# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

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

data_exp_8186
_database_code_depnum_ccdc_archive 'CCDC 2073809'
loop_
_audit_author_name
_audit_author_address
'Kai Yang'
;School of Chemistry and Environment,South China Normal University
China
;
_audit_update_record             
;
2021-03-29 deposited with the CCDC.	2022-01-13 downloaded from the CCDC.
;
_audit_creation_date             2020-08-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H20 Cl2 N4'
_chemical_formula_sum            'C31 H20 Cl2 N4'
_chemical_formula_weight         519.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.1302(6)
_cell_length_b                   11.9492(9)
_cell_length_c                   12.8521(7)
_cell_angle_alpha                78.067(5)
_cell_angle_beta                 75.145(5)
_cell_angle_gamma                67.721(6)
_cell_volume                     1244.66(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3450
_cell_measurement_temperature    290
_cell_measurement_theta_max      28.5650
_cell_measurement_theta_min      4.0310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10948
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.325
_diffrn_reflns_theta_min         3.546
_diffrn_ambient_temperature      290
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -23.00  40.00   1.00    5.00    --  -16.43  19.00 -60.00   63
  2  ω      4.00  83.00   1.00    5.00    --   15.65  57.00-150.00   79
  3  ω      1.00  63.00   1.00    5.00    --   15.65  19.00-180.00   62
  4  ω    -14.00  27.00   1.00    5.00    --   15.65 -57.00 -60.00   41
  5  ω     -7.00  21.00   1.00    5.00    --  -16.43 -99.00-150.00   28
  6  ω    -30.00  51.00   1.00    5.00    --   15.65 -92.00  42.00   81
  7  ω    -22.00  22.00   1.00    5.00    --  -16.43 -99.00  90.00   44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0128844000
_diffrn_orient_matrix_UB_12      0.0633306000
_diffrn_orient_matrix_UB_13      -0.0092878000
_diffrn_orient_matrix_UB_21      0.0157872000
_diffrn_orient_matrix_UB_22      -0.0029975000
_diffrn_orient_matrix_UB_23      0.0519349000
_diffrn_orient_matrix_UB_31      0.0831656000
_diffrn_orient_matrix_UB_32      -0.0125670000
_diffrn_orient_matrix_UB_33      -0.0229426000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3919
_reflns_number_total             5742
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5742
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      1.012
_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)+(0.0463P)²+0.4685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1327
_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:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29),
  C30(H30), C31(H31)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.25746(11) 0.13315(8) 0.87909(5) 0.0859(3) Uani 1 1 d . . . . .
Cl2 Cl 0.96367(11) 0.36080(8) 0.50570(6) 0.0889(3) Uani 1 1 d . . . . .
N1 N 0.7448(2) 0.22728(15) 0.25246(12) 0.0362(4) Uani 1 1 d . . . . .
N2 N 0.6884(2) 0.34340(16) 0.08361(13) 0.0395(4) Uani 1 1 d . . . . .
N3 N 0.7491(2) 0.47316(17) -0.05737(13) 0.0435(4) Uani 1 1 d . . . . .
N4 N 0.8224(2) 0.12143(16) 0.40850(13) 0.0398(4) Uani 1 1 d . . . . .
C1 C 0.6963(2) 0.45868(19) 0.04693(16) 0.0376(5) Uani 1 1 d . . . . .
C2 C 0.6982(2) 0.18177(19) 0.36152(15) 0.0363(5) Uani 1 1 d . . . . .
C3 C 0.9556(3) 0.12820(19) 0.33073(16) 0.0381(5) Uani 1 1 d . . . . .
C4 C 0.9122(2) 0.19349(18) 0.23259(15) 0.0355(5) Uani 1 1 d . . . . .
C5 C 0.7760(2) 0.3636(2) -0.09323(16) 0.0409(5) Uani 1 1 d . . . . .
C6 C 0.6309(3) 0.2959(2) 0.18969(15) 0.0397(5) Uani 1 1 d . . . . .
C7 C 1.0256(3) 0.2158(2) 0.14374(17) 0.0427(5) Uani 1 1 d . . . . .
H7 H 0.996453 0.257550 0.078440 0.051 Uiso 1 1 calc R U . . .
C8 C 0.4743(3) 0.1767(2) 0.52354(16) 0.0408(5) Uani 1 1 d . . . . .
C9 C 0.5308(3) 0.2083(2) 0.40624(16) 0.0412(5) Uani 1 1 d . . . . .
C10 C 0.5423(3) 0.1956(2) 0.60038(17) 0.0452(5) Uani 1 1 d . . . . .
H10 H 0.633615 0.218062 0.577969 0.054 Uiso 1 1 calc R U . . .
C11 C 0.7217(3) 0.51553(19) 0.21811(16) 0.0403(5) Uani 1 1 d . . . . .
C12 C 1.1827(3) 0.1734(2) 0.15677(18) 0.0483(6) Uani 1 1 d . . . . .
H12 H 1.261352 0.188909 0.099518 0.058 Uiso 1 1 calc R U . . .
C13 C 1.1167(3) 0.0831(2) 0.34064(18) 0.0451(5) Uani 1 1 d . . . . .
H13 H 1.147768 0.037759 0.404399 0.054 Uiso 1 1 calc R U . . .
C14 C 0.8839(3) 0.4934(2) 0.20786(18) 0.0456(5) Uani 1 1 d . . . . .
H14 H 0.944503 0.509059 0.140037 0.055 Uiso 1 1 calc R U . . .
