# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_202209167
_database_code_depnum_ccdc_archive 'CCDC 2217551'
loop_
_audit_author_name
_audit_author_address
'Qingjie Liu'
;Zhengzhou University
China
;
_audit_update_record             
;
2022-11-04 deposited with the CCDC.	2024-08-26 downloaded from the CCDC.
;
_audit_creation_date             2022-09-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 F3 I N2'
_chemical_formula_sum            'C14 H8 F3 I N2'
_chemical_formula_weight         388.12
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N2F6
_chemical_oxdiff_usercomment     r
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'
I I -0.3257 6.8362 '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                   24.8694(3)
_cell_length_b                   7.34027(12)
_cell_length_c                   15.1137(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.0839(13)
_cell_angle_gamma                90
_cell_volume                     2697.85(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4280
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8790
_cell_measurement_theta_min      5.1710
_shelx_estimated_absorpt_T_max   0.313
_shelx_estimated_absorpt_T_min   0.141
_exptl_absorpt_coefficient_mu    18.920
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53378
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.911
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10691
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.969
_diffrn_reflns_theta_min         3.635
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00   1.40   0.60    5.00    --  -33.50  37.00-180.00   94
  2  ω     21.00  71.40   0.60    5.00    --   36.47  57.00-180.00   84
  3  ω     48.00  77.40   0.60    5.00    --   36.47  19.00 120.00   49
  4  ω    -32.00  -5.00   0.60    5.00    --   36.47 -77.00  90.00   45
  5  ω     31.00 103.00   0.60    5.00    --   36.47  37.00-120.00  120
  6  ω     17.00  44.00   0.60    5.00    --   36.47  19.00 120.00   45
  7  ω     12.00  62.40   0.60    5.00    --   36.47  77.00  60.00   84
  8  ω     40.00  66.40   0.60    5.00    --   36.47  57.00  30.00   44
  9  ω      0.00  30.00   0.60    5.00    --   36.47 -99.00  90.00   50
 10  ω     27.00  63.00   0.60    5.00    --   36.47 -77.00  90.00   60
 11  ω     81.00 107.40   0.60    5.00    --   36.47 178.00 150.00   44
 12  ω     34.00 104.20   0.60    5.00    --   36.47  77.00  90.00  117
 13  ω     -7.00  18.20   0.60    5.00    --   36.47 106.00-159.68   42
 14  ω      9.00  54.00   0.60    5.00    --   36.47  77.00   0.00   75
 15  ω     35.00  61.40   0.60    5.00    --   36.47 -99.00  90.00   44
 16  ω    -34.00  33.20   0.60    5.00    --   36.47 -37.00 -30.00  112
 17  ω     79.00 105.40   0.60    8.50    --  108.00  77.00 -30.00   44
 18  ω     88.00 114.40   0.60    8.50    --  108.00  61.00 -30.00   44
 19  ω     82.00 111.40   0.60    8.50    --  108.00  30.00  60.00   49
 20  ω    115.00 175.00   0.60    8.50    --  108.00  77.00 -60.00  100
 21  ω     37.00 110.20   0.60    8.50    --  108.00-111.00-120.00  122
 22  ω     39.00 120.00   0.60    8.50    --  108.00 -45.00 -90.00  135
 23  ω     79.00 105.40   0.60    8.50    --  108.00  77.00 -60.00   44
 24  ω     38.00 108.20   0.60    8.50    --  108.00 -94.00 -90.00  117
 25  ω     88.00 114.40   0.60    8.50    --  108.00  61.00  30.00   44
 26  ω     82.00 115.60   0.60    8.50    --  108.00  30.00  90.00   56
 27  ω    121.00 160.60   0.60    8.50    --  108.00  45.00 120.00   66
 28  ω    112.00 174.40   0.60    8.50    --  108.00  77.00  60.00  104
 29  ω     79.00 104.20   0.60    8.50    --  108.00  77.00  60.00   42
 30  ω     88.00 114.40   0.60    8.50    --  108.00  45.00 120.00   44
 31  ω    124.00 154.60   0.60    8.50    --  108.00  77.00  30.00   51
 32  ω     89.00 115.40   0.60    8.50    --  108.00  61.00  90.00   44
 33  ω     81.00 107.40   0.60    8.50    --  108.00  77.00  90.00   44
 34  ω     84.00 114.00   0.60    8.50    --  108.00  30.00  30.00   50
 35  ω    111.00 176.40   0.60    8.50    --  108.00  77.00   0.00  109
 36  ω     83.00 109.40   0.60    8.50    --  108.00  30.00   0.00   44
 37  ω     87.00 113.40   0.60    8.50    --  108.00  30.00 -30.00   44
 38  ω     88.00 114.40   0.60    8.50    --  108.00  61.00  60.00   44
 39  ω     88.00 151.60   0.60    8.50    --  108.00  61.00   0.00  106
 40  ω     79.00 104.20   0.60    8.50    --  108.00  77.00   0.00   42
 41  ω     88.00 113.20   0.60    8.50    --  108.00  45.00  30.00   42
 42  ω     83.00 108.20   0.60    8.50    --  108.00  30.00 120.00   42
 43  ω     79.00 112.60   0.60    8.50    --  108.00  77.00  30.00   56
 44  ω     80.00 106.40   0.60    8.50    --  108.00  77.00 -90.00   44
 45  ω     67.00  96.40   0.60    8.50    --  108.00  15.00   0.00   49
 46  ω    133.00 166.00   0.60    8.50    --  108.00  15.00   0.00   55
 47  ω     66.80 109.40   0.60    8.50    --  108.00 -94.00  90.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0012906000
_diffrn_orient_matrix_UB_12      0.0350130000
_diffrn_orient_matrix_UB_13      0.1009321000
_diffrn_orient_matrix_UB_21      0.0629383000
_diffrn_orient_matrix_UB_22      0.0223341000
_diffrn_orient_matrix_UB_23      0.0177687000
_diffrn_orient_matrix_UB_31      -0.0070592000
_diffrn_orient_matrix_UB_32      0.2057252000
_diffrn_orient_matrix_UB_33      -0.0191227000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2282
_reflns_number_total             2577
_reflns_odcompleteness_completeness 99.92
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.568
_refine_diff_density_min         -1.696
_refine_diff_density_rms         0.225
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2577
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0714P)²+4.4191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1224
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F1-F2 \\sim F1-F3 \\sim F2-F3 \\sim F1A-F2A \\sim F1A-F3A \\sim F2A-F3A
 with sigma of 0.04
 C14-F1 \\sim C14-F2 \\sim C14-F3 \\sim C14-F1A \\sim C14-F2A \\sim C14-F3A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F3) \\sim Ueq, Uanis(F3A) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F1)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F1) = Uanis(F1A)
Uanis(F2) = Uanis(F2A)
Uanis(F3) = Uanis(F3A)
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
I1 I 0.91785(2) 0.73793(4) 0.69366(2) 0.04855(17) Uani 1 1 d . . . . .
