# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_0062
_database_code_depnum_ccdc_archive 'CCDC 2213792'
loop_
_audit_author_name
_audit_author_address
'Zhi Zhou'
;Guangzhou Medical University
China
;
_audit_update_record             
;
2022-10-18 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
_audit_creation_date             2021-04-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H11 Cl F N3'
_chemical_formula_sum            'C17 H11 Cl F N3'
_chemical_formula_weight         311.74
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   19.5807(14)
_cell_length_b                   4.7294(3)
_cell_length_c                   14.8063(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.738(7)
_cell_angle_gamma                90
_cell_volume                     1313.04(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2362
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.2250
_cell_measurement_theta_min      2.7410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95312
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5097
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.172
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -83.00  15.00   1.00    4.00    --  -11.27 -57.00 150.00   98
  2  ω    -86.00  -3.00   1.00    4.00    --  -11.27 -38.00-120.00   83
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0354341000
_diffrn_orient_matrix_UB_12      0.0164916000
_diffrn_orient_matrix_UB_13      0.0024278000
_diffrn_orient_matrix_UB_21      0.0130554000
_diffrn_orient_matrix_UB_22      0.0200307000
_diffrn_orient_matrix_UB_23      0.0494862000
_diffrn_orient_matrix_UB_31      0.0022381000
_diffrn_orient_matrix_UB_32      0.1476652000
_diffrn_orient_matrix_UB_33      -0.0069700000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1968
_reflns_number_total             2317
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.036
_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)+(0.0393P)²+0.5253P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0837
_refine_ls_wR_factor_ref         0.0897
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17)
;
_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
Cl1 Cl 0.01183(3) 0.93072(11) 0.36064(4) 0.03755(17) Uani 1 1 d . . . . .
F1 F 0.39278(6) 0.1282(2) 0.40925(8) 0.0373(3) Uani 1 1 d . . . . .
N1 N 0.21024(8) 0.2815(3) 0.51378(10) 0.0242(4) Uani 1 1 d . . . . .
N2 N 0.27069(8) -0.0712(3) 0.61389(10) 0.0235(4) Uani 1 1 d . . . . .
N3 N 0.32094(8) 0.0635(3) 0.50101(10) 0.0219(3) Uani 1 1 d . . . . .
C1 C 0.12493(10) 0.5913(4) 0.43472(12) 0.0228(4) Uani 1 1 d . . . . .
C2 C 0.09297(10) 0.7753(4) 0.36267(13) 0.0269(4) Uani 1 1 d . . . . .
C3 C 0.12406(11) 0.8338(4) 0.29190(13) 0.0302(5) Uani 1 1 d . . . . .
H3 H 0.102873 0.960189 0.243884 0.036 Uiso 1 1 calc R U . . .
C4 C 0.18745(10) 0.7000(4) 0.29412(13) 0.0280(4) Uani 1 1 d . . . . .
H4 H 0.208016 0.738045 0.246104 0.034 Uiso 1 1 calc R U . . .
C5 C 0.22199(9) 0.5107(4) 0.36506(12) 0.0226(4) Uani 1 1 d . . . . .
C6 C 0.18835(9) 0.4601(3) 0.43510(12) 0.0209(4) Uani 1 1 d . . . . .
C7 C 0.10135(10) 0.4981(4) 0.51797(13) 0.0292(4) Uani 1 1 d . . . . .
H7A H 0.056046 0.399570 0.497753 0.035 Uiso 1 1 calc R U . . .
H7B H 0.096707 0.658545 0.556596 0.035 Uiso 1 1 calc R U . . .
C8 C 0.16077(10) 0.3000(4) 0.57194(13) 0.0284(4) Uani 1 1 d . . . . .
H8A H 0.184701 0.376309 0.633785 0.034 Uiso 1 1 calc R U . . .
H8B H 0.141750 0.115092 0.579586 0.034 Uiso 1 1 calc R U . . .
C9 C 0.26528(9) 0.0949(4) 0.54201(12) 0.0209(4) Uani 1 1 d . . . . .
C10 C 0.33004(10) 0.2052(4) 0.42239(13) 0.0248(4) Uani 1 1 d . . . . .
