# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_adaaf115_auto
_database_code_depnum_ccdc_archive 'CCDC 2311113'
loop_
_audit_author_name
_audit_author_address
'Animesh Das'
;IISER KOLKATA
India
;
_audit_update_record             
;
2023-11-29 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;
_audit_creation_date             2023-11-02
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H10 F5 N3'
_chemical_formula_sum            'C17 H10 F5 N3'
_chemical_formula_weight         351.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N F'
_chemical_oxdiff_usercomment     '100 K'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   14.4065(2)
_cell_length_b                   6.17670(10)
_cell_length_c                   17.7705(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.917(2)
_cell_angle_gamma                90
_cell_volume                     1486.72(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12348
_cell_measurement_temperature    99.99(11)
_cell_measurement_theta_max      67.9590
_cell_measurement_theta_min      2.6370
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.711
_exptl_absorpt_coefficient_mu    1.223
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19619
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.141
_diffrn_reflns_theta_min         3.263
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    105.00 170.00   0.50    0.40    --   96.35  96.00-120.00  130
  2  ω    -29.00  31.00   0.50    0.20    --   40.58 -25.00-180.00  120
  3  ω    -25.00  43.00   0.50    0.20    --   40.58 -38.00-120.00  136
  4  ω    -35.00  24.00   0.50    0.20    --   40.58 -12.00-150.00  118
  5  ω    -35.00  24.00   0.50    0.20    --   40.58 -12.00  60.00  118
  6  ω    -25.00  51.00   0.50    0.20    --   40.58 -45.00   7.00  152
  7  ω     44.00 127.00   0.50    0.40    --   96.35-145.00-120.00  166
  8  ω     23.00 106.00   0.50    0.40    --   96.35 -96.00-150.00  166
  9  ω     18.00  78.00   0.50    0.20    --   40.58-104.00 -60.00  120
 10  ω     33.00 110.00   0.50    0.40    --   96.35-117.00  60.00  154
 11  ω     33.00 110.00   0.50    0.40    --   96.35-117.00  30.00  154
 12  ω     30.00  57.00   0.50    0.40    --   96.35 -50.00 -90.00   54
 13  ω     29.00  83.00   0.50    0.40    --   96.35 -68.00-120.00  108
 14  ω     29.00  83.00   0.50    0.40    --   96.35 -68.00-150.00  108
 15  ω     29.00  83.00   0.50    0.40    --   96.35 -68.00 -90.00  108
 16  ω     30.00  57.00   0.50    0.40    --   96.35 -50.00   0.00   54
 17  ω     30.00  57.00   0.50    0.40    --   96.35 -50.00 -30.00   54
 18  ω     28.00  68.00   0.50    0.40    --   96.35 -59.00  30.00   80
 19  ω     30.00  57.00   0.50    0.40    --   96.35 -50.00  60.00   54
 20  ω     30.00  57.00   0.50    0.40    --   96.35 -50.00  90.00   54
 21  ω     30.00  57.00   0.50    0.40    --   96.35 -50.00 150.00   54
 22  ω     28.00 105.00   0.50    0.40    --   96.35 -77.00  60.00  154
 23  ω     30.00  57.00   0.50    0.40    --   96.35 -50.00 -60.00   54
 24  ω     30.00  57.00   0.50    0.40    --   96.35 -50.00-120.00   54
 25  ω     70.00 165.00   0.50    0.40    --   96.35  77.00 -60.00  190
 26  ω     75.00 165.00   0.50    0.40    --   96.35  59.00-180.00  180
 27  ω     77.00 163.00   0.50    0.40    --   96.35  50.00-150.00  172
 28  ω     72.00 164.00   0.50    0.40    --   96.35  68.00-120.00  184
 29  ω     80.00 164.00   0.50    0.40    --   96.35  42.00 -60.00  168
 30  ω     80.00 164.00   0.50    0.40    --   96.35  42.00   0.00  168