F1 F 0.5091(2) 0.6317(12) 0.6381(6) 0.100(3) Uani 0.752(14) 1 d D U P A 1
F1A F 0.5016(8) 0.744(4) 0.6683(13) 0.100(3) Uani 0.248(14) 1 d D U P A 2
F2 F 0.5201(5) 0.7495(16) 0.5177(5) 0.095(3) Uani 0.752(14) 1 d D . P A 1
F2A F 0.5151(17) 0.694(5) 0.5313(16) 0.095(3) Uani 0.248(14) 1 d D . P A 2
F3 F 0.4999(3) 0.9208(12) 0.6166(8) 0.106(3) Uani 0.752(14) 1 d D U P A 1
F3A F 0.5104(12) 0.950(2) 0.587(2) 0.106(3) Uani 0.248(14) 1 d D U P A 2
N1 N 0.79131(12) 0.8591(4) 0.83186(19) 0.0280(6) Uani 1 1 d . . . . .
N2 N 0.79708(14) 0.7946(5) 0.6899(2) 0.0317(7) Uani 1 1 d . . . . .
C1 C 0.77506(17) 0.9218(6) 0.9088(2) 0.0366(9) Uani 1 1 d . . . . .
H1 H 0.7385 0.9513 0.9069 0.044 Uiso 1 1 calc R . . . .
C2 C 0.8128(2) 0.9393(7) 0.9860(3) 0.0461(11) Uani 1 1 d . . . . .
H2 H 0.8021 0.9811 1.0377 0.055 Uiso 1 1 calc R . . . .
C3 C 0.8691(2) 0.8951(7) 0.9901(3) 0.0498(12) Uani 1 1 d . . . . .
H3 H 0.8942 0.9012 1.0451 0.060 Uiso 1 1 calc R . . . .
C4 C 0.88585(17) 0.8448(6) 0.9148(3) 0.0406(10) Uani 1 1 d . . . . .
H4 H 0.9228 0.8202 0.9171 0.049 Uiso 1 1 calc R . . . .
C5 C 0.84705(15) 0.8292(6) 0.8320(2) 0.0299(8) Uani 1 1 d . . . . .
C6 C 0.84811(16) 0.7916(6) 0.7436(3) 0.0307(8) Uani 1 1 d . . . . .
C7 C 0.76285(15) 0.8338(6) 0.7443(2) 0.0283(7) Uani 1 1 d . . . . .
C8 C 0.70307(15) 0.8325(6) 0.7135(2) 0.0281(7) Uani 1 1 d . . . . .
C9 C 0.68041(17) 0.8781(6) 0.6236(2) 0.0379(9) Uani 1 1 d . . . . .
H9 H 0.7034 0.9195 0.5865 0.045 Uiso 1 1 calc R . . . .
C10 C 0.62503(17) 0.8631(7) 0.5890(3) 0.0408(10) Uani 1 1 d . . . . .
H10 H 0.6106 0.8939 0.5290 0.049 Uiso 1 1 calc R . . . .
C11 C 0.59041(17) 0.8013(6) 0.6442(3) 0.0380(9) Uani 1 1 d . . . . .
C12 C 0.6117(2) 0.7574(6) 0.7337(3) 0.0391(10) Uani 1 1 d . . . . .
H12 H 0.5886 0.7184 0.7709 0.047 Uiso 1 1 calc R . . . .
C13 C 0.6680(2) 0.7718(6) 0.7676(3) 0.0360(10) Uani 1 1 d . . . . .
H13 H 0.6823 0.7404 0.8275 0.043 Uiso 1 1 calc R . . . .
C14 C 0.5304(2) 0.7795(8) 0.6067(4) 0.0572(14) Uani 1 1 d 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
I1 C6 2.069(4) . ?
F1 C14 1.337(8) . ?
F1A C14 1.315(14) . ?
F2 C14 1.334(9) . ?
F2A C14 1.285(14) . ?
F3 C14 1.312(8) . ?
F3A C14 1.356(14) . ?
N1 C1 1.387(5) . ?
N1 C5 1.403(5) . ?
N1 C7 1.376(4) . ?
N2 C6 1.356(5) . ?
N2 C7 1.333(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.342(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.425(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.344(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.416(5) . ?
C5 C6 1.369(6) . ?
C7 C8 1.462(5) . ?
C8 C9 1.399(5) . ?
C8 C13 1.388(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.372(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.394(7) . ?
C11 C12 1.383(7) . ?
C11 C14 1.490(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.390(7) . ?
C13 H13 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
C1 N1 C5 120.8(3) . . ?
C7 N1 C1 132.0(3) . . ?