C15 C 0.7387(3) 0.2815(2) -0.00670(16) 0.0427(5) Uani 1 1 d . . . . .
C16 C 0.4740(3) 0.3146(2) 0.23080(17) 0.0491(6) Uani 1 1 d . . . . .
H16 H 0.398055 0.356139 0.187160 0.059 Uiso 1 1 calc R U . . .
C17 C 0.4768(3) 0.1815(2) 0.70918(18) 0.0507(6) Uani 1 1 d . . . . .
H17 H 0.521790 0.196128 0.760025 0.061 Uiso 1 1 calc R U . . .
C18 C 1.2280(3) 0.1075(2) 0.25367(19) 0.0492(6) Uani 1 1 d . . . . .
H18 H 1.335963 0.079724 0.259205 0.059 Uiso 1 1 calc R U . . .
C19 C 0.4233(3) 0.2715(2) 0.34000(18) 0.0502(6) Uani 1 1 d . . . . .
H19 H 0.313775 0.286537 0.367357 0.060 Uiso 1 1 calc R U . . .
C20 C 0.6443(3) 0.5551(2) 0.11976(18) 0.0479(6) Uani 1 1 d . . . . .
H20A H 0.528018 0.580476 0.143831 0.057 Uiso 1 1 calc R U . . .
H20B H 0.669851 0.625278 0.078400 0.057 Uiso 1 1 calc R U . . .
C21 C 0.3436(3) 0.1362(2) 0.55980(18) 0.0516(6) Uani 1 1 d . . . . .
H21 H 0.299282 0.119739 0.509638 0.062 Uiso 1 1 calc R U . . .
C22 C 0.3443(3) 0.1458(2) 0.74169(18) 0.0523(6) Uani 1 1 d . . . . .
C23 C 0.8684(3) 0.4259(2) 0.39577(18) 0.0520(6) Uani 1 1 d . . . . .
C24 C 0.8261(3) 0.3299(3) -0.19755(18) 0.0534(6) Uani 1 1 d . . . . .
H24 H 0.851675 0.383314 -0.256975 0.064 Uiso 1 1 calc R U . . .
C25 C 0.6327(3) 0.4964(2) 0.32079(18) 0.0502(6) Uani 1 1 d . . . . .
H25 H 0.522073 0.514238 0.330025 0.060 Uiso 1 1 calc R U . . .
C26 C 0.9580(3) 0.4486(2) 0.29599(19) 0.0535(6) Uani 1 1 d . . . . .
H26 H 1.067668 0.433879 0.287820 0.064 Uiso 1 1 calc R U . . .
C27 C 0.7061(3) 0.4512(2) 0.40943(18) 0.0551(6) Uani 1 1 d . . . . .
H27 H 0.645592 0.438052 0.477984 0.066 Uiso 1 1 calc R U . . .
C28 C 0.2788(3) 0.1201(2) 0.6686(2) 0.0580(7) Uani 1 1 d . . . . .
H28 H 0.191951 0.092350 0.692181 0.070 Uiso 1 1 calc R U . . .
C29 C 0.8366(3) 0.2166(3) -0.2101(2) 0.0644(7) Uani 1 1 d . . . . .
H29 H 0.867869 0.193294 -0.279401 0.077 Uiso 1 1 calc R U . . .
C30 C 0.7516(4) 0.1665(2) -0.0184(2) 0.0651(8) Uani 1 1 d . . . . .
H30 H 0.727590 0.112228 0.040775 0.078 Uiso 1 1 calc R U . . .
C31 C 0.8019(4) 0.1354(3) -0.1225(2) 0.0728(8) Uani 1 1 d . . . . .
H31 H 0.812775 0.058064 -0.134002 0.087 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C22 1.742(2) . ?
Cl2 C23 1.738(2) . ?
N1 C2 1.413(2) . ?
N1 C4 1.392(3) . ?
N1 C6 1.384(3) . ?
N2 C1 1.384(3) . ?
N2 C6 1.413(2) . ?
N2 C15 1.389(3) . ?
N3 C1 1.302(2) . ?
N3 C5 1.391(3) . ?
N4 C2 1.312(3) . ?
N4 C3 1.379(3) . ?
C1 C20 1.494(3) . ?
C2 C9 1.423(3) . ?
C3 C4 1.404(3) . ?
C3 C13 1.392(3) . ?
C4 C7 1.387(3) . ?
C5 C15 1.387(3) . ?
C5 C24 1.392(3) . ?
C6 C16 1.342(3) . ?
C7 H7 0.9300 . ?
C7 C12 1.371(3) . ?
C8 C9 1.481(3) . ?
C8 C10 1.387(3) . ?
C8 C21 1.391(3) . ?
C9 C19 1.363(3) . ?
C10 H10 0.9300 . ?
C10 C17 1.375(3) . ?
C11 C14 1.377(3) . ?
C11 C20 1.509(3) . ?
C11 C25 1.386(3) . ?
C12 H12 0.9300 . ?
C12 C18 1.398(3) . ?
C13 H13 0.9300 . ?
C13 C18 1.369(3) . ?
C14 H14 0.9300 . ?
C14 C26 1.377(3) . ?
C15 C30 1.371(3) . ?
C16 H16 0.9300 . ?
C16 C19 1.414(3) . ?
C17 H17 0.9300 . ?
C17 C22 1.371(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21 0.9300 . ?
C21 C28 1.376(3) . ?
C22 C28 1.372(4) . ?
C23 C26 1.369(3) . ?