 31  ω     77.00 163.00   0.50    0.40    --   96.35  50.00  30.00  172
 32  ω     77.00 163.00   0.50    0.40    --   96.35  50.00 120.00  172
 33  ω     81.00 167.00   0.50    0.40    --   96.35  25.00  90.00  172
 34  ω     79.00 164.00   0.50    0.40    --   96.35  45.00 157.00  170
 35  ω     14.00 109.00   0.50    0.20    --   40.58  77.00 150.00  190
 36  ω     14.00 109.00   0.50    0.20    --   40.58  77.00  90.00  190
 37  ω     23.00 108.00   0.50    0.20    --   40.58  45.00 157.00  170
 38  ω     26.00 111.00   0.50    0.20    --   40.58  25.00  90.00  170
 39  ω     14.00 109.00   0.50    0.20    --   40.58  77.00  30.00  190
 40  ω     14.00 109.00   0.50    0.20    --   40.58  77.00 -60.00  190
 41  ω     14.00 109.00   0.50    0.20    --   40.58  77.00-150.00  190
 42  ω    -31.00  30.00   0.50    0.20    --  -40.58  25.00-150.00  122
 43  ω    -47.00 -15.00   0.50    0.40    --  -82.50  42.00 -60.00   64
 44  ω    -47.00 -15.00   0.50    0.40    --  -82.50  42.00  30.00   64
 45  ω    -47.00 -15.00   0.50    0.40    --  -82.50  42.00 120.00   64
 46  ω    -51.00 -15.00   0.50    0.40    --  -82.50  45.00 157.00   72
 47  ω    -51.00  27.00   0.50    0.20    --  -40.58  45.00 157.00  156
 48  ω    -96.00 -19.00   0.50    0.20    --  -40.58 138.00 150.00  154
 49  ω    -80.00  -9.00   0.50    0.40    --  -82.50  96.00-150.00  142
 50  ω   -108.00 -23.00   0.50    0.20    --  -40.58 -45.00   7.00  170
 51  ω   -108.00 -17.00   0.50    0.20    --  -40.58 -64.00 -30.00  182
 52  ω   -109.00 -14.00   0.50    0.20    --  -40.58 -77.00-150.00  190
 53  ω   -107.00 -25.00   0.50    0.20    --  -40.58 -38.00-180.00  164
 54  ω   -108.00 -17.00   0.50    0.20    --  -40.58 -64.00 -90.00  182
 55  ω   -150.00 -65.00   0.50    0.40    --  -82.50 -45.00   7.00  170
 56  ω   -151.00 -55.00   0.50    0.40    --  -82.50 -77.00 150.00  192
 57  ω   -151.00 -55.00   0.50    0.40    --  -82.50 -77.00  90.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0969309000
_diffrn_orient_matrix_UB_12      -0.0177311000
_diffrn_orient_matrix_UB_13      -0.0717738000
_diffrn_orient_matrix_UB_21      -0.0452650000
_diffrn_orient_matrix_UB_22      -0.1386702000
_diffrn_orient_matrix_UB_23      0.0507348000
_diffrn_orient_matrix_UB_31      -0.0386911000
_diffrn_orient_matrix_UB_32      0.2064927000
_diffrn_orient_matrix_UB_33      0.0279341000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2482
_reflns_number_total             2708
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_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         0.251
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2708
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.045
_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)+(0.0483P)²+0.6326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0912
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C5(H5), C16(H16), C6(H6), C17(H17), C1(H1), C2(H2)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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
F1 F 0.81682(6) 0.71846(14) 0.47069(5) 0.0316(2) Uani 1 1 d . . . . .
F5 F 0.75150(6) 0.04359(14) 0.33918(5) 0.0322(2) Uani 1 1 d . . . . .
F4 F 0.91598(7) 0.08822(15) 0.29904(5) 0.0363(2) Uani 1 1 d . . . . .
F2 F 0.97921(6) 0.76429(15) 0.42887(5) 0.0358(2) Uani 1 1 d . . . . .
F3 F 1.02825(6) 0.44851(16) 0.34172(5) 0.0373(2) Uani 1 1 d . . . . .
N3 N 0.54125(8) 0.48277(19) 0.42392(6) 0.0226(3) Uani 1 1 d . . . . .
