# Supplementary Information (SI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_2
_database_code_depnum_ccdc_archive 'CCDC 2355948'
loop_
_audit_author_name
_audit_author_address
'Gao Lei'
;DongHua University
China
;
_audit_update_record             
;
2024-05-16 deposited with the CCDC.	2024-10-08 downloaded from the CCDC.
;
_audit_creation_date             2024-03-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1
_chemical_formula_moiety         'C15 H9 Cl N4'
_chemical_formula_sum            'C15 H9 Cl N4'
_chemical_formula_weight         280.71
_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 0.0181 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'

_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        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   13.6775(8)
_cell_length_b                   7.0104(3)
_cell_length_c                   26.4013(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.209(5)
_cell_angle_gamma                90
_cell_volume                     2521.0(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3029
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.6310
_cell_measurement_theta_min      3.3760
_shelx_estimated_absorpt_T_max   0.880
_shelx_estimated_absorpt_T_min   0.837
_exptl_absorpt_coefficient_mu    2.630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1249
_diffrn_reflns_av_unetI/netI     0.1026
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            9244
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.732
_diffrn_reflns_theta_min         3.362
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00  72.00   0.50    0.80    --   42.30 -43.00-180.00   78
  2  ω    -46.00 -14.00   0.50    0.80    --   42.30 -65.00 120.00   64
  3  ω     34.00  70.00   0.50    0.80    --   42.30 -82.00 -30.00   72
  4  ω     12.00  69.00   0.50    0.80    --   42.30 -82.00-120.00  114
  5  ω     57.00  93.00   0.50    0.80    --   42.30  82.00 -60.00   72
  6  ω    -10.00  20.00   0.50    0.80    --   42.30 -65.00 120.00   60
  7  ω    -13.00  12.00   0.50    0.80    --   42.30 -77.00   0.00   50
  8  ω    -43.00 -17.00   0.50    0.80    --   42.30 -77.00   0.00   52
  9  ω    -47.00  63.00   0.50    0.80    --   42.30 -82.00 120.00  220
 10  ω    -24.00  37.00   0.50    0.80    --   42.30 -65.00  30.00  122
 11  ω     96.00 127.00   0.50    0.80    --   42.30  82.00 -60.00   62
 12  ω    -44.00  12.00   0.50    0.80    --   42.30 -43.00-180.00  112
 13  ω     29.00  54.00   0.50    0.80    --   42.30  82.00 -60.00   50
 14  ω     32.00  66.00   0.50    0.80    --   42.30 -65.00 120.00   68
 15  ω     55.00 131.00   0.50    0.80    --   42.30  65.00  30.00  152
 16  ω     34.00  67.00   0.50    0.80    --   42.30 -77.00   0.00   66
 17  ω     20.00  45.00   0.50    0.80    --   42.30  65.00 -90.00   50
 18  ω     18.00  47.00   0.50    0.80    --   42.30  65.00  30.00   58
 19  ω      6.00  65.00   0.50    1.00    --   93.70 -82.00 -90.00  118
 20  ω      5.00 121.00   0.50    1.00    --   93.70 -82.00-120.00  232
 21  ω      4.00  99.00   0.50    1.00    --   93.70 -82.00 -30.00  190
 22  ω     19.00  93.00   0.50    1.00    --   93.70 -82.00-180.00  148
 23  ω     25.00  93.00   0.50    1.00    --   93.70 -82.00  60.00  136
 24  ω    151.00 176.00   0.50    1.00    --   93.70  33.00  60.00   50
 25  ω     62.00 183.00   0.50    1.00    --   93.70  33.00-180.00  242
