# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_kjk-etcetoh-needle
_database_code_depnum_ccdc_archive 'CCDC 2260509'
loop_
_audit_author_name
_audit_author_address
'Kalyan Jyoti Kalita'
;Indian Institute of Science Education and Research Kolkata
India
;
_audit_update_record             
;
2023-05-04 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_audit_creation_date             2023-04-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 F2 N, C14 H13 N'
_chemical_formula_sum            'C18 H13 F2 N2'
_chemical_formula_weight         295.30
_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                   9.21813(19)
_cell_length_b                   19.4553(3)
_cell_length_c                   8.39007(17)
_cell_angle_alpha                90
_cell_angle_beta                 108.890(2)
_cell_angle_gamma                90
_cell_volume                     1423.65(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5424
_cell_measurement_temperature    100.00(13)
_cell_measurement_theta_max      68.0390
_cell_measurement_theta_min      4.5270
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.680
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9254
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.226
_diffrn_reflns_theta_min         4.545
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  28.00   0.50    1.20    --  -41.33  29.00  57.00  124
  2  ω    -24.00  35.00   0.50    1.20    --  -41.33  11.00  90.00  118
  3  ω     29.00 110.00   0.50    1.20    --   41.33  29.00  57.00  162
  4  ω     84.00 166.00   0.50    4.79    --   96.67  29.00  57.00  164
  5  ω     90.00 124.00   0.50    4.79    --   96.67 145.00 -90.00   68
  6  ω    135.00 163.00   0.50    4.79    --   96.67 145.00 -90.00   56
  7  ω     90.00 123.00   0.50    4.79    --   96.67 145.00 -60.00   66
  8  ω     80.00 160.00   0.50    4.79    --   96.67  42.00-120.00  160
  9  ω     39.00  64.00   0.50    4.79    --   96.67 -68.00 120.00   50
 10  ω     41.00  82.00   0.50    4.79    --   96.67 -68.00 150.00   82
 11  ω     37.00  97.00   0.50    4.79    --   96.67-117.00 150.00  120
 12  ω     44.00 110.00   0.50    4.79    --   96.67-145.00  60.00  132
 13  ω     41.00  67.00   0.50    4.79    --   96.67 -59.00 -90.00   52
 14  ω     38.00  92.00   0.50    4.79    --   96.67 -77.00 -90.00  108
 15  ω     40.00  83.00   0.50    4.79    --   96.67 -68.00-180.00   86
 16  ω     30.00  55.00   0.50    4.79    --   96.67 -50.00 -90.00   50
 17  ω     30.00  55.00   0.50    4.79    --   96.67 -50.00 -60.00   50
 18  ω     29.00  54.00   0.50    4.79    --   96.67 -59.00 -60.00   50
 19  ω     30.00  56.00   0.50    4.79    --   96.67 -50.00 -30.00   52
 20  ω     36.00  68.00   0.50    4.79    --   96.67 -59.00   0.00   64
 21  ω     30.00  55.00   0.50    4.79    --   96.67 -50.00  30.00   50
 22  ω     30.00  55.00   0.50    4.79    --   96.67 -50.00  90.00   50
 23  ω    -25.00  48.00   0.50    1.20    --   41.33 -43.00  60.00  146
 24  ω    -25.00  48.00   0.50    1.20    --   41.33 -43.00  90.00  146
 25  ω    -27.00  34.00   0.50    1.20    --   41.33 -29.00-103.00  122
 26  ω     18.00  80.00   0.50    1.20    --   41.33-104.00-120.00  124
 27  ω     30.00  56.00   0.50    4.79    --   96.67 -50.00-120.00   52
 28  ω     31.00  57.00   0.50    4.79    --   96.67 -50.00-150.00   52
 29  ω     29.00  55.00   0.50    4.79    --   96.67 -59.00-150.00   52
 30  ω    -65.00  26.00   0.50    1.20    --  -41.33  65.00 120.00  182
 31  ω    -47.00 -15.00   0.50    4.79    --  -82.50  42.00   0.00   64
 32  ω    -47.00 -15.00   0.50    4.79    --  -82.50  42.00  60.00   64
 33  ω    -47.00 -15.00   0.50    4.79    --  -82.50  42.00  30.00   64
 34  ω    -47.00 -15.00   0.50    4.79    --  -82.50  42.00 -90.00   64
 35  ω    -47.00 -15.00   0.50    4.79    --  -82.50  42.00-120.00   64
 36  ω    -83.00 -14.00   0.50    4.79    --  -82.50  68.00-180.00  138
 37  ω   -110.00 -29.00   0.50    1.20    --  -41.33 -29.00-103.00  162
 38  ω   -151.00 -70.00   0.50    4.79    --  -82.50 -29.00-103.00  162
;
_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      -0.1655206000
_diffrn_orient_matrix_UB_12      0.0275048000
_diffrn_orient_matrix_UB_13      -0.0519043000
_diffrn_orient_matrix_UB_21      -0.0167777000
_diffrn_orient_matrix_UB_22      -0.0115901000
_diffrn_orient_matrix_UB_23      -0.1867882000
_diffrn_orient_matrix_UB_31      -0.0593533000
_diffrn_orient_matrix_UB_32      -0.0733362000
_diffrn_orient_matrix_UB_33      0.0101315000
_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                2164
_reflns_number_total             2566
_reflns_odcompleteness_completeness 99.85
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2566
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0563P)²+0.2398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1028
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C17(H17), C20(H20), C18(H18), C13(H13), C12(H12), C19(H19)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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
F4 F 0.79647(9) 0.45861(4) 0.62982(11) 0.0310(2) Uani 1 1 d . . . . .
F5 F 0.61078(10) 0.45133(4) 0.81976(10) 0.0336(2) Uani 1 1 d . . . . .
N16 N 0.81024(13) 0.61705(6) 0.75326(14) 0.0237(3) Uani 1 1 d . . . . .
N7 N 0.22827(15) 0.49246(6) 0.78481(17) 0.0330(3) Uani 1 1 d . . . . .
C8 C 0.82954(16) 0.63666(7) 0.60236(17) 0.0227(3) Uani 1 1 d . . . . .
C9 C 0.69185(16) 0.66599(7) 0.49671(17) 0.0222(3) Uani 1 1 d . . . . .
C15 C 0.66327(16) 0.63503(7) 0.74874(18) 0.0234(3) Uani 1 1 d . . . . .
C10 C 0.58452(16) 0.66435(6) 0.58928(17) 0.0223(3) Uani 1 1 d . . . . .
C2 C 0.40324(16) 0.49630(7) 0.59906(18) 0.0247(3) Uani 1 1 d . . . . .
C3 C 0.55585(17) 0.47544(7) 0.66221(17) 0.0253(3) Uani 1 1 d . . . . .
C11 C 0.43256(16) 0.68592(7) 0.55402(18) 0.0247(3) Uani 1 1 d . . . . .
H11 H 0.377836 0.705180 0.447431 0.030 Uiso 1 1 calc R U . . .
C14 C 0.59310(17) 0.62701(7) 0.87180(18) 0.0262(3) Uani 1 1 d . . . . .
H14 H 0.646034 0.606848 0.977838 0.031 Uiso 1 1 calc R U . . .
C6 C 0.30560(17) 0.49355(7) 0.70166(19) 0.0268(3) Uani 1 1 d . . . . .
C17 C 0.95861(16) 0.63059(7) 0.55148(18) 0.0251(3) Uani 1 1 d . . . . .
H17 H 1.049840 0.609411 0.621549 0.030 Uiso 1 1 calc R U . . .
C20 C 0.68444(16) 0.69099(7) 0.33777(17) 0.0241(3) Uani 1 1 d . . . . .
H20 H 0.592366 0.710523 0.264919 0.029 Uiso 1 1 calc R U . . .
C18 C 0.94861(17) 0.65671(7) 0.39433(18) 0.0259(3) Uani 1 1 d . . . . .
H18 H 1.035606 0.654162 0.357399 0.031 Uiso 1 1 calc R U . . .
C13 C 0.44287(17) 0.64963(7) 0.83348(19) 0.0279(3) Uani 1 1 d . . . . .
H13 H 0.392702 0.645241 0.915621 0.033 Uiso 1 1 calc R U . . .
C12 C 0.36323(17) 0.67879(7) 0.67667(19) 0.0278(3) Uani 1 1 d . . . . .
H12 H 0.260502 0.693809 0.654444 0.033 Uiso 1 1 calc R U . . .
C19 C 0.81366(17) 0.68670(7) 0.28892(18) 0.0265(3) Uani 1 1 d . . . . .
H19 H 0.810821 0.704342 0.182377 0.032 Uiso 1 1 calc R U . . .
C1 C 0.65047(16) 0.47919(7) 0.56567(18) 0.0247(3) Uani 1 1 d . . . . .
C21 C 0.93446(17) 0.59311(8) 0.90053(18) 0.0288(3) Uani 1 1 d . . . . .
H21A H 0.992365 0.556552 0.865317 0.035 Uiso 1 1 calc R U . . .
H21B H 0.889985 0.572857 0.982590 0.035 Uiso 1 1 calc R U . . .
C22 C 1.04392(17) 0.65038(9) 0.98559(19) 0.0341(4) Uani 1 1 d . . . . .
H22A H 1.091195 0.669502 0.906169 0.051 Uiso 1 1 calc R U . . .
H22B H 1.123925 0.632013 1.084147 0.051 Uiso 1 1 calc R U . . .
H22C H 0.987341 0.686601 1.021396 0.051 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
F4 C1 1.3388(16) . ?
F5 C3 1.3380(16) . ?
N16 C8 1.3878(18) . ?
N16 C15 1.3878(18) . ?
N16 C21 1.4624(18) . ?
N7 C6 1.148(2) . ?
C8 C9 1.4121(19) . ?
C8 C17 1.393(2) . ?
C9 C10 1.443(2) . ?
C9 C20 1.400(2) . ?
C15 C10 1.419(2) . ?
C15 C14 1.393(2) . ?
C10 C11 1.399(2) . ?
C2 C3 1.394(2) . ?
C2 C6 1.434(2) . ?
C2 C1 1.393(2) 3_666 ?
C3 C1 1.371(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.388(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(2) . ?
C20 H20 0.9500 . ?
C20 C19 1.382(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.399(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.402(2) . ?
C12 H12 0.9500 . ?
C19 H19 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.517(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

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
C8 N16 C15 108.55(11) . . ?
C8 N16 C21 124.18(12) . . ?
C15 N16 C21 126.43(12) . . ?
N16 C8 C9 109.22(12) . . ?
N16 C8 C17 129.11(13) . . ?
C17 C8 C9 121.68(13) . . ?
C8 C9 C10 106.67(12) . . ?
C20 C9 C8 119.67(13) . . ?
C20 C9 C10 133.63(13) . . ?
N16 C15 C10 108.90(13) . . ?
N16 C15 C14 129.41(13) . . ?
C14 C15 C10 121.68(13) . . ?
C15 C10 C9 106.61(12) . . ?
C11 C10 C9 133.93(13) . . ?
C11 C10 C15 119.44(13) . . ?
C3 C2 C6 120.90(13) . . ?
C1 C2 C3 117.89(13) 3_666 . ?
C1 C2 C6 121.21(13) 3_666 . ?
F5 C3 C2 119.36(13) . . ?
F5 C3 C1 119.52(13) . . ?
C1 C3 C2 121.12(13) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.00(13) . . ?
C12 C11 H11 120.5 . . ?
C15 C14 H14 121.3 . . ?
C13 C14 C15 117.43(13) . . ?
C13 C14 H14 121.3 . . ?
N7 C6 C2 178.83(15) . . ?
C8 C17 H17 121.3 . . ?
C18 C17 C8 117.35(13) . . ?
C18 C17 H17 121.3 . . ?
C9 C20 H20 120.6 . . ?
C19 C20 C9 118.72(13) . . ?
C19 C20 H20 120.6 . . ?
C17 C18 H18 119.2 . . ?
C17 C18 C19 121.68(14) . . ?
C19 C18 H18 119.2 . . ?
C14 C13 H13 119.1 . . ?
C14 C13 C12 121.71(14) . . ?
C12 C13 H13 119.1 . . ?
C11 C12 C13 120.73(14) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C20 C19 C18 120.87(13) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
F4 C1 C2 119.30(13) . 3_666 ?
F4 C1 C3 119.71(12) . . ?
C3 C1 C2 120.98(13) . 3_666 ?
N16 C21 H21A 109.1 . . ?
N16 C21 H21B 109.1 . . ?
N16 C21 C22 112.52(12) . . ?
H21A C21 H21B 107.8 . . ?
C22 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
F5 C3 C1 F4 0.13(19) . . . . ?
F5 C3 C1 C2 179.68(12) . . . 3_666 ?
N16 C8 C9 C10 0.38(14) . . . . ?
N16 C8 C9 C20 178.77(11) . . . . ?
N16 C8 C17 C18 -177.88(13) . . . . ?
N16 C15 C10 C9 -2.01(14) . . . . ?
N16 C15 C10 C11 179.30(11) . . . . ?
N16 C15 C14 C13 -179.82(13) . . . . ?
C8 N16 C15 C10 2.28(15) . . . . ?
C8 N16 C15 C14 -178.56(14) . . . . ?
C8 N16 C21 C22 70.91(17) . . . . ?
C8 C9 C10 C15 0.99(14) . . . . ?
C8 C9 C10 C11 179.41(14) . . . . ?
C8 C9 C20 C19 -0.52(19) . . . . ?
C8 C17 C18 C19 -1.3(2) . . . . ?
C9 C8 C17 C18 2.1(2) . . . . ?
C9 C10 C11 C12 -177.55(14) . . . . ?
C9 C20 C19 C18 1.3(2) . . . . ?
C15 N16 C8 C9 -1.65(15) . . . . ?
C15 N16 C8 C17 178.38(14) . . . . ?
C15 N16 C21 C22 -97.35(16) . . . . ?
C15 C10 C11 C12 0.71(19) . . . . ?
C15 C14 C13 C12 0.7(2) . . . . ?
C10 C9 C20 C19 177.35(14) . . . . ?
C10 C15 C14 C13 -0.8(2) . . . . ?
C10 C11 C12 C13 -0.8(2) . . . . ?
C2 C3 C1 F4 -179.86(12) . . . . ?
C2 C3 C1 C2 -0.3(2) . . . 3_666 ?
C14 C15 C10 C9 178.75(12) . . . . ?
C14 C15 C10 C11 0.1(2) . . . . ?
C14 C13 C12 C11 0.1(2) . . . . ?
C6 C2 C3 F5 1.3(2) . . . . ?
C6 C2 C3 C1 -178.75(12) . . . . ?
C17 C8 C9 C10 -179.64(12) . . . . ?
C17 C8 C9 C20 -1.2(2) . . . . ?
C17 C18 C19 C20 -0.4(2) . . . . ?
C20 C9 C10 C15 -177.08(14) . . . . ?
C20 C9 C10 C11 1.3(3) . . . . ?
C1 C2 C3 F5 -179.69(12) 3_666 . . . ?
C1 C2 C3 C1 0.3(2) 3_666 . . . ?
C21 N16 C8 C9 -171.70(12) . . . . ?
C21 N16 C8 C17 8.3(2) . . . . ?
C21 N16 C15 C10 172.05(12) . . . . ?
C21 N16 C15 C14 -8.8(2) . . . . ?