N2 N 0.61756(8) 0.60455(19) 0.33039(6) 0.0228(3) Uani 1 1 d . . . . .
N1 N 0.69475(8) 0.35427(19) 0.42807(6) 0.0230(3) Uani 1 1 d . . . . .
C7 C 0.70342(10) 0.2115(2) 0.49401(8) 0.0219(3) Uani 1 1 d . . . . .
C14 C 0.61383(9) 0.4863(2) 0.39276(7) 0.0207(3) Uani 1 1 d . . . . .
C15 C 0.53957(10) 0.7325(2) 0.29696(8) 0.0243(3) Uani 1 1 d . . . . .
H15 H 0.538684 0.819574 0.252660 0.029 Uiso 1 1 calc R . . . .
C5 C 0.64735(10) -0.0891(2) 0.55265(8) 0.0242(3) Uani 1 1 d . . . . .
H5 H 0.598746 -0.196224 0.549179 0.029 Uiso 1 1 calc R . . . .
C8 C 0.77948(9) 0.3806(2) 0.40547(8) 0.0221(3) Uani 1 1 d . . . . .
C16 C 0.46005(10) 0.7444(2) 0.32366(8) 0.0250(3) Uani 1 1 d . . . . .
H16 H 0.405216 0.836308 0.299006 0.030 Uiso 1 1 calc R . . . .
C9 C 0.83937(10) 0.5627(2) 0.42761(8) 0.0242(3) Uani 1 1 d . . . . .
C6 C 0.63424(10) 0.0513(2) 0.48888(8) 0.0233(3) Uani 1 1 d . . . . .
H6 H 0.577930 0.037602 0.441818 0.028 Uiso 1 1 calc R . . . .
C3 C 0.73059(10) -0.0760(2) 0.62183(8) 0.0252(3) Uani 1 1 d . . . . .
C17 C 0.46507(10) 0.6145(2) 0.38845(8) 0.0236(3) Uani 1 1 d . . . . .
H17 H 0.411972 0.619039 0.408677 0.028 Uiso 1 1 calc R . . . .
C13 C 0.80715(10) 0.2215(2) 0.36220(8) 0.0243(3) Uani 1 1 d . . . . .
C10 C 0.92266(10) 0.5868(2) 0.40661(8) 0.0262(3) Uani 1 1 d . . . . .
C12 C 0.89088(11) 0.2425(2) 0.34140(8) 0.0267(3) Uani 1 1 d . . . . .
C1 C 0.78553(10) 0.2298(3) 0.56289(8) 0.0284(3) Uani 1 1 d . . . . .
H1 H 0.832536 0.341237 0.567198 0.034 Uiso 1 1 calc R . . . .
C11 C 0.94819(10) 0.4260(3) 0.36336(8) 0.0270(3) Uani 1 1 d . . . . .
C2 C 0.79895(11) 0.0853(3) 0.62550(8) 0.0308(3) Uani 1 1 d . . . . .
H2 H 0.856225 0.097150 0.671897 0.037 Uiso 1 1 calc R . . . .
C4 C 0.74640(12) -0.2324(3) 0.69018(9) 0.0326(3) Uani 1 1 d . . . . .
H4A H 0.706027 -0.188496 0.722169 0.049 Uiso 1 1 calc GR . . . .
H4B H 0.816230 -0.232138 0.723892 0.049 Uiso 1 1 calc GR . . . .
H4C H 0.727218 -0.378348 0.668907 0.049 Uiso 1 1 calc GR . . . .


_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
F1 C9 1.3368(16) . ?
F5 C13 1.3394(16) . ?
F4 C12 1.3382(16) . ?
F2 C10 1.3425(16) . ?
F3 C11 1.3416(16) . ?
N3 C14 1.3396(17) . ?
N3 C17 1.3387(18) . ?
N2 C14 1.3438(17) . ?
N2 C15 1.3360(18) . ?
N1 C7 1.4376(17) . ?
N1 C14 1.3854(17) . ?
N1 C8 1.4184(16) . ?
C7 C6 1.3852(19) . ?
C7 C1 1.3871(19) . ?
C15 C16 1.3832(19) . ?