 26  ω     88.00 183.00   0.50    1.00    --   93.70  33.00 120.00  190
 27  ω    120.00 146.00   0.50    1.00    --   93.70  33.00  60.00   52
 28  ω    114.00 182.00   0.50    1.00    --   93.70  77.00 -30.00  136
 29  ω     72.00 112.00   0.50    1.00    --   93.70 -82.00  90.00   80
 30  ω     99.00 124.00   0.50    1.00    --   93.70 -33.00-180.00   50
 31  ω     19.00  94.00   0.50    1.00    --   93.70 -82.00 -60.00  150
 32  ω    102.00 127.00   0.50    1.00    --   93.70  68.00 -90.00   50
 33  ω     94.00 183.00   0.50    1.00    --   93.70  42.00-120.00  178
 34  ω     61.00  96.00   0.50    1.00    --   93.70 -82.00-150.00   70
 35  ω     21.00  91.00   0.50    1.00    --   93.70 -82.00   0.00  140
 36  ω     64.00  92.00   0.50    1.00    --   93.70 -82.00 150.00   56
 37  ω      6.00 110.00   0.50    1.00    --   93.70 -59.00  60.00  208
 38  ω      4.00  93.00   0.50    1.00    --   93.70 -82.00  30.00  178
 39  ω      7.00  33.00   0.50    1.00    --   93.70 -33.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0101714000
_diffrn_orient_matrix_UB_12      -0.1202270000
_diffrn_orient_matrix_UB_13      0.0490396000
_diffrn_orient_matrix_UB_21      -0.0443032000
_diffrn_orient_matrix_UB_22      0.1646317000
_diffrn_orient_matrix_UB_23      0.0290670000
_diffrn_orient_matrix_UB_31      -0.1035782000
_diffrn_orient_matrix_UB_32      -0.0821643000
_diffrn_orient_matrix_UB_33      -0.0134971000
_diffrn_oxdiff_digest_frames     
;
01aebeafaaac06d15bbe642309790e83c4000290d7a
;
_diffrn_oxdiff_digest_hkl        
;
011ffb660640cf90c31a8f4a799276be1f4d22
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1523
_reflns_number_total             2267
_reflns_odcompleteness_completeness 99.47
_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 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.523
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2267
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1269
_refine_ls_R_factor_gt           0.1047
_refine_ls_restrained_S_all      1.106
_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)+(0.1850P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2757
_refine_ls_wR_factor_ref         0.3062
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
N14 \\sim C15: within 3A with sigma of 0.004 and sigma for terminal atoms of
0.008
3.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C10(H10), C2(H2), C12(H12), C15(H15), C3(H3A), C5(H5), C4(H4), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.45175(10) 0.19874(15) 0.65108(5) 0.0708(6) Uani 1 1 d . . . . .
N3 N 0.3711(3) 0.3211(4) 0.47113(13) 0.0530(10) Uani 1 1 d . . . . .
H3 H 0.375589 0.233668 0.494080 0.064 Uiso 1 1 calc R . . . .
N2 N 0.3654(2) 0.6125(5) 0.43657(13) 0.0535(9) Uani 1 1 d . . . . .
N14 N 0.3901(3) 0.6518(6) 0.72986(15) 0.0688(11) Uani 1 1 d . U . . .
C8 C 0.3786(3) 0.5994(6) 0.52954(15) 0.0496(10) Uani 1 1 d . . . . .
C7 C 0.3718(3) 0.5147(6) 0.47909(15) 0.0495(10) Uani 1 1 d . . . . .
C1 C 0.3589(3) 0.4757(6) 0.39837(16) 0.0496(10) Uani 1 1 d . . . . .
C11 C 0.3878(3) 0.5564(6) 0.62559(15) 0.0498(10) Uani 1 1 d . . . . .
C10 C 0.3842(3) 0.4966(6) 0.57280(15) 0.0518(10) Uani 1 1 d . . . . .
H10 H 0.385959 0.365250 0.568061 0.062 Uiso 1 1 calc R . . . .
C6 C 0.3617(3) 0.2943(5) 0.41960(17) 0.0519(11) Uani 1 1 d . . . . .
C16 C 0.4172(3) 0.4276(6) 0.66461(16) 0.0524(11) Uani 1 1 d . . . . .
C2 C 0.3483(3) 0.4957(7) 0.34535(16) 0.0579(11) Uani 1 1 d . . . . .