_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 1.349
_oxdiff_exptl_absorpt_empirical_full_min 0.722
####################################################################### 
# 
# 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_kjkj_dtdc_1
_database_code_depnum_ccdc_archive 'CCDC 2260512'
loop_
_audit_author_name
_audit_author_address
'Kalyan Jyoti Kalita'
;Indian Institute of Science Education and Research Kolkata
India
;
_audit_update_record             
;
2023-05-04 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_audit_creation_date             2023-04-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 F4 N2, C20 H25 N'
_chemical_formula_sum            'C28 H25 F4 N3'
_chemical_formula_weight         479.51
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7353(3)
_cell_length_b                   11.3696(5)
_cell_length_c                   16.8733(8)
_cell_angle_alpha                70.393(4)
_cell_angle_beta                 86.036(4)
_cell_angle_gamma                79.883(4)
_cell_volume                     1198.20(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4354
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      67.7320
_cell_measurement_theta_min      2.7710
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.590
_exptl_absorpt_coefficient_mu    0.842
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10240
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.214
_diffrn_reflns_theta_min         2.780
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  29.00   0.50    0.35    --  -41.33  21.00 -30.00  104
  2  ω    -21.00  19.00   0.50    0.35    --  -41.33  21.00  30.00   80
  3  ω     -9.00  29.00   0.50    0.35    --  -41.33  11.00 120.00   76
  4  ω    -24.00  32.00   0.50    0.35    --  -41.33  11.00  90.00  112
  5  ω    -26.00   3.00   0.50    0.35    --  -41.33  21.00   0.00   58
  6  ω    -47.00 -22.00   0.50    1.42    --  -82.50  42.00 -90.00   50
  7  ω    -27.00  26.00   0.50    0.35    --  -41.33  21.00-150.00  106
  8  ω    -45.00 -15.00   0.50    1.42    --  -82.50  42.00-180.00   60
  9  ω    -68.00 -27.00   0.50    0.35    --  -41.33 128.00-164.00   82
 10  ω    -45.00 -17.00   0.50    1.42    --  -82.50  42.00  30.00   56
 11  ω    -45.00 -16.00   0.50    1.42    --  -82.50  42.00  90.00   58
 12  ω    -57.00 -21.00   0.50    1.42    --  -82.50  50.00  60.00   72
 13  ω    -87.00 -40.00   0.50    0.35    --  -41.33 142.00   6.00   94
 14  ω    -84.00 -31.00   0.50    1.42    --  -82.50 117.00 120.00  106
 15  ω    -17.00  14.00   0.50    0.35    --   41.33 -43.00-120.00   62
 16  ω     23.00  48.00   0.50    0.35    --   41.33 -43.00-120.00   50
 17  ω     83.00 163.00   0.50    1.42    --   96.67  33.00 -30.00  160
 18  ω    107.00 140.00   0.50    1.42    --   96.67  96.00-120.00   66
 19  ω    130.00 163.00   0.50    1.42    --   96.67  96.00-180.00   66
 20  ω    134.00 162.00   0.50    1.42    --   96.67 145.00-120.00   56
 21  ω    111.00 164.00   0.50    1.42    --   96.67 117.00 -30.00  106
 22  ω     99.00 129.00   0.50    1.42    --   96.67 117.00-120.00   60
 23  ω     87.00 113.00   0.50    1.42    --   96.67 145.00-120.00   52
 24  ω     95.00 123.00   0.50    1.42    --   96.67 142.00   6.00   56
 25  ω     84.00 164.00   0.50    1.42    --   96.67  59.00  60.00  160
 26  ω    101.00 156.00   0.50    1.42    --   96.67  33.00  30.00  110
 27  ω     90.00 163.00   0.50    1.42    --   96.67  50.00   0.00  146
 28  ω     80.00 105.00   0.50    0.35    --   41.33  54.00-150.00   50
 29  ω     83.00 135.00   0.50    1.42    --   96.67  33.00-180.00  104
 30  ω     72.00 101.00   0.50    1.42    --   96.67 -77.00 -30.00   58
 31  ω     84.00 109.00   0.50    1.42    --   96.67-117.00  30.00   50
 32  ω     84.00 109.00   0.50    1.42    --   96.67-142.00 -49.00   50
 33  ω     83.00 108.00   0.50    1.42    --   96.67-117.00-150.00   50
 34  ω     72.00  98.00   0.50    0.35    --   41.33-142.00 -49.00   52
 35  ω     46.00  81.00   0.50    1.42    --   96.67 -68.00 -90.00   70
 36  ω     37.00  68.00   0.50    1.42    --   96.67 -77.00 -30.00   62
 37  ω     34.00 108.00   0.50    1.42    --   96.67-117.00 -90.00  148
 38  ω     35.00  82.00   0.50    1.42    --   96.67 -68.00   0.00   94
 39  ω     30.00  55.00   0.50    1.42    --   96.67 -50.00   0.00   50
 40  ω     31.00  57.00   0.50    1.42    --   96.67 -50.00  60.00   52
 41  ω     32.00  57.00   0.50    1.42    --   96.67 -50.00  90.00   50
 42  ω     53.00  92.00   0.50    1.42    --   96.67 -77.00 120.00   78
 43  ω     71.00  97.00   0.50    1.42    --   96.67-128.00 121.00   52
 44  ω     39.00  64.00   0.50    0.35    --   41.33-128.00 121.00   50
 45  ω     35.00  67.00   0.50    1.42    --   96.67 -59.00 150.00   64
 46  ω     30.00  55.00   0.50    1.42    --   96.67 -50.00 150.00   50
 47  ω     31.00  56.00   0.50    1.42    --   96.67 -50.00 120.00   50
 48  ω     29.00  67.00   0.50    1.42    --   96.67 -59.00  60.00   76
 49  ω     32.00  58.00   0.50    1.42    --   96.67-117.00  30.00   52
 50  ω     30.00  55.00   0.50    1.42    --   96.67 -50.00 -60.00   50
 51  ω     28.00 114.00   0.50    1.42    --   96.67 -87.00 -90.00  172
 52  ω     32.00  57.00   0.50    1.42    --   96.67 -50.00-120.00   50
 53  ω     31.00  56.00   0.50    1.42    --   96.67 -50.00 -90.00   50
 54  ω     30.00  55.00   0.50    1.42    --   96.67 -50.00-180.00   50
 55  ω     22.00  48.00   0.50    0.35    --   41.33  54.00-150.00   52
 56  ω    -33.00  -8.00   0.50    0.35    --   41.33 -11.00 -30.00   50
 57  ω     73.00  99.00   0.50    0.35    --   41.33  77.00 150.00   52
 58  ω     37.00  62.00   0.50    0.35    --   41.33  77.00 150.00   50
 59  ω    -97.00 -71.00   0.50    0.35    --  -41.33-142.00 -49.00   52
 60  ω   -111.00 -85.00   0.50    1.42    --  -82.50-142.00 -49.00   52
 61  ω   -107.00 -82.00   0.50    1.42    --  -82.50-128.00 121.00   50
 62  ω   -151.00 -74.00   0.50    1.42    --  -82.50  -8.00 120.00  154
 63  ω    -76.00 -51.00   0.50    1.42    --  -82.50 128.00-164.00   50
;
_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      -0.0121359000
_diffrn_orient_matrix_UB_12      0.0064255000
_diffrn_orient_matrix_UB_13      0.0899902000
_diffrn_orient_matrix_UB_21      -0.0527270000
_diffrn_orient_matrix_UB_22      0.1453075000
_diffrn_orient_matrix_UB_23      -0.0356812000
_diffrn_orient_matrix_UB_31      -0.2259610000
_diffrn_orient_matrix_UB_32      -0.0099299000
_diffrn_orient_matrix_UB_33      0.0045920000
_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                3567
_reflns_number_total             4280
_reflns_odcompleteness_completeness 99.01
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         4280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0906P)²+0.1254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1413
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N005(H005), C008(H008), C009(H009), C00B(H00B), C00J(H00J), C00L(H00L),
 C00M(H00M)
2.b Idealised Me refined as rotating group:
 C00T(H00A,H00C,H00D), C00U(H00E,H00F,H00G), C00W(H00H,H00I,H00K), C00X(H00N,
 H00O,H00P), C00Y(H00Q,H00R,H00S), C00Z(H00T,H00U,H00V)
;
_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 0.80337(14) 0.34681(9) 0.76763(6) 0.0288(2) Uani 1 1 d . . . . .
F002 F 1.01535(15) 0.22053(10) 0.53219(6) 0.0312(3) Uani 1 1 d . . . . .
F003 F 0.92624(14) 0.10798(10) 0.87066(6) 0.0320(3) Uani 1 1 d . . . . .
F004 F 1.14398(14) -0.01715(9) 0.63500(7) 0.0318(3) Uani 1 1 d . . . . .
N005 N 0.54512(19) 0.72569(12) 0.39974(8) 0.0217(3) Uani 1 1 d . . . . .
H005 H 0.557252 0.667917 0.450012 0.026 Uiso 1 1 calc R U . . .
N006 N 0.7668(2) 0.50977(14) 0.54740(9) 0.0324(4) Uani 1 1 d . . . . .
C007 C 0.4692(2) 0.85349(15) 0.38250(10) 0.0205(3) Uani 1 1 d . . . . .
C008 C 0.4097(2) 1.04635(15) 0.26205(10) 0.0205(3) Uani 1 1 d . . . . .
H008 H 0.413923 1.088276 0.203010 0.025 Uiso 1 1 calc R U . . .
C009 C 0.3295(2) 1.04823(15) 0.40293(10) 0.0232(3) Uani 1 1 d . . . . .
H009 H 0.276129 1.094068 0.439566 0.028 Uiso 1 1 calc R U . . .
N00A N 1.1609(2) -0.18566(16) 0.85321(11) 0.0424(4) Uani 1 1 d . . . . .
C00B C 0.5890(2) 0.82155(15) 0.17399(10) 0.0215(3) Uani 1 1 d . . . . .
H00B H 0.559171 0.898941 0.128936 0.026 Uiso 1 1 calc R U . . .
C00C C 0.5544(2) 0.81915(15) 0.25734(10) 0.0199(3) Uani 1 1 d . . . . .
C00D C 0.9948(2) 0.19293(16) 0.61548(10) 0.0249(4) Uani 1 1 d . . . . .
C00E C 0.4731(2) 0.91552(15) 0.29498(10) 0.0197(3) Uani 1 1 d . . . . .
C00F C 0.3405(2) 1.11506(15) 0.31571(10) 0.0210(3) Uani 1 1 d . . . . .
C00G C 0.8868(2) 0.25734(16) 0.73512(10) 0.0242(3) Uani 1 1 d . . . . .
C00H C 0.5985(2) 0.70490(15) 0.32401(10) 0.0209(3) Uani 1 1 d . . . . .
C00I C 0.9069(2) 0.28755(15) 0.64835(10) 0.0233(3) Uani 1 1 d . . . . .
C00J C 0.7111(2) 0.59757(15) 0.22612(10) 0.0240(4) Uani 1 1 d . . . . .
H00J H 0.765277 0.521643 0.214969 0.029 Uiso 1 1 calc R U . . .
C00K C 0.6673(2) 0.71001(15) 0.15723(10) 0.0221(3) Uani 1 1 d . . . . .
C00L C 0.3928(2) 0.91940(15) 0.43724(10) 0.0226(3) Uani 1 1 d . . . . .
H00L H 0.384568 0.877163 0.496123 0.027 Uiso 1 1 calc R U . . .
C00M C 0.6794(2) 0.59214(15) 0.30896(10) 0.0229(3) Uani 1 1 d . . . . .
H00M H 0.711315 0.514892 0.353945 0.027 Uiso 1 1 calc R U . . .
C00N C 1.0601(2) 0.07201(16) 0.66770(11) 0.0257(4) Uani 1 1 d . . . . .
C00O C 0.2876(2) 1.25996(15) 0.28452(10) 0.0235(4) Uani 1 1 d . . . . .
C00P C 0.7016(2) 0.70458(16) 0.06761(10) 0.0263(4) Uani 1 1 d . . . . .
C00Q C 1.0380(2) 0.04169(16) 0.75449(11) 0.0252(4) Uani 1 1 d . . . . .
C00R C 0.9503(2) 0.13621(17) 0.78731(10) 0.0250(4) Uani 1 1 d . . . . .
C00S C 0.8310(2) 0.41201(16) 0.59251(10) 0.0260(4) Uani 1 1 d . . . . .
C00T C 0.2984(3) 1.31697(16) 0.18883(11) 0.0288(4) Uani 1 1 d . . . . .
H00A H 0.435050 1.293163 0.169173 0.043 Uiso 1 1 calc R U . . .
H00C H 0.265375 1.409364 0.172214 0.043 Uiso 1 1 calc R U . . .
H00D H 0.201869 1.285000 0.163660 0.043 Uiso 1 1 calc R U . . .
C00U C 0.0748(3) 1.30258(17) 0.31371(11) 0.0315(4) Uani 1 1 d . . . . .
H00E H -0.024075 1.272574 0.288321 0.047 Uiso 1 1 calc R U . . .
H00F H 0.047101 1.395173 0.296325 0.047 Uiso 1 1 calc R U . . .
H00G H 0.065228 1.267243 0.375144 0.047 Uiso 1 1 calc R U . . .
C00V C 1.1061(2) -0.08473(17) 0.80958(12) 0.0312(4) Uani 1 1 d . . . . .
C00W C 0.4410(3) 1.31209(17) 0.32179(12) 0.0343(4) Uani 1 1 d . . . . .
H00H H 0.429311 1.281992 0.383300 0.051 Uiso 1 1 calc R U . . .
H00I H 0.413659 1.404786 0.300840 0.051 Uiso 1 1 calc R U . . .
H00K H 0.577783 1.282678 0.304945 0.051 Uiso 1 1 calc R U . . .
C00X C 0.9229(3) 0.65022(19) 0.05597(12) 0.0371(4) Uani 1 1 d . . . . .
H00N H 1.010715 0.704500 0.065208 0.056 Uiso 1 1 calc R U . . .
H00O H 0.944018 0.646721 -0.001304 0.056 Uiso 1 1 calc R U . . .
H00P H 0.955228 0.564757 0.096569 0.056 Uiso 1 1 calc R U . . .
C00Y C 0.6540(3) 0.83512(18) 0.00078(11) 0.0380(4) Uani 1 1 d . . . . .
H00Q H 0.511083 0.869532 0.004760 0.057 Uiso 1 1 calc R U . . .
H00R H 0.683158 0.827643 -0.055202 0.057 Uiso 1 1 calc R U . . .
H00S H 0.737217 0.891875 0.009930 0.057 Uiso 1 1 calc R U . . .
C00Z C 0.5648(3) 0.6184(2) 0.05395(12) 0.0396(5) Uani 1 1 d . . . . .
H00T H 0.598350 0.533211 0.094747 0.059 Uiso 1 1 calc R U . . .
H00U H 0.585412 0.614494 -0.003232 0.059 Uiso 1 1 calc R U . . .
H00V H 0.423518 0.652566 0.061625 0.059 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
F001 C00G 1.3352(19) . ?
F002 C00D 1.3360(18) . ?
F003 C00R 1.3383(18) . ?
F004 C00N 1.3351(19) . ?
N005 H005 0.8800 . ?
N005 C007 1.390(2) . ?
N005 C00H 1.388(2) . ?
N006 C00S 1.145(2) . ?
C007 C00E 1.407(2) . ?
C007 C00L 1.394(2) . ?
C008 H008 0.9500 . ?
C008 C00E 1.400(2) . ?
C008 C00F 1.391(2) . ?
C009 H009 0.9500 . ?
C009 C00F 1.415(2) . ?
C009 C00L 1.381(2) . ?
N00A C00V 1.148(2) . ?
C00B H00B 0.9500 . ?
C00B C00C 1.402(2) . ?
C00B C00K 1.397(2) . ?
C00C C00E 1.453(2) . ?
C00C C00H 1.404(2) . ?
C00D C00I 1.395(2) . ?
C00D C00N 1.374(2) . ?
C00F C00O 1.535(2) . ?
C00G C00I 1.390(2) . ?
C00G C00R 1.373(2) . ?
C00H C00M 1.400(2) . ?
C00I C00S 1.438(2) . ?
C00J H00J 0.9500 . ?
C00J C00K 1.411(2) . ?
C00J C00M 1.381(2) . ?
C00K C00P 1.534(2) . ?
C00L H00L 0.9500 . ?
