# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

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

data_ed-178-lc
_database_code_depnum_ccdc_archive 'CCDC 2259714'
loop_
_audit_author_name
_audit_author_address
'Xinsong Lin'
;Florida State University
United States of America
;
_audit_update_record             
;
2023-04-28 deposited with the CCDC.	2023-10-11 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V118 by Daniel Kratzert, Freiburg 2023,
https://dkratzert.de/finalcif.html
;
_audit_creation_date             2023-04-28
_chemical_oxdiff_formula         C21H16N4O
_chemical_oxdiff_usercomment     '100 K'
_diffrn_orient_matrix_UB_11      -0.0908478000
_diffrn_orient_matrix_UB_12      -0.1057854000
_diffrn_orient_matrix_UB_13      -0.0251646000
_diffrn_orient_matrix_UB_21      0.1376405000
_diffrn_orient_matrix_UB_22      -0.1288100000
_diffrn_orient_matrix_UB_23      0.0537345000
_diffrn_orient_matrix_UB_31      -0.1224878000
_diffrn_orient_matrix_UB_32      -0.0277919000
_diffrn_orient_matrix_UB_33      0.1265601000
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_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:
 C10(H10A,H10B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13), C14(H14), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.755
_oxdiff_exptl_absorpt_empirical_full_min 0.808
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C21 H16 N4 O'
_chemical_formula_moiety         'C21 H16 N4 O'
_chemical_formula_weight         340.38
_chemical_melting_point          ?
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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'
'-x, -y, -z'

_cell_length_a                   7.8488(2)
_cell_length_b                   9.8954(3)
_cell_length_c                   12.1031(4)
_cell_angle_alpha                68.423(3)
_cell_angle_beta                 74.665(3)
_cell_angle_gamma                77.346(3)
_cell_volume                     835.21(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    99.9(6)
_cell_measurement_reflns_used    23752
_cell_measurement_theta_min      4.0140
_cell_measurement_theta_max      76.7720
_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_recrystallization_method 'by a slow evaporation method'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.195
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.018
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.988
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      99.9(6)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -121.00 -35.00   0.50    1.50    --  -47.84 -33.00-144.00  172
  2  ω     35.00 122.00   0.50    1.50    --   47.84  33.00  14.00  174
  3  ω    -26.00  56.00   0.50    1.50    --   47.84 -33.00-144.00  164
  4  ω   -160.00 -72.00   0.50    6.50    --  -86.25 -33.00-144.00  176
  5  ω     94.00 178.00   0.50    6.50    --  107.75  33.00  14.00  168
  6  ω    -17.00   9.00   0.50    1.50    --   14.00  97.00 -87.43   52
  7  ω    -17.00  10.00   0.50    1.50    --   14.00  95.00 101.14   54
  8  ω      0.00  26.00   0.50    1.50    --   22.00  76.00 126.06   52
  9  ω      2.00  33.00   0.50    1.50    --   22.00  70.00   7.86   62
 10  ω     12.00  39.00   0.50    1.50    --   30.00  66.00 -72.80   54
 11  ω     12.00  39.00   0.50    1.50    --   30.00  66.00 -95.26   54
 12  ω    -42.00 -16.00   0.50    1.50    --  -34.00 -64.00-110.47   52
 13  ω    -44.00 -17.00   0.50    1.50    --  -34.00 -63.00  76.33   54
 14  ω     22.00  52.00   0.50    1.50    --   38.00  59.00  96.78   60
 15  ω     23.00  55.00   0.50    1.50    --   38.00  58.00-154.11   64
 16  ω     22.00  50.00   0.50    1.50    --   38.00  60.00  51.50   56
 17  ω    -52.00 -26.00   0.50    1.50    --  -42.00 -59.00  28.83   52
 18  ω    -65.00 -27.00   0.50    1.50    --  -42.00 -56.00 157.90   76
 19  ω     27.00  65.00   0.50    1.50    --   42.00  56.00 -32.79   76
 20  ω      1.00  28.00   0.50    1.50    --  -47.84  19.00-180.00   54
 21  ω      1.00  28.00   0.50    1.50    --  -47.84  19.00-150.00   54
 22  ω    -14.00  26.00   0.50    1.50    --  -47.84  33.00  14.00   80
 23  ω     34.00  94.00   0.50    1.50    --   47.84-125.00   0.00  120
 24  ω     34.00  94.00   0.50    1.50    --   47.84-125.00  90.00  120
 25  ω     34.00 120.00   0.50    1.50    --   47.84  55.00 172.00  172
 26  ω   -121.00 -35.00   0.50    1.50    --  -50.00 -56.00-156.99  172
 27  ω   -125.00 -39.00   0.50    1.50    --  -54.00 -55.00-134.36  172
 28  ω   -125.00 -39.00   0.50    1.50    --  -54.00 -55.00 -55.23  172
 29  ω   -130.00 -43.00   0.50    1.50    --  -58.00 -56.00 163.44  174
 30  ω     43.00 131.00   0.50    1.50    --   58.00  56.00 -22.04  176
 31  ω   -134.00 -48.00   0.50    1.50    --  -62.00 -50.00  73.27  172
 32  ω   -138.00 -52.00   0.50    1.50    --  -66.00 -52.00  12.57  172
 33  ω   -142.00 -55.00   0.50    1.50    --  -70.00 -55.00-114.32  174
 34  ω   -142.00 -56.00   0.50    1.50    --  -70.00 -52.00  31.65  172
 35  ω   -142.00 -56.00   0.50    1.50    --  -70.00 -54.00 149.23  172
 36  ω   -142.00 -56.00   0.50    1.50    --  -70.00 -54.00 -64.69  172
 37  ω   -142.00 -56.00   0.50    1.50    --  -70.00 -52.00  -5.29  172