H2 H 0.345335 0.615220 0.330020 0.069 Uiso 1 1 calc R . . . .
C9 C 0.3790(4) 0.8043(6) 0.52906(17) 0.0583(12) Uani 1 1 d . . . . .
N1 N 0.3806(4) 0.9663(6) 0.52883(16) 0.0872(15) Uani 1 1 d . . . . .
C12 C 0.3593(3) 0.7350(7) 0.64202(17) 0.0601(12) Uani 1 1 d . . . . .
H12 H 0.339043 0.828010 0.618224 0.072 Uiso 1 1 calc R . . . .
C15 C 0.4188(3) 0.4822(7) 0.71455(17) 0.0643(11) Uani 1 1 d . U . . .
H15 H 0.441459 0.394526 0.739323 0.077 Uiso 1 1 calc R . . . .
C3 C 0.3424(3) 0.3311(7) 0.31697(18) 0.0628(12) Uani 1 1 d . . . . .
H3A H 0.334815 0.340730 0.281701 0.075 Uiso 1 1 calc R . . . .
C5 C 0.3568(3) 0.1268(7) 0.39061(17) 0.0626(12) Uani 1 1 d . . . . .
H5 H 0.359759 0.006494 0.405518 0.075 Uiso 1 1 calc R . . . .
C4 C 0.3473(3) 0.1511(8) 0.33889(19) 0.0669(13) Uani 1 1 d . . . . .
H4 H 0.344000 0.044237 0.317948 0.080 Uiso 1 1 calc R . . . .
C13 C 0.3607(4) 0.7752(7) 0.69294(19) 0.0666(13) Uani 1 1 d . . . . .
H13 H 0.339919 0.895347 0.702347 0.080 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
Cl1 C16 1.719(4) . ?
N3 H3 0.8600 . ?
N3 C7 1.373(5) . ?
N3 C6 1.368(6) . ?
N2 C7 1.312(5) . ?
N2 C1 1.389(5) . ?
N14 C15 1.326(6) . ?
N14 C13 1.338(7) . ?
C8 C7 1.454(5) . ?
C8 C10 1.347(6) . ?
C8 C9 1.436(6) . ?
C1 C6 1.389(5) . ?
C1 C2 1.401(6) . ?
C11 C10 1.452(5) . ?
C11 C16 1.401(6) . ?
C11 C12 1.392(6) . ?
C10 H10 0.9300 . ?
C6 C5 1.400(6) . ?
C16 C15 1.371(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(6) . ?
C9 N1 1.136(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(6) . ?
C15 H15 0.9300 . ?
C3 H3A 0.9300 . ?
C3 C4 1.387(7) . ?
C5 H5 0.9300 . ?
C5 C4 1.370(6) . ?
C4 H4 0.9300 . ?
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
C7 N3 H3 126.7 . . ?
C6 N3 H3 126.7 . . ?
C6 N3 C7 106.6(3) . . ?
C7 N2 C1 104.8(3) . . ?
C15 N14 C13 115.8(4) . . ?
C10 C8 C7 123.5(4) . . ?
C10 C8 C9 122.9(4) . . ?
C9 C8 C7 113.6(3) . . ?
N3 C7 C8 122.9(3) . . ?
N2 C7 N3 112.8(4) . . ?
N2 C7 C8 124.3(4) . . ?
N2 C1 C2 130.6(4) . . ?
C6 C1 N2 110.0(4) . . ?
C6 C1 C2 119.4(4) . . ?
C16 C11 C10 120.2(4) . . ?
C12 C11 C10 124.9(4) . . ?
C12 C11 C16 114.8(4) . . ?
C8 C10 C11 130.8(4) . . ?
C8 C10 H10 114.6 . . ?
C11 C10 H10 114.6 . . ?
N3 C6 C1 105.8(3) . . ?
N3 C6 C5 130.9(4) . . ?
C1 C6 C5 123.3(4) . . ?
C11 C16 Cl1 121.0(3) . . ?
C15 C16 Cl1 118.7(3) . . ?