C00M H00M 0.9500 . ?
C00N C00Q 1.391(2) . ?
C00O C00T 1.527(2) . ?
C00O C00U 1.533(2) . ?
C00O C00W 1.539(2) . ?
C00P C00X 1.536(2) . ?
C00P C00Y 1.529(2) . ?
C00P C00Z 1.536(2) . ?
C00Q C00R 1.393(2) . ?
C00Q C00V 1.439(2) . ?
C00T H00A 0.9800 . ?
C00T H00C 0.9800 . ?
C00T H00D 0.9800 . ?
C00U H00E 0.9800 . ?
C00U H00F 0.9800 . ?
C00U H00G 0.9800 . ?
C00W H00H 0.9800 . ?
C00W H00I 0.9800 . ?
C00W H00K 0.9800 . ?
C00X H00N 0.9800 . ?
C00X H00O 0.9800 . ?
C00X H00P 0.9800 . ?
C00Y H00Q 0.9800 . ?
C00Y H00R 0.9800 . ?
C00Y H00S 0.9800 . ?
C00Z H00T 0.9800 . ?
C00Z H00U 0.9800 . ?
C00Z H00V 0.9800 . ?

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
C007 N005 H005 125.9 . . ?
C00H N005 H005 125.9 . . ?
C00H N005 C007 108.25(13) . . ?
N005 C007 C00E 109.31(13) . . ?
N005 C007 C00L 129.76(15) . . ?
C00L C007 C00E 120.91(15) . . ?
C00E C008 H008 120.0 . . ?
C00F C008 H008 120.0 . . ?
C00F C008 C00E 120.05(14) . . ?
C00F C009 H009 118.5 . . ?
C00L C009 H009 118.5 . . ?
C00L C009 C00F 123.00(14) . . ?
C00C C00B H00B 120.0 . . ?
C00K C00B H00B 120.0 . . ?
C00K C00B C00C 119.93(15) . . ?
C00B C00C C00E 133.29(14) . . ?
C00B C00C C00H 120.12(14) . . ?
C00H C00C C00E 106.59(13) . . ?
F002 C00D C00I 119.44(15) . . ?
F002 C00D C00N 119.76(14) . . ?
C00N C00D C00I 120.79(15) . . ?
C007 C00E C00C 106.41(13) . . ?
C008 C00E C007 120.05(14) . . ?
C008 C00E C00C 133.52(14) . . ?
C008 C00F C009 118.13(14) . . ?
C008 C00F C00O 122.58(14) . . ?
C009 C00F C00O 119.19(13) . . ?
F001 C00G C00I 119.51(15) . . ?
F001 C00G C00R 120.00(14) . . ?
C00R C00G C00I 120.49(15) . . ?
N005 C00H C00C 109.43(13) . . ?
N005 C00H C00M 129.47(15) . . ?
C00M C00H C00C 121.08(14) . . ?
C00D C00I C00S 119.91(14) . . ?
C00G C00I C00D 118.73(15) . . ?
C00G C00I C00S 121.30(14) . . ?
C00K C00J H00J 118.3 . . ?
C00M C00J H00J 118.3 . . ?
C00M C00J C00K 123.41(14) . . ?
C00B C00K C00J 118.06(14) . . ?
C00B C00K C00P 122.78(14) . . ?
C00J C00K C00P 119.13(14) . . ?
C007 C00L H00L 121.1 . . ?
C009 C00L C007 117.73(15) . . ?
C009 C00L H00L 121.1 . . ?
C00H C00M H00M 121.3 . . ?
C00J C00M C00H 117.39(14) . . ?
C00J C00M H00M 121.3 . . ?
F004 C00N C00D 119.87(15) . . ?
F004 C00N C00Q 119.76(15) . . ?
C00D C00N C00Q 120.37(15) . . ?
C00F C00O C00W 107.98(13) . . ?
C00T C00O C00F 112.64(12) . . ?
C00T C00O C00U 108.32(13) . . ?
C00T C00O C00W 108.01(14) . . ?
C00U C00O C00F 110.69(13) . . ?
C00U C00O C00W 109.11(13) . . ?
C00K C00P C00X 109.76(14) . . ?
C00K C00P C00Z 108.85(14) . . ?
C00Y C00P C00K 112.28(13) . . ?
C00Y C00P C00X 108.00(15) . . ?
C00Y C00P C00Z 108.66(15) . . ?
C00Z C00P C00X 109.24(15) . . ?
C00N C00Q C00R 118.83(15) . . ?
C00N C00Q C00V 120.68(15) . . ?
C00R C00Q C00V 120.49(15) . . ?
F003 C00R C00G 119.79(15) . . ?
F003 C00R C00Q 119.43(15) . . ?
C00G C00R C00Q 120.78(15) . . ?
N006 C00S C00I 178.24(18) . . ?
C00O C00T H00A 109.5 . . ?
C00O C00T H00C 109.5 . . ?
C00O C00T H00D 109.5 . . ?
H00A C00T H00C 109.5 . . ?
H00A C00T H00D 109.5 . . ?
H00C C00T H00D 109.5 . . ?
C00O C00U H00E 109.5 . . ?
C00O C00U H00F 109.5 . . ?
C00O C00U H00G 109.5 . . ?
H00E C00U H00F 109.5 . . ?
H00E C00U H00G 109.5 . . ?
H00F C00U H00G 109.5 . . ?
N00A C00V C00Q 179.7(2) . . ?
C00O C00W H00H 109.5 . . ?
C00O C00W H00I 109.5 . . ?
C00O C00W H00K 109.5 . . ?
H00H C00W H00I 109.5 . . ?
H00H C00W H00K 109.5 . . ?
H00I C00W H00K 109.5 . . ?
C00P C00X H00N 109.5 . . ?
C00P C00X H00O 109.5 . . ?
C00P C00X H00P 109.5 . . ?
H00N C00X H00O 109.5 . . ?
H00N C00X H00P 109.5 . . ?
H00O C00X H00P 109.5 . . ?
C00P C00Y H00Q 109.5 . . ?
C00P C00Y H00R 109.5 . . ?
C00P C00Y H00S 109.5 . . ?
H00Q C00Y H00R 109.5 . . ?
H00Q C00Y H00S 109.5 . . ?
H00R C00Y H00S 109.5 . . ?
C00P C00Z H00T 109.5 . . ?
C00P C00Z H00U 109.5 . . ?
C00P C00Z H00V 109.5 . . ?
H00T C00Z H00U 109.5 . . ?
H00T C00Z H00V 109.5 . . ?
H00U C00Z H00V 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
F001 C00G C00I C00D 179.88(13) . . . . ?
F001 C00G C00I C00S -2.9(2) . . . . ?
F001 C00G C00R F003 0.7(2) . . . . ?
F001 C00G C00R C00Q -179.92(13) . . . . ?
F002 C00D C00I C00G -179.92(13) . . . . ?
F002 C00D C00I C00S 2.9(2) . . . . ?
F002 C00D C00N F004 0.1(2) . . . . ?
F002 C00D C00N C00Q -179.42(13) . . . . ?
F004 C00N C00Q C00R 179.89(13) . . . . ?
F004 C00N C00Q C00V 0.5(2) . . . . ?
N005 C007 C00E C008 -178.01(12) . . . . ?
N005 C007 C00E C00C 0.57(16) . . . . ?
N005 C007 C00L C009 178.99(14) . . . . ?
N005 C00H C00M C00J 177.41(14) . . . . ?
C007 N005 C00H C00C -0.86(16) . . . . ?
C007 N005 C00H C00M -179.36(15) . . . . ?
C008 C00F C00O C00T 6.0(2) . . . . ?
C008 C00F C00O C00U 127.41(15) . . . . ?
C008 C00F C00O C00W -113.22(16) . . . . ?
C009 C00F C00O C00T -177.60(14) . . . . ?
C009 C00F C00O C00U -56.16(18) . . . . ?
C009 C00F C00O C00W 63.21(18) . . . . ?
C00B C00C C00E C007 177.86(16) . . . . ?
C00B C00C C00E C008 -3.8(3) . . . . ?
C00B C00C C00H N005 -177.90(13) . . . . ?
C00B C00C C00H C00M 0.7(2) . . . . ?
C00B C00K C00P C00X 124.00(17) . . . . ?
C00B C00K C00P C00Y 3.9(2) . . . . ?
C00B C00K C00P C00Z -116.49(17) . . . . ?
C00C C00B C00K C00J -0.6(2) . . . . ?
C00C C00B C00K C00P 177.65(14) . . . . ?
C00C C00H C00M C00J -0.9(2) . . . . ?
C00D C00N C00Q C00R -0.6(2) . . . . ?
C00D C00N C00Q C00V -179.97(14) . . . . ?
C00E C007 C00L C009 -2.7(2) . . . . ?
C00E C008 C00F C009 -2.3(2) . . . . ?
C00E C008 C00F C00O 174.12(13) . . . . ?
C00E C00C C00H N005 1.19(16) . . . . ?
C00E C00C C00H C00M 179.84(13) . . . . ?
C00F C008 C00E C007 -0.7(2) . . . . ?
C00F C008 C00E C00C -178.86(15) . . . . ?
C00F C009 C00L C007 -0.5(2) . . . . ?
C00H N005 C007 C00E 0.16(17) . . . . ?
C00H N005 C007 C00L 178.59(15) . . . . ?
C00H C00C C00E C007 -1.06(16) . . . . ?
C00H C00C C00E C008 177.24(15) . . . . ?
C00I C00D C00N F004 -179.94(13) . . . . ?
C00I C00D C00N C00Q 0.5(2) . . . . ?
C00I C00G C00R F003 -178.64(13) . . . . ?
C00I C00G C00R C00Q 0.7(2) . . . . ?
C00J C00K C00P C00X -57.7(2) . . . . ?
C00J C00K C00P C00Y -177.89(15) . . . . ?
C00J C00K C00P C00Z 61.77(19) . . . . ?
C00K C00B C00C C00E -178.74(14) . . . . ?
C00K C00B C00C C00H 0.1(2) . . . . ?
C00K C00J C00M C00H 0.4(2) . . . . ?
C00L C007 C00E C008 3.4(2) . . . . ?
C00L C007 C00E C00C -178.03(13) . . . . ?
C00L C009 C00F C008 3.0(2) . . . . ?
C00L C009 C00F C00O -173.55(14) . . . . ?
C00M C00J C00K C00B 0.4(2) . . . . ?
C00M C00J C00K C00P -177.92(14) . . . . ?
C00N C00D C00I C00G 0.1(2) . . . . ?
C00N C00D C00I C00S -177.09(14) . . . . ?
C00N C00Q C00R F003 179.31(13) . . . . ?
C00N C00Q C00R C00G 0.0(2) . . . . ?
C00R C00G C00I C00D -0.8(2) . . . . ?
C00R C00G C00I C00S 176.43(14) . . . . ?
C00V C00Q C00R F003 -1.3(2) . . . . ?
C00V C00Q C00R C00G 179.35(14) . . . . ?


_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 1.576
_oxdiff_exptl_absorpt_empirical_full_min 0.656
####################################################################### 
# 
# 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_kjk_czc2_tcnq_1
_database_code_depnum_ccdc_archive 'CCDC 2260511'
loop_
_audit_author_name
_audit_author_address
'Kalyan Jyoti Kalita'
;Indian Institute of Science Education and Research Kolkata
India
;
_audit_update_record             
;
2023-05-04 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_audit_creation_date             2023-04-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 N, C12 H4 N4'
_chemical_formula_sum            'C26 H17 N5'
_chemical_formula_weight         399.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N'
_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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6187(2)
_cell_length_b                   9.1334(3)
_cell_length_c                   16.8821(5)
_cell_angle_alpha                95.636(3)
_cell_angle_beta                 94.087(2)
_cell_angle_gamma                94.166(3)
_cell_volume                     1009.76(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6815
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      67.9270
_cell_measurement_theta_min      2.6300
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.630
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0731
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14382
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.548
_diffrn_reflns_theta_min         2.638
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00  24.00   0.50    0.40    --  -40.33  99.00  64.00  200
  2  ω     -2.00  76.00   0.50    0.40    --   40.33 -99.00 -41.00  156
  3  ω    -81.00  -9.00   0.50    2.10    --  -82.50  99.00  64.00  144
  4  ω   -156.00 -85.00   0.50    2.10    --  -82.50 -99.00 -41.00  142
  5  ω    107.00 170.00   0.50    2.10    --   96.67  99.00  64.00  126
  6  ω     24.00 106.00   0.50    2.10    --   96.67 -99.00 -41.00  164
  7  ω   -107.00 -21.00   0.50    0.40    --  -40.33 -50.00-180.00  172
  8  ω    -43.00  26.00   0.50    0.40    --  -40.33  38.00  30.00  138
  9  ω    -56.00  26.00   0.50    0.40    --  -40.33  50.00-180.00  164
 10  ω    -43.00  26.00   0.50    0.40    --  -40.33  38.00-180.00  138
 11  ω    -24.00  35.00   0.50    0.40    --  -40.33  12.00 -60.00  118
 12  ω    -24.00  35.00   0.50    0.40    --  -40.33  12.00 120.00  118
 13  ω    -24.00  35.00   0.50    0.40    --  -40.33  12.00 -30.00  118
 14  ω     41.00  99.00   0.50    0.40    --   40.33-138.00 -90.00  116
 15  ω    -30.00  31.00   0.50    0.40    --   40.33 -25.00 -30.00  122
 16  ω    -26.00  43.00   0.50    0.40    --   40.33 -38.00-150.00  138
 17  ω   -156.00 -58.00   0.50    2.10    --  -82.50 -17.00  60.00  196
 18  ω    -47.00 -15.00   0.50    2.10    --  -82.50  42.00  90.00   64
 19  ω   -151.00 -55.00   0.50    2.10    --  -82.50 -77.00   0.00  192
 20  ω   -149.00 -78.00   0.50    2.10    --  -82.50-117.00  60.00  142
 21  ω    -68.00 -14.00   0.50    2.10    --  -82.50  59.00 -30.00  108
 22  ω     29.00  83.00   0.50    2.10    --   96.67 -68.00-120.00  108
 23  ω     70.00 165.00   0.50    2.10    --   96.67  77.00 120.00  190
 24  ω     70.00 165.00   0.50    2.10    --   96.67  77.00 150.00  190
 25  ω     75.00 164.00   0.50    2.10    --   96.67  59.00  60.00  178
 26  ω     28.00 105.00   0.50    2.10    --   96.67 -77.00-180.00  154
 27  ω    105.00 170.00   0.50    2.10    --   96.67  96.00 -60.00  130
 28  ω    105.00 170.00   0.50    2.10    --   96.67  96.00  90.00  130
 29  ω     30.00  57.00   0.50    2.10    --   96.67 -50.00-180.00   54
 30  ω     30.00 109.00   0.50    2.10    --   96.67-117.00 -90.00  158
 31  ω     22.00 106.00   0.50    2.10    --   96.67 -96.00 150.00  168
 32  ω     99.00 164.00   0.50    2.10    --   96.67 117.00 -30.00  130
 33  ω     29.00  83.00   0.50    2.10    --   96.67 -68.00 -60.00  108
 34  ω     30.00  57.00   0.50    2.10    --   96.67 -50.00-120.00   54
 35  ω     22.00 106.00   0.50    2.10    --   96.67 -96.00-120.00  168
 36  ω     44.00 127.00   0.50    2.10    --   96.67-145.00-120.00  166
 37  ω     29.00  83.00   0.50    2.10    --   96.67 -68.00 -30.00  108
 38  ω     28.00 105.00   0.50    2.10    --   96.67 -77.00  60.00  154
 39  ω     73.00 165.00   0.50    2.10    --   96.67  68.00  30.00  184
 40  ω     71.00 170.00   0.50    2.10    --   96.67  17.00  30.00  198
 41  ω     83.00 164.00   0.50    2.10    --   96.67  33.00-150.00  162
 42  ω     30.00 109.00   0.50    2.10    --   96.67-117.00 120.00  158
 43  ω     29.00  83.00   0.50    2.10    --   96.67 -68.00   0.00  108
 44  ω     99.00 164.00   0.50    2.10    --   96.67 117.00-120.00  130
 45  ω   -106.00 -25.00   0.50    0.40    --  -40.33 -38.00  30.00  162
 46  ω   -108.00 -17.00   0.50    0.40    --  -40.33 -64.00   0.00  182
 47  ω   -109.00 -13.00   0.50    0.40    --  -40.33 -77.00 120.00  192
 48  ω   -109.00 -13.00   0.50    0.40    --  -40.33 -77.00 -90.00  192
 49  ω   -109.00 -13.00   0.50    0.40    --  -40.33 -77.00 -30.00  192
 50  ω     14.00 109.00   0.50    0.40    --   40.33  77.00-180.00  190
 51  ω     14.00 109.00   0.50    0.40    --   40.33  77.00-120.00  190
 52  ω     14.00 109.00   0.50    0.40    --   40.33  77.00 120.00  190
 53  ω     21.00 107.00   0.50    0.40    --   40.33  50.00 -30.00  172
;
_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      0.0452865000
_diffrn_orient_matrix_UB_12      -0.0566602000
_diffrn_orient_matrix_UB_13      -0.0853898000
_diffrn_orient_matrix_UB_21      0.0554667000
_diffrn_orient_matrix_UB_22      0.1597185000
_diffrn_orient_matrix_UB_23      -0.0175595000
_diffrn_orient_matrix_UB_31      0.2228888000
_diffrn_orient_matrix_UB_32      -0.0139053000
_diffrn_orient_matrix_UB_33      0.0293507000
_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                3098
_reflns_number_total             3652
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.911
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.173
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3652
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0786
_refine_ls_restrained_S_all      1.051
_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)+(0.1754P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2065
_refine_ls_wR_factor_ref         0.2183
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00U(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00F), C00D(H00G), C00H(H00H), C00K(H00K), C00L(H00L), C00N(H00N),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T)
2.c Idealised Me refined as rotating group:
 C00V(H00C,H00D,H00E)
;
_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
N001 N 0.8921(2) 0.32857(18) 0.79721(9) 0.0267(4) Uani 1 1 d . . . . .