 38  ω   -145.00 -59.00   0.50    1.50    --  -74.00 -56.00 117.75  172
 39  ω   -145.00 -59.00   0.50    1.50    --  -74.00 -55.00  71.25  172
 40  ω   -145.00 -60.00   0.50    1.50    --  -74.00 -51.00 -19.20  170
 41  ω   -150.00 -63.00   0.50    6.50    --  -78.00 -56.00 -39.43  174
 42  ω   -150.00 -63.00   0.50    6.50    --  -78.00 -56.00 -80.61  174
 43  ω   -150.00 -64.00   0.50    6.50    --  -78.00 -51.00  49.43  172
 44  ω   -150.00 -63.00   0.50    6.50    --  -78.00 -56.00-169.91  174
 45  ω   -150.00 -63.00   0.50    6.50    --  -78.00 -56.00-144.40  174
 46  ω   -153.00 -67.00   0.50    6.50    --  -82.00 -55.00 154.64  172
 47  ω   -159.00 -73.00   0.50    6.50    --  -86.25 -50.00-129.47  172
 48  ω   -159.00 -73.00   0.50    6.50    --  -86.25 -49.00-165.51  172
 49  ω   -159.00 -72.00   0.50    6.50    --  -86.25 -54.00 137.35  174
 50  ω   -159.00 -72.00   0.50    6.50    --  -86.25 -55.00 -90.87  174
 51  ω    -52.00 -13.00   0.50    6.50    --  -86.25  61.00-180.00   78
 52  ω   -159.00 -72.00   0.50    6.50    --  -86.25 -55.00  43.58  174
 53  ω     91.00 178.00   0.50    6.50    --  107.75  61.00-120.00  174
 54  ω     35.00 106.00   0.50    6.50    --  107.75 -94.00  60.00  142
 55  ω     91.00 178.00   0.50    6.50    --  107.75  61.00  60.00  174
 56  ω     35.00 106.00   0.50    6.50    --  107.75 -94.00  30.00  142
 57  ω     38.00 112.00   0.50    6.50    --  107.75-125.00-150.00  148
 58  ω     35.00 106.00   0.50    6.50    --  107.75 -94.00 -60.00  142
 59  ω     95.00 178.00   0.50    6.50    --  107.75  30.00-180.00  166
 60  ω     91.00 178.00   0.50    6.50    --  107.75  61.00 -60.00  174
 61  ω     91.00 178.00   0.50    6.50    --  107.75  61.00-150.00  174
 62  ω     35.00 131.00   0.50    6.50    --  107.75 -77.00 150.00  192
 63  ω     36.00  71.00   0.50    6.50    --  107.75 -45.00  90.00   70
 64  ω     36.00  71.00   0.50    6.50    --  107.75 -45.00 -60.00   70
 65  ω     95.00 178.00   0.50    6.50    --  107.75  45.00 -30.00  166
 66  ω     91.00 178.00   0.50    6.50    --  107.75  61.00 150.00  174
 67  ω     35.00  94.00   0.50    6.50    --  107.75 -61.00-150.00  118
 68  ω    101.00 178.00   0.50    6.50    --  107.75  77.00  30.00  154
 69  ω     35.00 106.00   0.50    6.50    --  107.75 -94.00   0.00  142
 70  ω     36.00  71.00   0.50    6.50    --  107.75 -45.00  30.00   70
 71  ω     95.00 178.00   0.50    6.50    --  107.75  45.00 120.00  166
 72  ω     91.00 178.00   0.50    6.50    --  107.75  61.00  30.00  174
 73  ω     35.00 106.00   0.50    6.50    --  107.75 -94.00  90.00  142
 74  ω     95.00 178.00   0.50    6.50    --  107.75  45.00 -60.00  166
 75  ω     35.00 106.00   0.50    6.50    --  107.75 -94.00-120.00  142
 76  ω     35.00 106.00   0.50    6.50    --  107.75 -94.00-180.00  142
 77  ω     91.00 178.00   0.50    6.50    --  107.75  61.00 120.00  174
 78  ω     91.00 178.00   0.50    6.50    --  107.75  61.00   0.00  174
 79  ω     36.00  71.00   0.50    6.50    --  107.75 -45.00  60.00   70
 80  ω     91.00 178.00   0.50    6.50    --  107.75  61.00  90.00  174
 81  ω     91.00 178.00   0.50    6.50    --  107.75  61.00 -30.00  174
 82  ω     35.00 106.00   0.50    6.50    --  107.75 -94.00-150.00  142
 83  ω     36.00  71.00   0.50    6.50    --  107.75 -45.00 -30.00   70
 84  ω     36.00  71.00   0.50    6.50    --  107.75 -45.00 150.00   70
 85  ω     91.00 178.00   0.50    6.50    --  107.75  61.00 -90.00  174
 86  ω     91.00 178.00   0.50    6.50    --  107.75  61.00-180.00  174
 87  ω     95.00 178.00   0.50    6.50    --  107.75  45.00  60.00  166
 88  ω     36.00  71.00   0.50    6.50    --  107.75 -45.00 -90.00   70
 89  ω     95.00 178.00   0.50    6.50    --  107.75  45.00   0.00  166
 90  ω     95.00 178.00   0.50    6.50    --  107.75  45.00  90.00  166
 91  ω     35.00 106.00   0.50    6.50    --  107.75 -94.00 120.00  142
 92  ω     35.00 106.00   0.50    6.50    --  107.75 -94.00 -30.00  142
 93  ω    101.00 178.00   0.50    6.50    --  107.75  77.00 150.00  154
 94  ω     95.00 178.00   0.50    6.50    --  107.75  45.00-150.00  166
 95  ω     35.00 106.00   0.50    6.50    --  107.75 -94.00 -90.00  142
 96  ω     36.00  71.00   0.50    6.50    --  107.75 -45.00-120.00   70
 97  ω     12.00  40.00   0.50    1.50    --   30.00  65.00-156.49   56
 98  ω   -119.00 -34.00   0.50    1.50    --  -47.84 -52.00 -59.04  170
 99  ω    -24.00 120.00   0.50    1.50    --   47.84   0.00 -60.00  288
100  ω     34.00 120.00   0.50    1.50    --   47.84  55.00 -67.14  172
101  ω    -24.00  -0.50   0.50    1.50    --   47.84   0.00 -30.00   47
;
_diffrn_reflns_number            38664
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_theta_min         4.011
_diffrn_reflns_theta_max         77.412
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3490
_reflns_number_gt                3229
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_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)+(0.0474P)²+0.2900P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3490
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0044(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0926
0 0 -1 0.0666
0 -1 0 0.0060
0 1 0 0.0120
-1 0 0 0.0733
1 0 0 0.0733
5 3 4 0.0526
-5 -3 -4 0.0406

loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0000 -0.0000 1.0000 -0.0252 0.0537 0.1266
-0.0000 0.0000 -1.0000 0.0252 -0.0537 -0.1266
-0.0000 -1.0000 -0.0000 0.1058 0.1288 0.0278
0.0000 1.0000 0.0000 -0.1058 -0.1288 -0.0278
-1.0000 -0.0000 -0.0000 0.0908 -0.1376 0.1225
1.0000 0.0000 0.0000 -0.0908 0.1376 -0.1225
5.0000 3.0000 4.0000 -0.8723 0.5167 -0.1896
-5.0000 -3.0000 -4.0000 0.8723 -0.5167 0.1896

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
O1 O 0.37484(12) 0.20094(9) 0.36428(8) 0.0296(2) Uani 1 1 d . . . . .
N1 N 0.16179(13) 0.67375(11) 0.36379(9) 0.0239(2) Uani 1 1 d . . . . .
C1 C 0.23447(15) 0.21453(13) 0.31149(11) 0.0231(2) Uani 1 1 d . . . . .
N2 N 0.29833(13) 0.69792(11) 0.09913(9) 0.0222(2) Uani 1 1 d . . . . .
C2 C 0.15051(17) 0.08782(13) 0.36166(11) 0.0258(3) Uani 1 1 d . . . . .
H2 H 0.1900 0.0095 0.4275 0.031 Uiso 1 1 calc R U . . .
N3 N 0.29913(13) 0.67244(11) -0.00329(9) 0.0252(2) Uani 1 1 d . . . . .
C3 C 0.01201(17) 0.07378(14) 0.31792(11) 0.0270(3) Uani 1 1 d . . . . .
H3 H -0.0418 -0.0137 0.3528 0.032 Uiso 1 1 calc R U . . .
N4 N 0.26362(13) 0.53764(11) 0.02883(9) 0.0243(2) Uani 1 1 d . . . . .
C4 C -0.04825(17) 0.18841(14) 0.22258(11) 0.0276(3) Uani 1 1 d . . . . .
H4 H -0.1431 0.1802 0.1913 0.033 Uiso 1 1 calc R U . . .
C5 C 0.03214(16) 0.31467(13) 0.17399(11) 0.0247(2) Uani 1 1 d . . . . .
H5 H -0.0111 0.3933 0.1099 0.030 Uiso 1 1 calc R U . . .
C6 C 0.17537(15) 0.33196(13) 0.21534(10) 0.0220(2) Uani 1 1 d . . . . .
C7 C 0.24268(15) 0.47548(13) 0.15218(10) 0.0213(2) Uani 1 1 d . . . . .
C8 C 0.26515(14) 0.57781(12) 0.19781(10) 0.0210(2) Uani 1 1 d . . . . .
C9 C 0.25750(15) 0.56409(12) 0.32396(10) 0.0211(2) Uani 1 1 d . . . . .
C10 C 0.46295(16) 0.32367(13) 0.34340(12) 0.0263(3) Uani 1 1 d . . . . .
H10A H 0.5026 0.3706 0.2549 0.032 Uiso 1 1 calc R U . . .
H10B H 0.5703 0.2878 0.3797 0.032 Uiso 1 1 calc R U . . .
C11 C 0.34488(15) 0.43674(13) 0.39611(11) 0.0227(2) Uani 1 1 d . . . . .
C12 C 0.32262(16) 0.41994(14) 0.51841(11) 0.0269(3) Uani 1 1 d . . . . .
H12 H 0.3786 0.3346 0.5711 0.032 Uiso 1 1 calc R U . . .
C13 C 0.21841(17) 0.52843(14) 0.56230(11) 0.0291(3) Uani 1 1 d . . . . .
H13 H 0.1979 0.5173 0.6459 0.035 Uiso 1 1 calc R U . . .
C14 C 0.14437(16) 0.65387(14) 0.48169(11) 0.0271(3) Uani 1 1 d . . . . .
H14 H 0.0775 0.7300 0.5118 0.033 Uiso 1 1 calc R U . . .
C15 C 0.33023(16) 0.84123(13) 0.09228(11) 0.0246(3) Uani 1 1 d . . . . .
H15A H 0.2295 0.8813 0.1457 0.030 Uiso 1 1 calc R U . . .
H15B H 0.3340 0.9092 0.0081 0.030 Uiso 1 1 calc R U . . .
C16 C 0.50199(15) 0.83446(12) 0.12935(10) 0.0214(2) Uani 1 1 d . . . . .
C17 C 0.50455(16) 0.91740(13) 0.19999(11) 0.0251(3) Uani 1 1 d . . . . .
H17 H 0.3977 0.9735 0.2269 0.030 Uiso 1 1 calc R U . . .
C18 C 0.66144(17) 0.91897(14) 0.23156(11) 0.0279(3) Uani 1 1 d . . . . .
H18 H 0.6617 0.9761 0.2797 0.033 Uiso 1 1 calc R U . . .
C19 C 0.81760(17) 0.83726(14) 0.19279(12) 0.0289(3) Uani 1 1 d . . . . .
H19 H 0.9253 0.8379 0.2143 0.035 Uiso 1 1 calc R U . . .
C20 C 0.81574(17) 0.75435(15) 0.12220(12) 0.0312(3) Uani 1 1 d . . . . .
H20 H 0.9228 0.6984 0.0953 0.037 Uiso 1 1 calc R U . . .
C21 C 0.65864(16) 0.75260(14) 0.09055(11) 0.0271(3) Uani 1 1 d . . . . .
H21 H 0.6585 0.6954 0.0424 0.033 Uiso 1 1 calc R U . . .


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
O1 C1 1.3727(14) . ?
O1 C10 1.4376(14) . ?
N1 C9 1.3455(15) . ?
N1 C14 1.3401(16) . ?
C1 C2 1.4020(17) . ?
C1 C6 1.4052(16) . ?
N2 N3 1.3510(13) . ?
N2 C8 1.3543(15) . ?
N2 C15 1.4624(14) . ?
C2 C3 1.3806(17) . ?
N3 N4 1.3161(14) . ?
C3 C4 1.3902(18) . ?
N4 C7 1.3687(15) . ?
C4 C5 1.3834(17) . ?
C5 C6 1.4100(16) . ?
C6 C7 1.4823(16) . ?
C7 C8 1.3793(15) . ?
C8 C9 1.4682(15) . ?
C9 C11 1.3963(16) . ?
C10 C11 1.5085(16) . ?
C11 C12 1.3942(16) . ?
C12 C13 1.3815(18) . ?
C13 C14 1.3869(18) . ?
C15 C16 1.5104(15) . ?
C16 C17 1.3919(16) . ?
C16 C21 1.3880(17) . ?
C17 C18 1.3871(17) . ?
C18 C19 1.3845(18) . ?
C19 C20 1.3894(18) . ?
C20 C21 1.3898(17) . ?

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 O1 C10 122.18(9) . . ?
C14 N1 C9 116.72(10) . . ?
O1 C1 C2 111.70(10) . . ?
O1 C1 C6 128.61(10) . . ?
C2 C1 C6 119.63(11) . . ?
N3 N2 C8 110.85(9) . . ?
N3 N2 C15 119.95(10) . . ?
C8 N2 C15 129.20(10) . . ?
C3 C2 C1 121.75(11) . . ?
N4 N3 N2 107.36(9) . . ?
C2 C3 C4 119.59(11) . . ?
N3 N4 C7 108.95(9) . . ?
C5 C4 C3 118.93(11) . . ?
C4 C5 C6 122.97(11) . . ?
C1 C6 C5 117.11(10) . . ?
C1 C6 C7 127.98(10) . . ?
C5 C6 C7 114.89(10) . . ?
N4 C7 C6 120.49(10) . . ?
N4 C7 C8 108.18(10) . . ?
C8 C7 C6 130.45(10) . . ?
N2 C8 C7 104.65(10) . . ?
N2 C8 C9 126.15(10) . . ?
C7 C8 C9 129.20(10) . . ?
N1 C9 C8 117.63(10) . . ?
N1 C9 C11 124.06(11) . . ?
C11 C9 C8 118.28(10) . . ?
O1 C10 C11 112.77(10) . . ?
C9 C11 C10 121.45(10) . . ?
C12 C11 C9 117.35(11) . . ?
C12 C11 C10 121.18(11) . . ?
C13 C12 C11 119.44(11) . . ?
C12 C13 C14 118.60(11) . . ?
N1 C14 C13 123.69(11) . . ?
N2 C15 C16 112.82(9) . . ?
C17 C16 C15 119.01(10) . . ?
C21 C16 C15 121.65(10) . . ?
C21 C16 C17 119.29(11) . . ?
C18 C17 C16 120.72(11) . . ?
C19 C18 C17 119.93(11) . . ?
C18 C19 C20 119.56(11) . . ?
C19 C20 C21 120.57(11) . . ?
C16 C21 C20 119.93(11) . . ?