C11 C 0.28979(10) 0.3878(4) 0.36353(12) 0.0252(4) Uani 1 1 d . . . . .
H11 H 0.307006 0.446400 0.314233 0.030 Uiso 1 1 calc R U . . .
C12 C 0.36619(10) -0.1472(4) 0.55528(12) 0.0233(4) Uani 1 1 d . . . . .
C13 C 0.33321(10) -0.2250(4) 0.62395(13) 0.0239(4) Uani 1 1 d . . . . .
C14 C 0.36281(10) -0.4296(4) 0.69009(14) 0.0303(5) Uani 1 1 d . . . . .
H14 H 0.340906 -0.481557 0.735601 0.036 Uiso 1 1 calc R U . . .
C15 C 0.42587(11) -0.5555(4) 0.68704(14) 0.0331(5) Uani 1 1 d . . . . .
H15 H 0.446603 -0.694614 0.730728 0.040 Uiso 1 1 calc R U . . .
C16 C 0.45845(11) -0.4754(4) 0.61915(14) 0.0330(5) Uani 1 1 d . . . . .
H16 H 0.500993 -0.562098 0.618747 0.040 Uiso 1 1 calc R U . . .
C17 C 0.42971(10) -0.2712(4) 0.55213(13) 0.0291(4) Uani 1 1 d . . . . .
H17 H 0.451959 -0.219232 0.506973 0.035 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
Cl1 C2 1.7430(19) . ?
F1 C10 1.348(2) . ?
N1 C6 1.402(2) . ?
N1 C8 1.472(2) . ?
N1 C9 1.362(2) . ?
N2 C9 1.302(2) . ?
N2 C13 1.395(2) . ?
N3 C9 1.400(2) . ?
N3 C10 1.398(2) . ?
N3 C12 1.419(2) . ?
C1 C2 1.379(3) . ?
C1 C6 1.387(3) . ?
C1 C7 1.501(2) . ?
C2 C3 1.383(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.398(3) . ?
C5 C6 1.400(2) . ?
C5 C11 1.455(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.528(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C11 1.316(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.402(3) . ?
C12 C17 1.388(3) . ?
C13 C14 1.380(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.383(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.389(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.383(3) . ?
C17 H17 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C8 110.78(14) . . ?
C9 N1 C6 132.12(15) . . ?
C9 N1 C8 117.04(15) . . ?
C9 N2 C13 105.33(15) . . ?
C9 N3 C12 105.42(14) . . ?
C10 N3 C9 127.75(15) . . ?
C10 N3 C12 126.82(15) . . ?
C2 C1 C6 119.45(16) . . ?
C2 C1 C7 129.92(17) . . ?
C6 C1 C7 110.62(16) . . ?
C1 C2 Cl1 119.19(14) . . ?
C1 C2 C3 120.77(18) . . ?
C3 C2 Cl1 120.03(15) . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.53(18) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 118.4 . . ?
C3 C4 C5 123.16(17) . . ?
C5 C4 H4 118.4 . . ?
C4 C5 C6 115.91(17) . . ?
C4 C5 C11 119.36(16) . . ?
C6 C5 C11 124.70(17) . . ?
C1 C6 N1 109.38(15) . . ?
C1 C6 C5 122.17(17) . . ?
C5 C6 N1 128.44(17) . . ?
C1 C7 H7A 111.0 . . ?
C1 C7 H7B 111.0 . . ?
C1 C7 C8 103.97(14) . . ?
H7A C7 H7B 109.0 . . ?
C8 C7 H7A 111.0 . . ?
C8 C7 H7B 111.0 . . ?
N1 C8 C7 105.11(14) . . ?
N1 C8 H8A 110.7 . . ?
N1 C8 H8B 110.7 . . ?
C7 C8 H8A 110.7 . . ?
C7 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
N1 C9 N3 125.56(16) . . ?
N2 C9 N1 120.83(16) . . ?
N2 C9 N3 113.60(15) . . ?
F1 C10 N3 109.32(15) . . ?
C11 C10 F1 118.60(16) . . ?
C11 C10 N3 132.09(17) . . ?
C5 C11 H11 115.6 . . ?
C10 C11 C5 128.83(16) . . ?
C10 C11 H11 115.6 . . ?
C13 C12 N3 104.61(15) . . ?