N002 N 0.4632(2) 0.9714(2) 0.81332(10) 0.0342(4) Uani 1 1 d . . . . .
N003 N 0.3273(2) 0.26223(19) 0.45117(10) 0.0338(4) Uani 1 1 d . . . . .
N004 N 0.4605(3) 0.6660(2) 0.99208(10) 0.0349(5) Uani 1 1 d . . . . .
N005 N 0.3085(3) -0.04821(19) 0.62859(10) 0.0343(4) Uani 1 1 d . . . . .
C006 C 0.9177(3) 0.5414(2) 0.73654(11) 0.0260(4) Uani 1 1 d . . . . .
C007 C 0.9143(3) 0.4801(2) 0.81054(11) 0.0271(5) Uani 1 1 d . . . . .
C008 C 0.3822(3) 0.3420(2) 0.66019(11) 0.0259(5) Uani 1 1 d . . . . .
C009 C 0.8779(3) 0.2888(2) 0.71536(11) 0.0280(5) Uani 1 1 d . . . . .
C00A C 0.4283(3) 0.5819(2) 0.78221(11) 0.0256(5) Uani 1 1 d . . . . .
C00B C 0.4191(3) 0.4306(2) 0.80152(11) 0.0263(5) Uani 1 1 d . . . . .
H00F H 0.428771 0.411391 0.855887 0.032 Uiso 1 1 calc R U . . .
C00C C 0.3540(3) 0.2254(2) 0.60129(11) 0.0271(5) Uani 1 1 d . . . . .
C00D C 0.4187(3) 0.6072(2) 0.69852(11) 0.0258(4) Uani 1 1 d . . . . .
H00G H 0.427423 0.705304 0.684179 0.031 Uiso 1 1 calc R U . . .
C00E C 0.3401(3) 0.2479(2) 0.51812(11) 0.0273(5) Uani 1 1 d . . . . .
C00F C 0.4459(3) 0.6983(2) 0.84137(11) 0.0261(4) Uani 1 1 d . . . . .
C00G C 0.4558(3) 0.8492(2) 0.82451(11) 0.0274(5) Uani 1 1 d . . . . .
C00H C 0.3976(3) 0.4929(2) 0.64106(11) 0.0255(4) Uani 1 1 d . . . . .
H00H H 0.392662 0.511888 0.586665 0.031 Uiso 1 1 calc R U . . .
C00I C 0.3302(3) 0.0740(2) 0.61797(11) 0.0278(5) Uani 1 1 d . . . . .
C00J C 0.8939(3) 0.4179(2) 0.67557(12) 0.0271(5) Uani 1 1 d . . . . .
C00K C 0.9379(3) 0.6938(2) 0.73464(12) 0.0289(5) Uani 1 1 d . . . . .
H00K H 0.939959 0.735341 0.685240 0.035 Uiso 1 1 calc R U . . .
C00L C 0.9314(3) 0.5708(2) 0.88281(12) 0.0317(5) Uani 1 1 d . . . . .
H00L H 0.929633 0.530274 0.932504 0.038 Uiso 1 1 calc R U . . .
C00M C 0.4540(3) 0.6777(2) 0.92489(11) 0.0279(5) Uani 1 1 d . . . . .
C00N C 0.8806(3) 0.4069(2) 0.59199(11) 0.0282(5) Uani 1 1 d . . . . .
H00N H 0.890615 0.493048 0.564744 0.034 Uiso 1 1 calc R U . . .
C00O C 0.3972(3) 0.3169(2) 0.74370(11) 0.0262(4) Uani 1 1 d . . . . .
H00O H 0.391367 0.218635 0.757892 0.031 Uiso 1 1 calc R U . . .
C00P C 0.9551(3) 0.7837(2) 0.80625(12) 0.0312(5) Uani 1 1 d . . . . .
H00P H 0.969679 0.887897 0.806067 0.037 Uiso 1 1 calc R U . . .
C00Q C 0.8528(3) 0.2686(2) 0.54998(12) 0.0318(5) Uani 1 1 d . . . . .
H00Q H 0.843957 0.259295 0.493274 0.038 Uiso 1 1 calc R U . . .
C00R C 0.9510(3) 0.7217(2) 0.87912(12) 0.0323(5) Uani 1 1 d . . . . .
H00R H 0.962022 0.785577 0.927430 0.039 Uiso 1 1 calc R U . . .
C00S C 0.8375(3) 0.1412(2) 0.59042(13) 0.0336(5) Uani 1 1 d . . . . .
H00S H 0.817688 0.047142 0.560263 0.040 Uiso 1 1 calc R U . . .
C00T C 0.8505(3) 0.1491(2) 0.67289(12) 0.0316(5) Uani 1 1 d . . . . .
H00T H 0.841034 0.062357 0.699653 0.038 Uiso 1 1 calc R U . . .
C00U C 0.8676(3) 0.2278(2) 0.85806(11) 0.0311(5) Uani 1 1 d . . . . .
H00A H 0.785128 0.137565 0.833993 0.037 Uiso 1 1 calc R U . . .
H00B H 0.791807 0.274971 0.900817 0.037 Uiso 1 1 calc R U . . .
C00V C 1.0674(3) 0.1842(2) 0.89492(12) 0.0334(5) Uani 1 1 d . . . . .
H00C H 1.147137 0.142647 0.852674 0.050 Uiso 1 1 calc R U . . .
H00D H 1.040361 0.110256 0.931965 0.050 Uiso 1 1 calc R U . . .
H00E H 1.143857 0.271450 0.923933 0.050 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
N001 C007 1.376(3) . ?
N001 C009 1.389(2) . ?
N001 C00U 1.454(2) . ?
N002 C00G 1.148(3) . ?
N003 C00E 1.148(2) . ?
N004 C00M 1.148(2) . ?
N005 C00I 1.148(3) . ?
C006 C007 1.419(3) . ?
C006 C00J 1.442(3) . ?
C006 C00K 1.393(3) . ?
C007 C00L 1.398(3) . ?
C008 C00C 1.377(3) . ?
C008 C00H 1.444(3) . ?
C008 C00O 1.448(3) . ?
C009 C00J 1.414(3) . ?
C009 C00T 1.394(3) . ?
C00A C00B 1.448(3) . ?
C00A C00D 1.451(3) . ?
C00A C00F 1.377(3) . ?
C00B H00F 0.9500 . ?
C00B C00O 1.346(3) . ?
C00C C00E 1.436(2) . ?
C00C C00I 1.438(3) . ?
C00D H00G 0.9500 . ?
C00D C00H 1.346(3) . ?
C00F C00G 1.432(3) . ?
C00F C00M 1.438(2) . ?
C00H H00H 0.9500 . ?
C00J C00N 1.401(3) . ?
C00K H00K 0.9500 . ?
C00K C00P 1.386(3) . ?
C00L H00L 0.9500 . ?
C00L C00R 1.383(3) . ?
C00N H00N 0.9500 . ?
C00N C00Q 1.380(3) . ?
C00O H00O 0.9500 . ?
C00P H00P 0.9500 . ?
C00P C00R 1.405(3) . ?
C00Q H00Q 0.9500 . ?
C00Q C00S 1.407(3) . ?
C00R H00R 0.9500 . ?
C00S H00S 0.9500 . ?
C00S C00T 1.383(3) . ?
C00T H00T 0.9500 . ?
C00U H00A 0.9900 . ?
C00U H00B 0.9900 . ?
C00U C00V 1.518(3) . ?
C00V H00C 0.9800 . ?
C00V H00D 0.9800 . ?
C00V H00E 0.9800 . ?

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
C007 N001 C009 108.36(16) . . ?
C007 N001 C00U 125.69(16) . . ?
C009 N001 C00U 125.69(17) . . ?
C007 C006 C00J 106.02(17) . . ?
C00K C006 C007 120.37(18) . . ?
C00K C006 C00J 133.60(17) . . ?
N001 C007 C006 109.72(17) . . ?
N001 C007 C00L 129.30(19) . . ?
C00L C007 C006 121.0(2) . . ?
C00C C008 C00H 121.40(17) . . ?
C00C C008 C00O 120.78(18) . . ?
C00H C008 C00O 117.82(17) . . ?
N001 C009 C00J 109.14(17) . . ?
N001 C009 C00T 129.66(19) . . ?
C00T C009 C00J 121.20(18) . . ?
C00B C00A C00D 117.92(17) . . ?
C00F C00A C00B 121.09(17) . . ?
C00F C00A C00D 120.99(18) . . ?
C00A C00B H00F 119.5 . . ?
C00O C00B C00A 121.10(17) . . ?
C00O C00B H00F 119.5 . . ?
C008 C00C C00E 121.66(18) . . ?
C008 C00C C00I 123.02(17) . . ?
C00E C00C C00I 115.29(16) . . ?
C00A C00D H00G 119.7 . . ?
C00H C00D C00A 120.62(18) . . ?
C00H C00D H00G 119.7 . . ?
N003 C00E C00C 178.3(2) . . ?
C00A C00F C00G 122.62(17) . . ?
C00A C00F C00M 122.65(17) . . ?
C00G C00F C00M 114.73(16) . . ?
N002 C00G C00F 178.0(2) . . ?
C008 C00H H00H 119.2 . . ?
C00D C00H C008 121.52(17) . . ?
C00D C00H H00H 119.2 . . ?
N005 C00I C00C 177.61(19) . . ?
C009 C00J C006 106.75(16) . . ?
C00N C00J C006 133.16(18) . . ?
C00N C00J C009 120.07(18) . . ?
C006 C00K H00K 120.7 . . ?
C00P C00K C006 118.67(18) . . ?
C00P C00K H00K 120.7 . . ?
C007 C00L H00L 121.3 . . ?
C00R C00L C007 117.41(19) . . ?
C00R C00L H00L 121.3 . . ?
N004 C00M C00F 177.9(2) . . ?
C00J C00N H00N 120.6 . . ?
C00Q C00N C00J 118.70(19) . . ?
C00Q C00N H00N 120.6 . . ?
C008 C00O H00O 119.5 . . ?
C00B C00O C008 120.98(18) . . ?
C00B C00O H00O 119.5 . . ?
C00K C00P H00P 119.8 . . ?
C00K C00P C00R 120.44(19) . . ?
C00R C00P H00P 119.8 . . ?
C00N C00Q H00Q 119.7 . . ?
C00N C00Q C00S 120.57(19) . . ?
C00S C00Q H00Q 119.7 . . ?
C00L C00R C00P 122.14(18) . . ?
C00L C00R H00R 118.9 . . ?
C00P C00R H00R 118.9 . . ?
C00Q C00S H00S 119.1 . . ?
C00T C00S C00Q 121.82(19) . . ?
C00T C00S H00S 119.1 . . ?
C009 C00T H00T 121.2 . . ?
C00S C00T C009 117.64(19) . . ?
C00S C00T H00T 121.2 . . ?
N001 C00U H00A 108.9 . . ?
N001 C00U H00B 108.9 . . ?
N001 C00U C00V 113.55(15) . . ?
H00A C00U H00B 107.7 . . ?
C00V C00U H00A 108.9 . . ?
C00V C00U H00B 108.9 . . ?
C00U C00V H00C 109.5 . . ?
C00U C00V H00D 109.5 . . ?
C00U C00V H00E 109.5 . . ?
H00C C00V H00D 109.5 . . ?
H00C C00V H00E 109.5 . . ?
H00D C00V H00E 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
N001 C007 C00L C00R -179.52(17) . . . . ?
N001 C009 C00J C006 -0.36(19) . . . . ?
N001 C009 C00J C00N -178.98(15) . . . . ?
N001 C009 C00T C00S 178.76(17) . . . . ?
C006 C007 C00L C00R 0.2(3) . . . . ?
C006 C00J C00N C00Q -178.48(18) . . . . ?
C006 C00K C00P C00R -0.3(3) . . . . ?
C007 N001 C009 C00J 0.74(19) . . . . ?
C007 N001 C009 C00T -178.71(18) . . . . ?
C007 N001 C00U C00V -88.6(2) . . . . ?
C007 C006 C00J C009 -0.14(19) . . . . ?
C007 C006 C00J C00N 178.22(18) . . . . ?
C007 C006 C00K C00P 0.2(3) . . . . ?
C007 C00L C00R C00P -0.4(3) . . . . ?
C009 N001 C007 C006 -0.84(19) . . . . ?
C009 N001 C007 C00L 178.90(18) . . . . ?
C009 N001 C00U C00V 97.8(2) . . . . ?
C009 C00J C00N C00Q -0.3(3) . . . . ?
C00A C00B C00O C008 0.1(3) . . . . ?
C00A C00D C00H C008 0.5(3) . . . . ?
C00B C00A C00D C00H 1.4(3) . . . . ?
C00B C00A C00F C00G 179.88(15) . . . . ?
C00B C00A C00F C00M -0.7(3) . . . . ?
C00C C008 C00H C00D 177.86(16) . . . . ?
C00C C008 C00O C00B -178.15(17) . . . . ?
C00D C00A C00B C00O -1.7(3) . . . . ?
C00D C00A C00F C00G 0.0(3) . . . . ?
C00D C00A C00F C00M 179.41(14) . . . . ?
C00F C00A C00B C00O 178.42(17) . . . . ?
C00F C00A C00D C00H -178.70(16) . . . . ?
C00H C008 C00C C00E 0.5(3) . . . . ?
C00H C008 C00C C00I -177.56(15) . . . . ?
C00H C008 C00O C00B 1.8(3) . . . . ?
C00J C006 C007 N001 0.60(19) . . . . ?
C00J C006 C007 C00L -179.16(16) . . . . ?
C00J C006 C00K C00P 178.92(18) . . . . ?