####################################################################### 
# 
# 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_ed-188-lc_auto
_database_code_depnum_ccdc_archive 'CCDC 2286852'
loop_
_audit_author_name
_audit_author_address
'Xinsong Lin'
;Florida State University
United States of America
;
_audit_update_record             
;
2023-08-04 deposited with the CCDC.	2023-10-11 downloaded from the CCDC.
;
_audit_creation_date             2022-11-04
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 N4 O'
_chemical_formula_sum            'C21 H16 N4 O'
_chemical_formula_weight         340.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H16N4O
_chemical_oxdiff_usercomment     150K
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.11690(10)
_cell_length_b                   12.31300(10)
_cell_length_c                   14.85260(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.1900(10)
_cell_angle_gamma                90
_cell_volume                     1662.84(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22601
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      77.7570
_cell_measurement_theta_min      4.6570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.548
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.67a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             712
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0854
1 0 0 0.0744
0 -1 0 0.1421
0 1 0 0.1421
0 0 1 0.1426
0 0 -1 0.1485
-1 -1 0 0.0477
2 5 3 0.0797
5 -1 -1 0.0687

_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.160
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 -0.0000 0.0000 0.1469 -0.0784 0.0314
1.0000 0.0000 -0.0000 -0.1469 0.0784 -0.0314
-0.0000 -1.0000 -0.0000 0.0296 0.0888 0.0830
0.0000 1.0000 0.0000 -0.0296 -0.0888 -0.0830
-0.0000 -0.0000 1.0000 -0.0521 -0.0516 0.0738
0.0000 0.0000 -1.0000 0.0521 0.0516 -0.0738
-1.0000 -1.0000 -0.0000 0.1765 0.0104 0.1144
2.0000 5.0000 3.0000 -0.5980 -0.4420 -0.2567
5.0000 -1.0000 -1.0000 -0.6529 0.5323 -0.1476