C7 N1 C5 106.8(3) . . ?
C7 N2 C6 105.8(3) . . ?
N1 C1 H1 120.4 . . ?
C2 C1 N1 119.2(4) . . ?
C2 C1 H1 120.4 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.2(4) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(4) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 118.6(4) . . ?
C6 C5 N1 104.6(3) . . ?
C6 C5 C4 136.9(4) . . ?
N2 C6 I1 122.3(3) . . ?
N2 C6 C5 112.0(3) . . ?
C5 C6 I1 125.7(3) . . ?
N1 C7 C8 126.2(3) . . ?
N2 C7 N1 110.9(3) . . ?
N2 C7 C8 122.7(3) . . ?
C9 C8 C7 118.9(3) . . ?
C13 C8 C7 122.6(3) . . ?
C13 C8 C9 118.3(4) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.3(4) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(4) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C14 120.1(4) . . ?
C12 C11 C10 120.2(4) . . ?
C12 C11 C14 119.7(5) . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.5(4) . . ?
C13 C12 H12 120.2 . . ?
C8 C13 C12 121.1(4) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
F1 C14 C11 113.1(5) . . ?
F1A C14 F3A 96.1(13) . . ?
F1A C14 C11 113.8(10) . . ?
F2 C14 F1 102.5(6) . . ?
F2 C14 C11 111.5(7) . . ?
F2A C14 F1A 115.2(17) . . ?
F2A C14 F3A 103.3(19) . . ?
F2A C14 C11 118(2) . . ?
F3 C14 F1 108.6(7) . . ?
F3 C14 F2 104.6(7) . . ?
F3 C14 C11 115.3(6) . . ?
F3A C14 C11 106.1(14) . . ?

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 C1 C2 C3 0.1(7) . . . . ?
N1 C5 C6 I1 178.8(3) . . . . ?
N1 C5 C6 N2 -0.6(5) . . . . ?
N1 C7 C8 C9 154.6(4) . . . . ?
N1 C7 C8 C13 -31.4(7) . . . . ?
N2 C7 C8 C9 -31.3(6) . . . . ?
N2 C7 C8 C13 142.8(4) . . . . ?
C1 N1 C5 C4 7.0(6) . . . . ?
C1 N1 C5 C6 -172.5(4) . . . . ?
C1 N1 C7 N2 171.3(4) . . . . ?
C1 N1 C7 C8 -13.9(7) . . . . ?
C1 C2 C3 C4 3.9(8) . . . . ?
C2 C3 C4 C5 -2.3(7) . . . . ?
C3 C4 C5 N1 -2.9(7) . . . . ?
C3 C4 C5 C6 176.4(5) . . . . ?
C4 C5 C6 I1 -0.5(8) . . . . ?
C4 C5 C6 N2 -179.9(5) . . . . ?
C5 N1 C1 C2 -5.5(6) . . . . ?
C5 N1 C7 N2 -1.4(5) . . . . ?
C5 N1 C7 C8 173.3(4) . . . . ?
C6 N2 C7 N1 1.0(5) . . . . ?
C6 N2 C7 C8 -173.9(4) . . . . ?
C7 N1 C1 C2 -177.4(4) . . . . ?
C7 N1 C5 C4 -179.3(4) . . . . ?
C7 N1 C5 C6 1.2(4) . . . . ?
C7 N2 C6 I1 -179.7(3) . . . . ?
C7 N2 C6 C5 -0.2(5) . . . . ?
C7 C8 C9 C10 174.0(4) . . . . ?
C7 C8 C13 C12 -174.3(4) . . . . ?
C8 C9 C10 C11 0.1(7) . . . . ?
C9 C8 C13 C12 -0.3(6) . . . . ?
C9 C10 C11 C12 0.7(7) . . . . ?
C9 C10 C11 C14 -178.3(5) . . . . ?
C10 C11 C12 C13 -1.3(7) . . . . ?
C10 C11 C14 F1 141.2(7) . . . . ?
C10 C11 C14 F1A -171.5(14) . . . . ?
C10 C11 C14 F2 26.2(9) . . . . ?
C10 C11 C14 F2A 48(2) . . . . ?
C10 C11 C14 F3 -92.9(8) . . . . ?
C10 C11 C14 F3A -67.1(16) . . . . ?
C11 C12 C13 C8 1.0(7) . . . . ?
C12 C11 C14 F1 -37.8(8) . . . . ?
C12 C11 C14 F1A 9.5(14) . . . . ?
C12 C11 C14 F2 -152.8(7) . . . . ?
C12 C11 C14 F2A -131(2) . . . . ?
C12 C11 C14 F3 88.0(8) . . . . ?
C12 C11 C14 F3A 113.9(15) . . . . ?
C13 C8 C9 C10 -0.3(7) . . . . ?
C14 C11 C12 C13 177.8(4) . . . . ?

_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 1.660
_oxdiff_exptl_absorpt_empirical_full_min 0.669
####################################################################### 
# 
# 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_202209166
_database_code_depnum_ccdc_archive 'CCDC 2217577'
loop_
_audit_author_name
_audit_author_address
'Qingjie Liu'
;Zhengzhou University
China
;
_audit_update_record             
;
2022-11-04 deposited with the CCDC.	2024-08-26 downloaded from the CCDC.