C00J C009 C00T C00S -0.6(3) . . . . ?
C00J C00N C00Q C00S 0.2(3) . . . . ?
C00K C006 C007 N001 179.67(15) . . . . ?
C00K C006 C007 C00L -0.1(3) . . . . ?
C00K C006 C00J C009 -179.03(19) . . . . ?
C00K C006 C00J C00N -0.7(4) . . . . ?
C00K C00P C00R C00L 0.4(3) . . . . ?
C00N C00Q C00S C00T -0.3(3) . . . . ?
C00O C008 C00C C00E -179.58(15) . . . . ?
C00O C008 C00C C00I 2.4(3) . . . . ?
C00O C008 C00H C00D -2.1(3) . . . . ?
C00Q C00S C00T C009 0.5(3) . . . . ?
C00T C009 C00J C006 179.14(16) . . . . ?
C00T C009 C00J C00N 0.5(3) . . . . ?
C00U N001 C007 C006 -175.30(15) . . . . ?
C00U N001 C007 C00L 4.4(3) . . . . ?
C00U N001 C009 C00J 175.20(15) . . . . ?
C00U N001 C009 C00T -4.2(3) . . . . ?


_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 1.715
_oxdiff_exptl_absorpt_empirical_full_min 0.416
####################################################################### 
# 
# 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_kjk-py-tfdcnb-2-100k_test1
_database_code_depnum_ccdc_archive 'CCDC 2260513'
loop_
_audit_author_name
_audit_author_address
'Kalyan Jyoti Kalita'
;Indian Institute of Science Education and Research Kolkata
India
;
_audit_update_record             
;
2023-05-04 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_audit_creation_date             2023-04-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C4 F2 N), C16 H10'
_chemical_formula_sum            'C24 H10 F4 N2'
_chemical_formula_weight         402.34
_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                   14.0212(3)
_cell_length_b                   8.3368(2)
_cell_length_c                   15.4457(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.715(2)
_cell_angle_gamma                90
_cell_volume                     1774.00(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9199
_cell_measurement_temperature    99.97(12)
_cell_measurement_theta_max      68.0220
_cell_measurement_theta_min      3.2020
_shelx_estimated_absorpt_T_max   0.905
_shelx_estimated_absorpt_T_min   0.631
_exptl_absorpt_coefficient_mu    1.015
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16874
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.076
_diffrn_reflns_theta_min         3.208
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  35.00   0.50    0.23    --  -40.58  12.00-150.00  118
  2  ω    -64.00  27.00   0.50    0.23    --  -40.58  64.00-120.00  182
  3  ω    -24.00  35.00   0.50    0.23    --  -40.58  12.00 -60.00  118
  4  ω    -47.00 -15.00   0.50    0.91    --  -82.50  42.00  90.00   64
  5  ω    -25.00  43.00   0.50    0.23    --   40.58 -38.00-120.00  136
  6  ω    -35.00  24.00   0.50    0.23    --   40.58 -12.00-180.00  118
  7  ω    -25.00  43.00   0.50    0.23    --   40.58 -38.00   0.00  136
  8  ω    -29.00  31.00   0.50    0.23    --   40.58 -25.00  60.00  120
  9  ω     83.00 164.00   0.50    0.91    --   96.35  33.00 120.00  162
 10  ω     81.00 165.00   0.50    0.91    --   96.35 145.00  60.00  168
 11  ω     99.00 160.00   0.50    0.91    --   96.35 117.00 -60.00  122
 12  ω    104.00 166.00   0.50    0.91    --   96.35 105.00 -76.00  124
 13  ω    105.00 170.00   0.50    0.91    --   96.35  96.00-150.00  130
 14  ω     14.00 109.00   0.50    0.23    --   40.58  77.00 -30.00  190
 15  ω     30.00  57.00   0.50    0.91    --   96.35 -50.00  60.00   54
 16  ω     29.00  83.00   0.50    0.91    --   96.35 -68.00   0.00  108
 17  ω     28.00  68.00   0.50    0.91    --   96.35 -59.00-150.00   80
 18  ω     28.00 105.00   0.50    0.91    --   96.35 -77.00-180.00  154
 19  ω     29.00  83.00   0.50    0.91    --   96.35 -68.00-180.00  108
 20  ω     28.00  68.00   0.50    0.91    --   96.35 -59.00-180.00   80
 21  ω     30.00  57.00   0.50    0.91    --   96.35 -50.00-180.00   54
 22  ω     30.00  57.00   0.50    0.91    --   96.35 -50.00-150.00   54
 23  ω     30.00  57.00   0.50    0.91    --   96.35 -50.00-120.00   54
 24  ω     30.00  57.00   0.50    0.91    --   96.35 -50.00   0.00   54
 25  ω     30.00  57.00   0.50    0.91    --   96.35 -50.00  30.00   54
 26  ω     30.00  57.00   0.50    0.91    --   96.35 -50.00  90.00   54
 27  ω     44.00 127.00   0.50    0.91    --   96.35-145.00  60.00  166
 28  ω     18.00  78.00   0.50    0.23    --   40.58-105.00-176.00  120
 29  ω     27.00 108.00   0.50    0.91    --   96.35-105.00-176.00  162
 30  ω     44.00 127.00   0.50    0.91    --   96.35-145.00  30.00  166
 31  ω     18.00  78.00   0.50    0.23    --   40.58-104.00-120.00  120
 32  ω   -107.00 -25.00   0.50    0.23    --  -40.58 -38.00   0.00  164
 33  ω   -109.00 -14.00   0.50    0.23    --  -40.58 -77.00-150.00  190
 34  ω   -109.00 -14.00   0.50    0.23    --  -40.58 -77.00 -30.00  190
 35  ω   -109.00 -14.00   0.50    0.23    --  -40.58 -77.00  30.00  190
 36  ω   -108.00 -17.00   0.50    0.23    --  -40.58 -64.00  90.00  182
 37  ω   -109.00 -14.00   0.50    0.23    --  -40.58 -77.00 150.00  190
 38  ω   -108.00 -17.00   0.50    0.23    --  -40.58 -64.00-120.00  182
 39  ω   -107.00 -21.00   0.50    0.23    --  -40.58 -50.00-120.00  172
 40  ω    -82.00 -12.00   0.50    0.91    --  -82.50 105.00 -76.00  140
 41  ω    -78.00   4.00   0.50    0.23    --  -40.58 105.00 -76.00  164
 42  ω   -107.00 -25.00   0.50    0.23    --  -40.58 -38.00 150.00  164
 43  ω   -150.00 -69.00   0.50    0.91    --  -82.50 -33.00   0.00  162
 44  ω   -153.00 -78.00   0.50    0.91    --  -82.50 -87.00 -60.00  150
 45  ω   -152.00 -83.00   0.50    0.91    --  -82.50-105.00-176.00  138
;
_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      -0.0081947000
_diffrn_orient_matrix_UB_12      -0.1064064000
_diffrn_orient_matrix_UB_13      -0.0825913000
_diffrn_orient_matrix_UB_21      0.0384027000
_diffrn_orient_matrix_UB_22      -0.1444737000
_diffrn_orient_matrix_UB_23      0.0585044000
_diffrn_orient_matrix_UB_31      -0.1046518000
_diffrn_orient_matrix_UB_32      -0.0445615000
_diffrn_orient_matrix_UB_33      0.0077511000
_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                2821
_reflns_number_total             3194
_reflns_odcompleteness_completeness 99.82
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+3.5939P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1485
_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:
 C00J(H00J), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T)
;
_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 0.99977(11) 0.26003(18) 0.61913(10) 0.0283(4) Uani 1 1 d . . . . .
F002 F 1.06874(11) 0.55344(19) 0.67373(9) 0.0274(4) Uani 1 1 d . . . . .
F003 F 0.48017(11) 0.21327(19) 0.57849(11) 0.0313(4) Uani 1 1 d . . . . .
F004 F 0.54919(11) 0.4695(2) 0.67745(10) 0.0317(4) Uani 1 1 d . . . . .
N005 N 0.90082(17) 0.0708(3) 0.41392(16) 0.0311(6) Uani 1 1 d . . . . .
N006 N 0.39377(17) 0.1238(3) 0.35463(17) 0.0339(6) Uani 1 1 d . . . . .
C007 C 0.99960(18) 0.3775(3) 0.56029(17) 0.0216(5) Uani 1 1 d . . . . .
C008 C 0.73102(17) 0.4080(3) 0.49072(17) 0.0211(5) Uani 1 1 d . . . . .
C009 C 1.03480(18) 0.5264(3) 0.58838(16) 0.0213(5) Uani 1 1 d . . . . .
C00A C 0.46291(17) 0.3678(3) 0.44883(17) 0.0229(6) Uani 1 1 d . . . . .
C00B C 0.77236(17) 0.5337(3) 0.54875(17) 0.0205(5) Uani 1 1 d . . . . .
C00C C 0.96485(17) 0.3482(3) 0.47174(17) 0.0214(5) Uani 1 1 d . . . . .
C00D C 0.78838(17) 0.6880(3) 0.51447(17) 0.0221(5) Uani 1 1 d . . . . .
C00E C 0.79965(18) 0.5043(3) 0.64067(17) 0.0232(6) Uani 1 1 d . . . . .
C00F C 0.48924(18) 0.3542(3) 0.53981(18) 0.0235(6) Uani 1 1 d . . . . .
C00G C 0.52546(18) 0.4842(3) 0.59043(17) 0.0240(6) Uani 1 1 d . . . . .
C00H C 0.71497(18) 0.2539(3) 0.52552(18) 0.0228(6) Uani 1 1 d . . . . .
C00I C 0.92923(18) 0.1933(3) 0.44042(17) 0.0234(6) Uani 1 1 d . . . . .
C00J C 0.83111(18) 0.8071(3) 0.57194(18) 0.0260(6) Uani 1 1 d . . . . .
H00J H 0.842268 0.910127 0.549491 0.031 Uiso 1 1 calc R U . . .
C00K C 0.70468(18) 0.4375(3) 0.39876(17) 0.0231(6) Uani 1 1 d . . . . .
C00L C 0.76052(18) 0.7130(3) 0.42054(17) 0.0249(6) Uani 1 1 d . . . . .
H00L H 0.770162 0.815553 0.396725 0.030 Uiso 1 1 calc R U . . .
C00M C 0.78298(19) 0.3469(3) 0.67353(18) 0.0261(6) Uani 1 1 d . . . . .
H00M H 0.800609 0.325799 0.734857 0.031 Uiso 1 1 calc R U . . .
C00N C 0.74297(19) 0.2297(3) 0.61902(18) 0.0258(6) Uani 1 1 d . . . . .
H00N H 0.732849 0.127462 0.642959 0.031 Uiso 1 1 calc R U . . .
C00O C 0.72128(18) 0.5949(3) 0.36600(18) 0.0264(6) Uani 1 1 d . . . . .
H00O H 0.704145 0.615707 0.304603 0.032 Uiso 1 1 calc R U . . .
C00P C 0.84200(19) 0.6282(3) 0.69571(18) 0.0268(6) Uani 1 1 d . . . . .
H00P H 0.860258 0.609635 0.757257 0.032 Uiso 1 1 calc R U . . .
C00Q C 0.67337(18) 0.1338(3) 0.46739(18) 0.0267(6) Uani 1 1 d . . . . .
H00Q H 0.662161 0.030684 0.489673 0.032 Uiso 1 1 calc R U . . .
C00R C 0.85769(19) 0.7775(3) 0.66172(18) 0.0270(6) Uani 1 1 d . . . . .
H00R H 0.886808 0.860207 0.700018 0.032 Uiso 1 1 calc R U . . .
C00S C 0.64823(19) 0.1631(3) 0.37763(19) 0.0278(6) Uani 1 1 d . . . . .
H00S H 0.620182 0.079701 0.339261 0.033 Uiso 1 1 calc R U . . .
C00T C 0.66350(18) 0.3124(3) 0.34318(18) 0.0268(6) Uani 1 1 d . . . . .
H00T H 0.645990 0.330302 0.281528 0.032 Uiso 1 1 calc R U . . .
C00U C 0.42460(18) 0.2322(3) 0.39625(18) 0.0264(6) Uani 1 1 d . . . . .


_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 C007 1.336(3) . ?
F002 C009 1.335(3) . ?
F003 C00F 1.335(3) . ?
F004 C00G 1.329(3) . ?
N005 C00I 1.144(4) . ?
N006 C00U 1.146(4) . ?
C007 C009 1.376(4) . ?
C007 C00C 1.385(4) . ?
C008 C00B 1.430(4) . ?
C008 C00H 1.426(4) . ?
C008 C00K 1.421(4) . ?
C009 C00C 1.399(4) 3_766 ?
C00A C00F 1.390(4) . ?
C00A C00G 1.397(4) 3_666 ?
C00A C00U 1.437(4) . ?
C00B C00D 1.424(4) . ?
C00B C00E 1.421(4) . ?
C00C C00I 1.436(4) . ?
C00D C00J 1.391(4) . ?
C00D C00L 1.446(4) . ?
C00E C00M 1.441(4) . ?
C00E C00P 1.398(4) . ?
C00F C00G 1.377(4) . ?
C00H C00N 1.439(4) . ?
C00H C00Q 1.398(4) . ?
C00J H00J 0.9500 . ?
C00J C00R 1.390(4) . ?
C00K C00O 1.441(4) . ?
C00K C00T 1.405(4) . ?
C00L H00L 0.9500 . ?
C00L C00O 1.345(4) . ?
C00M H00M 0.9500 . ?
C00M C00N 1.343(4) . ?
C00N H00N 0.9500 . ?
C00O H00O 0.9500 . ?
C00P H00P 0.9500 . ?
C00P C00R 1.384(4) . ?
C00Q H00Q 0.9500 . ?
C00Q C00S 1.387(4) . ?
C00R H00R 0.9500 . ?
C00S H00S 0.9500 . ?
C00S C00T 1.386(4) . ?
C00T H00T 0.9500 . ?

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
F001 C007 C009 119.5(2) . . ?
F001 C007 C00C 119.9(2) . . ?
C009 C007 C00C 120.6(2) . . ?
C00H C008 C00B 119.9(2) . . ?
C00K C008 C00B 120.0(2) . . ?
C00K C008 C00H 120.2(2) . . ?
F002 C009 C007 120.3(2) . . ?
F002 C009 C00C 119.0(2) . 3_766 ?
C007 C009 C00C 120.7(2) . 3_766 ?
C00F C00A C00G 118.7(2) . 3_666 ?
C00F C00A C00U 120.5(2) . . ?
C00G C00A C00U 120.7(2) 3_666 . ?
C00D C00B C008 120.1(2) . . ?
C00E C00B C008 120.1(2) . . ?
C00E C00B C00D 119.7(2) . . ?
C007 C00C C009 118.7(2) . 3_766 ?
C007 C00C C00I 121.8(2) . . ?
C009 C00C C00I 119.5(2) 3_766 . ?
C00B C00D C00L 118.1(2) . . ?
C00J C00D C00B 119.1(2) . . ?
C00J C00D C00L 122.8(2) . . ?
C00B C00E C00M 118.5(2) . . ?
C00P C00E C00B 119.0(2) . . ?
C00P C00E C00M 122.5(2) . . ?
F003 C00F C00A 119.7(2) . . ?
F003 C00F C00G 119.6(2) . . ?
C00G C00F C00A 120.7(2) . . ?
F004 C00G C00A 119.6(2) . 3_666 ?
F004 C00G C00F 119.9(2) . . ?
C00F C00G C00A 120.6(2) . 3_666 ?
C008 C00H C00N 118.2(2) . . ?
C00Q C00H C008 118.6(2) . . ?
C00Q C00H C00N 123.2(2) . . ?
N005 C00I C00C 178.7(3) . . ?
C00D C00J H00J 119.5 . . ?
C00R C00J C00D 120.9(3) . . ?
C00R C00J H00J 119.5 . . ?