C17 C12 N3 134.19(17) . . ?
C17 C12 C13 121.20(17) . . ?
N2 C13 C12 111.05(16) . . ?
C14 C13 N2 128.17(17) . . ?
C14 C13 C12 120.78(17) . . ?
C13 C14 H14 120.8 . . ?
C13 C14 C15 118.37(19) . . ?
C15 C14 H14 120.8 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.43(19) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 118.9 . . ?
C17 C16 C15 122.20(19) . . ?
C17 C16 H16 118.9 . . ?
C12 C17 H17 121.5 . . ?
C16 C17 C12 117.02(18) . . ?
C16 C17 H17 121.5 . . ?

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
Cl1 C2 C3 C4 -178.06(14) . . . . ?
F1 C10 C11 C5 -177.37(16) . . . . ?
N2 C13 C14 C15 -179.85(17) . . . . ?
N3 C10 C11 C5 2.8(3) . . . . ?
N3 C12 C13 N2 -0.23(19) . . . . ?
N3 C12 C13 C14 179.81(16) . . . . ?
N3 C12 C17 C16 179.99(18) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C1 C7 C8 N1 -3.37(19) . . . . ?
C2 C1 C6 N1 -179.30(15) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
C2 C1 C7 C8 -178.63(18) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C3 C4 C5 C11 -177.79(17) . . . . ?
C4 C5 C6 N1 179.68(16) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C4 C5 C11 C10 -179.18(19) . . . . ?
C6 N1 C8 C7 3.6(2) . . . . ?
C6 N1 C9 N2 -172.80(17) . . . . ?
C6 N1 C9 N3 8.6(3) . . . . ?
C6 C1 C2 Cl1 177.99(13) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
C6 C1 C7 C8 2.2(2) . . . . ?
C6 C5 C11 C10 2.8(3) . . . . ?
C7 C1 C2 Cl1 -1.1(3) . . . . ?
C7 C1 C2 C3 179.80(19) . . . . ?
C7 C1 C6 N1 0.0(2) . . . . ?
C7 C1 C6 C5 -179.90(16) . . . . ?
C8 N1 C6 C1 -2.3(2) . . . . ?
C8 N1 C6 C5 177.54(17) . . . . ?
C8 N1 C9 N2 4.2(2) . . . . ?
C8 N1 C9 N3 -174.35(16) . . . . ?
C9 N1 C6 C1 174.85(17) . . . . ?
C9 N1 C6 C5 -5.3(3) . . . . ?
C9 N1 C8 C7 -174.04(15) . . . . ?
C9 N2 C13 C12 0.0(2) . . . . ?
C9 N2 C13 C14 179.94(18) . . . . ?
C9 N3 C10 F1 176.04(15) . . . . ?
C9 N3 C10 C11 -4.1(3) . . . . ?
C9 N3 C12 C13 0.37(18) . . . . ?
C9 N3 C12 C17 -179.22(19) . . . . ?
C10 N3 C9 N1 -2.7(3) . . . . ?
C10 N3 C9 N2 178.67(16) . . . . ?
C10 N3 C12 C13 -178.73(16) . . . . ?
C10 N3 C12 C17 1.7(3) . . . . ?
C11 C5 C6 N1 -2.2(3) . . . . ?
C11 C5 C6 C1 177.61(16) . . . . ?
C12 N3 C9 N1 178.24(16) . . . . ?
C12 N3 C9 N2 -0.42(19) . . . . ?
C12 N3 C10 F1 -5.1(2) . . . . ?
C12 N3 C10 C11 174.77(19) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 N2 C9 N1 -178.45(15) . . . . ?
C13 N2 C9 N3 0.27(19) . . . . ?
C13 C12 C17 C16 0.5(3) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C12 0.0(3) . . . . ?
C17 C12 C13 N2 179.42(15) . . . . ?