C23 C27 1.367(3) . ?
C24 H24 0.9300 . ?
C24 C29 1.361(4) . ?
C25 H25 0.9300 . ?
C25 C27 1.379(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C29 C31 1.381(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.378(4) . ?
C31 H31 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
C4 N1 C2 106.24(15) . . ?
C6 N1 C2 121.08(17) . . ?
C6 N1 C4 132.60(17) . . ?
C1 N2 C6 128.62(18) . . ?
C1 N2 C15 106.78(16) . . ?
C15 N2 C6 124.47(18) . . ?
C1 N3 C5 105.76(17) . . ?
C2 N4 C3 105.25(16) . . ?
N2 C1 C20 122.94(18) . . ?
N3 C1 N2 112.16(19) . . ?
N3 C1 C20 124.87(19) . . ?
N1 C2 C9 118.61(17) . . ?
N4 C2 N1 112.28(18) . . ?
N4 C2 C9 129.08(18) . . ?
N4 C3 C4 111.72(18) . . ?
N4 C3 C13 128.33(19) . . ?
C13 C3 C4 119.92(19) . . ?
N1 C4 C3 104.49(16) . . ?
C7 C4 N1 133.45(18) . . ?
C7 C4 C3 122.01(19) . . ?
N3 C5 C24 130.4(2) . . ?
C15 C5 N3 110.29(18) . . ?
C15 C5 C24 119.2(2) . . ?
N1 C6 N2 117.01(18) . . ?
C16 C6 N1 119.75(18) . . ?
C16 C6 N2 123.24(18) . . ?
C4 C7 H7 121.6 . . ?
C12 C7 C4 116.8(2) . . ?
C12 C7 H7 121.6 . . ?
C10 C8 C9 120.8(2) . . ?
C10 C8 C21 118.2(2) . . ?
C21 C8 C9 120.8(2) . . ?
C2 C9 C8 120.77(18) . . ?
C19 C9 C2 118.24(19) . . ?
C19 C9 C8 120.8(2) . . ?
C8 C10 H10 119.5 . . ?
C17 C10 C8 121.0(2) . . ?
C17 C10 H10 119.5 . . ?
C14 C11 C20 120.93(19) . . ?
C14 C11 C25 118.2(2) . . ?
C25 C11 C20 120.9(2) . . ?
C7 C12 H12 119.1 . . ?
C7 C12 C18 121.9(2) . . ?
C18 C12 H12 119.1 . . ?
C3 C13 H13 121.0 . . ?
C18 C13 C3 118.0(2) . . ?
C18 C13 H13 121.0 . . ?
C11 C14 H14 119.3 . . ?
C26 C14 C11 121.3(2) . . ?
C26 C14 H14 119.3 . . ?
C5 C15 N2 105.0(2) . . ?
C30 C15 N2 132.0(2) . . ?
C30 C15 C5 123.0(2) . . ?
C6 C16 H16 119.8 . . ?
C6 C16 C19 120.4(2) . . ?
C19 C16 H16 119.8 . . ?
C10 C17 H17 120.4 . . ?
C22 C17 C10 119.1(2) . . ?
C22 C17 H17 120.4 . . ?
C12 C18 H18 119.3 . . ?
C13 C18 C12 121.3(2) . . ?
C13 C18 H18 119.3 . . ?
C9 C19 C16 121.7(2) . . ?
C9 C19 H19 119.2 . . ?
C16 C19 H19 119.2 . . ?
C1 C20 C11 114.13(18) . . ?
C1 C20 H20A 108.7 . . ?
C1 C20 H20B 108.7 . . ?
C11 C20 H20A 108.7 . . ?
C11 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C8 C21 H21 119.4 . . ?
C28 C21 C8 121.1(2) . . ?
C28 C21 H21 119.4 . . ?
C17 C22 Cl1 119.0(2) . . ?
C17 C22 C28 121.6(2) . . ?
C28 C22 Cl1 119.4(2) . . ?
C26 C23 Cl2 119.4(2) . . ?
C27 C23 Cl2 119.70(19) . . ?
C27 C23 C26 120.9(2) . . ?
C5 C24 H24 121.0 . . ?
C29 C24 C5 118.1(2) . . ?
C29 C24 H24 121.0 . . ?
C11 C25 H25 119.6 . . ?
C27 C25 C11 120.8(2) . . ?
C27 C25 H25 119.6 . . ?
C14 C26 H26 120.4 . . ?
C23 C26 C14 119.2(2) . . ?
C23 C26 H26 120.4 . . ?
C23 C27 C25 119.5(2) . . ?
C23 C27 H27 120.3 . . ?
C25 C27 H27 120.3 . . ?
C21 C28 H28 120.6 . . ?
C22 C28 C21 118.9(2) . . ?
C22 C28 H28 120.6 . . ?
C24 C29 H29 119.2 . . ?
C24 C29 C31 121.7(2) . . ?
C31 C29 H29 119.2 . . ?
C15 C30 H30 121.7 . . ?
C15 C30 C31 116.5(2) . . ?
C31 C30 H30 121.7 . . ?
C29 C31 H31 119.3 . . ?
C30 C31 C29 121.4(3) . . ?
C30 C31 H31 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C22 C28 C21 176.85(19) . . . . ?
Cl2 C23 C26 C14 176.18(19) . . . . ?
Cl2 C23 C27 C25 -176.34(19) . . . . ?
N1 C2 C9 C8 -172.08(19) . . . . ?
N1 C2 C9 C19 3.2(3) . . . . ?