C5 C6 1.388(2) . ?
C5 C3 1.397(2) . ?
C8 C9 1.390(2) . ?
C8 C13 1.388(2) . ?
C16 C17 1.3850(19) . ?
C9 C10 1.381(2) . ?
C3 C2 1.387(2) . ?
C3 C4 1.5073(19) . ?
C13 C12 1.383(2) . ?
C10 C11 1.380(2) . ?
C12 C11 1.378(2) . ?
C1 C2 1.388(2) . ?

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
C17 N3 C14 115.19(11) . . ?
C15 N2 C14 115.11(11) . . ?
C14 N1 C7 123.80(11) . . ?
C14 N1 C8 118.47(11) . . ?
C8 N1 C7 117.20(10) . . ?
C6 C7 N1 121.59(12) . . ?
C6 C7 C1 119.65(13) . . ?
C1 C7 N1 118.71(12) . . ?
N3 C14 N2 127.30(12) . . ?
N3 C14 N1 117.27(11) . . ?
N2 C14 N1 115.44(11) . . ?
N2 C15 C16 123.25(12) . . ?
C6 C5 C3 121.31(13) . . ?
C9 C8 N1 121.60(12) . . ?
C13 C8 N1 120.86(12) . . ?
C13 C8 C9 117.52(12) . . ?
C15 C16 C17 116.07(13) . . ?
F1 C9 C8 119.72(12) . . ?
F1 C9 C10 118.70(13) . . ?
C10 C9 C8 121.58(13) . . ?
C7 C6 C5 119.86(12) . . ?
C5 C3 C4 121.39(13) . . ?
C2 C3 C5 117.77(13) . . ?
C2 C3 C4 120.84(13) . . ?
N3 C17 C16 123.08(12) . . ?
F5 C13 C8 119.70(12) . . ?
F5 C13 C12 118.76(12) . . ?
C12 C13 C8 121.55(13) . . ?
F2 C10 C9 120.30(13) . . ?
F2 C10 C11 120.10(12) . . ?
C11 C10 C9 119.60(13) . . ?
F4 C12 C13 120.74(13) . . ?
F4 C12 C11 119.63(12) . . ?
C11 C12 C13 119.62(13) . . ?
C7 C1 C2 119.93(13) . . ?
F3 C11 C10 120.23(13) . . ?
F3 C11 C12 119.64(13) . . ?
C12 C11 C10 120.13(13) . . ?
C3 C2 C1 121.45(13) . . ?

_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 1.914
_oxdiff_exptl_absorpt_empirical_full_min 0.528
####################################################################### 
# 
# 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_ada_ab_272_auto_1
_database_code_depnum_ccdc_archive 'CCDC 2327240'
loop_
_audit_author_name
_audit_author_address
'Animesh Das'
;IISER KOLKATA
India
;
_audit_update_record             
;
2024-01-22 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;
_audit_creation_date             2023-11-29
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 F5 N3'
_chemical_formula_sum            'C15 H14 F5 N3'
_chemical_formula_weight         331.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N F'
_chemical_oxdiff_usercomment     100K
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.4951(3)
_cell_length_b                   7.6806(2)
_cell_length_c                   16.1712(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.511(3)
_cell_angle_gamma                90
_cell_volume                     1471.65(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10122
_cell_measurement_temperature    100.4(9)
_cell_measurement_theta_max      67.9940
_cell_measurement_theta_min      3.7320
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.797
_exptl_absorpt_coefficient_mu    1.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16716
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.072
_diffrn_reflns_theta_min         3.731
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.4(9)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  30.00   0.50    0.30    --  -40.58  89.00 -22.00  204
  2  ω    -21.00  72.00   0.50    0.30    --   40.58 -89.00-138.00  186
  3  ω   -153.00 -78.00   0.50    1.50    --  -82.50 -89.00-138.00  150
  4  ω    -81.00 -12.00   0.50    1.50    --  -82.50  89.00 -22.00  138
  5  ω     26.00 106.00   0.50    1.50    --   96.35 -89.00-138.00  160
  6  ω    -96.00 -19.00   0.50    0.30    --  -40.58 138.00-180.00  154
  7  ω    -24.00  35.00   0.50    0.30    --  -40.58  12.00 120.00  118
  8  ω    -31.00  30.00   0.50    0.30    --  -40.58  25.00 -90.00  122
  9  ω    -25.00  43.00   0.50    0.30    --   40.58 -38.00 -60.00  136
 10  ω     22.00 107.00   0.50    0.30    --   40.58  50.00  60.00  170
 11  ω    -35.00  24.00   0.50    0.30    --   40.58 -12.00  90.00  118
 12  ω    -29.00  31.00   0.50    0.30    --   40.58 -25.00-120.00  120
 13  ω   -151.00 -61.00   0.50    1.50    --  -82.50 -59.00 150.00  180