C15 C16 C11 120.4(4) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.2(4) . . ?
C3 C2 H2 121.4 . . ?
N1 C9 C8 179.1(6) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12 119.7 . . ?
N14 C15 C16 124.3(4) . . ?
N14 C15 H15 117.8 . . ?
C16 C15 H15 117.8 . . ?
C2 C3 H3A 118.7 . . ?
C2 C3 C4 122.5(5) . . ?
C4 C3 H3A 118.7 . . ?
C6 C5 H5 122.1 . . ?
C4 C5 C6 115.8(5) . . ?
C4 C5 H5 122.1 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.7(5) . . ?
C5 C4 H4 119.1 . . ?
N14 C13 C12 123.9(5) . . ?
N14 C13 H13 118.1 . . ?
C12 C13 H13 118.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C16 C15 N14 -177.2(4) . . . . ?
N3 C6 C5 C4 -180.0(4) . . . . ?
N2 C1 C6 N3 -0.7(5) . . . . ?
N2 C1 C6 C5 -179.9(4) . . . . ?
N2 C1 C2 C3 -179.0(4) . . . . ?
C7 N3 C6 C1 1.1(4) . . . . ?
C7 N3 C6 C5 -179.9(4) . . . . ?
C7 N2 C1 C6 0.1(4) . . . . ?
C7 N2 C1 C2 178.3(4) . . . . ?
C7 C8 C10 C11 -177.6(4) . . . . ?
C1 N2 C7 N3 0.6(4) . . . . ?
C1 N2 C7 C8 -179.0(3) . . . . ?
C1 C6 C5 C4 -1.1(7) . . . . ?
C1 C2 C3 C4 -0.5(7) . . . . ?
C11 C16 C15 N14 2.8(7) . . . . ?
C11 C12 C13 N14 1.2(7) . . . . ?
C10 C8 C7 N3 -0.4(6) . . . . ?
C10 C8 C7 N2 179.3(4) . . . . ?
C10 C11 C16 Cl1 1.3(5) . . . . ?
C10 C11 C16 C15 -178.6(4) . . . . ?
C10 C11 C12 C13 176.7(4) . . . . ?
C6 N3 C7 N2 -1.1(5) . . . . ?
C6 N3 C7 C8 178.6(3) . . . . ?
C6 C1 C2 C3 -0.9(6) . . . . ?
C6 C5 C4 C3 -0.3(7) . . . . ?
C16 C11 C10 C8 -164.5(4) . . . . ?
C16 C11 C12 C13 -0.2(6) . . . . ?
C2 C1 C6 N3 -179.2(3) . . . . ?
C2 C1 C6 C5 1.7(6) . . . . ?
C2 C3 C4 C5 1.1(7) . . . . ?
C9 C8 C7 N3 179.5(4) . . . . ?
C9 C8 C7 N2 -0.9(5) . . . . ?
C9 C8 C10 C11 2.6(7) . . . . ?
C12 C11 C10 C8 18.8(7) . . . . ?
C12 C11 C16 Cl1 178.4(3) . . . . ?
C12 C11 C16 C15 -1.6(6) . . . . ?
C15 N14 C13 C12 -0.2(7) . . . . ?
C13 N14 C15 C16 -1.8(7) . . . . ?

_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 3.685
_oxdiff_exptl_absorpt_empirical_full_min 0.230
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2355949'
loop_
_audit_author_name
_audit_author_address
'Gao Lei'
;DongHua University
China
;
_audit_update_record             
;
2024-05-16 deposited with the CCDC.	2024-10-08 downloaded from the CCDC.