N1 C4 C7 C12 175.6(2) . . . . ?
N1 C6 C16 C19 4.2(4) . . . . ?
N2 C1 C20 C11 53.1(3) . . . . ?
N2 C6 C16 C19 -175.7(2) . . . . ?
N2 C15 C30 C31 177.9(2) . . . . ?
N3 C1 C20 C11 -129.1(2) . . . . ?
N3 C5 C15 N2 -0.1(2) . . . . ?
N3 C5 C15 C30 179.0(2) . . . . ?
N3 C5 C24 C29 -177.4(2) . . . . ?
N4 C2 C9 C8 5.8(4) . . . . ?
N4 C2 C9 C19 -178.9(2) . . . . ?
N4 C3 C4 N1 -0.1(2) . . . . ?
N4 C3 C4 C7 177.67(19) . . . . ?
N4 C3 C13 C18 -175.9(2) . . . . ?
C1 N2 C6 N1 -97.4(3) . . . . ?
C1 N2 C6 C16 82.4(3) . . . . ?
C1 N2 C15 C5 0.6(2) . . . . ?
C1 N2 C15 C30 -178.5(3) . . . . ?
C1 N3 C5 C15 -0.4(2) . . . . ?
C1 N3 C5 C24 177.1(2) . . . . ?
C2 N1 C4 C3 0.8(2) . . . . ?
C2 N1 C4 C7 -176.6(2) . . . . ?
C2 N1 C6 N2 176.41(18) . . . . ?
C2 N1 C6 C16 -3.5(3) . . . . ?
C2 N4 C3 C4 -0.7(2) . . . . ?
C2 N4 C3 C13 177.2(2) . . . . ?
C2 C9 C19 C16 -2.6(4) . . . . ?
C3 N4 C2 N1 1.2(2) . . . . ?
C3 N4 C2 C9 -176.8(2) . . . . ?
C3 C4 C7 C12 -1.5(3) . . . . ?
C3 C13 C18 C12 -1.4(4) . . . . ?
C4 N1 C2 N4 -1.4(2) . . . . ?
C4 N1 C2 C9 176.89(19) . . . . ?
C4 N1 C6 N2 0.1(3) . . . . ?
C4 N1 C6 C16 -179.8(2) . . . . ?
C4 C3 C13 C18 1.8(3) . . . . ?
C4 C7 C12 C18 1.9(3) . . . . ?
C5 N3 C1 N2 0.8(2) . . . . ?
C5 N3 C1 C20 -177.18(19) . . . . ?
C5 C15 C30 C31 -1.0(4) . . . . ?
C5 C24 C29 C31 -1.2(4) . . . . ?
C6 N1 C2 N4 -178.50(19) . . . . ?
C6 N1 C2 C9 -0.3(3) . . . . ?
C6 N1 C4 C3 177.5(2) . . . . ?
C6 N1 C4 C7 0.1(4) . . . . ?
C6 N2 C1 N3 -176.86(19) . . . . ?
C6 N2 C1 C20 1.2(3) . . . . ?
C6 N2 C15 C5 176.74(18) . . . . ?
C6 N2 C15 C30 -2.3(4) . . . . ?
C6 C16 C19 C9 -1.1(4) . . . . ?
C7 C12 C18 C13 -0.5(4) . . . . ?
C8 C9 C19 C16 172.7(2) . . . . ?
C8 C10 C17 C22 1.4(3) . . . . ?
C8 C21 C28 C22 0.6(4) . . . . ?
C9 C8 C10 C17 171.4(2) . . . . ?
C9 C8 C21 C28 -172.4(2) . . . . ?
C10 C8 C9 C2 41.7(3) . . . . ?
C10 C8 C9 C19 -133.5(2) . . . . ?
C10 C8 C21 C28 2.7(4) . . . . ?
C10 C17 C22 Cl1 -177.82(18) . . . . ?
C10 C17 C22 C28 2.0(4) . . . . ?
C11 C14 C26 C23 -0.2(4) . . . . ?
C11 C25 C27 C23 0.5(4) . . . . ?
C13 C3 C4 N1 -178.20(19) . . . . ?
C13 C3 C4 C7 -0.4(3) . . . . ?
C14 C11 C20 C1 68.9(3) . . . . ?
C14 C11 C25 C27 -2.9(3) . . . . ?
C15 N2 C1 N3 -1.0(2) . . . . ?
C15 N2 C1 C20 177.11(19) . . . . ?
C15 N2 C6 N1 87.3(3) . . . . ?
C15 N2 C6 C16 -92.8(3) . . . . ?
C15 C5 C24 C29 -0.1(3) . . . . ?
C15 C30 C31 C29 -0.3(4) . . . . ?
C17 C22 C28 C21 -3.0(4) . . . . ?
C20 C11 C14 C26 -175.1(2) . . . . ?
C20 C11 C25 C27 174.9(2) . . . . ?
C21 C8 C9 C2 -143.3(2) . . . . ?
C21 C8 C9 C19 41.5(3) . . . . ?
C21 C8 C10 C17 -3.7(3) . . . . ?
C24 C5 C15 N2 -177.98(19) . . . . ?
C24 C5 C15 C30 1.2(3) . . . . ?
C24 C29 C31 C30 1.5(5) . . . . ?
C25 C11 C14 C26 2.7(3) . . . . ?
C25 C11 C20 C1 -108.9(2) . . . . ?
C26 C23 C27 C25 2.2(4) . . . . ?