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            34000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.047
_diffrn_reflns_theta_min         4.670
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  27.00   0.50    0.05    --  -47.05  37.00-150.00   92
  2  ω    -59.00  26.00   0.50    0.05    --  -47.05  65.00 -40.00  170
  3  ω      1.00  28.00   0.50    0.05    --  -47.05  19.00 -30.00   54
  4  ω      1.00  28.00   0.50    0.05    --  -47.05  19.00  90.00   54
  5  ω      1.00  28.00   0.50    0.05    --  -47.05  19.00 120.00   54
  6  ω    -19.00  27.00   0.50    0.05    --  -47.05  37.00 150.00   92
  7  ω     28.00 119.00   0.50    0.05    --   47.05  65.00 -40.00  182
  8  ω     82.00 119.00   0.50    0.05    --   47.05  57.00  30.00   74
  9  ω    113.00 154.00   0.50    0.19    --  110.00  77.00  90.00   82
 10  ω    101.00 168.00   0.50    0.19    --  110.00  77.00  30.00  134
 11  ω    101.00 178.00   0.50    0.19    --  110.00  77.00   0.00  154
 12  ω     93.00 178.00   0.50    0.19    --  110.00  61.00  90.00  170
 13  ω     93.00 129.00   0.50    0.19    --  110.00  61.00  30.00   72
 14  ω    137.00 164.00   0.50    0.19    --  110.00  61.00  30.00   54
 15  ω     93.00 178.00   0.50    0.19    --  110.00  61.00   0.00  170
 16  ω     98.00 123.00   0.50    0.19    --  110.00  61.00  60.00   50
 17  ω     91.00 178.00   0.50    0.19    --  110.00  65.00 -40.00  174
 18  ω     96.00 178.00   0.50    0.19    --  110.00  45.00-120.00  164
 19  ω    120.00 166.00   0.50    0.19    --  110.00  77.00-150.00   92
 20  ω     98.00 147.00   0.50    0.19    --  110.00  30.00-150.00   98
 21  ω     82.00 119.00   0.50    0.05    --   47.05  57.00-120.00   74
 22  ω     96.00 178.00   0.50    0.19    --  110.00  30.00-180.00  164
 23  ω     92.00 178.00   0.50    0.19    --  110.00  15.00 -60.00  172
 24  ω     96.00 178.00   0.50    0.19    --  110.00  45.00  60.00  164
 25  ω     96.00 155.00   0.50    0.19    --  110.00  45.00  90.00  118
 26  ω    104.00 130.00   0.50    0.19    --  110.00  45.00 120.00   52
 27  ω     39.00  70.00   0.50    0.19    --  110.00 -45.00 -30.00   62
 28  ω     38.00 134.00   0.50    0.19    --  110.00 -77.00  60.00  192
 29  ω     99.00 133.00   0.50    0.19    --  110.00 -77.00 -60.00   68
 30  ω     53.00  89.00   0.50    0.19    --  110.00 -61.00 -30.00   72
 31  ω     38.00  95.00   0.50    0.19    --  110.00 -77.00 -60.00  114
 32  ω    -25.00  66.00   0.50    0.05    --   47.05 -65.00-176.00  182
 33  ω     38.00 101.00   0.50    0.19    --  110.00 -65.00-176.00  126
 34  ω     38.00  71.00   0.50    0.19    --  110.00 -45.00-180.00   66
 35  ω     39.00  71.00   0.50    0.19    --  110.00 -45.00-120.00   64
 36  ω     38.00  71.00   0.50    0.19    --  110.00 -45.00 -90.00   66
 37  ω     38.00  71.00   0.50    0.19    --  110.00 -45.00 -60.00   66
 38  ω     38.00  63.00   0.50    0.19    --  110.00 -45.00   0.00   50
 39  ω     38.00  71.00   0.50    0.19    --  110.00 -45.00 120.00   66
 40  ω     34.00  94.00   0.50    0.05    --   47.05-125.00   0.00  120
 41  ω     38.00 106.00   0.50    0.19    --  110.00 -94.00 120.00  136
 42  ω     40.00 112.00   0.50    0.19    --  110.00-125.00 -30.00  144
 43  ω     64.00  90.00   0.50    0.19    --  110.00 -94.00 -30.00   52
 44  ω     39.00  89.00   0.50    0.19    --  110.00 -94.00 -90.00  100
 45  ω     38.00 106.00   0.50    0.19    --  110.00 -94.00-120.00  136
 46  ω     38.00 106.00   0.50    0.19    --  110.00 -94.00-150.00  136
 47  ω    -59.00 -15.00   0.50    0.19    --  -88.50  65.00 -40.00   88
 48  ω   -121.00 -32.00   0.50    0.05    --  -47.05 -37.00  60.00  178
 49  ω   -161.00 -74.00   0.50    0.19    --  -88.50 -45.00  60.00  174
 50  ω   -119.00 -82.00   0.50    0.05    --  -47.05 -57.00   0.00   74
 51  ω   -119.00 -28.00   0.50    0.05    --  -47.05 -65.00-176.00  182
 52  ω   -160.00 -69.00   0.50    0.19    --  -88.50 -65.00-176.00  182
 53  ω   -161.00 -15.00   0.50    0.19    --  -88.50   0.00   0.00  292
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1469095000
_diffrn_orient_matrix_UB_12      -0.0295817000
_diffrn_orient_matrix_UB_13      -0.0520859000
_diffrn_orient_matrix_UB_21      0.0783803000
_diffrn_orient_matrix_UB_22      -0.0887820000
_diffrn_orient_matrix_UB_23      -0.0516172000
_diffrn_orient_matrix_UB_31      -0.0313752000
_diffrn_orient_matrix_UB_32      -0.0830343000
_diffrn_orient_matrix_UB_33      0.0737537000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3373
_reflns_number_total             3550
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.67a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0025(3)
_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   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3550
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.061
_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)+(0.0406P)²+0.5535P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0891
_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:
 C1(H1A,H1B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
;
_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
O1 O 0.94984(8) 0.64030(7) 0.67909(5) 0.02814(19) Uani 1 1 d . . . . .
N1 N 0.80116(10) 0.66346(7) 0.44125(6) 0.0238(2) Uani 1 1 d . . . . .
N2 N 0.54554(9) 0.73250(7) 0.52934(6) 0.02032(19) Uani 1 1 d . . . . .
N3 N 0.41239(9) 0.70855(7) 0.55762(6) 0.0238(2) Uani 1 1 d . . . . .
N4 N 0.42707(9) 0.62118(7) 0.60840(6) 0.02320(19) Uani 1 1 d . . . . .
C1 C 0.82909(11) 0.62336(9) 0.73491(7) 0.0241(2) Uani 1 1 d . . . . .
H1A H 0.7534 0.6795 0.7203 0.029 Uiso 1 1 calc R U . . .
H1B H 0.8650 0.6328 0.7990 0.029 Uiso 1 1 calc R U . . .
C2 C 0.75917(11) 0.51303(9) 0.72343(6) 0.0212(2) Uani 1 1 d . . . . .
C3 C 0.81976(12) 0.42454(9) 0.77181(7) 0.0252(2) Uani 1 1 d . . . . .
H3 H 0.9091 0.4332 0.8082 0.030 Uiso 1 1 calc R U . . .
C4 C 0.75093(13) 0.32430(9) 0.76723(7) 0.0281(2) Uani 1 1 d . . . . .
H4 H 0.7937 0.2643 0.7997 0.034 Uiso 1 1 calc R U . . .
C5 C 0.61886(12) 0.31145(9) 0.71503(7) 0.0265(2) Uani 1 1 d . . . . .
H5 H 0.5704 0.2431 0.7133 0.032 Uiso 1 1 calc R U . . .
C6 C 0.55783(11) 0.39781(9) 0.66558(7) 0.0225(2) Uani 1 1 d . . . . .
H6 H 0.4678 0.3886 0.6300 0.027 Uiso 1 1 calc R U . . .
C7 C 0.62892(11) 0.49839(8) 0.66822(6) 0.0198(2) Uani 1 1 d . . . . .
C8 C 0.57084(10) 0.59009(8) 0.61360(6) 0.0196(2) Uani 1 1 d . . . . .
C9 C 0.64885(10) 0.66054(8) 0.56289(6) 0.0191(2) Uani 1 1 d . . . . .
C10 C 0.79960(11) 0.65675(8) 0.53220(7) 0.0197(2) Uani 1 1 d . . . . .
C11 C 0.93038(11) 0.64305(8) 0.58706(7) 0.0213(2) Uani 1 1 d . . . . .
C12 C 1.06238(11) 0.63514(9) 0.54528(8) 0.0245(2) Uani 1 1 d . . . . .
H12 H 1.1523 0.6246 0.5807 0.029 Uiso 1 1 calc R U . . .
C13 C 1.06241(11) 0.64250(9) 0.45302(8) 0.0261(2) Uani 1 1 d . . . . .
H13 H 1.1516 0.6380 0.4239 0.031 Uiso 1 1 calc R U . . .
C14 C 0.92854(12) 0.65664(9) 0.40328(7) 0.0265(2) Uani 1 1 d . . . . .
H14 H 0.9280 0.6616 0.3394 0.032 Uiso 1 1 calc R U . . .
C15 C 0.56515(11) 0.83294(8) 0.47938(7) 0.0225(2) Uani 1 1 d . . . . .
H15A H 0.4676 0.8640 0.4605 0.027 Uiso 1 1 calc R U . . .
H15B H 0.6159 0.8166 0.4242 0.027 Uiso 1 1 calc R U . . .
C16 C 0.65395(11) 0.91554(8) 0.53575(7) 0.0212(2) Uani 1 1 d . . . . .
C17 C 0.63185(13) 0.93075(9) 0.62650(7) 0.0289(2) Uani 1 1 d . . . . .
H17 H 0.5625 0.8869 0.6545 0.035 Uiso 1 1 calc R U . . .
C18 C 0.71044(14) 1.00959(10) 0.67650(8) 0.0335(3) Uani 1 1 d . . . . .
H18 H 0.6957 1.0188 0.7387 0.040 Uiso 1 1 calc R U . . .
C19 C 0.81021(12) 1.07471(10) 0.63578(9) 0.0326(3) Uani 1 1 d . . . . .
H19 H 0.8634 1.1290 0.6698 0.039 Uiso 1 1 calc R U . . .
C20 C 0.83219(13) 1.06046(10) 0.54549(9) 0.0357(3) Uani 1 1 d . . . . .
H20 H 0.9000 1.1054 0.5173 0.043 Uiso 1 1 calc R U . . .
C21 C 0.75501(13) 0.98036(10) 0.49594(8) 0.0296(2) Uani 1 1 d . . . . .
H21 H 0.7718 0.9700 0.4342 0.036 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
O1 C1 1.4409(12) . ?
O1 C11 1.3659(12) . ?
N1 C10 1.3545(13) . ?
N1 C14 1.3302(14) . ?
N2 N3 1.3459(11) . ?
N2 C9 1.3608(13) . ?
N2 C15 1.4600(13) . ?
N3 N4 1.3151(13) . ?
N4 C8 1.3622(13) . ?
C1 C2 1.5050(15) . ?
C2 C3 1.3966(15) . ?
C2 C7 1.4045(14) . ?
C3 C4 1.3841(17) . ?
C4 C5 1.3927(16) . ?
C5 C6 1.3856(15) . ?
C6 C7 1.3970(14) . ?
C7 C8 1.4665(14) . ?
C8 C9 1.3799(14) . ?
C9 C10 1.4800(13) . ?
C10 C11 1.4042(14) . ?
C11 C12 1.3971(14) . ?
C12 C13 1.3733(16) . ?
C13 C14 1.3907(16) . ?
C15 C16 1.5139(14) . ?
C16 C17 1.3901(15) . ?
C16 C21 1.3838(15) . ?
C17 C18 1.3890(16) . ?
C18 C19 1.3843(18) . ?
C19 C20 1.3815(18) . ?
C20 C21 1.3906(17) . ?