;
_audit_creation_date             2023-07-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1
_chemical_formula_moiety         'H2 O, C19 H12 N4'
_chemical_formula_sum            'C19 H14 N4 O'
_chemical_formula_weight         314.34
_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 0.0181 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                   10.8369(8)
_cell_length_b                   7.3671(7)
_cell_length_c                   20.0273(14)
_cell_angle_alpha                90
_cell_angle_beta                 104.078(7)
_cell_angle_gamma                90
_cell_volume                     1550.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7104
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.1980
_cell_measurement_theta_min      2.2310
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11198
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.904
_diffrn_reflns_theta_min         4.206
_diffrn_ambient_temperature      293
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  66.00   0.50    0.50    --   41.80 -77.00 -30.00   62
  2  ω    -36.00  32.00   0.50    0.50    --   41.80 -82.00 -60.00  136
  3  ω     23.00  95.00   0.50    0.50    --   41.80  65.00   0.00  144
  4  ω     11.00  62.00   0.50    0.50    --   41.80 -65.00-180.00  102
  5  ω     36.00  63.00   0.50    0.50    --   41.80 -65.00  60.00   54
  6  ω     42.00  68.00   0.50    0.50    --   41.80 -82.00 -60.00   52
  7  ω     32.00  69.00   0.50    0.50    --   41.80 -82.00-180.00   74
  8  ω    -47.00  -9.00   0.50    0.50    --   41.80 -77.00-120.00   76
  9  ω     85.00 111.00   0.50    0.50    --   41.80  65.00 -30.00   52
 10  ω      7.00  61.00   0.50    0.50    --   41.80 -77.00-120.00  108
 11  ω    -39.00 -13.00   0.50    0.50    --   41.80 -77.00 -30.00   52
 12  ω    -48.00  32.00   0.50    0.50    --   41.80 -77.00 120.00  160
 13  ω     25.00  79.00   0.50    0.50    --   41.80  65.00 -30.00  108
 14  ω    -46.00  29.00   0.50    0.50    --   41.80 -65.00  60.00  150
 15  ω    -48.00 -14.00   0.50    0.50    --   41.80 -54.00   0.00   68
 16  ω     93.00 129.00   0.50    0.50    --   41.80  54.00-150.00   72
 17  ω     19.00  45.00   0.50    0.50    --   41.80 -54.00   0.00   52
 18  ω     15.00  82.00   0.50    0.50    --   41.80  54.00-150.00  134
 19  ω     26.00  69.00   0.50    0.50    --   41.80 -82.00 120.00   86
 20  ω    -25.00   0.00   0.50    0.50    --   41.80 -82.00 120.00   50
 21  ω     17.00 168.00   0.50    0.50    --   93.70  25.00-150.00  302
 22  ω     12.00 118.00   0.50    0.50    --   93.70 -82.00  60.00  212
 23  ω     42.00 121.00   0.50    0.50    --   93.70 -59.00 150.00  158
 24  ω     65.00  97.00   0.50    0.50    --   93.70 -82.00-120.00   64
 25  ω      6.00 116.00   0.50    0.50    --   93.70 -82.00 -60.00  220
 26  ω     66.00  91.00   0.50    0.50    --   93.70 -82.00 120.00   50
 27  ω     72.00  98.00   0.50    0.50    --   93.70 -82.00 150.00   52
 28  ω     68.00  94.00   0.50    0.50    --   93.70 -82.00   0.00   52
 29  ω     80.00 105.00   0.50    0.50    --   93.70 -82.00 -30.00   50
 30  ω     32.00  66.00   0.50    0.50    --   93.70 -82.00   0.00   68
 31  ω     91.00 183.00   0.50    0.50    --   93.70   8.00 120.00  184
 32  ω     33.00  63.00   0.50    0.50    --   93.70 -82.00 -30.00   60
 33  ω     68.00  94.00   0.50    0.50    --   93.70 -82.00 -90.00   52