 14  ω    -47.00 -15.00   0.50    1.50    --  -82.50  42.00 -90.00   64
 15  ω    -47.00 -15.00   0.50    1.50    --  -82.50  42.00-180.00   64
 16  ω   -156.00 -83.00   0.50    1.50    --  -82.50 -96.00  30.00  146
 17  ω    -47.00 -15.00   0.50    1.50    --  -82.50  42.00 150.00   64
 18  ω     30.00  57.00   0.50    1.50    --   96.35 -50.00  90.00   54
 19  ω     29.00  83.00   0.50    1.50    --   96.35 -68.00-120.00  108
 20  ω     30.00  57.00   0.50    1.50    --   96.35 -50.00 120.00   54
 21  ω     44.00 127.00   0.50    1.50    --   96.35-145.00-120.00  166
 22  ω     28.00  68.00   0.50    1.50    --   96.35 -59.00  30.00   80
 23  ω     30.00  57.00   0.50    1.50    --   96.35 -50.00  30.00   54
 24  ω    105.00 170.00   0.50    1.50    --   96.35  96.00   0.00  130
 25  ω     44.00 127.00   0.50    1.50    --   96.35-145.00  60.00  166
 26  ω     81.00 167.00   0.50    1.50    --   96.35  25.00 -60.00  172
 27  ω     44.00 127.00   0.50    1.50    --   96.35-145.00  90.00  166
 28  ω     33.00 110.00   0.50    1.50    --   96.35-117.00  90.00  154
 29  ω     28.00 105.00   0.50    1.50    --   96.35 -77.00 -90.00  154
 30  ω     30.00  57.00   0.50    1.50    --   96.35 -50.00 -60.00   54
 31  ω     29.00  83.00   0.50    1.50    --   96.35 -68.00  90.00  108
 32  ω    100.00 167.00   0.50    1.50    --   96.35  89.00 -22.00  134
 33  ω   -109.00 -14.00   0.50    0.30    --  -40.58 -77.00  60.00  190
 34  ω   -109.00 -14.00   0.50    0.30    --  -40.58 -77.00 120.00  190
 35  ω   -108.00 -17.00   0.50    0.30    --  -40.58 -64.00-120.00  182
 36  ω   -109.00 -14.00   0.50    0.30    --  -40.58 -77.00-180.00  190
 37  ω   -109.00 -14.00   0.50    0.30    --  -40.58 -77.00 -30.00  190
 38  ω    -25.00  43.00   0.50    0.30    --   40.58 -38.00   0.00  136
 39  ω     14.00 109.00   0.50    0.30    --   40.58  77.00  60.00  190
 40  ω     22.00 107.00   0.50    0.30    --   40.58  50.00   0.00  170
 41  ω     18.00 108.00   0.50    0.30    --   40.58  64.00-150.00  180
 42  ω     14.00 109.00   0.50    0.30    --   40.58  77.00 -90.00  190
 43  ω   -151.00 -72.00   0.50    1.50    --  -82.50 -77.00 -90.00  158
 44  ω     77.00 163.00   0.50    1.50    --   96.35  50.00-180.00  172
 45  ω     72.00 164.00   0.50    1.50    --   96.35  68.00  90.00  184
 46  ω     75.00 165.00   0.50    1.50    --   96.35  59.00 -30.00  180
 47  ω     83.00 164.00   0.50    1.50    --   96.35  33.00-120.00  162
 48  ω     80.00 164.00   0.50    1.50    --   96.35  42.00  60.00  168
 49  ω     70.00 165.00   0.50    1.50    --   96.35  77.00 120.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1245792000
_diffrn_orient_matrix_UB_12      0.0314184000
_diffrn_orient_matrix_UB_13      0.0533557000
_diffrn_orient_matrix_UB_21      0.0045820000
_diffrn_orient_matrix_UB_22      -0.1792434000
_diffrn_orient_matrix_UB_23      0.0437665000
_diffrn_orient_matrix_UB_31      0.0367369000
_diffrn_orient_matrix_UB_32      -0.0845139000
_diffrn_orient_matrix_UB_33      -0.0730836000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2323
_reflns_number_total             2682
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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         0.319
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2682
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.054
_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)+(0.0781P)²+0.4736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1326
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C12(H12a,H12b)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C9(H9), C8(H8)
2.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C13(H13a,H13b,H13c)
;
_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
F1 F 0.56673(9) 0.18624(13) 0.66567(7) 0.0352(3) Uani 1 1 d . . . . .