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
C11 O1 C1 122.05(8) . . ?
C14 N1 C10 119.48(9) . . ?
N3 N2 C9 111.04(8) . . ?
N3 N2 C15 119.40(8) . . ?
C9 N2 C15 129.08(8) . . ?
N4 N3 N2 107.57(8) . . ?
N3 N4 C8 108.64(8) . . ?
O1 C1 C2 113.61(8) . . ?
C3 C2 C1 119.84(9) . . ?
C3 C2 C7 119.08(10) . . ?
C7 C2 C1 121.00(9) . . ?
C4 C3 C2 120.63(10) . . ?
C3 C4 C5 119.94(10) . . ?
C6 C5 C4 120.35(10) . . ?
C5 C6 C7 119.86(10) . . ?
C2 C7 C8 118.67(9) . . ?
C6 C7 C2 120.06(9) . . ?
C6 C7 C8 121.26(9) . . ?
N4 C8 C7 123.70(9) . . ?
N4 C8 C9 108.94(9) . . ?
C9 C8 C7 127.32(9) . . ?
N2 C9 C8 103.80(8) . . ?
N2 C9 C10 122.77(9) . . ?
C8 C9 C10 132.50(9) . . ?
N1 C10 C9 112.51(8) . . ?
N1 C10 C11 121.04(9) . . ?
C11 C10 C9 126.40(9) . . ?
O1 C11 C10 128.78(9) . . ?
O1 C11 C12 112.93(9) . . ?
C12 C11 C10 118.23(9) . . ?
C13 C12 C11 120.10(10) . . ?
C12 C13 C14 118.30(10) . . ?
N1 C14 C13 122.84(10) . . ?
N2 C15 C16 111.62(8) . . ?
C17 C16 C15 121.15(9) . . ?
C21 C16 C15 119.80(9) . . ?
C21 C16 C17 119.00(10) . . ?
C18 C17 C16 120.46(10) . . ?
C19 C18 C17 120.06(11) . . ?
C20 C19 C18 119.80(11) . . ?
C19 C20 C21 120.01(11) . . ?
C16 C21 C20 120.65(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.445
_oxdiff_exptl_absorpt_empirical_full_min 0.676
####################################################################### 
# 
# 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_ed-20-lc_auto
_database_code_depnum_ccdc_archive 'CCDC 2286853'
loop_
_audit_author_name
_audit_author_address
'Xinsong Lin'
;Florida State University
United States of America
;
_audit_update_record             
;
2023-08-04 deposited with the CCDC.	2023-10-11 downloaded from the CCDC.
;
_audit_creation_method           
;FinalCif V119 by Daniel Kratzert, Freiburg 2023,
https://dkratzert.de/finalcif.html
;
_audit_creation_date             2022-08-19
_chemical_oxdiff_formula         CHNCl
_chemical_oxdiff_usercomment     150
_diffrn_orient_matrix_UB_11      -0.1393568000
_diffrn_orient_matrix_UB_12      -0.0127949000
_diffrn_orient_matrix_UB_13      -0.0040479000
_diffrn_orient_matrix_UB_21      0.0274431000
_diffrn_orient_matrix_UB_22      0.0183933000
_diffrn_orient_matrix_UB_23      0.1943154000
_diffrn_orient_matrix_UB_31      -0.0335964000
_diffrn_orient_matrix_UB_32      0.0682259000
_diffrn_orient_matrix_UB_33      -0.0532209000
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_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:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C10(H10), C11(H11), C12(H12), C18(H18), C19(H19),
 C20(H20), C21(H21), C22(H22)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.940
_oxdiff_exptl_absorpt_empirical_full_min 0.407
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_sum            'C22 H17 Cl N4'
_chemical_formula_moiety         'C22 H17 Cl N4'
_chemical_formula_weight         372.85
_chemical_melting_point          ?
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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'
_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'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.93403(10)
_cell_length_b                   21.4604(2)
_cell_length_c                   7.91748(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.1277(9)
_cell_angle_gamma                90
_cell_volume                     1793.45(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    149.99(10)
_cell_measurement_reflns_used    25365
_cell_measurement_theta_min      4.1290
_cell_measurement_theta_max      77.5660
_exptl_crystal_description       plate
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_recrystallization_method 'by a slow evaporation method'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.825
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    1.990
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.010
_exptl_absorpt_correction_T_max  0.606
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.61a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_shelx_estimated_absorpt_T_min   0.291
_shelx_estimated_absorpt_T_max   0.823
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_special_details           ?
_diffrn_ambient_temperature      149.99(10)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_ambient_temperature_device_make 'Oxford Cryostream 800'
_diffrn_radiation_probe          x-ray
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            HyPix
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00 -24.00   0.50    0.72    --  -86.25  61.00-180.00   52
  2  ω    -15.00  23.00   0.50    0.18    --  -48.74  37.00-180.00   76
  3  ω     -4.00  26.00   0.50    0.18    --  -48.74  24.00  27.00   60
  4  ω    -19.00  23.00   0.50    0.18    --  -48.74  37.00 150.00   84
  5  ω     36.00  86.00   0.50    0.18    --   48.74  56.00 120.31  100
  6  ω     38.00  63.00   0.50    0.18    --   48.74  55.00 161.19   50
  7  ω     38.00  67.00   0.50    0.18    --   48.74  55.00 174.34   58
  8  ω     40.00  96.00   0.50    0.18    --   48.74  37.00  90.00  112
  9  ω     39.00 123.00   0.50    0.18    --   48.74  24.00  27.00  168
 10  ω     36.00 108.00   0.50    0.18    --   48.74  55.00-139.39  144