;
_audit_creation_date             2022-09-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 N2'
_chemical_formula_sum            'C17 H12 N2'
_chemical_formula_weight         244.29
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N2
_chemical_oxdiff_usercomment     r
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.4481(3)
_cell_length_b                   12.5608(7)
_cell_length_c                   13.0832(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1223.99(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1705
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9890
_cell_measurement_theta_min      5.9440
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.897
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90567
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6812
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.988
_diffrn_reflns_theta_min         4.881
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -93.00 -67.00   1.00    4.50    --  -33.50 -19.00 120.00   26
  2  ω    -55.00  -3.00   1.00    4.50    --  -33.50 -19.00 120.00   52
  3  ω     -5.00  29.00   1.00    4.50    --  -33.50  57.00  90.00   34
  4  ω     76.00 107.00   1.00    4.50    --   36.47 178.00  90.00   31
  5  ω     -3.00  41.00   1.00    4.50    --   36.47 -99.00  30.00   44
  6  ω     47.00 103.00   1.00   13.50    --  108.00 -94.00 -30.00   56
  7  ω     42.00  68.00   1.00   13.50    --  108.00 -61.00  30.00   26
  8  ω     40.00  86.00   1.00   13.50    --  108.00 -94.00  90.00   46
  9  ω     95.00 177.00   1.00   14.00    --  108.00  45.00 -60.00   82
 10  ω     97.00 176.00   1.00   14.00    --  108.00  61.00-180.00   79
 11  ω     51.00 106.00   1.00   14.00    --  108.00-111.00-150.00   55
 12  ω     64.00 105.00   1.00    4.50    --   36.47  57.00-180.00   41
 13  ω     27.00  60.00   1.00    4.50    --   36.47 -99.00  90.00   33
 14  ω     24.00  78.00   1.00    4.50    --   36.47  57.00 -90.00   54
 15  ω     98.00 124.00   1.00   14.00    --  108.00 -45.00 -90.00   26
 16  ω     47.00  91.00   1.00   14.00    --  108.00 -45.00 -90.00   44
 17  ω     91.00 133.00   1.00   14.00    --  108.00  61.00 120.00   42
 18  ω     56.00  95.00   1.00   14.00    --  108.00 -30.00-150.00   39
 19  ω     65.00  91.00   1.00    4.50    --   36.47 178.00  30.00   26
 20  ω     52.00  77.00   1.00    4.50    --   36.47 -99.00   0.00   25
 21  ω      9.00  35.00   1.00    4.50    --   36.47 -99.00   0.00   26
 22  ω     94.00 120.00   1.00   14.00    --  108.00  45.00 120.00   26
 23  ω    127.00 177.00   1.00   14.00    --  108.00  45.00  30.00   50
 24  ω    141.00 167.00   1.00   14.00    --  108.00  61.00  90.00   26
 25  ω     45.00  72.00   1.00   14.00    --  108.00 -61.00-180.00   27
 26  ω     89.00 128.00   1.00   14.00    --  108.00 -61.00 -90.00   39
 27  ω    143.00 178.00   1.00   14.00    --  108.00  45.00 120.00   35
 28  ω    146.00 176.00   1.00   14.00    --  108.00 111.00  60.00   30
 29  ω    101.00 127.00   1.00   14.00    --  108.00 -45.00 -30.00   26
 30  ω     88.00 114.00   1.00   14.00    --  108.00  61.00 -90.00   26
 31  ω    153.00 178.00   1.00   14.00    --  108.00  45.00 -90.00   25
 32  ω     94.00 120.00   1.00   14.00    --  108.00  61.00 150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0567865000
_diffrn_orient_matrix_UB_12      -0.0277558000
_diffrn_orient_matrix_UB_13      -0.1100831000
_diffrn_orient_matrix_UB_21      0.0944749000
_diffrn_orient_matrix_UB_22      -0.1086400000
_diffrn_orient_matrix_UB_23      0.0094287000
_diffrn_orient_matrix_UB_31      -0.1749546000
_diffrn_orient_matrix_UB_32      -0.0496919000
_diffrn_orient_matrix_UB_33      0.0408152000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                1975
_reflns_number_total             2344
_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 1.171.40.53 (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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 697 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(6)
_refine_ls_extinction_coef       0.0015(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.059
_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)+(0.0455P)²+0.0136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1043
_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:
 C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C9(H9), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
N1 N 0.7793(3) 0.53377(18) 0.33137(16) 0.0465(5) Uani 1 1 d . . . . .
N2 N 0.8616(4) 0.4502(2) 0.18968(18) 0.0601(6) Uani 1 1 d . . . . .
C1 C 0.7046(4) 0.5628(2) 0.4238(2) 0.0534(6) Uani 1 1 d . . . . .
H1 H 0.6459 0.5124 0.4637 0.064 Uiso 1 1 calc R . . . .
C2 C 0.7169(5) 0.6643(2) 0.4560(2) 0.0625(8) Uani 1 1 d . . . . .
H2 H 0.6672 0.6837 0.5185 0.075 Uiso 1 1 calc R . . . .
C3 C 0.8053(5) 0.7421(3) 0.3952(3) 0.0635(8) Uani 1 1 d . . . . .
H3 H 0.8158 0.8116 0.4190 0.076 Uiso 1 1 calc R . . . .
C4 C 0.8740(4) 0.7157(2) 0.3034(3) 0.0591(7) Uani 1 1 d . . . . .
H4 H 0.9303 0.7670 0.2635 0.071 Uiso 1 1 calc R . . . .
C5 C 0.8601(4) 0.6098(2) 0.2681(2) 0.0520(6) Uani 1 1 d . . . . .
C6 C 0.9081(4) 0.5544(3) 0.1817(2) 0.0601(7) Uani 1 1 d . . . . .
H6 H 0.9649 0.5843 0.1253 0.072 Uiso 1 1 calc R . . . .
C7 C 0.7850(4) 0.4380(2) 0.2802(2) 0.0485(6) Uani 1 1 d . . . . .
C8 C 0.7290(3) 0.3349(2) 0.3217(2) 0.0475(6) Uani 1 1 d . . . . .
C9 C 0.6495(4) 0.2593(2) 0.2545(2) 0.0558(7) Uani 1 1 d . . . . .
H9 H 0.6266 0.2779 0.1870 0.067 Uiso 1 1 calc R . . . .