C27 C23 C26 C14 -2.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.656
_oxdiff_exptl_absorpt_empirical_full_min 0.716
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_7056
_database_code_depnum_ccdc_archive 'CCDC 2073813'
loop_
_audit_author_name
_audit_author_address
'Kai Yang'
;School of Chemistry and Environment,South China Normal University
China
;
_audit_update_record             
;
2021-03-29 deposited with the CCDC.	2022-01-13 downloaded from the CCDC.
;
_audit_creation_date             2019-07-18
_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        ?
_chemical_formula_moiety         'C19 H14 N4'
_chemical_formula_sum            'C19 H14 N4'
_chemical_formula_weight         298.34
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.8364(10)
_cell_length_b                   16.955(3)
_cell_length_c                   11.2061(19)
_cell_angle_alpha                90
_cell_angle_beta                 94.406(13)
_cell_angle_gamma                90
_cell_volume                     1484.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    826
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      21.3680
_cell_measurement_theta_min      4.0620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.1089
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6190
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.507
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00  49.00   1.00   10.00    --  -16.28   0.00   0.00  107
  2  ω    -16.00  11.00   1.00   10.00    --  -16.28 -99.00 120.00   27
  3  ω    -47.00  20.00   1.00   10.00    --   15.49 -57.00-150.00   67
  4  ω     63.00  88.00   1.00   10.00    --   15.49-178.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0183991000
_diffrn_orient_matrix_UB_12      0.0218636000
_diffrn_orient_matrix_UB_13      -0.0514037000
_diffrn_orient_matrix_UB_21      -0.0323888000
_diffrn_orient_matrix_UB_22      -0.0313366000
_diffrn_orient_matrix_UB_23      -0.0371215000
_diffrn_orient_matrix_UB_31      -0.0827679000
_diffrn_orient_matrix_UB_32      0.0171136000
_diffrn_orient_matrix_UB_33      -0.0022782000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1436
_reflns_number_total             2613
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2613
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1349
_refine_ls_R_factor_gt           0.0647
_refine_ls_restrained_S_all      1.012
_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)+(0.0193P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.1115
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C16(H16),
 C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.7392(3) 0.54477(15) 0.5892(2) 0.0338(6) Uani 1 1 d . . . . .
N2 N 0.7136(3) 0.63742(14) 0.7461(2) 0.0371(7) Uani 1 1 d . . . . .
N3 N 0.8633(3) 0.66992(15) 0.9174(2) 0.0422(7) Uani 1 1 d . . . . .
N4 N 0.7788(3) 0.44905(17) 0.4529(2) 0.0445(7) Uani 1 1 d . . . . .
C1 C 0.6817(3) 0.61760(19) 0.6238(3) 0.0369(8) Uani 1 1 d . . . . .
C2 C 0.8667(3) 0.66310(19) 0.8027(3) 0.0400(8) Uani 1 1 d . . . . .
C3 C 0.6984(3) 0.64643(18) 0.9412(3) 0.0374(8) Uani 1 1 d . . . . .
C4 C 0.6028(3) 0.62609(18) 0.8356(3) 0.0362(8) Uani 1 1 d . . . . .
C5 C 0.4342(3) 0.60172(19) 0.8320(3) 0.0514(10) Uani 1 1 d . . . . .
H5 H 0.372477 0.588586 0.760581 0.062 Uiso 1 1 calc R . . . .
C6 C 0.3636(4) 0.5981(2) 0.9400(4) 0.0627(11) Uani 1 1 d . . . . .
H6 H 0.250203 0.582199 0.941923 0.075 Uiso 1 1 calc R . . . .
C7 C 0.4566(4) 0.6175(2) 1.0471(3) 0.0613(11) Uani 1 1 d . . . . .
H7 H 0.404566 0.613734 1.118690 0.074 Uiso 1 1 calc R . . . .
C8 C 0.6239(4) 0.64195(19) 1.0486(3) 0.0500(10) Uani 1 1 d . . . . .
H8 H 0.685195 0.655167 1.120159 0.060 Uiso 1 1 calc R . . . .
C9 C 1.0149(3) 0.6803(2) 0.7312(3) 0.0537(10) Uani 1 1 d . . . . .
H9A H 1.050221 0.632638 0.693804 0.081 Uiso 1 1 calc GR . . . .
H9B H 1.108031 0.700531 0.782897 0.081 Uiso 1 1 calc GR . . . .
H9C H 0.981992 0.718643 0.670784 0.081 Uiso 1 1 calc GR . . . .
C10 C 0.5981(3) 0.6650(2) 0.5434(3) 0.0471(9) Uani 1 1 d . . . . .
H10 H 0.559035 0.714031 0.566891 0.056 Uiso 1 1 calc R . . . .
C11 C 0.5693(4) 0.6405(2) 0.4224(3) 0.0528(10) Uani 1 1 d . . . . .
H11 H 0.508583 0.672960 0.367401 0.063 Uiso 1 1 calc R . . . .
C12 C 0.6288(4) 0.5707(2) 0.3865(3) 0.0467(9) Uani 1 1 d . . . . .
H12 H 0.611930 0.555921 0.306582 0.056 Uiso 1 1 calc R . . . .
C13 C 0.7167(3) 0.5198(2) 0.4698(3) 0.0393(8) Uani 1 1 d . . . . .
C14 C 0.8438(3) 0.4257(2) 0.5657(3) 0.0400(8) Uani 1 1 d . . . . .
C15 C 0.8213(3) 0.48324(18) 0.6522(3) 0.0344(8) Uani 1 1 d . . . . .