C008 C00K C00O 118.7(2) . . ?
C00T C00K C008 118.9(2) . . ?
C00T C00K C00O 122.4(2) . . ?
C00D C00L H00L 119.2 . . ?
C00O C00L C00D 121.7(2) . . ?
C00O C00L H00L 119.2 . . ?
C00E C00M H00M 119.4 . . ?
C00N C00M C00E 121.2(2) . . ?
C00N C00M H00M 119.4 . . ?
C00H C00N H00N 119.0 . . ?
C00M C00N C00H 122.1(3) . . ?
C00M C00N H00N 119.0 . . ?
C00K C00O H00O 119.3 . . ?
C00L C00O C00K 121.4(2) . . ?
C00L C00O H00O 119.3 . . ?
C00E C00P H00P 119.6 . . ?
C00R C00P C00E 120.9(3) . . ?
C00R C00P H00P 119.6 . . ?
C00H C00Q H00Q 119.5 . . ?
C00S C00Q C00H 120.9(3) . . ?
C00S C00Q H00Q 119.5 . . ?
C00J C00R H00R 119.8 . . ?
C00P C00R C00J 120.4(3) . . ?
C00P C00R H00R 119.8 . . ?
C00Q C00S H00S 119.6 . . ?
C00T C00S C00Q 120.9(3) . . ?
C00T C00S H00S 119.6 . . ?
C00K C00T H00T 119.8 . . ?
C00S C00T C00K 120.5(3) . . ?
C00S C00T H00T 119.8 . . ?
N006 C00U C00A 179.6(3) . . ?

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
F001 C007 C009 F002 -0.1(4) . . . . ?
F001 C007 C009 C00C -179.8(2) . . . 3_766 ?
F001 C007 C00C C009 179.8(2) . . . 3_766 ?
F001 C007 C00C C00I -0.6(4) . . . . ?
F003 C00F C00G F004 -1.4(4) . . . . ?
F003 C00F C00G C00A 178.9(2) . . . 3_666 ?
C008 C00B C00D C00J -178.3(2) . . . . ?
C008 C00B C00D C00L 0.8(3) . . . . ?
C008 C00B C00E C00M -1.2(3) . . . . ?
C008 C00B C00E C00P 178.5(2) . . . . ?
C008 C00H C00N C00M 0.2(4) . . . . ?
C008 C00H C00Q C00S 0.1(4) . . . . ?
C008 C00K C00O C00L -0.2(4) . . . . ?
C008 C00K C00T C00S 0.4(4) . . . . ?
C009 C007 C00C C009 -0.7(4) . . . 3_766 ?
C009 C007 C00C C00I 178.9(2) . . . . ?
C00A C00F C00G F004 179.2(2) . . . . ?
C00A C00F C00G C00A -0.5(4) . . . 3_666 ?
C00B C008 C00H C00N -1.1(3) . . . . ?
C00B C008 C00H C00Q 179.2(2) . . . . ?
C00B C008 C00K C00O 0.5(3) . . . . ?
C00B C008 C00K C00T -179.5(2) . . . . ?
C00B C00D C00J C00R -0.3(4) . . . . ?
C00B C00D C00L C00O -0.6(4) . . . . ?
C00B C00E C00M C00N 0.3(4) . . . . ?
C00B C00E C00P C00R -0.2(4) . . . . ?
C00C C007 C009 F002 -179.6(2) . . . . ?
C00C C007 C009 C00C 0.8(4) . . . 3_766 ?
C00D C00B C00E C00M -179.7(2) . . . . ?
C00D C00B C00E C00P -0.1(3) . . . . ?
C00D C00J C00R C00P 0.0(4) . . . . ?
C00D C00L C00O C00K 0.3(4) . . . . ?
C00E C00B C00D C00J 0.3(3) . . . . ?
C00E C00B C00D C00L 179.4(2) . . . . ?
C00E C00M C00N C00H 0.2(4) . . . . ?
C00E C00P C00R C00J 0.3(4) . . . . ?
C00G C00A C00F F003 -178.9(2) 3_666 . . . ?
C00G C00A C00F C00G 0.5(4) 3_666 . . . ?
C00H C008 C00B C00D -179.9(2) . . . . ?
C00H C008 C00B C00E 1.6(3) . . . . ?
C00H C008 C00K C00O 179.5(2) . . . . ?
C00H C008 C00K C00T -0.5(3) . . . . ?
C00H C00Q C00S C00T -0.1(4) . . . . ?
C00J C00D C00L C00O 178.5(2) . . . . ?
C00K C008 C00B C00D -0.8(3) . . . . ?
C00K C008 C00B C00E -179.4(2) . . . . ?
C00K C008 C00H C00N 179.9(2) . . . . ?
C00K C008 C00H C00Q 0.2(4) . . . . ?
C00L C00D C00J C00R -179.3(2) . . . . ?
C00M C00E C00P C00R 179.4(2) . . . . ?
C00N C00H C00Q C00S -179.6(2) . . . . ?
C00O C00K C00T C00S -179.6(2) . . . . ?
C00P C00E C00M C00N -179.4(2) . . . . ?
C00Q C00H C00N C00M 179.9(3) . . . . ?
C00Q C00S C00T C00K -0.1(4) . . . . ?
C00T C00K C00O C00L 179.8(2) . . . . ?
C00U C00A C00F F003 1.0(4) . . . . ?
C00U C00A C00F C00G -179.6(2) . . . . ?


_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 1.398
_oxdiff_exptl_absorpt_empirical_full_min 0.759
####################################################################### 
# 
# 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_kjk-tcnb_1
_database_code_depnum_ccdc_archive 'CCDC 2260514'
loop_
_audit_author_name
_audit_author_address
'Kalyan Jyoti Kalita'
;Indian Institute of Science Education and Research Kolkata
India
;
_audit_update_record             
;
2023-05-04 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_audit_creation_date             2023-04-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C5 H N2), C14 H13 N'
_chemical_formula_sum            'C24 H15 N5'
_chemical_formula_weight         373.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N'
_chemical_oxdiff_usercomment     @RT
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'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.2576(2)
_cell_length_b                   29.1258(4)
_cell_length_c                   9.46920(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.6360(10)
_cell_angle_gamma                90
_cell_volume                     3924.30(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5505
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.9460
_cell_measurement_theta_min      3.4440
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.886
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orangish orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9209
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.194
_diffrn_reflns_theta_min         3.035
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00  25.00   0.50    3.00    --  -41.33  32.00   0.00  124
  2  ω    -27.00  67.00   0.50    3.00    --   41.33 -72.00  42.00  188
  3  ω     26.00  80.00   0.50    3.00    --   41.33-104.00 -30.00  108
  4  ω     75.00 100.00   0.50    3.00    --   41.33-138.00   0.00   50
  5  ω     44.00 127.00   0.50   18.00    --   96.67-145.00 -90.00  166
  6  ω     36.00  83.00   0.50   18.00    --   96.67 -68.00 -30.00   94
  7  ω     30.00  57.00   0.50   18.00    --   96.67 -50.00   0.00   54
  8  ω     31.00  56.00   0.50   18.00    --   96.67 -50.00 -30.00   50
  9  ω     29.00  54.00   0.50   18.00    --   96.67 -59.00 -60.00   50
 10  ω     28.00  96.00   0.50   18.00    --   96.67 -77.00 -90.00  136
 11  ω     30.00 107.00   0.50   18.00    --   96.67-117.00 -90.00  154
 12  ω     28.00  91.00   0.50   18.00    --   96.67 -72.00  42.00  126
 13  ω     31.00  56.00   0.50   18.00    --   96.67 -50.00 120.00   50
 14  ω     32.00  83.00   0.50   18.00    --   96.67 -68.00  90.00  102
 15  ω     30.00  55.00   0.50   18.00    --   96.67 -50.00 150.00   50
 16  ω     32.00  58.00   0.50   18.00    --   96.67 -59.00 120.00   52
 17  ω     31.00  56.00   0.50   18.00    --   96.67 -50.00  90.00   50
 18  ω     34.00  60.00   0.50   18.00    --   96.67 -59.00  60.00   52
 19  ω     83.00 159.00   0.50   18.00    --   96.67  50.00  90.00  152
 20  ω    106.00 132.00   0.50   18.00    --   96.67  96.00   0.00   52
 21  ω     99.00 164.00   0.50   18.00    --   96.67 117.00  30.00  130
 22  ω    122.00 148.00   0.50   18.00    --   96.67 117.00-120.00   52
 23  ω     16.00 111.00   0.50    3.00    --   41.33  72.00 172.00  190
 24  ω     71.00 163.00   0.50   18.00    --   96.67  72.00 172.00  184
 25  ω     -4.00  22.00   0.50    3.00    --  -41.33  72.00 172.00   52
;
_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      -0.0324780000
_diffrn_orient_matrix_UB_12      -0.0137117000
_diffrn_orient_matrix_UB_13      -0.1524631000
_diffrn_orient_matrix_UB_21      0.0566203000
_diffrn_orient_matrix_UB_22      0.0402038000
_diffrn_orient_matrix_UB_23      -0.0573509000
_diffrn_orient_matrix_UB_31      0.0863639000
_diffrn_orient_matrix_UB_32      -0.0315209000
_diffrn_orient_matrix_UB_33      -0.0067817000
_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                2953
_reflns_number_total             3541
_reflns_odcompleteness_completeness 99.02
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0963P)²+0.5007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1497
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C1(0.5) C3(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C00U(H00A,H00B)
3.b Aromatic/amide H refined with riding coordinates:
 C003(H003), C005(H005), C00C(H00F), C00E(H00G), C00M(H00M), C00N(H00N),
 C00O(H00O), C00Q(H00Q), C2(H2)
3.c Idealised Me refined as rotating group:
 C00V(H00C,H00D,H00E)
;
_atom_sites_solution_hydrogens   mixed
_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
C001 C 0.97246(7) 0.36173(4) 0.62710(11) 0.0480(3) Uani 1 1 d . . . . .
N002 N 0.92373(9) 0.31558(5) 0.40240(13) 0.0740(4) Uani 1 1 d . . . . .
C003 C 1.000000 0.33806(6) 0.750000 0.0500(4) Uani 1 2 d S T P . .
H003 H 0.999999 0.306133 0.750002 0.060 Uiso 1 2 calc R U P . .
C004 C 0.97262(7) 0.41008(4) 0.62727(11) 0.0498(3) Uani 1 1 d . . . . .
C005 C 1.000000 0.43380(6) 0.750000 0.0542(4) Uani 1 2 d S T P . .
H005 H 0.999998 0.465733 0.750001 0.065 Uiso 1 2 calc R U P . .
C006 C 0.94474(9) 0.33660(4) 0.50065(13) 0.0551(3) Uani 1 1 d . . . . .
C007 C 0.52616(8) 0.30773(4) 0.87295(13) 0.0548(3) Uani 1 1 d . . . . .
N008 N 0.92214(11) 0.45682(5) 0.40414(14) 0.0814(4) Uani 1 1 d . . . . .
N009 N 0.74933(8) 0.42112(4) 0.70378(14) 0.0693(3) Uani 1 1 d . . . . .
C00A C 0.94462(10) 0.43534(5) 0.50119(13) 0.0602(3) Uani 1 1 d . . . . .
C00B C 0.52607(8) 0.35588(5) 0.87317(14) 0.0570(3) Uani 1 1 d . . . . .
C00C C 0.500000 0.28410(6) 0.750000 0.0588(4) Uani 1 2 d S T P . .
H00F H 0.500001 0.252173 0.749998 0.071 Uiso 1 2 calc R U P . .
N00D N 0.57531(11) 0.26510(5) 1.10419(15) 0.0876(4) Uani 1 1 d . . . . .
C00E C 0.500000 0.37933(6) 0.750000 0.0617(5) Uani 1 2 d S T P . .
H00G H 0.500000 0.411262 0.750001 0.074 Uiso 1 2 calc R U P . .
C00F C 0.55343(10) 0.28369(5) 1.00182(15) 0.0653(4) Uani 1 1 d . . . . .
C00G C 0.73295(8) 0.34417(5) 0.68371(14) 0.0551(3) Uani 1 1 d . . . . .
C00H C 0.76455(8) 0.35468(5) 0.82739(13) 0.0570(3) Uani 1 1 d . . . . .
C00I C 0.55266(11) 0.38116(5) 0.99912(18) 0.0695(4) Uani 1 1 d . . . . .
N00J N 0.57363(12) 0.40272(6) 1.09709(19) 0.0981(5) Uani 1 1 d . . . . .
C00K C 0.72351(9) 0.38588(5) 0.61202(15) 0.0597(3) Uani 1 1 d . . . . .
C00L C 0.77350(9) 0.40252(5) 0.83611(16) 0.0634(4) Uani 1 1 d . . . . .
C00M C 0.71054(10) 0.30348(6) 0.61198(19) 0.0746(4) Uani 1 1 d . . . . .
H00M H 0.716418 0.275435 0.658649 0.090 Uiso 1 1 calc R U . . .
C00N C 0.69205(12) 0.38736(7) 0.46897(18) 0.0836(5) Uani 1 1 d . . . . .
H00N H 0.685605 0.415093 0.420651 0.100 Uiso 1 1 calc R U . . .
C00O C 0.67983(11) 0.30515(8) 0.4723(2) 0.0924(6) Uani 1 1 d . . . . .
H00O H 0.664768 0.278050 0.424133 0.111 Uiso 1 1 calc R U . . .
C00Q C 0.67100(12) 0.34627(9) 0.40248(19) 0.0967(7) Uani 1 1 d . . . . .
H00Q H 0.650169 0.346425 0.307398 0.116 Uiso 1 1 calc R U . . .
C00U C 0.74008(14) 0.46986(6) 0.6738(3) 0.1013(7) Uani 1 1 d . . . . .
H00A H 0.749296 0.475107 0.574475 0.122 Uiso 1 1 calc R U . . .
H00B H 0.788804 0.486404 0.728874 0.122 Uiso 1 1 calc R U . . .
C00V C 0.64565(18) 0.48843(7) 0.7075(4) 0.1368(11) Uani 1 1 d . . . . .
H00C H 0.598298 0.476750 0.640356 0.205 Uiso 1 1 calc R U . . .
H00D H 0.646603 0.521344 0.702642 0.205 Uiso 1 1 calc R U . . .
H00E H 0.631775 0.479038 0.801123 0.205 Uiso 1 1 calc R U . . .
C2 C 0.78615(10) 0.32816(8) 0.94730(17) 0.0841(5) Uani 1 1 d . . . . .
H2 H 0.780527 0.296369 0.943592 0.101 Uiso 1 1 calc R U . . .
C1 C 0.8053(10) 0.4173(4) 0.9762(14) 0.073(2) Uani 0.5 1 d . . P . .
C4 C 0.81577(14) 0.34960(15) 1.0707(2) 0.1133(9) Uani 1 1 d . . . . .
C5 C 0.82486(15) 0.39687(17) 1.0773(3) 0.1230(12) Uani 1 1 d . . . . .
C3 C 0.8027(10) 0.4305(4) 0.9482(15) 0.073(2) Uani 0.5 1 d . . P . .
H4 H 0.8297(18) 0.3301(9) 1.152(3) 0.137(9) Uiso 1 1 d . . . . .
H1 H 0.806(2) 0.4595(11) 0.956(3) 0.145(12) Uiso 1 1 d . . . . .
H5 H 0.8451(19) 0.4097(10) 1.161(3) 0.142(9) Uiso 1 1 d . . . . .


_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
C001 C003 1.3877(14) . ?
C001 C004 1.4081(18) . ?
C001 C006 1.4372(16) . ?
N002 C006 1.1380(17) . ?
C003 H003 0.9300 . ?
C004 C005 1.3867(14) . ?
C004 C00A 1.4372(17) . ?
C005 H005 0.9300 . ?
C007 C00B 1.4024(19) . ?
C007 C00C 1.3831(15) . ?