C10 C 0.6068(4) 0.1602(3) 0.2881(2) 0.0599(8) Uani 1 1 d . . . . .
H10 H 0.5536 0.1123 0.2431 0.072 Uiso 1 1 calc R . . . .
C11 C 0.6416(4) 0.1282(2) 0.3897(2) 0.0516(7) Uani 1 1 d . . . . .
C12 C 0.7216(4) 0.2025(2) 0.4579(2) 0.0468(6) Uani 1 1 d . . . . .
C13 C 0.7636(3) 0.3057(2) 0.4210(2) 0.0475(6) Uani 1 1 d . . . . .
H13 H 0.8160 0.3548 0.4650 0.057 Uiso 1 1 calc R . . . .
C14 C 0.6034(4) 0.0247(3) 0.4268(3) 0.0654(9) Uani 1 1 d . . . . .
H14 H 0.5497 -0.0247 0.3836 0.078 Uiso 1 1 calc R . . . .
C15 C 0.6437(5) -0.0036(2) 0.5239(3) 0.0685(9) Uani 1 1 d . . . . .
H15 H 0.6194 -0.0725 0.5460 0.082 Uiso 1 1 calc R . . . .
C16 C 0.7220(4) 0.0700(3) 0.5919(3) 0.0658(8) Uani 1 1 d . . . . .
H16 H 0.7474 0.0501 0.6589 0.079 Uiso 1 1 calc R . . . .
C17 C 0.7604(4) 0.1710(2) 0.5591(2) 0.0558(7) Uani 1 1 d . . . . .
H17 H 0.8127 0.2193 0.6040 0.067 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.380(4) . ?
N1 C5 1.400(4) . ?
N1 C7 1.377(3) . ?
N2 C6 1.357(4) . ?
N2 C7 1.324(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.346(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.422(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.347(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.411(4) . ?
C5 C6 1.375(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.464(4) . ?
C8 C9 1.423(4) . ?
C8 C13 1.374(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.358(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.413(5) . ?
C11 C12 1.422(4) . ?
C11 C14 1.416(4) . ?
C12 C13 1.418(4) . ?
C12 C17 1.412(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.353(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.410(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.370(4) . ?
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
C1 N1 C5 120.7(3) . . ?
C7 N1 C1 132.0(2) . . ?
C7 N1 C5 107.2(2) . . ?
C7 N2 C6 106.9(3) . . ?
N1 C1 H1 120.1 . . ?
C2 C1 N1 119.8(3) . . ?
C2 C1 H1 120.1 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 118.7(3) . . ?
C6 C5 N1 104.6(3) . . ?
C6 C5 C4 136.7(3) . . ?
N2 C6 C5 111.0(3) . . ?
N2 C6 H6 124.5 . . ?
C5 C6 H6 124.5 . . ?
N1 C7 C8 125.7(2) . . ?
N2 C7 N1 110.2(2) . . ?
N2 C7 C8 123.9(3) . . ?
C9 C8 C7 118.7(3) . . ?
C13 C8 C7 122.2(2) . . ?
C13 C8 C9 118.9(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.4(3) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C12 118.7(3) . . ?
C10 C11 C14 123.1(3) . . ?
C14 C11 C12 118.1(3) . . ?
C13 C12 C11 118.6(3) . . ?
C17 C12 C11 119.3(3) . . ?
C17 C12 C13 122.1(3) . . ?
C8 C13 C12 121.7(2) . . ?
C8 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C11 C14 H14 119.4 . . ?
C15 C14 C11 121.3(3) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.8(3) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.7(3) . . ?
C16 C17 H17 119.6 . . ?

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 C1 C2 C3 0.4(5) . . . . ?
N1 C5 C6 N2 -0.2(3) . . . . ?
N1 C7 C8 C9 145.9(3) . . . . ?
N1 C7 C8 C13 -39.5(4) . . . . ?
N2 C7 C8 C9 -39.3(4) . . . . ?
N2 C7 C8 C13 135.3(3) . . . . ?
C1 N1 C5 C4 3.9(4) . . . . ?
C1 N1 C5 C6 -176.3(3) . . . . ?
C1 N1 C7 N2 175.6(3) . . . . ?
C1 N1 C7 C8 -9.0(5) . . . . ?
C1 C2 C3 C4 1.7(5) . . . . ?
C2 C3 C4 C5 -0.9(5) . . . . ?
C3 C4 C5 N1 -1.9(4) . . . . ?
C3 C4 C5 C6 178.5(4) . . . . ?
C4 C5 C6 N2 179.5(3) . . . . ?
C5 N1 C1 C2 -3.2(4) . . . . ?
C5 N1 C7 N2 -0.8(3) . . . . ?
C5 N1 C7 C8 174.6(3) . . . . ?
C6 N2 C7 N1 0.7(3) . . . . ?
C6 N2 C7 C8 -174.8(3) . . . . ?
C7 N1 C1 C2 -179.2(3) . . . . ?
C7 N1 C5 C4 -179.2(3) . . . . ?
C7 N1 C5 C6 0.6(3) . . . . ?
C7 N2 C6 C5 -0.3(4) . . . . ?
C7 C8 C9 C10 175.4(3) . . . . ?
C7 C8 C13 C12 -174.8(2) . . . . ?
C8 C9 C10 C11 -0.8(5) . . . . ?
C9 C8 C13 C12 -0.3(4) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
C9 C10 C11 C14 -178.3(3) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C10 C11 C12 C17 -178.7(3) . . . . ?
C10 C11 C14 C15 178.0(3) . . . . ?
C11 C12 C13 C8 0.0(4) . . . . ?
C11 C12 C17 C16 0.0(4) . . . . ?
C11 C14 C15 C16 1.3(5) . . . . ?