 34  ω     36.00 104.00   0.50    0.50    --   93.70 -82.00  90.00  136
 35  ω     13.00 116.00   0.50    0.50    --   93.70 -33.00 -90.00  206
 36  ω     75.00 104.00   0.50    0.50    --   93.70 -82.00-180.00   58
 37  ω      5.00 110.00   0.50    0.50    --   93.70 -50.00  60.00  210
 38  ω      5.00  49.00   0.50    0.50    --   93.70 -68.00 -90.00   88
 39  ω      4.00  42.00   0.50    0.50    --   93.70   8.00 120.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1392256000
_diffrn_orient_matrix_UB_12      -0.0191655000
_diffrn_orient_matrix_UB_13      0.0047765000
_diffrn_orient_matrix_UB_21      -0.0459749000
_diffrn_orient_matrix_UB_22      0.0595965000
_diffrn_orient_matrix_UB_23      -0.0757531000
_diffrn_orient_matrix_UB_31      -0.0005350000
_diffrn_orient_matrix_UB_32      -0.1993828000
_diffrn_orient_matrix_UB_33      -0.0230300000
_diffrn_oxdiff_digest_frames     
;
014adcc9efc15c2ee6a647e0c73b9f25130003076ed
;
_diffrn_oxdiff_digest_hkl        
;
01eab1ea960da7255b84b931c8cbb7054c99b3
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2446
_reflns_number_total             2766
_reflns_odcompleteness_completeness 99.30
_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 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.533
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.170
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2766
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0728
_refine_ls_restrained_S_all      1.116
_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)+(0.1195P)²+0.1310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.1791
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4), C7(H7), C10(H10), C6(H6), C9(H9), C3(H3), C19(H19), C2(H2), C1(H1),
 C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.90892(15) 0.89263(16) 0.36791(7) 0.0577(4) Uani 1 1 d . . . . .
H1A H 0.911718 0.974314 0.398180 0.086 Uiso 1 1 d G . . . .
H1B H 0.900988 0.942052 0.328719 0.086 Uiso 1 1 d G . . . .
N4 N 0.96963(13) 0.53291(18) 0.40701(7) 0.0391(4) Uani 1 1 d . . . . .
H4 H 0.946555 0.641410 0.393754 0.047 Uiso 1 1 calc R . . . .
N3 N 0.95406(14) 0.24002(18) 0.43449(7) 0.0443(4) Uani 1 1 d . . . . .
N1 N 0.16276(14) 0.6422(2) 0.25040(7) 0.0480(4) Uani 1 1 d . . . . .
C11 C 0.75362(17) 0.4026(2) 0.39285(8) 0.0394(4) Uani 1 1 d . . . . .
C13 C 0.89164(16) 0.3915(2) 0.41249(8) 0.0378(4) Uani 1 1 d . . . . .
C7 C 0.47345(17) 0.4269(2) 0.30494(8) 0.0441(4) Uani 1 1 d . . . . .
H7 H 0.509511 0.313639 0.301810 0.053 Uiso 1 1 calc R . . . .
C4 C 0.36443(16) 0.7652(2) 0.31655(8) 0.0395(4) Uani 1 1 d . . . . .
C5 C 0.28914(16) 0.6220(2) 0.28093(8) 0.0394(4) Uani 1 1 d . . . . .
C8 C 0.55085(16) 0.5708(2) 0.33987(8) 0.0397(4) Uani 1 1 d . . . . .
C14 C 1.09211(16) 0.4689(2) 0.42671(7) 0.0399(4) Uani 1 1 d . . . . .
C10 C 0.68786(16) 0.5517(2) 0.36657(8) 0.0410(4) Uani 1 1 d . . . . .
H10 H 0.735858 0.655755 0.365294 0.049 Uiso 1 1 calc R . . . .
N2 N 0.6336(2) 0.1210(2) 0.41997(12) 0.0809(7) Uani 1 1 d . . . . .
C6 C 0.34808(18) 0.4530(2) 0.27626(9) 0.0469(5) Uani 1 1 d . . . . .
H6 H 0.299780 0.357739 0.253002 0.056 Uiso 1 1 calc R . . . .
C9 C 0.49500(16) 0.7363(2) 0.34461(9) 0.0414(4) Uani 1 1 d . . . . .
H9 H 0.544806 0.831409 0.366931 0.050 Uiso 1 1 calc R . . . .
C15 C 1.08126(17) 0.2857(2) 0.44373(8) 0.0428(4) Uani 1 1 d . . . . .