F5 F 0.84840(9) 0.62330(14) 0.74238(7) 0.0365(3) Uani 1 1 d . . . . .
F4 F 1.00209(9) 0.38176(16) 0.81991(8) 0.0438(3) Uani 1 1 d . . . . .
F2 F 0.72121(11) -0.05098(14) 0.74605(8) 0.0455(3) Uani 1 1 d . . . . .
F3 F 0.94054(11) 0.04244(16) 0.82144(8) 0.0475(3) Uani 1 1 d . . . . .
N3 N 0.37951(12) 0.90449(19) 0.53955(10) 0.0288(4) Uani 1 1 d . . . . .
H3 H 0.399618 0.990142 0.511472 0.035 Uiso 1 1 calc R . . . .
N2 N 0.55848(12) 0.79514(19) 0.56492(10) 0.0289(3) Uani 1 1 d . . . . .
N1 N 0.43099(12) 0.66940(19) 0.63290(10) 0.0306(4) Uani 1 1 d . . . . .
C10 C 0.45766(14) 0.7865(2) 0.57995(11) 0.0273(4) Uani 1 1 d . . . . .
C6 C 0.70122(15) 0.4149(2) 0.70081(11) 0.0271(4) Uani 1 1 d . . . . .
C1 C 0.67353(15) 0.2397(2) 0.70394(11) 0.0290(4) Uani 1 1 d . . . . .
C7 C 0.61507(15) 0.5470(2) 0.65849(11) 0.0275(4) Uani 1 1 d . . . . .
C5 C 0.81431(15) 0.4569(2) 0.74036(12) 0.0298(4) Uani 1 1 d . . . . .
C9 C 0.63351(15) 0.6750(2) 0.60371(12) 0.0291(4) Uani 1 1 d . . . . .
H9 H 0.704316 0.676256 0.593529 0.035 Uiso 1 1 calc R . . . .
C8 C 0.50985(15) 0.5529(2) 0.67098(12) 0.0294(4) Uani 1 1 d . . . . .
H8 H 0.493630 0.469311 0.708650 0.035 Uiso 1 1 calc R . . . .
C11 C 0.26295(14) 0.8983(2) 0.53968(12) 0.0275(4) Uani 1 1 d . . . . .
H11 H 0.263299 0.869665 0.600079 0.033 Uiso 1 1 calc R . . . .
C2 C 0.75231(17) 0.1150(2) 0.74411(12) 0.0327(4) Uani 1 1 d . . . . .
C4 C 0.89471(15) 0.3342(3) 0.78049(12) 0.0327(4) Uani 1 1 d . . . . .
C3 C 0.86334(17) 0.1624(3) 0.78186(12) 0.0352(5) Uani 1 1 d . . . . .
C14 C 0.20961(15) 1.0773(2) 0.51563(13) 0.0334(4) Uani 1 1 d . . . . .
H14A H 0.210757 1.107735 0.456422 0.040 Uiso 1 1 calc R . . . .