C12 C11 C14 C15 -0.9(4) . . . . ?
C13 C8 C9 C10 0.7(4) . . . . ?
C13 C12 C17 C16 -178.5(3) . . . . ?
C14 C11 C12 C13 178.8(2) . . . . ?
C14 C11 C12 C17 0.2(4) . . . . ?
C14 C15 C16 C17 -1.0(5) . . . . ?
C15 C16 C17 C12 0.4(5) . . . . ?
C17 C12 C13 C8 178.5(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 1.202
_oxdiff_exptl_absorpt_empirical_full_min 0.918
####################################################################### 
# 
# 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_202210190
_database_code_depnum_ccdc_archive 'CCDC 2235837'
loop_
_audit_author_name
_audit_author_address
'Qingjie Liu'
;Zhengzhou University
China
;
_audit_update_record             
;
2023-01-12 deposited with the CCDC.	2024-08-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 N2'
_chemical_formula_weight         208.26

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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x, z+1/4'
'-x, -y, z+1/2'
'y, -x, z+3/4'

_cell_length_a                   8.8835(11)
_cell_length_b                   8.8835(11)
_cell_length_c                   14.400(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1136.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.568
_shelx_estimated_absorpt_T_min   0.885
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7582
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.978
_diffrn_reflns_theta_max         66.947
_diffrn_reflns_theta_full        66.947
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_point_group_measured_fraction_full 0.928
_reflns_number_total             1882
_reflns_number_gt                1586
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_max     0.851
_reflns_Friedel_fraction_full    0.851

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0641P)²+0.0292P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0158(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 590 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1882
_refine_ls_number_parameters     151
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
N1 N 0.3640(3) 0.6960(3) 0.60684(18) 0.0435(7) Uani 1 1 d . . . . .
H1 H 0.417(5) 0.718(4) 0.560(3) 0.056(11) Uiso 1 1 d . . . . .
N2 N 0.2282(3) 0.5455(3) 0.6988(2) 0.0473(7) Uani 1 1 d . . . . .
C1 C 0.3015(5) 0.9437(4) 0.6839(3) 0.0590(10) Uani 1 1 d . . . . .
H1A H 0.3576 1.0062 0.6454 0.071 Uiso 1 1 calc R U . . .
C2 C 0.2181(5) 1.0002(5) 0.7568(3) 0.0684(12) Uani 1 1 d . . . . .
H2 H 0.2173 1.1035 0.7672 0.082 Uiso 1 1 calc R U . . .
C3 C 0.1350(5) 0.9071(5) 0.8154(3) 0.0671(11) Uani 1 1 d . . . . .
H3 H 0.0816 0.9493 0.8645 0.081 Uiso 1 1 calc R U . . .
C4 C 0.1306(4) 0.7544(5) 0.8020(3) 0.0575(9) Uani 1 1 d . . . . .
H4 H 0.0742 0.6927 0.8409 0.069 Uiso 1 1 calc R U . . .
C5 C 0.2128(4) 0.6945(4) 0.7285(2) 0.0442(7) Uani 1 1 d . . . . .
C6 C 0.2973(4) 0.7894(4) 0.6711(2) 0.0430(8) Uani 1 1 d . . . . .
C7 C 0.3188(4) 0.5521(4) 0.6264(2) 0.0427(7) Uani 1 1 d . . . . .
C8 C 0.3772(4) 0.4227(4) 0.5728(2) 0.0484(8) Uani 1 1 d . . . . .
C9 C 0.5310(5) 0.4148(5) 0.5575(3) 0.0619(10) Uani 1 1 d . . . . .
H9 H 0.5930 0.4912 0.5795 0.074 Uiso 1 1 calc R U . . .
C10 C 0.5942(7) 0.2940(6) 0.5095(3) 0.0817(16) Uani 1 1 d . . . . .
H10 H 0.6977 0.2884 0.5008 0.098 Uiso 1 1 calc R U . . .
C11 C 0.5012(7) 0.1830(5) 0.4751(3) 0.0823(15) Uani 1 1 d . . . . .
H11 H 0.5418 0.1021 0.4427 0.099 Uiso 1 1 calc R U . . .
C12 C 0.3482(7) 0.1921(5) 0.4889(3) 0.0763(14) Uani 1 1 d . . . . .
H12 H 0.2869 0.1167 0.4648 0.092 Uiso 1 1 calc R U . . .
C13 C 0.2820(5) 0.3106(4) 0.5377(3) 0.0593(10) Uani 1 1 d . . . . .
C14 C 0.1143(6) 0.3149(6) 0.5491(4) 0.0865(15) Uani 1 1 d . . . . .
H14A H 0.0888 0.2910 0.6122 0.130 Uiso 1 1 calc R U . . .
H14B H 0.0689 0.2426 0.5082 0.130 Uiso 1 1 calc R U . . .
H14C H 0.0780 0.4137 0.5342 0.130 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
N1 C7 1.369(4) . ?
N1 C6 1.376(4) . ?
N1 H1 0.84(4) . ?
N2 C7 1.319(4) . ?
N2 C5 1.398(4) . ?
C1 C2 1.379(6) . ?
C1 C6 1.384(5) . ?
C1 H1A 0.9300 . ?
C2 C3 1.393(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.392(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(5) . ?
C7 C8 1.479(4) . ?
C8 C9 1.386(5) . ?
C8 C13 1.401(6) . ?
C9 C10 1.394(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.396(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.498(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C7 N1 C6 107.4(3) . . ?
C7 N1 H1 123(3) . . ?
C6 N1 H1 129(3) . . ?
C7 N2 C5 105.0(3) . . ?
C2 C1 C6 116.6(4) . . ?
C2 C1 H1A 121.7 . . ?
C6 C1 H1A 121.7 . . ?