C16 C 0.8736(3) 0.47129(19) 0.7719(3) 0.0424(9) Uani 1 1 d . . . . .
H16 H 0.857861 0.509665 0.829362 0.051 Uiso 1 1 calc R . . . .
C17 C 0.9495(3) 0.4005(2) 0.8018(3) 0.0495(9) Uani 1 1 d . . . . .
H17 H 0.987094 0.390955 0.881268 0.059 Uiso 1 1 calc R . . . .
C18 C 0.9718(4) 0.3424(2) 0.7164(4) 0.0532(10) Uani 1 1 d . . . . .
H18 H 1.023178 0.294833 0.740011 0.064 Uiso 1 1 calc R . . . .
C19 C 0.9195(4) 0.3541(2) 0.5988(3) 0.0511(10) Uani 1 1 d . . . . .
H19 H 0.934090 0.315011 0.542235 0.061 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.381(4) . ?
N1 C13 1.402(3) . ?
N1 C15 1.390(3) . ?
N2 C1 1.414(3) . ?
N2 C2 1.384(3) . ?
N2 C4 1.390(3) . ?
N3 C2 1.294(4) . ?
N3 C3 1.397(3) . ?
N4 C13 1.314(4) . ?
N4 C14 1.383(4) . ?
C1 C10 1.340(4) . ?
C2 C9 1.489(4) . ?
C3 C4 1.395(4) . ?
C3 C8 1.379(4) . ?
C4 C5 1.381(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.395(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.373(4) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C11 1.420(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.344(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.410(4) . ?
C14 C15 1.397(4) . ?
C14 C19 1.389(4) . ?
C15 C16 1.388(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.369(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.394(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.364(4) . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C13 121.2(3) . . ?
C1 N1 C15 132.6(3) . . ?
C15 N1 C13 106.1(2) . . ?
C2 N2 C1 127.0(2) . . ?
C2 N2 C4 106.3(2) . . ?
C4 N2 C1 126.3(2) . . ?
C2 N3 C3 104.7(2) . . ?
C13 N4 C14 104.2(3) . . ?
N1 C1 N2 116.6(3) . . ?
C10 C1 N1 120.1(3) . . ?
C10 C1 N2 123.3(3) . . ?
N2 C2 C9 120.0(3) . . ?
N3 C2 N2 113.6(3) . . ?
N3 C2 C9 126.4(3) . . ?
C4 C3 N3 110.7(3) . . ?
C8 C3 N3 130.0(3) . . ?
C8 C3 C4 119.4(3) . . ?
N2 C4 C3 104.7(2) . . ?
C5 C4 N2 132.0(3) . . ?
C5 C4 C3 123.3(3) . . ?
C4 C5 H5 122.0 . . ?
C6 C5 C4 116.0(3) . . ?
C6 C5 H5 122.0 . . ?
C5 C6 H6 119.0 . . ?
C5 C6 C7 121.9(3) . . ?
C7 C6 H6 119.0 . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.2(3) . . ?
C8 C7 H7 119.4 . . ?
C3 C8 H8 120.9 . . ?
C7 C8 C3 118.3(3) . . ?
C7 C8 H8 120.9 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C10 H10 120.0 . . ?
C1 C10 C11 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
N1 C13 C12 117.8(3) . . ?
N4 C13 N1 113.1(3) . . ?
N4 C13 C12 129.1(3) . . ?
N4 C14 C15 112.1(3) . . ?
N4 C14 C19 127.9(3) . . ?
C19 C14 C15 119.9(3) . . ?
N1 C15 C14 104.5(3) . . ?
C16 C15 N1 133.8(3) . . ?
C16 C15 C14 121.7(3) . . ?
C15 C16 H16 121.5 . . ?
C17 C16 C15 117.1(3) . . ?
C17 C16 H16 121.5 . . ?
C16 C17 H17 119.1 . . ?
C16 C17 C18 121.8(3) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.1(3) . . ?
C19 C18 H18 119.5 . . ?
C14 C19 H19 120.8 . . ?
C18 C19 C14 118.4(3) . . ?
C18 C19 H19 120.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C10 C11 -0.2(4) . . . . ?
N1 C15 C16 C17 178.6(3) . . . . ?
N2 C1 C10 C11 -179.2(3) . . . . ?
N2 C4 C5 C6 -179.3(3) . . . . ?
N3 C3 C4 N2 0.2(3) . . . . ?
N3 C3 C4 C5 -179.0(3) . . . . ?
N3 C3 C8 C7 179.3(3) . . . . ?
N4 C14 C15 N1 -0.3(3) . . . . ?
N4 C14 C15 C16 178.5(2) . . . . ?
N4 C14 C19 C18 -178.5(3) . . . . ?
C1 N1 C13 N4 -179.8(2) . . . . ?
C1 N1 C13 C12 -1.8(4) . . . . ?
C1 N1 C15 C14 179.5(3) . . . . ?
C1 N1 C15 C16 1.0(5) . . . . ?
C1 N2 C2 N3 -173.9(3) . . . . ?
C1 N2 C2 C9 6.3(5) . . . . ?
C1 N2 C4 C3 173.5(3) . . . . ?
C1 N2 C4 C5 -7.3(5) . . . . ?
C1 C10 C11 C12 -1.7(5) . . . . ?
C2 N2 C1 N1 77.9(4) . . . . ?
C2 N2 C1 C10 -103.0(3) . . . . ?
C2 N2 C4 C3 0.3(3) . . . . ?