C17 C12 C13 C14 -0.5(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 1.205
_oxdiff_exptl_absorpt_empirical_full_min 0.937
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_2968
_database_code_depnum_ccdc_archive 'CCDC 2213793'
loop_
_audit_author_name
_audit_author_address
'Zhi Zhou'
;Guangzhou Medical University
China
;
_audit_update_record             
;
2022-10-18 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
_audit_creation_date             2021-04-10
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 F2 N3'
_chemical_formula_sum            'C17 H13 F2 N3'
_chemical_formula_weight         297.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   11.6045(10)
_cell_length_b                   8.9631(8)
_cell_length_c                   13.1233(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.803(7)
_cell_angle_gamma                90
_cell_volume                     1345.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2859
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.1490
_cell_measurement_theta_min      2.8890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5944
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.765
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  -4.00   1.00    2.50    --   11.90 -38.00 -30.00   30
  2  ω    -19.00  21.00   1.00    2.50    --  -11.27 -99.00 -30.00   40
  3  ω    -58.00  28.00   1.00    2.50    --   11.90 -38.00  30.00   86
  4  ω     42.00  90.00   1.00    2.50    --   11.90 178.00 -30.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0603264000
_diffrn_orient_matrix_UB_12      0.0019197000
_diffrn_orient_matrix_UB_13      -0.0215618000
_diffrn_orient_matrix_UB_21      0.0035525000
_diffrn_orient_matrix_UB_22      -0.0743387000
_diffrn_orient_matrix_UB_23      -0.0176009000
_diffrn_orient_matrix_UB_31      -0.0140164000
_diffrn_orient_matrix_UB_32      -0.0269737000
_diffrn_orient_matrix_UB_33      0.0472697000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2054
_reflns_number_total             2370
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.070
_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)+(0.0385P)²+0.4629P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0936
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.50297(9) 0.56663(12) 0.17936(7) 0.0333(3) Uani 1 1 d . . . . .
F2 F 0.57842(9) 0.36710(11) 0.25507(7) 0.0341(3) Uani 1 1 d . . . . .
N1 N 0.37293(11) 0.66377(15) 0.41262(9) 0.0219(3) Uani 1 1 d . . . . .
N2 N 0.56291(11) 0.71065(15) 0.49483(9) 0.0230(3) Uani 1 1 d . . . . .
N3 N 0.54748(11) 0.56049(15) 0.35491(9) 0.0208(3) Uani 1 1 d . . . . .
C1 C 0.18473(14) 0.7147(2) 0.33472(12) 0.0263(4) Uani 1 1 d . . . . .
C2 C 0.08540(15) 0.6969(2) 0.26098(13) 0.0329(4) Uani 1 1 d . . . . .
H2 H 0.019895 0.756114 0.262349 0.040 Uiso 1 1 calc R U . . .
C3 C 0.08490(15) 0.5893(2) 0.18496(14) 0.0349(5) Uani 1 1 d . . . . .
H3 H 0.018944 0.576948 0.134441 0.042 Uiso 1 1 calc R U . . .
C4 C 0.18204(15) 0.5005(2) 0.18394(12) 0.0305(4) Uani 1 1 d . . . . .
H4 H 0.179829 0.428409 0.132675 0.037 Uiso 1 1 calc R U . . .
C5 C 0.28330(14) 0.51576(19) 0.25755(11) 0.0233(4) Uani 1 1 d . . . . .
C6 C 0.28260(14) 0.62688(18) 0.33116(11) 0.0209(4) Uani 1 1 d . . . . .
C7 C 0.38286(14) 0.40951(19) 0.26078(12) 0.0253(4) Uani 1 1 d . . . . .
H7A H 0.385819 0.346519 0.321272 0.030 Uiso 1 1 calc R U . . .
H7B H 0.366814 0.345513 0.200424 0.030 Uiso 1 1 calc R U . . .
C8 C 0.50040(14) 0.47835(19) 0.26383(11) 0.0232(4) Uani 1 1 d . . . . .
C9 C 0.49049(13) 0.64506(17) 0.42088(11) 0.0194(3) Uani 1 1 d . . . . .
C10 C 0.67369(14) 0.67250(19) 0.47782(12) 0.0236(4) Uani 1 1 d . . . . .
C11 C 0.78171(15) 0.7135(2) 0.53393(13) 0.0314(4) Uani 1 1 d . . . . .
H11 H 0.786570 0.773005 0.592561 0.038 Uiso 1 1 calc R U . . .
C12 C 0.88141(16) 0.6639(2) 0.50057(14) 0.0364(5) Uani 1 1 d . . . . .