C1 C2 C3 122.0(4) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 118.1(4) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C4 C5 N2 130.2(3) . . ?
C4 C5 C6 120.0(3) . . ?
N2 C5 C6 109.7(3) . . ?
N1 C6 C1 132.5(3) . . ?
N1 C6 C5 105.4(3) . . ?
C1 C6 C5 122.2(3) . . ?
N2 C7 N1 112.5(3) . . ?
N2 C7 C8 126.3(3) . . ?
N1 C7 C8 121.1(3) . . ?
C9 C8 C13 120.2(3) . . ?
C9 C8 C7 117.9(3) . . ?
C13 C8 C7 121.9(3) . . ?
C8 C9 C10 121.0(5) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 119.2(5) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 122.2(5) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 H12 118.9 . . ?
C12 C13 C8 117.6(4) . . ?
C12 C13 C14 119.6(4) . . ?
C8 C13 C14 122.9(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C6 C1 C2 C3 0.7(6) . . . . ?
C1 C2 C3 C4 -1.1(7) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C3 C4 C5 N2 -179.8(4) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C7 N2 C5 C4 -179.9(4) . . . . ?
C7 N2 C5 C6 0.0(4) . . . . ?
C7 N1 C6 C1 -179.1(4) . . . . ?
C7 N1 C6 C5 0.2(3) . . . . ?
C2 C1 C6 N1 179.5(4) . . . . ?
C2 C1 C6 C5 0.3(5) . . . . ?
C4 C5 C6 N1 179.8(3) . . . . ?
N2 C5 C6 N1 -0.1(4) . . . . ?
C4 C5 C6 C1 -0.8(5) . . . . ?
N2 C5 C6 C1 179.3(3) . . . . ?
C5 N2 C7 N1 0.2(4) . . . . ?
C5 N2 C7 C8 176.4(3) . . . . ?
C6 N1 C7 N2 -0.3(4) . . . . ?
C6 N1 C7 C8 -176.7(3) . . . . ?
N2 C7 C8 C9 -128.9(4) . . . . ?
N1 C7 C8 C9 47.0(4) . . . . ?
N2 C7 C8 C13 51.2(5) . . . . ?
N1 C7 C8 C13 -132.8(4) . . . . ?
C13 C8 C9 C10 -1.8(6) . . . . ?
C7 C8 C9 C10 178.4(4) . . . . ?
C8 C9 C10 C11 1.5(7) . . . . ?
C9 C10 C11 C12 -0.3(7) . . . . ?
C10 C11 C12 C13 -0.5(7) . . . . ?
C11 C12 C13 C8 0.3(6) . . . . ?
C11 C12 C13 C14 179.2(5) . . . . ?
C9 C8 C13 C12 0.9(5) . . . . ?
C7 C8 C13 C12 -179.3(3) . . . . ?
C9 C8 C13 C14 -178.0(4) . . . . ?
C7 C8 C13 C14 1.8(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N2 0.84(4) 2.03(4) 2.869(4) 180(5) 4_564

_refine_diff_density_max         0.126
_refine_diff_density_min         -0.119
_refine_diff_density_rms         0.027



####################################################################### 
# 
# 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_lqj-1
_database_code_depnum_ccdc_archive 'CCDC 2235130'
loop_
_audit_author_name
_audit_author_address
'Qingjie Liu'
;Zhengzhou University
China
;
_audit_update_record             
;
2023-01-07 deposited with the CCDC.	2024-08-26 downloaded from the CCDC.
;
_audit_creation_date             2023-01-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 N3'
_chemical_formula_sum            'C14 H9 N3'
_chemical_formula_weight         219.24
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.2378(10)
_cell_length_b                   11.8288(14)
_cell_length_c                   12.7296(17)
_cell_angle_alpha                90
_cell_angle_beta                 92.175(5)
_cell_angle_gamma                90
_cell_volume                     1089.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9020
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      26.55
_cell_measurement_theta_min      3.19
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6879
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1310 before and 0.0603 after correction.
The Ratio of minimum to maximum transmission is 0.9226.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            27964
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.187
_diffrn_ambient_temperature      300.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1601
_reflns_number_total             1928
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.104
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1928
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.107
_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)+(0.0396P)²+0.2428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0935
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C13(H13), C12(H12), C1(H1A), C10(H10), C9(H9), C5(H5), C6(H6)
;
_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
N1 N 0.26768(16) 0.51607(10) 0.57815(9) 0.0383(3) Uani 1 1 d . . . . .
H1 H 0.215309 0.466585 0.537472 0.046 Uiso 1 1 calc R U . . .
N2 N 0.41799(17) 0.67347(10) 0.62801(9) 0.0411(3) Uani 1 1 d . . . . .
N3 N 0.3873(2) 0.81597(12) 0.04624(11) 0.0557(4) Uani 1 1 d . . . . .
C2 C 0.28673(19) 0.51055(11) 0.68606(11) 0.0364(3) Uani 1 1 d . . . . .
C3 C 0.38125(19) 0.60940(12) 0.71581(11) 0.0373(3) Uani 1 1 d . . . . .
C7 C 0.34759(18) 0.61494(11) 0.54779(11) 0.0364(3) Uani 1 1 d . . . . .
C8 C 0.35102(18) 0.65357(12) 0.43813(11) 0.0368(3) Uani 1 1 d . . . . .
C11 C 0.3640(2) 0.73426(12) 0.23345(11) 0.0393(3) Uani 1 1 d . . . . .
C4 C 0.4216(2) 0.63093(13) 0.82223(11) 0.0455(4) Uani 1 1 d . . . . .
H4 H 0.485567 0.695686 0.843505 0.055 Uiso 1 1 calc R U . . .
C14 C 0.3748(2) 0.77771(13) 0.12807(12) 0.0432(4) Uani 1 1 d . . . . .