C2 N2 C4 C5 179.4(3) . . . . ?
C2 N3 C3 C4 -0.7(3) . . . . ?
C2 N3 C3 C8 180.0(3) . . . . ?
C3 N3 C2 N2 0.9(3) . . . . ?
C3 N3 C2 C9 -179.4(3) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C4 N2 C1 N1 -94.0(3) . . . . ?
C4 N2 C1 C10 85.1(4) . . . . ?
C4 N2 C2 N3 -0.7(4) . . . . ?
C4 N2 C2 C9 179.5(3) . . . . ?
C4 C3 C8 C7 -0.1(5) . . . . ?
C4 C5 C6 C7 -0.3(5) . . . . ?
C5 C6 C7 C8 0.6(6) . . . . ?
C6 C7 C8 C3 -0.4(5) . . . . ?
C8 C3 C4 N2 179.7(3) . . . . ?
C8 C3 C4 C5 0.4(5) . . . . ?
C10 C11 C12 C13 1.8(5) . . . . ?
C11 C12 C13 N1 -0.1(4) . . . . ?
C11 C12 C13 N4 177.6(3) . . . . ?
C13 N1 C1 N2 -179.0(2) . . . . ?
C13 N1 C1 C10 1.9(4) . . . . ?
C13 N1 C15 C14 0.5(3) . . . . ?
C13 N1 C15 C16 -178.0(3) . . . . ?
C13 N4 C14 C15 -0.1(3) . . . . ?
C13 N4 C14 C19 177.8(3) . . . . ?
C14 N4 C13 N1 0.5(3) . . . . ?
C14 N4 C13 C12 -177.3(3) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 N1 C1 N2 2.2(4) . . . . ?
C15 N1 C1 C10 -176.9(3) . . . . ?
C15 N1 C13 N4 -0.7(3) . . . . ?
C15 N1 C13 C12 177.4(2) . . . . ?
C15 C14 C19 C18 -0.7(5) . . . . ?
C15 C16 C17 C18 -0.7(4) . . . . ?
C16 C17 C18 C19 0.4(5) . . . . ?
C17 C18 C19 C14 0.3(5) . . . . ?
C19 C14 C15 N1 -178.4(2) . . . . ?
C19 C14 C15 C16 0.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.083
_oxdiff_exptl_absorpt_empirical_full_min 0.910
####################################################################### 
# 
# 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_yk
_database_code_depnum_ccdc_archive 'CCDC 2107172'
loop_
_audit_author_name
_audit_author_address
'Kai Yang'
;School of Chemistry,South China Normal University
China
;
_audit_update_record             
;
2021-09-02 deposited with the CCDC.	2022-01-13 downloaded from the CCDC.
;
_audit_creation_date             2021-09-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 N4 O'
_chemical_formula_sum            'C21 H16 N4 O'
_chemical_formula_weight         340.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHON
_chemical_oxdiff_usercomment     YK414
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                   14.90184(14)
_cell_length_b                   25.7373(3)
_cell_length_c                   8.75564(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.9084(9)
_cell_angle_gamma                90
_cell_volume                     3350.27(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13133
_cell_measurement_temperature    149.94(13)
_cell_measurement_theta_max      74.1100
_cell_measurement_theta_min      3.3920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            23917
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.166
_diffrn_reflns_theta_min         2.972
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.94(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  32.00   1.00    1.00    --  -41.14  57.00 -30.00   86
  2  ω   -121.00  -1.00   1.00    1.00    --  -41.14 -19.00 -30.00  120
  3  ω   -112.00 -15.00   1.00    1.00    --  -41.14 -77.00-150.00   97
  4  ω    -66.00  -8.00   1.00    1.00    --  -41.14  57.00  60.00   58
  5  ω     24.00  51.00   1.00    1.00    --   41.14-125.00-120.00   27
  6  ω     48.00  96.00   1.00    1.00    --   41.14-125.00-180.00   48
  7  ω     27.00 108.00   1.00    1.21    --  107.79 -94.00-120.00   81
  8  ω     95.00 176.00   1.00    1.21    --  107.79 125.00 -60.00   81
  9  ω    106.00 172.00   1.00    1.21    --  107.79  30.00  30.00   66
 10  ω    150.00 177.00   1.00    1.21    --  107.79  30.00   0.00   27
 11  ω     38.00 136.00   1.00    1.21    --  107.79 -30.00 -90.00   98
 12  ω     88.00 118.00   1.00    1.21    --  107.79-125.00-180.00   30
 13  ω     81.00 141.00   1.00    1.21    --  107.79  30.00   0.00   60
 14  ω     83.00 118.00   1.00    1.21    --  107.79-125.00  90.00   35
 15  ω     44.00 136.00   1.00    1.21    --  107.79 -15.00-180.00   92
 16  ω     32.00 133.00   1.00    1.21    --  107.79 -77.00 -90.00  101
 17  ω     37.00 122.00   1.00    1.21    --  107.79 -61.00  30.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0584833000
_diffrn_orient_matrix_UB_12      -0.0492142000
_diffrn_orient_matrix_UB_13      0.0193033000
_diffrn_orient_matrix_UB_21      0.0853500000
_diffrn_orient_matrix_UB_22      0.0339260000
_diffrn_orient_matrix_UB_23      0.0143235000
_diffrn_orient_matrix_UB_31      -0.0063590000
_diffrn_orient_matrix_UB_32      0.0026135000
_diffrn_orient_matrix_UB_33      0.1747215000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5971
_reflns_number_total             6731
_reflns_odcompleteness_completeness 99.98
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.00144(10)
_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   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     472
_refine_ls_number_reflns         6731
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+0.9397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1036
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C010(H010), C011(H011), C012(H012), C013(H013), C014(H014), C015(H015),
 C016(H016), C017(H017), C018(H018), C01B(H01B), C01C(H01C), C01D(H01D),
 C01E(H01E), C01G(H01H)
2.b Idealised Me refined as rotating group:
 C01A(H01I,H01J,H01K), C01F(H01A,H01F,H01G)
;
_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
O001 O 0.29393(6) 0.49086(3) 0.40898(11) 0.0348(2) Uani 1 1 d . . . . .