C12 C 0.68765(18) 0.2420(2) 0.40672(10) 0.0513(5) Uani 1 1 d . . . . .
C3 C 0.30353(18) 0.9326(3) 0.32107(10) 0.0507(5) Uani 1 1 d . . . . .
H3 H 0.349269 1.030103 0.344221 0.061 Uiso 1 1 calc R . . . .
C19 C 1.20887(17) 0.5518(3) 0.43124(9) 0.0508(5) Uani 1 1 d . . . . .
H19 H 1.215082 0.673916 0.420734 0.061 Uiso 1 1 calc R . . . .
C2 C 0.1776(2) 0.9495(3) 0.29128(11) 0.0572(5) Uani 1 1 d . . . . .
H2 H 0.135738 1.058223 0.294283 0.069 Uiso 1 1 calc R . . . .
C1 C 0.11144(18) 0.8015(3) 0.25598(10) 0.0529(5) Uani 1 1 d . . . . .
H1 H 0.025538 0.816789 0.235082 0.063 Uiso 1 1 calc R . . . .
C16 C 1.1901(2) 0.1801(3) 0.46560(10) 0.0557(5) Uani 1 1 d . . . . .
H16 H 1.184742 0.058820 0.477427 0.067 Uiso 1 1 calc R . . . .
C17 C 1.3058(2) 0.2611(3) 0.46915(10) 0.0628(6) Uani 1 1 d . . . . .
H17 H 1.379804 0.192966 0.483217 0.075 Uiso 1 1 calc R . . . .
C18 C 1.31452(19) 0.4444(3) 0.45198(9) 0.0596(6) Uani 1 1 d . . . . .
H18 H 1.394361 0.494572 0.454756 0.072 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
O1 H1A 0.8495 . ?
O1 H1B 0.8503 . ?
N4 H4 0.8600 . ?
N4 C13 1.363(2) . ?
N4 C14 1.373(2) . ?
N3 C13 1.323(2) . ?
N3 C15 1.387(2) . ?
N1 C5 1.365(2) . ?
N1 C1 1.315(2) . ?
C11 C13 1.453(2) . ?
C11 C10 1.345(2) . ?
C11 C12 1.444(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.425(2) . ?
C7 C6 1.354(2) . ?
C4 C5 1.416(2) . ?
C4 C9 1.406(2) . ?
C4 C3 1.412(2) . ?
C5 C6 1.413(2) . ?
C8 C10 1.457(2) . ?
C8 C9 1.375(2) . ?
C14 C15 1.404(3) . ?
C14 C19 1.388(2) . ?
C10 H10 0.9300 . ?
N2 C12 1.133(3) . ?
C6 H6 0.9300 . ?
C9 H9 0.9300 . ?
C15 C16 1.392(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.355(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.370(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.399(3) . ?
C1 H1 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.375(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.402(3) . ?
C18 H18 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
H1A O1 H1B 109.5 . . ?
C13 N4 H4 126.6 . . ?
C13 N4 C14 106.82(14) . . ?
C14 N4 H4 126.6 . . ?
C13 N3 C15 104.51(14) . . ?
C1 N1 C5 117.25(16) . . ?
C10 C11 C13 124.35(15) . . ?
C10 C11 C12 120.30(16) . . ?
C12 C11 C13 115.27(14) . . ?
N4 C13 C11 123.55(14) . . ?
N3 C13 N4 113.25(15) . . ?
N3 C13 C11 123.13(15) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.84(16) . . ?
C9 C4 C5 119.26(15) . . ?
C9 C4 C3 123.20(16) . . ?
C3 C4 C5 117.53(16) . . ?
N1 C5 C4 122.46(15) . . ?
N1 C5 C6 119.13(15) . . ?
C6 C5 C4 118.41(16) . . ?
C7 C8 C10 122.27(15) . . ?
C9 C8 C7 118.50(16) . . ?
C9 C8 C10 119.10(15) . . ?
N4 C14 C15 105.52(14) . . ?
N4 C14 C19 132.06(17) . . ?