C007 C00F 1.4389(19) . ?
N008 C00A 1.1408(17) . ?
N009 C00K 1.3798(19) . ?
N009 C00L 1.388(2) . ?
N009 C00U 1.452(2) . ?
C00B C00E 1.3821(16) . ?
C00B C00I 1.432(2) . ?
C00C H00F 0.9300 . ?
N00D C00F 1.1366(19) . ?
C00E H00G 0.9300 . ?
C00G C00H 1.4388(19) . ?
C00G C00K 1.3939(19) . ?
C00G C00M 1.393(2) . ?
C00H C00L 1.401(2) . ?
C00H C2 1.391(2) . ?
C00I N00J 1.144(2) . ?
C00K C00N 1.400(2) . ?
C00L C1 1.440(15) . ?
C00L C3 1.381(16) . ?
C00M H00M 0.9300 . ?
C00M C00O 1.367(3) . ?
C00N H00N 0.9300 . ?
C00N C00Q 1.377(3) . ?
C00O H00O 0.9300 . ?
C00O C00Q 1.370(3) . ?
C00Q H00Q 0.9300 . ?
C00U H00A 0.9700 . ?
C00U H00B 0.9700 . ?
C00U C00V 1.504(3) . ?
C00V H00C 0.9600 . ?
C00V H00D 0.9600 . ?
C00V H00E 0.9600 . ?
C2 H2 0.9300 . ?
C2 C4 1.368(4) . ?
C1 C5 1.146(11) . ?
C1 H1 1.25(3) . ?
C4 C5 1.384(4) . ?
C4 H4 0.97(3) . ?
C5 C3 1.582(10) . ?
C5 H5 0.91(3) . ?
C3 H1 0.85(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
C003 C001 C004 119.70(11) . . ?
C003 C001 C006 119.60(12) . . ?
C004 C001 C006 120.70(10) . . ?
C001 C003 C001 120.43(15) . 2_756 ?
C001 C003 H003 119.8 2_756 . ?
C001 C003 H003 119.8 . . ?
C001 C004 C00A 120.71(10) . . ?
C005 C004 C001 119.97(11) . . ?
C005 C004 C00A 119.32(12) . . ?
C004 C005 C004 120.22(16) 2_756 . ?
C004 C005 H005 119.9 2_756 . ?
C004 C005 H005 119.9 . . ?
N002 C006 C001 178.02(14) . . ?
C00B C007 C00F 119.05(12) . . ?
C00C C007 C00B 119.90(12) . . ?
C00C C007 C00F 121.05(12) . . ?
C00K N009 C00L 108.61(12) . . ?
C00K N009 C00U 125.94(16) . . ?
C00L N009 C00U 124.91(16) . . ?
N008 C00A C004 177.45(15) . . ?
C007 C00B C00I 121.01(13) . . ?
C00E C00B C007 119.55(12) . . ?
C00E C00B C00I 119.44(13) . . ?
C007 C00C C007 120.33(17) . 2_656 ?
C007 C00C H00F 119.8 2_656 . ?
C007 C00C H00F 119.8 . . ?
C00B C00E C00B 120.76(17) 2_656 . ?
C00B C00E H00G 119.6 . . ?
C00B C00E H00G 119.6 2_656 . ?
N00D C00F C007 179.32(17) . . ?
C00K C00G C00H 106.85(12) . . ?
C00M C00G C00H 133.67(14) . . ?
C00M C00G C00K 119.46(14) . . ?
C00L C00H C00G 106.80(11) . . ?
C2 C00H C00G 133.90(16) . . ?
C2 C00H C00L 119.29(15) . . ?
N00J C00I C00B 177.65(18) . . ?
N009 C00K C00G 109.15(12) . . ?
N009 C00K C00N 129.98(15) . . ?
C00G C00K C00N 120.87(15) . . ?
N009 C00L C00H 108.57(12) . . ?
N009 C00L C1 139.5(4) . . ?
C00H C00L C1 111.9(4) . . ?
C3 C00L N009 120.6(4) . . ?
C3 C00L C00H 130.8(4) . . ?
C3 C00L C1 19.0(6) . . ?
C00G C00M H00M 120.3 . . ?
C00O C00M C00G 119.39(17) . . ?
C00O C00M H00M 120.3 . . ?
C00K C00N H00N 121.2 . . ?
C00Q C00N C00K 117.57(17) . . ?
C00Q C00N H00N 121.2 . . ?
C00M C00O H00O 119.6 . . ?
C00M C00O C00Q 120.80(18) . . ?
C00Q C00O H00O 119.6 . . ?
C00N C00Q H00Q 119.0 . . ?
C00O C00Q C00N 121.91(17) . . ?
C00O C00Q H00Q 119.0 . . ?
N009 C00U H00A 109.1 . . ?
N009 C00U H00B 109.1 . . ?
N009 C00U C00V 112.43(15) . . ?
H00A C00U H00B 107.9 . . ?
C00V C00U H00A 109.1 . . ?
C00V C00U H00B 109.1 . . ?
C00U C00V H00C 109.5 . . ?
C00U C00V H00D 109.5 . . ?
C00U C00V H00E 109.5 . . ?
H00C C00V H00D 109.5 . . ?
H00C C00V H00E 109.5 . . ?
H00D C00V H00E 109.5 . . ?
C00H C2 H2 120.5 . . ?
C4 C2 C00H 119.0(2) . . ?
C4 C2 H2 120.5 . . ?
C00L C1 H1 99.3(16) . . ?
C5 C1 C00L 131.4(11) . . ?
C5 C1 H1 129.3(18) . . ?
C2 C4 C5 121.0(2) . . ?
C2 C4 H4 116.7(17) . . ?
C5 C4 H4 122.3(17) . . ?
C1 C5 C4 117.5(8) . . ?
C1 C5 C3 7.2(13) . . ?
C1 C5 H5 124(2) . . ?
C4 C5 C3 124.6(6) . . ?
C4 C5 H5 118.1(19) . . ?
C3 C5 H5 117(2) . . ?
C00L C3 C5 105.3(7) . . ?
C00L C3 H1 132(2) . . ?
C5 C3 H1 123(3) . . ?

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
C001 C004 C005 C004 0.08(7) . . . 2_756 ?
C003 C001 C004 C005 -0.15(14) . . . . ?
C003 C001 C004 C00A 179.84(9) . . . . ?
C004 C001 C003 C001 0.07(7) . . . 2_756 ?
C006 C001 C003 C001 179.61(11) . . . 2_756 ?
C006 C001 C004 C005 -179.69(9) . . . . ?
C006 C001 C004 C00A 0.30(16) . . . . ?
C007 C00B C00E C00B 0.09(8) . . . 2_656 ?
N009 C00K C00N C00Q 179.95(14) . . . . ?
N009 C00L C1 C5 -178.0(8) . . . . ?
N009 C00L C3 C5 -179.1(4) . . . . ?
C00A C004 C005 C004 -179.91(12) . . . 2_756 ?
C00B C007 C00C C007 0.09(8) . . . 2_656 ?
C00C C007 C00B C00E -0.18(15) . . . . ?
C00C C007 C00B C00I 179.87(10) . . . . ?
C00F C007 C00B C00E 180.00(10) . . . . ?
C00F C007 C00B C00I 0.05(18) . . . . ?
C00F C007 C00C C007 179.91(12) . . . 2_656 ?
C00G C00H C00L N009 -0.43(13) . . . . ?
C00G C00H C00L C1 -179.8(6) . . . . ?
C00G C00H C00L C3 -178.8(8) . . . . ?
C00G C00H C2 C4 179.47(14) . . . . ?
C00G C00K C00N C00Q 0.0(2) . . . . ?
C00G C00M C00O C00Q 0.1(2) . . . . ?
C00H C00G C00K N009 1.08(14) . . . . ?
C00H C00G C00K C00N -178.94(12) . . . . ?
C00H C00G C00M C00O 178.54(13) . . . . ?
C00H C00L C1 C5 1.1(17) . . . . ?
C00H C00L C3 C5 -0.9(12) . . . . ?
C00H C2 C4 C5 -0.3(3) . . . . ?
C00I C00B C00E C00B -179.96(13) . . . 2_656 ?
C00K N009 C00L C00H 1.11(14) . . . . ?
C00K N009 C00L C1 -179.8(9) . . . . ?
C00K N009 C00L C3 179.7(7) . . . . ?
C00K N009 C00U C00V 87.8(3) . . . . ?
C00K C00G C00H C00L -0.39(13) . . . . ?
C00K C00G C00H C2 179.98(13) . . . . ?
C00K C00G C00M C00O 0.1(2) . . . . ?
C00K C00N C00Q C00O 0.2(3) . . . . ?
C00L N009 C00K C00G -1.37(15) . . . . ?
C00L N009 C00K C00N 178.65(14) . . . . ?
C00L N009 C00U C00V -82.8(3) . . . . ?
C00L C00H C2 C4 -0.1(2) . . . . ?
C00L C1 C5 C4 -1.6(18) . . . . ?
C00L C1 C5 C3 172(11) . . . . ?
C00M C00G C00H C00L -178.94(14) . . . . ?
C00M C00G C00H C2 1.4(2) . . . . ?
C00M C00G C00K N009 179.88(11) . . . . ?
C00M C00G C00K C00N -0.1(2) . . . . ?
C00M C00O C00Q C00N -0.2(3) . . . . ?
C00U N009 C00K C00G -173.19(14) . . . . ?
C00U N009 C00K C00N 6.8(2) . . . . ?
C00U N009 C00L C00H 173.04(14) . . . . ?
C00U N009 C00L C1 -7.8(9) . . . . ?
C00U N009 C00L C3 -8.4(7) . . . . ?
C2 C00H C00L N009 179.26(11) . . . . ?
C2 C00H C00L C1 -0.1(7) . . . . ?
C2 C00H C00L C3 0.9(8) . . . . ?
C2 C4 C5 C1 1.2(9) . . . . ?
C2 C4 C5 C3 0.2(7) . . . . ?
C1 C00L C3 C5 2(3) . . . . ?
C1 C5 C3 C00L -6(9) . . . . ?
C4 C5 C3 C00L 0.4(12) . . . . ?
C3 C00L C1 C5 -177(5) . . . . ?


_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 1.431
_oxdiff_exptl_absorpt_empirical_full_min 0.789
####################################################################### 
# 
# 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_kjk-etc-tf1_test1
_database_code_depnum_ccdc_archive 'CCDC 2260510'
loop_
_audit_author_name
_audit_author_address
'Kalyan Jyoti Kalita'
;Indian Institute of Science Education and Research Kolkata
India
;
_audit_update_record             
;
2023-05-04 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_audit_creation_date             2023-04-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 F2 N, C14 H13 N'
_chemical_formula_sum            'C18 H13 F2 N2'
_chemical_formula_weight         295.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N F'
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                   9.2342(3)
_cell_length_b                   19.7739(4)
_cell_length_c                   8.5738(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.396(3)
_cell_angle_gamma                90
_cell_volume                     1493.94(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14912
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.0490
_cell_measurement_theta_min      2.1760
_shelx_estimated_absorpt_T_max   0.925
_shelx_estimated_absorpt_T_min   0.692
_exptl_absorpt_coefficient_mu    0.795
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50115
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            36060
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         4.472
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00   1.00   0.50    0.20    --  -40.27 108.00   8.00  160
  2  ω     21.00  79.00   0.50    0.20    --   40.27-108.00 -89.00  116
  3  ω   -150.00 -82.00   0.50    0.50    --  -82.50-108.00 -89.00  136
  4  ω    -83.00 -15.00   0.50    0.50    --  -82.50 108.00   8.00  136
  5  ω    103.00 164.00   0.50    0.50    --   96.35 108.00   8.00  122
  6  ω     29.00 108.00   0.50    0.50    --   96.35-108.00 -89.00  158
  7  ω   -110.00 -26.00   0.50    0.20    --  -40.27 -25.00   0.00  168
  8  ω   -108.00 -17.00   0.50    0.20    --  -40.27 -64.00-150.00  182
  9  ω     41.00  99.00   0.50    0.20    --   40.27-138.00-150.00  116
 10  ω    -35.00  24.00   0.50    0.20    --   40.27 -12.00 -90.00  118
 11  ω    -35.00  24.00   0.50    0.20    --   40.27 -12.00-150.00  118
 12  ω    -26.00  57.00   0.50    0.20    --   40.27 -50.00 -90.00  166
 13  ω    -47.00 -15.00   0.50    0.50    --  -82.50  42.00-150.00   64
 14  ω    -47.00 -15.00   0.50    0.50    --  -82.50  42.00 150.00   64
 15  ω   -156.00 -83.00   0.50    0.50    --  -82.50 -96.00  30.00  146
 16  ω    -68.00 -14.00   0.50    0.50    --  -82.50  59.00 -60.00  108
 17  ω     99.00 160.00   0.50    0.50    --   96.35 117.00-120.00  122
 18  ω     30.00  57.00   0.50    0.50    --   96.35 -50.00 -30.00   54
 19  ω     70.00 165.00   0.50    0.50    --   96.35  77.00   0.00  190
 20  ω     26.00 127.00   0.50    0.50    --   96.35 -87.00 -90.00  202
 21  ω    105.00 170.00   0.50    0.50    --   96.35  96.00 -30.00  130
 22  ω     30.00  57.00   0.50    0.50    --   96.35 -50.00  90.00   54
 23  ω     30.00  57.00   0.50    0.50    --   96.35 -50.00 -60.00   54
 24  ω     28.00  68.00   0.50    0.50    --   96.35 -59.00 -60.00   80
 25  ω     30.00  57.00   0.50    0.50    --   96.35 -50.00  60.00   54
 26  ω    105.00 170.00   0.50    0.50    --   96.35  96.00 -90.00  130
 27  ω     28.00  68.00   0.50    0.50    --   96.35 -59.00 120.00   80
 28  ω     30.00  57.00   0.50    0.50    --   96.35 -50.00 -90.00   54
 29  ω     44.00 127.00   0.50    0.50    --   96.35-145.00 120.00  166
 30  ω     99.00 160.00   0.50    0.50    --   96.35 117.00 -60.00  122
 31  ω     29.00  83.00   0.50    0.50    --   96.35 -68.00   0.00  108
 32  ω     28.00 105.00   0.50    0.50    --   96.35 -77.00 -90.00  154
 33  ω     99.00 160.00   0.50    0.50    --   96.35 117.00 -30.00  122
 34  ω   -109.00 -13.00   0.50    0.20    --  -40.27 -77.00 -90.00  192
 35  ω   -109.00 -13.00   0.50    0.20    --  -40.27 -77.00   0.00  192
 36  ω    -24.00  35.00   0.50    0.20    --  -40.27  12.00 150.00  118
 37  ω   -109.00 -13.00   0.50    0.20    --  -40.27 -77.00 120.00  192
 38  ω   -109.00 -13.00   0.50    0.20    --  -40.27 -77.00-180.00  192
 39  ω   -109.00 -13.00   0.50    0.20    --  -40.27 -77.00  60.00  192
 40  ω   -106.00 -25.00   0.50    0.20    --  -40.27 -38.00 -90.00  162
 41  ω   -109.00 -13.00   0.50    0.20    --  -40.27 -77.00 150.00  192
 42  ω   -109.00 -13.00   0.50    0.20    --  -40.27 -77.00 -30.00  192
 43  ω    -30.00  31.00   0.50    0.20    --   40.27 -25.00 -30.00  122
 44  ω   -151.00 -55.00   0.50    0.50    --  -82.50 -77.00-180.00  192
 45  ω   -151.00 -55.00   0.50    0.50    --  -82.50 -77.00 150.00  192
 46  ω   -151.00 -55.00   0.50    0.50    --  -82.50 -77.00-150.00  192
 47  ω   -151.00 -55.00   0.50    0.50    --  -82.50 -77.00 -60.00  192
 48  ω   -151.00 -55.00   0.50    0.50    --  -82.50 -77.00 120.00  192
 49  ω   -151.00 -55.00   0.50    0.50    --  -82.50 -77.00-120.00  192
 50  ω   -151.00 -55.00   0.50    0.50    --  -82.50 -77.00 -90.00  192
 51  ω   -151.00 -55.00   0.50    0.50    --  -82.50 -77.00 -30.00  192
 52  ω   -151.00 -55.00   0.50    0.50    --  -82.50 -77.00  60.00  192
 53  ω     77.00 163.00   0.50    0.50    --   96.35  50.00 -60.00  172
 54  ω     77.00 163.00   0.50    0.50    --   96.35  50.00-180.00  172
 55  ω     83.00 164.00   0.50    0.50    --   96.35  33.00-120.00  162
 56  ω     33.00 110.00   0.50    0.50    --   96.35-117.00-150.00  154
 57  ω     83.00 164.00   0.50    0.50    --   96.35  33.00  90.00  162
 58  ω     72.00 164.00   0.50    0.50    --   96.35  68.00  90.00  184
 59  ω     81.00 167.00   0.50    0.50    --   96.35  25.00 150.00  172
 60  ω     72.00 164.00   0.50    0.50    --   96.35  68.00 -30.00  184
 61  ω     70.00 165.00   0.50    0.50    --   96.35  77.00-120.00  190
 62  ω     70.00 165.00   0.50    0.50    --   96.35  77.00  30.00  190
 63  ω     23.00 106.00   0.50    0.50    --   96.35 -96.00  90.00  166
 64  ω    -96.00 -19.00   0.50    0.20    --  -40.27 138.00 -30.00  154
 65  ω   -109.00 -13.00   0.50    0.20    --  -40.27 -77.00 -60.00  192
 66  ω   -109.00 -13.00   0.50    0.20    --  -40.27 -77.00  30.00  192
 67  ω   -109.00 -13.00   0.50    0.20    --  -40.27 -77.00-150.00  192
 68  ω   -109.00 -13.00   0.50    0.20    --  -40.27 -77.00  90.00  192
 69  ω    -30.00  31.00   0.50    0.20    --   40.27 -25.00 150.00  122
 70  ω     13.00 109.00   0.50    0.20    --   40.27  77.00 -60.00  192
 71  ω     13.00 109.00   0.50    0.20    --   40.27  77.00  90.00  192
 72  ω     18.00  78.00   0.50    0.20    --   40.27-104.00 150.00  120
 73  ω     13.00 109.00   0.50    0.20    --   40.27  77.00 150.00  192
 74  ω   -151.00 -55.00   0.50    0.50    --  -82.50 -77.00  30.00  192
 75  ω   -151.00 -55.00   0.50    0.50    --  -82.50 -77.00  90.00  192
 76  ω   -151.00 -55.00   0.50    0.50    --  -82.50 -77.00   0.00  192
 77  ω     70.00 165.00   0.50    0.50    --   96.35  77.00-180.00  190
 78  ω     72.00 164.00   0.50    0.50    --   96.35  68.00 120.00  184
 79  ω     72.00 164.00   0.50    0.50    --   96.35  68.00 -90.00  184
 80  ω     70.00 165.00   0.50    0.50    --   96.35  77.00-150.00  190
 81  ω     70.00 165.00   0.50    0.50    --   96.35  77.00  60.00  190
 82  ω     70.00 165.00   0.50    0.50    --   96.35  77.00 -60.00  190
 83  ω     70.00 165.00   0.50    0.50    --   96.35  77.00 150.00  190
 84  ω     70.00 165.00   0.50    0.50    --   96.35  77.00 120.00  190
 85  ω     80.00 164.00   0.50    0.50    --   96.35  42.00  30.00  168
 86  ω     26.00 127.00   0.50    0.50    --   96.35 -87.00 120.00  202
;
_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      0.1188041000
_diffrn_orient_matrix_UB_12      0.0570748000
_diffrn_orient_matrix_UB_13      0.0429289000
_diffrn_orient_matrix_UB_21      0.1174800000
_diffrn_orient_matrix_UB_22      -0.0496547000
_diffrn_orient_matrix_UB_23      0.1057145000
_diffrn_orient_matrix_UB_31      0.0513332000
_diffrn_orient_matrix_UB_32      -0.0186166000
_diffrn_orient_matrix_UB_33      -0.1498154000
_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                2359
_reflns_number_total             2718
_reflns_odcompleteness_completeness 100.00
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.093
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.0028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2718
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.076
_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)+(0.0563P)²+0.1530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1132
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00L(H00A,H00C)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00B), C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00I),
 C00J(H00J), C00K(H00K)
2.c Idealised Me refined as rotating group:
 C00M(H00D,H00H,H00L)
;
_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 0.21026(10) 0.45630(5) 0.38389(12) 0.0952(3) Uani 1 1 d . . . . .