H12 H 0.954358 0.689791 0.537393 0.044 Uiso 1 1 calc R U . . .
C13 C 0.87437(15) 0.5756(2) 0.41263(15) 0.0365(5) Uani 1 1 d . . . . .
H13 H 0.943041 0.544899 0.391308 0.044 Uiso 1 1 calc R U . . .
C14 C 0.76818(15) 0.5321(2) 0.35599(13) 0.0313(4) Uani 1 1 d . . . . .
H14 H 0.763935 0.472585 0.297403 0.038 Uiso 1 1 calc R U . . .
C15 C 0.66804(14) 0.58132(19) 0.39065(12) 0.0234(4) Uani 1 1 d . . . . .
C16 C 0.33273(15) 0.7839(2) 0.47693(12) 0.0278(4) Uani 1 1 d . . . . .
H16A H 0.380802 0.872393 0.476734 0.033 Uiso 1 1 calc R U . . .
H16B H 0.336389 0.750647 0.547746 0.033 Uiso 1 1 calc R U . . .
C17 C 0.20711(15) 0.8160(2) 0.42698(14) 0.0383(5) Uani 1 1 d . . . . .
H17A H 0.153746 0.794313 0.474456 0.046 Uiso 1 1 calc R U . . .
H17B H 0.197899 0.919699 0.405965 0.046 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
F1 C8 1.3664(18) . ?
F2 C8 1.3648(19) . ?
N1 C6 1.403(2) . ?
N1 C9 1.360(2) . ?
N1 C16 1.491(2) . ?
N2 C9 1.310(2) . ?
N2 C10 1.385(2) . ?
N3 C8 1.431(2) . ?
N3 C9 1.3988(19) . ?
N3 C15 1.410(2) . ?
C1 C2 1.382(2) . ?
C1 C6 1.389(2) . ?
C1 C17 1.501(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.395(2) . ?
C5 C6 1.388(2) . ?
C5 C7 1.492(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.491(2) . ?
C10 C11 1.391(2) . ?
C10 C15 1.398(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.390(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.390(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.521(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?

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
C6 N1 C16 109.65(13) . . ?
C9 N1 C6 129.83(13) . . ?
C9 N1 C16 116.75(13) . . ?
C9 N2 C10 105.42(13) . . ?
C9 N3 C8 129.97(13) . . ?
C9 N3 C15 105.62(12) . . ?
C15 N3 C8 124.20(13) . . ?
C2 C1 C6 120.02(16) . . ?
C2 C1 C17 130.08(16) . . ?
C6 C1 C17 109.87(14) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.00(17) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.26(16) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.0 . . ?
C3 C4 C5 121.94(17) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C7 120.93(15) . . ?
C6 C5 C4 116.62(16) . . ?
C6 C5 C7 122.29(14) . . ?
C1 C6 N1 110.48(14) . . ?
C5 C6 N1 127.37(15) . . ?
C5 C6 C1 122.10(15) . . ?
C5 C7 H7A 108.3 . . ?
C5 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C8 C7 C5 115.90(14) . . ?
C8 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
F1 C8 N3 108.77(13) . . ?
F1 C8 C7 111.35(13) . . ?
F2 C8 F1 104.38(11) . . ?
F2 C8 N3 106.37(12) . . ?
F2 C8 C7 108.20(14) . . ?
N3 C8 C7 116.92(13) . . ?
N1 C9 N3 126.22(14) . . ?
N2 C9 N1 120.79(14) . . ?
N2 C9 N3 112.98(13) . . ?
N2 C10 C11 128.85(15) . . ?
N2 C10 C15 111.14(14) . . ?
C11 C10 C15 120.01(15) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 C10 118.43(17) . . ?
C12 C11 H11 120.8 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.89(17) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.1 . . ?
C14 C13 C12 121.87(17) . . ?
C14 C13 H13 119.1 . . ?
C13 C14 H14 121.5 . . ?
C13 C14 C15 116.92(17) . . ?
C15 C14 H14 121.5 . . ?
C10 C15 N3 104.78(13) . . ?
C14 C15 N3 133.35(16) . . ?
C14 C15 C10 121.87(16) . . ?
N1 C16 H16A 110.7 . . ?