 11  ω     37.00  62.00   0.50    0.18    --   48.74  54.00-160.69   50
 12  ω     67.00 108.00   0.50    0.18    --   48.74  54.00-160.69   82
 13  ω     93.00 177.00   0.50    0.72    --  107.75  61.00-180.00  168
 14  ω     93.00 155.00   0.50    0.72    --  107.75  61.00-150.00  124
 15  ω    141.00 177.00   0.50    0.72    --  107.75  61.00  60.00   72
 16  ω     93.00 136.00   0.50    0.72    --  107.75  61.00  60.00   86
 17  ω     94.00 143.00   0.50    0.72    --  107.75  61.00  90.00   98
 18  ω    150.00 176.00   0.50    0.72    --  107.75  45.00 120.00   52
 19  ω     93.00 159.00   0.50    0.72    --  107.75  61.00 150.00  132
 20  ω    100.00 153.00   0.50    0.72    --  107.75  45.00 150.00  106
 21  ω     93.00 148.00   0.50    0.72    --  107.75  61.00 120.00  110
 22  ω     99.00 141.00   0.50    0.72    --  107.75  45.00 120.00   84
 23  ω    131.00 178.00   0.50    0.72    --  107.75  30.00 120.00   94
 24  ω    134.00 166.00   0.50    0.72    --  107.75   0.00 150.00   64
 25  ω    102.00 132.00   0.50    0.72    --  107.75  45.00  90.00   60
 26  ω    114.00 139.00   0.50    0.72    --  107.75  24.00  27.00   50
 27  ω    128.00 166.00   0.50    0.72    --  107.75   0.00 -30.00   76
 28  ω    129.00 155.00   0.50    0.72    --  107.75   0.00 -60.00   52
 29  ω    140.00 166.00   0.50    0.72    --  107.75  30.00-180.00   52
 30  ω    101.00 146.00   0.50    0.72    --  107.75  45.00-150.00   90
 31  ω    127.00 159.00   0.50    0.72    --  107.75   0.00  90.00   64
 32  ω     73.00 125.00   0.50    0.72    --  107.75 -77.00 150.00  104
 33  ω     40.00  87.00   0.50    0.72    --  107.75 -61.00  90.00   94
 34  ω     36.00  61.00   0.50    0.72    --  107.75 -45.00  90.00   50
 35  ω     45.00  71.00   0.50    0.72    --  107.75 -45.00   0.00   52
 36  ω     36.00  82.00   0.50    0.72    --  107.75 -61.00 -30.00   92
 37  ω     45.00  84.00   0.50    0.72    --  107.75 -61.00-150.00   78
 38  ω     36.00  69.00   0.50    0.72    --  107.75 -45.00 -90.00   66
 39  ω     36.00  70.00   0.50    0.72    --  107.75 -45.00-120.00   68
 40  ω     36.00  71.00   0.50    0.72    --  107.75 -45.00 -30.00   70
 41  ω    -25.00  46.00   0.50    0.18    --   48.74 -24.00-137.00  142
 42  ω     36.00  70.00   0.50    0.72    --  107.75 -45.00  30.00   68
 43  ω     41.00  66.00   0.50    0.72    --  107.75 -45.00  60.00   50
 44  ω     46.00  71.00   0.50    0.72    --  107.75 -45.00 150.00   50
 45  ω     67.00 106.00   0.50    0.72    --  107.75 -94.00  90.00   78
 46  ω     78.00 104.00   0.50    0.72    --  107.75 -94.00   0.00   52
 47  ω     41.00  71.00   0.50    0.72    --  107.75 -94.00   0.00   60
 48  ω     56.00 108.00   0.50    0.72    --  107.75-125.00-150.00  104
 49  ω     75.00 107.00   0.50    0.72    --  107.75-125.00-180.00   64
 50  ω     41.00  67.00   0.50    0.72    --  107.75-125.00-180.00   52
 51  ω   -123.00 -38.00   0.50    0.18    --  -48.74 -24.00-137.00  170
 52  ω    -99.00 -73.00   0.50    0.72    --  -86.25 -55.00  54.50   52
 53  ω   -103.00 -78.00   0.50    0.72    --  -86.25 -56.00  94.13   50
 54  ω    -99.00 -73.00   0.50    0.72    --  -86.25 -55.00 100.40   52
 55  ω   -104.00 -78.00   0.50    0.72    --  -86.25 -56.00 127.14   52
 56  ω   -101.00 -75.00   0.50    0.72    --  -86.25 -53.00 168.62   52
 57  ω    -99.00 -73.00   0.50    0.72    --  -86.25 -55.00 144.74   52
 58  ω    -99.00 -73.00   0.50    0.72    --  -86.25 -53.00 159.72   52
 59  ω    -98.00 -73.00   0.50    0.72    --  -86.25 -53.00 138.73   50
 60  ω    -99.00 -74.00   0.50    0.72    --  -86.25 -52.00 146.94   50
 61  ω   -102.00 -73.00   0.50    0.72    --  -86.25 -55.00 114.31   58
 62  ω   -100.00 -74.00   0.50    0.72    --  -86.25 -52.00 127.34   52
 63  ω    -98.00 -73.00   0.50    0.72    --  -86.25 -54.00  92.96   50
 64  ω   -101.00 -75.00   0.50    0.72    --  -86.25 -50.00  61.50   52
 65  ω   -102.00 -75.00   0.50    0.72    --  -86.25 -52.00  61.25   54
 66  ω   -133.00 -74.00   0.50    0.72    --  -86.25 -52.00  69.51  118
 67  ω   -138.00 -74.00   0.50    0.72    --  -86.25 -54.00  44.40  128
 68  ω   -161.00 -76.00   0.50    0.72    --  -86.25 -24.00-137.00  170
 69  ω   -108.00 -62.00   0.50    0.18    --  -48.74 -37.00-180.00   92
 70  ω   -117.00 -75.00   0.50    0.72    --  -86.25 -48.00  49.76   84
 71  ω   -100.00 -75.00   0.50    0.72    --  -86.25 -46.00 163.62   50
 72  ω    -99.00 -74.00   0.50    0.72    --  -86.25 -50.00  78.58   50
 73  ω   -117.00 -87.00   0.50    0.18    --  -48.74-125.00 -30.00   60
;
_diffrn_reflns_number            35683
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0817
_diffrn_reflns_theta_min         4.120
_diffrn_reflns_theta_max         77.865
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3757
_reflns_number_gt                3510
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.61a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_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)+(0.0911P)²+0.3679P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3757
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1348
_refine_ls_wR_factor_gt          0.1328
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