F002 F 0.39535(12) 0.44900(5) 0.19463(12) 0.1031(3) Uani 1 1 d . . . . .
N003 N 0.19498(12) 0.61614(6) 0.24643(14) 0.0711(3) Uani 1 1 d . . . . .
C004 C 0.41548(14) 0.66440(6) 0.39749(17) 0.0640(3) Uani 1 1 d . . . . .
C005 C 0.30965(14) 0.66659(6) 0.49076(16) 0.0627(3) Uani 1 1 d . . . . .
C006 C 0.17436(15) 0.63658(6) 0.39302(17) 0.0652(3) Uani 1 1 d . . . . .
C007 C 0.34003(15) 0.63416(6) 0.24601(18) 0.0667(3) Uani 1 1 d . . . . .
C008 C 0.59641(16) 0.49626(6) 0.40152(18) 0.0700(4) Uani 1 1 d . . . . .
C009 C 0.31483(17) 0.69162(7) 0.64409(17) 0.0718(4) Uani 1 1 d . . . . .
H009 H 0.403364 0.711128 0.710837 0.086 Uiso 1 1 calc R U . . .
C00A C 0.35341(16) 0.47795(7) 0.44160(19) 0.0721(4) Uani 1 1 d . . . . .
C00B C 0.56515(16) 0.68627(7) 0.4257(2) 0.0747(4) Uani 1 1 d . . . . .
H00B H 0.617450 0.706156 0.524883 0.090 Uiso 1 1 calc R U . . .
C00C C 0.44711(17) 0.47420(7) 0.34513(18) 0.0737(4) Uani 1 1 d . . . . .
N00D N 0.77055(19) 0.49234(8) 0.2175(2) 0.1023(5) Uani 1 1 d . . . . .
C00E C 0.40983(18) 0.62594(8) 0.1246(2) 0.0802(4) Uani 1 1 d . . . . .
H00E H 0.359055 0.605996 0.025070 0.096 Uiso 1 1 calc R U . . .
C00F C 0.04769(16) 0.63093(8) 0.44639(19) 0.0753(4) Uani 1 1 d . . . . .
H00F H -0.040392 0.610209 0.382140 0.090 Uiso 1 1 calc R U . . .
C00G C 0.18833(19) 0.68726(8) 0.6959(2) 0.0802(4) Uani 1 1 d . . . . .
H00G H 0.190803 0.704678 0.797389 0.096 Uiso 1 1 calc R U . . .
C00H C 0.69387(19) 0.49353(7) 0.2995(2) 0.0809(4) Uani 1 1 d . . . . .
C00I C 0.05620(19) 0.65701(8) 0.5980(2) 0.0813(4) Uani 1 1 d . . . . .
H00I H -0.028165 0.654344 0.635731 0.098 Uiso 1 1 calc R U . . .
C00J C 0.63406(18) 0.67808(8) 0.3055(2) 0.0850(5) Uani 1 1 d . . . . .
H00J H 0.733551 0.692597 0.323807 0.102 Uiso 1 1 calc R U . . .
C00K C 0.55730(19) 0.64844(8) 0.1571(2) 0.0868(5) Uani 1 1 d . . . . .
H00K H 0.606457 0.643624 0.077584 0.104 Uiso 1 1 calc R U . . .
C00L C 0.07498(19) 0.58988(10) 0.1074(2) 0.0916(5) Uani 1 1 d . . . . .
H00A H 0.017218 0.556242 0.145891 0.110 Uiso 1 1 calc R U . . .
H00C H 0.120560 0.567718 0.032691 0.110 Uiso 1 1 calc R U . . .
C00M C -0.0314(2) 0.64454(13) 0.0167(2) 0.1138(7) Uani 1 1 d . . . . .
H00D H -0.106637 0.625008 -0.074866 0.171 Uiso 1 1 calc R U . . .
H00H H 0.025155 0.678054 -0.021561 0.171 Uiso 1 1 calc R U . . .
H00L H -0.080353 0.665309 0.088721 0.171 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
F001 C00A 1.3358(16) . ?
F002 C00C 1.3315(17) . ?
N003 C006 1.3864(18) . ?
N003 C007 1.3870(18) . ?
N003 C00L 1.4589(18) . ?
C004 C005 1.437(2) . ?
C004 C007 1.4102(19) . ?
C004 C00B 1.3985(19) . ?
C005 C006 1.4104(18) . ?
C005 C009 1.392(2) . ?
C006 C00F 1.382(2) . ?
C007 C00E 1.388(2) . ?
C008 C00A 1.383(2) 3_666 ?
C008 C00C 1.388(2) . ?
C008 C00H 1.432(2) . ?
C009 H009 0.9300 . ?
C009 C00G 1.371(2) . ?
C00A C00C 1.366(2) . ?
C00B H00B 0.9300 . ?
C00B C00J 1.373(2) . ?
N00D C00H 1.137(2) . ?
C00E H00E 0.9300 . ?
C00E C00K 1.379(2) . ?
C00F H00F 0.9300 . ?
C00F C00I 1.379(2) . ?
C00G H00G 0.9300 . ?
C00G C00I 1.392(2) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00J C00K 1.388(3) . ?
C00K H00K 0.9300 . ?
C00L H00A 0.9700 . ?
C00L H00C 0.9700 . ?
C00L C00M 1.511(3) . ?
C00M H00D 0.9600 . ?
C00M H00H 0.9600 . ?
C00M H00L 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
C006 N003 C007 108.78(11) . . ?
C006 N003 C00L 124.59(12) . . ?
C007 N003 C00L 125.98(12) . . ?
C007 C004 C005 107.12(11) . . ?
C00B C004 C005 134.09(13) . . ?
C00B C004 C007 118.77(14) . . ?
C006 C005 C004 106.60(12) . . ?
C009 C005 C004 134.38(12) . . ?
C009 C005 C006 119.01(13) . . ?
N003 C006 C005 108.90(12) . . ?
C00F C006 N003 129.48(12) . . ?
C00F C006 C005 121.62(13) . . ?
N003 C007 C004 108.55(13) . . ?
N003 C007 C00E 129.59(13) . . ?
C00E C007 C004 121.86(14) . . ?
C00A C008 C00C 117.64(14) 3_666 . ?
C00A C008 C00H 121.30(13) 3_666 . ?
C00C C008 C00H 121.05(14) . . ?
C005 C009 H009 120.3 . . ?
C00G C009 C005 119.43(13) . . ?
C00G C009 H009 120.3 . . ?
F001 C00A C008 119.03(14) . 3_666 ?
F001 C00A C00C 119.61(14) . . ?
C00C C00A C008 121.36(13) . 3_666 ?
C004 C00B H00B 120.4 . . ?
C00J C00B C004 119.29(15) . . ?
C00J C00B H00B 120.4 . . ?
F002 C00C C008 119.12(14) . . ?
F002 C00C C00A 119.88(13) . . ?
C00A C00C C008 121.00(14) . . ?
C007 C00E H00E 121.2 . . ?
C00K C00E C007 117.57(16) . . ?
C00K C00E H00E 121.2 . . ?
C006 C00F H00F 121.1 . . ?
C00I C00F C006 117.81(13) . . ?
C00I C00F H00F 121.1 . . ?
C009 C00G H00G 119.7 . . ?
C009 C00G C00I 120.66(14) . . ?
C00I C00G H00G 119.7 . . ?
N00D C00H C008 178.94(18) . . ?
C00F C00I C00G 121.43(15) . . ?
C00F C00I H00I 119.3 . . ?
C00G C00I H00I 119.3 . . ?
C00B C00J H00J 119.5 . . ?
C00B C00J C00K 120.92(15) . . ?
C00K C00J H00J 119.5 . . ?
C00E C00K C00J 121.60(16) . . ?
C00E C00K H00K 119.2 . . ?
C00J C00K H00K 119.2 . . ?
N003 C00L H00A 109.1 . . ?
N003 C00L H00C 109.1 . . ?
N003 C00L C00M 112.60(15) . . ?
H00A C00L H00C 107.8 . . ?
C00M C00L H00A 109.1 . . ?
C00M C00L H00C 109.1 . . ?
C00L C00M H00D 109.5 . . ?
C00L C00M H00H 109.5 . . ?
C00L C00M H00L 109.5 . . ?
H00D C00M H00H 109.5 . . ?
H00D C00M H00L 109.5 . . ?
H00H C00M H00L 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
F001 C00A C00C F002 -0.1(2) . . . . ?
F001 C00A C00C C008 180.00(12) . . . . ?
N003 C006 C00F C00I -178.62(14) . . . . ?
N003 C007 C00E C00K -179.67(14) . . . . ?
C004 C005 C006 N003 0.45(14) . . . . ?
C004 C005 C006 C00F -179.54(12) . . . . ?
C004 C005 C009 C00G 177.89(13) . . . . ?
C004 C007 C00E C00K 0.1(2) . . . . ?
C004 C00B C00J C00K -0.1(2) . . . . ?
C005 C004 C007 N003 -1.89(14) . . . . ?
C005 C004 C007 C00E 178.30(12) . . . . ?
C005 C004 C00B C00J -177.88(13) . . . . ?
C005 C006 C00F C00I 1.4(2) . . . . ?
C005 C009 C00G C00I 1.2(2) . . . . ?
C006 N003 C007 C004 2.20(15) . . . . ?
C006 N003 C007 C00E -178.01(14) . . . . ?
C006 N003 C00L C00M 74.4(2) . . . . ?
C006 C005 C009 C00G -0.72(19) . . . . ?
C006 C00F C00I C00G -0.9(2) . . . . ?
C007 N003 C006 C005 -1.64(15) . . . . ?
C007 N003 C006 C00F 178.35(14) . . . . ?
C007 N003 C00L C00M -95.30(18) . . . . ?
C007 C004 C005 C006 0.88(13) . . . . ?
C007 C004 C005 C009 -177.86(14) . . . . ?
C007 C004 C00B C00J 0.33(19) . . . . ?
C007 C00E C00K C00J 0.2(2) . . . . ?
C008 C00A C00C F002 179.90(13) 3_666 . . . ?
C008 C00A C00C C008 0.0(2) 3_666 . . . ?
C009 C005 C006 N003 179.41(11) . . . . ?
C009 C005 C006 C00F -0.6(2) . . . . ?
C009 C00G C00I C00F -0.4(2) . . . . ?
C00A C008 C00C F002 -179.90(12) 3_666 . . . ?
C00A C008 C00C C00A 0.0(2) 3_666 . . . ?
C00B C004 C005 C006 179.24(14) . . . . ?
C00B C004 C005 C009 0.5(2) . . . . ?
C00B C004 C007 N003 179.46(11) . . . . ?
C00B C004 C007 C00E -0.36(19) . . . . ?
C00B C00J C00K C00E -0.2(2) . . . . ?
C00H C008 C00C F002 1.3(2) . . . . ?
C00H C008 C00C C00A -178.82(13) . . . . ?
C00L N003 C006 C005 -172.86(14) . . . . ?
C00L N003 C006 C00F 7.1(2) . . . . ?
C00L N003 C007 C004 173.26(14) . . . . ?
C00L N003 C007 C00E -6.9(2) . . . . ?


_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 1.595
_oxdiff_exptl_absorpt_empirical_full_min 0.609