N1 C16 H16B 110.7 . . ?
N1 C16 C17 105.20(13) . . ?
H16A C16 H16B 108.8 . . ?
C17 C16 H16A 110.7 . . ?
C17 C16 H16B 110.7 . . ?
C1 C17 C16 104.75(14) . . ?
C1 C17 H17A 110.8 . . ?
C1 C17 H17B 110.8 . . ?
C16 C17 H17A 110.8 . . ?
C16 C17 H17B 110.8 . . ?
H17A C17 H17B 108.9 . . ?

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
N1 C16 C17 C1 -1.70(19) . . . . ?
N2 C10 C11 C12 -178.60(16) . . . . ?
N2 C10 C15 N3 -1.51(18) . . . . ?
N2 C10 C15 C14 178.02(15) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C1 C6 N1 179.79(15) . . . . ?
C2 C1 C6 C5 -2.6(2) . . . . ?
C2 C1 C17 C16 -179.73(18) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C3 C4 C5 C7 174.29(16) . . . . ?
C4 C5 C6 N1 179.87(15) . . . . ?
C4 C5 C6 C1 2.7(2) . . . . ?
C4 C5 C7 C8 129.74(16) . . . . ?
C5 C7 C8 F1 -59.29(17) . . . . ?
C5 C7 C8 F2 -173.43(12) . . . . ?
C5 C7 C8 N3 66.59(19) . . . . ?
C6 N1 C9 N2 167.48(15) . . . . ?
C6 N1 C9 N3 -11.5(3) . . . . ?
C6 N1 C16 C17 0.62(18) . . . . ?
C6 C1 C2 C3 0.8(3) . . . . ?
C6 C1 C17 C16 2.3(2) . . . . ?
C6 C5 C7 C8 -55.1(2) . . . . ?
C7 C5 C6 N1 4.5(3) . . . . ?
C7 C5 C6 C1 -172.64(15) . . . . ?
C8 N3 C9 N1 1.9(3) . . . . ?
C8 N3 C9 N2 -177.12(14) . . . . ?
C8 N3 C15 C10 177.40(14) . . . . ?
C8 N3 C15 C14 -2.0(3) . . . . ?
C9 N1 C6 C1 -156.09(16) . . . . ?
C9 N1 C6 C5 26.5(3) . . . . ?
C9 N1 C16 C17 160.93(14) . . . . ?
C9 N2 C10 C11 179.68(17) . . . . ?
C9 N2 C10 C15 0.18(18) . . . . ?
C9 N3 C8 F1 94.70(18) . . . . ?
C9 N3 C8 F2 -153.38(14) . . . . ?
C9 N3 C8 C7 -32.4(2) . . . . ?
C9 N3 C15 C10 2.16(16) . . . . ?
C9 N3 C15 C14 -177.29(18) . . . . ?
C10 N2 C9 N1 -177.79(14) . . . . ?
C10 N2 C9 N3 1.31(18) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C10 C15 N3 178.94(15) . . . . ?
C11 C10 C15 C14 -1.5(2) . . . . ?
C11 C12 C13 C14 -1.0(3) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C14 C15 N3 -179.71(17) . . . . ?
C13 C14 C15 C10 0.9(2) . . . . ?
C15 N3 C8 F1 -79.31(18) . . . . ?
C15 N3 C8 F2 32.60(19) . . . . ?
C15 N3 C8 C7 153.54(15) . . . . ?
C15 N3 C9 N1 176.78(15) . . . . ?
C15 N3 C9 N2 -2.26(17) . . . . ?
C15 C10 C11 C12 0.9(2) . . . . ?
C16 N1 C6 C1 0.84(18) . . . . ?
C16 N1 C6 C5 -176.59(15) . . . . ?
C16 N1 C9 N2 11.9(2) . . . . ?
C16 N1 C9 N3 -167.08(14) . . . . ?
C17 C1 C2 C3 -176.97(18) . . . . ?
C17 C1 C6 N1 -2.00(19) . . . . ?
C17 C1 C6 C5 175.59(15) . . . . ?

_olex2_date_sample_data_collection 2021-04-10
_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 1.210
_oxdiff_exptl_absorpt_empirical_full_min 0.825