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'
Cl Cl 0.3639 0.7018 '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'

_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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.3871
0 1 0 0.0800
0 -1 0 0.0570
-1 0 0 0.0668
1 0 0 0.0348
0 5 4 0.3262
-1 5 -1 0.1816

loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0001 -0.0001 -0.9995 0.0040 -0.1942 0.0532
0.0001 0.9991 -0.0001 -0.0128 0.0184 0.0682
-0.0001 -0.9991 0.0001 0.0128 -0.0184 -0.0682
-0.9995 0.0000 0.0000 0.1393 -0.0274 0.0336
0.9995 -0.0000 -0.0000 -0.1393 0.0274 -0.0336
0.0003 4.9961 3.9975 -0.0801 0.8687 0.1281
-0.9989 4.9955 -0.9999 0.0793 -0.1298 0.4276

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 0.87071(3) 0.31596(2) 0.07583(5) 0.03926(16) Uani 1 1 d . . . . .
N1 N 0.42135(12) 0.49434(6) 0.28374(15) 0.0295(3) Uani 1 1 d . . . . .
N2 N 0.30891(12) 0.50758(6) 0.30522(16) 0.0311(3) Uani 1 1 d . . . . .
N3 N 0.25667(11) 0.45378(5) 0.34005(14) 0.0273(3) Uani 1 1 d . . . . .
N4 N 0.20520(12) 0.31481(6) 0.26777(17) 0.0318(3) Uani 1 1 d . . . . .
C1 C 0.74550(13) 0.34829(7) 0.14473(18) 0.0291(3) Uani 1 1 d . . . . .
C2 C 0.66740(13) 0.39175(7) 0.04077(17) 0.0290(3) Uani 1 1 d . . . . .
H2 H 0.6799 0.4040 -0.0688 0.035 Uiso 1 1 calc R U . . .
C3 C 0.57035(13) 0.41679(6) 0.10172(17) 0.0279(3) Uani 1 1 d . . . . .
H3 H 0.5143 0.4458 0.0302 0.033 Uiso 1 1 calc R U . . .
C4 C 0.55160(12) 0.40097(6) 0.26515(16) 0.0250(3) Uani 1 1 d . . . . .
C5 C 0.63279(12) 0.35693(6) 0.37004(16) 0.0255(3) Uani 1 1 d . . . . .
C6 C 0.72785(13) 0.33041(7) 0.30432(18) 0.0283(3) Uani 1 1 d . . . . .
H6 H 0.7815 0.2994 0.3709 0.034 Uiso 1 1 calc R U . . .
C7 C 0.44234(13) 0.43185(6) 0.30796(16) 0.0254(3) Uani 1 1 d . . . . .
C8 C 0.33667(13) 0.40544(6) 0.34358(16) 0.0258(3) Uani 1 1 d . . . . .
C9 C 0.31203(13) 0.33940(6) 0.37039(17) 0.0263(3) Uani 1 1 d . . . . .
C10 C 0.19149(15) 0.25334(8) 0.2769(2) 0.0377(4) Uani 1 1 d . . . . .
H10 H 0.1161 0.2350 0.2070 0.045 Uiso 1 1 calc R U . . .
C11 C 0.28111(16) 0.21448(7) 0.3828(2) 0.0388(4) Uani 1 1 d . . . . .
H11 H 0.2696 0.1706 0.3795 0.047 Uiso 1 1 calc R U . . .
C12 C 0.38746(15) 0.24109(7) 0.4931(2) 0.0343(3) Uani 1 1 d . . . . .
H12 H 0.4488 0.2157 0.5696 0.041 Uiso 1 1 calc R U . . .
C13 C 0.40409(13) 0.30532(7) 0.49123(17) 0.0268(3) Uani 1 1 d . . . . .
C14 C 0.51332(13) 0.33771(7) 0.61543(17) 0.0287(3) Uani 1 1 d . . . . .
H14A H 0.5297 0.3172 0.7312 0.034 Uiso 1 1 calc R U . . .
H14B H 0.4888 0.3814 0.6299 0.034 Uiso 1 1 calc R U . . .
C15 C 0.63623(13) 0.33766(7) 0.55651(17) 0.0301(3) Uani 1 1 d . . . . .
H15A H 0.6970 0.3655 0.6366 0.036 Uiso 1 1 calc R U . . .
H15B H 0.6718 0.2950 0.5746 0.036 Uiso 1 1 calc R U . . .
C16 C 0.12678(13) 0.45313(7) 0.35850(18) 0.0307(3) Uani 1 1 d . . . . .
H16A H 0.0773 0.4216 0.2776 0.037 Uiso 1 1 calc R U . . .
H16B H 0.0876 0.4943 0.3229 0.037 Uiso 1 1 calc R U . . .
C17 C 0.11781(12) 0.43892(6) 0.54188(17) 0.0264(3) Uani 1 1 d . . . . .
C18 C 0.02685(13) 0.39714(7) 0.56450(19) 0.0320(3) Uani 1 1 d . . . . .
H18 H -0.0241 0.3757 0.4661 0.038 Uiso 1 1 calc R U . . .
C19 C 0.00941(14) 0.38633(7) 0.7291(2) 0.0349(3) Uani 1 1 d . . . . .
H19 H -0.0538 0.3579 0.7431 0.042 Uiso 1 1 calc R U . . .
C20 C 0.08410(15) 0.41703(8) 0.87328(19) 0.0359(3) Uani 1 1 d . . . . .
H20 H 0.0724 0.4098 0.9864 0.043 Uiso 1 1 calc R U . . .
C21 C 0.17598(16) 0.45839(8) 0.85163(19) 0.0381(4) Uani 1 1 d . . . . .
H21 H 0.2278 0.4792 0.9505 0.046 Uiso 1 1 calc R U . . .
C22 C 0.19297(15) 0.46965(7) 0.6869(2) 0.0340(3) Uani 1 1 d . . . . .
H22 H 0.2558 0.4983 0.6730 0.041 Uiso 1 1 calc R U . . .


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 C1 1.7443(14) . ?
N1 N2 1.3154(18) . ?
N1 C7 1.3657(18) . ?
N2 N3 1.3482(17) . ?
N3 C8 1.3525(18) . ?
N3 C16 1.4653(18) . ?
N4 C9 1.3445(19) . ?
N4 C10 1.332(2) . ?
C1 C2 1.382(2) . ?
C1 C6 1.3814(19) . ?
C2 C3 1.384(2) . ?
C3 C4 1.4036(18) . ?
C4 C5 1.4094(18) . ?
C4 C7 1.4807(19) . ?
C5 C6 1.3989(19) . ?
C5 C15 1.5241(17) . ?
C7 C8 1.3806(19) . ?
C8 C9 1.4682(19) . ?
C9 C13 1.4002(19) . ?
C10 C11 1.389(2) . ?
C11 C12 1.382(2) . ?
C12 C13 1.391(2) . ?
C13 C14 1.5045(19) . ?
C14 C15 1.5332(19) . ?
C16 C17 1.5116(18) . ?
C17 C18 1.385(2) . ?
C17 C22 1.3915(19) . ?
C18 C19 1.385(2) . ?
C19 C20 1.385(2) . ?
C20 C21 1.384(2) . ?
C21 C22 1.386(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C7 108.81(12) . . ?
N1 N2 N3 107.55(11) . . ?
N2 N3 C8 110.79(12) . . ?
N2 N3 C16 120.13(12) . . ?
C8 N3 C16 128.99(12) . . ?
C10 N4 C9 116.64(13) . . ?
C2 C1 Cl1 119.71(11) . . ?
C6 C1 Cl1 118.95(11) . . ?
C6 C1 C2 121.33(13) . . ?
C1 C2 C3 117.73(12) . . ?
C2 C3 C4 122.50(13) . . ?
C3 C4 C5 118.97(12) . . ?
C3 C4 C7 115.05(12) . . ?
C5 C4 C7 125.94(12) . . ?
C4 C5 C15 127.24(12) . . ?
C6 C5 C4 117.93(12) . . ?
C6 C5 C15 114.65(12) . . ?
C1 C6 C5 121.47(13) . . ?
N1 C7 C4 121.56(12) . . ?
N1 C7 C8 108.23(12) . . ?
C8 C7 C4 129.14(13) . . ?
N3 C8 C7 104.60(12) . . ?
N3 C8 C9 126.96(12) . . ?
C7 C8 C9 128.37(12) . . ?
N4 C9 C8 117.04(12) . . ?
N4 C9 C13 124.34(13) . . ?
C13 C9 C8 118.47(12) . . ?
N4 C10 C11 123.76(14) . . ?
C12 C11 C10 118.54(14) . . ?
C11 C12 C13 119.57(14) . . ?
C9 C13 C14 120.78(12) . . ?
C12 C13 C9 116.88(13) . . ?
C12 C13 C14 122.31(13) . . ?
C13 C14 C15 114.21(11) . . ?
C5 C15 C14 119.51(11) . . ?
N3 C16 C17 113.90(11) . . ?
C18 C17 C16 118.92(12) . . ?
C18 C17 C22 119.31(13) . . ?
C22 C17 C16 121.64(13) . . ?
C19 C18 C17 120.66(13) . . ?
C20 C19 C18 119.98(14) . . ?
C21 C20 C19 119.60(14) . . ?
C20 C21 C22 120.54(14) . . ?
C21 C22 C17 119.91(14) . . ?