C13 C 0.4429(2) 0.75398(13) 0.41678(11) 0.0439(4) Uani 1 1 d . . . . .
H13 H 0.500932 0.794092 0.471503 0.053 Uiso 1 1 calc R U . . .
C12 C 0.4486(2) 0.79443(13) 0.31573(12) 0.0444(4) Uani 1 1 d . . . . .
H12 H 0.509065 0.862015 0.302456 0.053 Uiso 1 1 calc R U . . .
C1 C 0.2310(2) 0.43099(12) 0.75892(12) 0.0450(4) Uani 1 1 d . . . . .
H1A H 0.169932 0.365047 0.738166 0.054 Uiso 1 1 calc R U . . .
C10 C 0.2727(2) 0.63397(13) 0.25343(12) 0.0464(4) Uani 1 1 d . . . . .
H10 H 0.216310 0.593428 0.198431 0.056 Uiso 1 1 calc R U . . .
C9 C 0.2658(2) 0.59448(13) 0.35520(11) 0.0452(4) Uani 1 1 d . . . . .
H9 H 0.203373 0.527571 0.368496 0.054 Uiso 1 1 calc R U . . .
C5 C 0.3637(2) 0.55342(13) 0.89441(12) 0.0497(4) Uani 1 1 d . . . . .
H5 H 0.386992 0.566961 0.965658 0.060 Uiso 1 1 calc R U . . .
C6 C 0.2708(2) 0.45469(14) 0.86317(12) 0.0507(4) Uani 1 1 d . . . . .
H6 H 0.234834 0.403728 0.914147 0.061 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
N1 H1 0.8600 . ?
N1 C2 1.3769(18) . ?
N1 C7 1.3670(18) . ?
N2 C3 1.3845(18) . ?
N2 C7 1.3199(18) . ?
N3 C14 1.1424(18) . ?
C2 C3 1.400(2) . ?
C2 C1 1.392(2) . ?
C3 C4 1.398(2) . ?
C7 C8 1.4699(19) . ?
C8 C13 1.393(2) . ?
C8 C9 1.391(2) . ?
C11 C14 1.441(2) . ?
C11 C12 1.389(2) . ?
C11 C10 1.386(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(2) . ?
C13 H13 0.9300 . ?
C13 C12 1.375(2) . ?
C12 H12 0.9300 . ?
C1 H1A 0.9300 . ?
C1 C6 1.376(2) . ?
C10 H10 0.9300 . ?
C10 C9 1.380(2) . ?
C9 H9 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.398(2) . ?
C6 H6 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
C2 N1 H1 126.4 . . ?
C7 N1 H1 126.4 . . ?
C7 N1 C2 107.17(11) . . ?
C7 N2 C3 104.90(12) . . ?
N1 C2 C3 105.05(12) . . ?
N1 C2 C1 132.56(13) . . ?
C1 C2 C3 122.39(13) . . ?
N2 C3 C2 110.23(12) . . ?
N2 C3 C4 130.01(13) . . ?
C4 C3 C2 119.75(13) . . ?
N1 C7 C8 123.86(12) . . ?
N2 C7 N1 112.64(12) . . ?
N2 C7 C8 123.48(13) . . ?
C13 C8 C7 118.41(13) . . ?
C9 C8 C7 122.79(13) . . ?
C9 C8 C13 118.80(13) . . ?
C12 C11 C14 118.74(13) . . ?
C10 C11 C14 121.28(14) . . ?
C10 C11 C12 119.98(13) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 117.93(14) . . ?
C5 C4 H4 121.0 . . ?
N3 C14 C11 177.15(17) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.73(14) . . ?
C12 C13 H13 119.6 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.94(14) . . ?
C13 C12 H12 120.0 . . ?
C2 C1 H1A 121.6 . . ?
C6 C1 C2 116.72(14) . . ?
C6 C1 H1A 121.6 . . ?
C11 C10 H10 120.1 . . ?
C9 C10 C11 119.77(14) . . ?
C9 C10 H10 120.1 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.78(14) . . ?
C10 C9 H9 119.6 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.50(15) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 121.69(14) . . ?
C1 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?

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 C2 C3 N2 0.21(15) . . . . ?
N1 C2 C3 C4 179.27(13) . . . . ?
N1 C2 C1 C6 -178.55(14) . . . . ?
N1 C7 C8 C13 -177.64(13) . . . . ?
N1 C7 C8 C9 2.7(2) . . . . ?
N2 C3 C4 C5 178.07(14) . . . . ?
N2 C7 C8 C13 3.9(2) . . . . ?
N2 C7 C8 C9 -175.71(14) . . . . ?
C2 N1 C7 N2 0.41(16) . . . . ?
C2 N1 C7 C8 -178.16(12) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
C3 N2 C7 N1 -0.27(16) . . . . ?
C3 N2 C7 C8 178.31(12) . . . . ?
C3 C2 C1 C6 1.0(2) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
C7 N1 C2 C3 -0.36(14) . . . . ?
C7 N1 C2 C1 179.24(15) . . . . ?
C7 N2 C3 C2 0.03(15) . . . . ?
C7 N2 C3 C4 -178.91(15) . . . . ?
C7 C8 C13 C12 -179.35(13) . . . . ?
C7 C8 C9 C10 -179.96(13) . . . . ?
C8 C13 C12 C11 -0.7(2) . . . . ?
C11 C10 C9 C8 -0.7(2) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C14 C11 C12 C13 -178.97(14) . . . . ?
C14 C11 C10 C9 179.65(14) . . . . ?
C13 C8 C9 C10 0.4(2) . . . . ?
C12 C11 C10 C9 0.2(2) . . . . ?
C1 C2 C3 N2 -179.44(13) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C10 C11 C12 C13 0.5(2) . . . . ?
C9 C8 C13 C12 0.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