C19 C14 C15 122.42(16) . . ?
C11 C10 C8 128.15(16) . . ?
C11 C10 H10 115.9 . . ?
C8 C10 H10 115.9 . . ?
C7 C6 C5 121.35(17) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C4 C9 H9 119.2 . . ?
C8 C9 C4 121.61(16) . . ?
C8 C9 H9 119.2 . . ?
N3 C15 C14 109.90(14) . . ?
N3 C15 C16 130.16(18) . . ?
C16 C15 C14 119.94(18) . . ?
N2 C12 C11 176.5(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 C4 119.22(17) . . ?
C2 C3 H3 120.4 . . ?
C14 C19 H19 121.7 . . ?
C18 C19 C14 116.5(2) . . ?
C18 C19 H19 121.7 . . ?
C3 C2 H2 120.4 . . ?
C3 C2 C1 119.25(18) . . ?
C1 C2 H2 120.4 . . ?
N1 C1 C2 124.27(18) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C15 C16 H16 121.1 . . ?
C17 C16 C15 117.8(2) . . ?
C17 C16 H16 121.1 . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.36(19) . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 121.9(2) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?

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
N4 C14 C15 N3 -0.07(17) . . . . ?
N4 C14 C15 C16 179.57(14) . . . . ?
N4 C14 C19 C18 -178.72(16) . . . . ?
N3 C15 C16 C17 179.04(17) . . . . ?
N1 C5 C6 C7 179.19(15) . . . . ?
C13 N4 C14 C15 -0.06(16) . . . . ?
C13 N4 C14 C19 179.98(17) . . . . ?
C13 N3 C15 C14 0.17(17) . . . . ?
C13 N3 C15 C16 -179.42(17) . . . . ?
C13 C11 C10 C8 174.02(15) . . . . ?
C7 C8 C10 C11 -33.8(3) . . . . ?
C7 C8 C9 C4 0.6(2) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C4 C3 C2 C1 -0.9(3) . . . . ?
C5 N1 C1 C2 -0.4(3) . . . . ?
C5 C4 C9 C8 -1.7(2) . . . . ?
C5 C4 C3 C2 -0.4(2) . . . . ?
C8 C7 C6 C5 -1.2(3) . . . . ?
C14 N4 C13 N3 0.18(17) . . . . ?
C14 N4 C13 C11 -176.82(14) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C14 C19 C18 C17 -1.3(3) . . . . ?
C10 C11 C13 N4 0.8(2) . . . . ?
C10 C11 C13 N3 -175.95(16) . . . . ?
C10 C8 C9 C4 176.63(14) . . . . ?
C6 C7 C8 C10 -175.05(15) . . . . ?
C6 C7 C8 C9 0.9(2) . . . . ?
C9 C4 C5 N1 -177.76(15) . . . . ?
C9 C4 C5 C6 1.4(2) . . . . ?
C9 C4 C3 C2 178.67(17) . . . . ?
C9 C8 C10 C11 150.36(17) . . . . ?
C15 N3 C13 N4 -0.21(17) . . . . ?
C15 N3 C13 C11 176.80(14) . . . . ?
C15 C14 C19 C18 1.3(2) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C12 C11 C13 N4 -176.10(15) . . . . ?
C12 C11 C13 N3 7.2(2) . . . . ?
C12 C11 C10 C8 -9.3(3) . . . . ?
C3 C4 C5 N1 1.3(2) . . . . ?
C3 C4 C5 C6 -179.54(15) . . . . ?
C3 C4 C9 C8 179.29(15) . . . . ?
C3 C2 C1 N1 1.3(3) . . . . ?
C19 C14 C15 N3 179.90(14) . . . . ?
C19 C14 C15 C16 -0.5(2) . . . . ?
C1 N1 C5 C4 -0.9(2) . . . . ?
C1 N1 C5 C6 179.94(15) . . . . ?
C16 C17 C18 C19 0.3(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 3.300
_oxdiff_exptl_absorpt_empirical_full_min 0.380