H14B H 0.129654 1.071120 0.513532 0.040 Uiso 1 1 calc R . . . .
C12 C 0.19835(16) 0.7548(2) 0.47813(13) 0.0342(4) Uani 1 1 d . . . . .
H12A H 0.195889 0.784096 0.417933 0.041 Uiso 1 1 calc R . . . .
H12B H 0.240335 0.644090 0.494288 0.041 Uiso 1 1 calc R . . . .
C15 C 0.26749(19) 1.2217(2) 0.57803(14) 0.0414(5) Uani 1 1 d . . . . .
H15A H 0.224921 1.330186 0.561082 0.062 Uiso 1 1 calc GR . . . .
H15B H 0.344334 1.237781 0.575816 0.062 Uiso 1 1 calc GR . . . .
H15C H 0.270563 1.190113 0.637464 0.062 Uiso 1 1 calc GR . . . .
C13 C 0.07861(18) 0.7278(3) 0.47934(15) 0.0493(6) Uani 1 1 d . . . . .
H13A H 0.048853 0.618473 0.449610 0.074 Uiso 1 1 calc GR . . . .
H13B H 0.031169 0.824862 0.449339 0.074 Uiso 1 1 calc GR . . . .
H13C H 0.078446 0.722434 0.539847 0.074 Uiso 1 1 calc GR . . . .


_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
F1 C1 1.345(2) . ?
F5 C5 1.344(2) . ?
F4 C4 1.340(2) . ?
F2 C2 1.336(2) . ?
F3 C3 1.340(2) . ?
N3 C10 1.340(2) . ?
N3 C11 1.458(2) . ?
N2 C10 1.358(2) . ?
N2 C9 1.323(2) . ?
N1 C10 1.354(2) . ?
N1 C8 1.329(2) . ?
C6 C1 1.394(2) . ?
C6 C7 1.479(2) . ?
C6 C5 1.391(3) . ?
C1 C2 1.379(3) . ?
C7 C9 1.391(2) . ?
C7 C8 1.393(3) . ?
C5 C4 1.380(3) . ?
C11 C14 1.523(2) . ?
C11 C12 1.532(2) . ?
C2 C3 1.375(3) . ?
C4 C3 1.379(3) . ?
C14 C15 1.519(3) . ?
C12 C13 1.517(3) . ?

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 N3 C11 123.43(15) . . ?
C9 N2 C10 116.03(15) . . ?
C8 N1 C10 116.43(15) . . ?
N3 C10 N2 116.95(15) . . ?
N3 C10 N1 118.02(16) . . ?
N1 C10 N2 125.03(16) . . ?
C1 C6 C7 121.74(16) . . ?
C5 C6 C1 115.74(16) . . ?
C5 C6 C7 122.52(16) . . ?
F1 C1 C6 119.98(16) . . ?
F1 C1 C2 117.40(16) . . ?
C2 C1 C6 122.62(17) . . ?
C9 C7 C6 122.41(16) . . ?
C9 C7 C8 115.12(16) . . ?
C8 C7 C6 122.47(15) . . ?
F5 C5 C6 119.94(15) . . ?
F5 C5 C4 117.39(16) . . ?
C4 C5 C6 122.65(17) . . ?
N2 C9 C7 124.01(16) . . ?
N1 C8 C7 123.35(16) . . ?
N3 C11 C14 109.07(14) . . ?
N3 C11 C12 110.06(15) . . ?
C14 C11 C12 112.69(15) . . ?
F2 C2 C1 120.29(18) . . ?
F2 C2 C3 120.11(16) . . ?
C3 C2 C1 119.60(17) . . ?
F4 C4 C5 120.45(18) . . ?
F4 C4 C3 119.99(17) . . ?
C3 C4 C5 119.53(18) . . ?
F3 C3 C2 120.12(18) . . ?
F3 C3 C4 120.02(18) . . ?
C2 C3 C4 119.85(17) . . ?
C15 C14 C11 114.30(15) . . ?
C13 C12 C11 114.13(16) . . ?

_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 1.475
_oxdiff_exptl_absorpt_empirical_full_min 0.625