O002 O -0.05664(7) 0.72016(4) 0.55978(11) 0.0369(2) Uani 1 1 d . . . . .
N003 N -0.02229(7) 0.44403(4) 0.16711(11) 0.0255(2) Uani 1 1 d . . . . .
N004 N 0.45854(7) 0.78208(4) 0.51152(12) 0.0295(2) Uani 1 1 d . . . . .
N005 N 0.07498(7) 0.51099(4) 0.21168(12) 0.0279(2) Uani 1 1 d . . . . .
N006 N -0.11501(7) 0.37117(4) 0.09311(12) 0.0275(2) Uani 1 1 d . . . . .
N007 N 0.41704(8) 0.86777(4) 0.42914(13) 0.0338(3) Uani 1 1 d . . . . .
N008 N 0.51000(7) 0.70467(5) 0.60567(13) 0.0347(3) Uani 1 1 d . . . . .
N009 N -0.14835(8) 0.31605(5) -0.09635(14) 0.0366(3) Uani 1 1 d . . . . .
C00A C -0.00701(8) 0.49384(5) 0.23198(13) 0.0255(2) Uani 1 1 d . . . . .
C00B C 0.11536(8) 0.47184(5) 0.13340(14) 0.0281(3) Uani 1 1 d . . . . .
C00C C 0.05761(8) 0.42952(5) 0.10419(13) 0.0266(3) Uani 1 1 d . . . . .
C00D C -0.06286(9) 0.66997(5) 0.50882(14) 0.0283(3) Uani 1 1 d . . . . .
C00E C -0.06754(8) 0.56936(5) 0.38312(14) 0.0259(3) Uani 1 1 d . . . . .
C00F C 0.40027(9) 0.81378(5) 0.42437(14) 0.0297(3) Uani 1 1 d . . . . .
C00G C -0.10462(8) 0.41956(5) 0.16934(14) 0.0277(3) Uani 1 1 d . . . . .
C00H C -0.07819(8) 0.51797(5) 0.30877(13) 0.0266(3) Uani 1 1 d . . . . .
C00I C 0.37424(8) 0.70524(5) 0.42325(14) 0.0285(3) Uani 1 1 d . . . . .
C00J C 0.35732(8) 0.64859(5) 0.42550(14) 0.0284(3) Uani 1 1 d . . . . .
C00K C 0.31948(9) 0.54185(5) 0.41414(14) 0.0293(3) Uani 1 1 d . . . . .
C00L C -0.11978(9) 0.63267(5) 0.56345(14) 0.0296(3) Uani 1 1 d . . . . .
H00L H -0.1567 0.6409 0.6415 0.036 Uiso 1 1 calc R . . . .
C00M C 0.44828(8) 0.72773(5) 0.51361(14) 0.0292(3) Uani 1 1 d . . . . .
C00N C 0.53363(9) 0.79322(6) 0.61089(15) 0.0333(3) Uani 1 1 d . . . . .
C00O C -0.00846(9) 0.60713(5) 0.33393(14) 0.0297(3) Uani 1 1 d . . . . .
H00O H 0.0301 0.5988 0.2584 0.036 Uiso 1 1 calc R . . . .
C00P C -0.17224(9) 0.44289(5) 0.23692(15) 0.0330(3) Uani 1 1 d . . . . .
H00P H -0.2279 0.4266 0.2379 0.040 Uiso 1 1 calc R . . . .
C00Q C -0.00617(9) 0.65651(5) 0.39515(15) 0.0319(3) Uani 1 1 d . . . . .
H00Q H 0.0335 0.6810 0.3603 0.038 Uiso 1 1 calc R . . . .
C00R C -0.12140(8) 0.58305(5) 0.50109(14) 0.0284(3) Uani 1 1 d . . . . .
H00R H -0.1594 0.5582 0.5390 0.034 Uiso 1 1 calc R . . . .
C00S C 0.26852(9) 0.63012(5) 0.41484(14) 0.0298(3) Uani 1 1 d . . . . .
H00S H 0.2213 0.6538 0.4118 0.036 Uiso 1 1 calc R . . . .
C00T C 0.33180(9) 0.79246(5) 0.33784(15) 0.0312(3) Uani 1 1 d . . . . .
H00T H 0.2928 0.8136 0.2783 0.037 Uiso 1 1 calc R . . . .
C00U C 0.08449(9) 0.38460(5) 0.03031(15) 0.0316(3) Uani 1 1 d . . . . .
H00U H 0.0455 0.3568 0.0111 0.038 Uiso 1 1 calc R . . . .
C00V C 0.31885(9) 0.73795(5) 0.33710(15) 0.0300(3) Uani 1 1 d . . . . .
H00V H 0.2713 0.7240 0.2762 0.036 Uiso 1 1 calc R . . . .
C00W C 0.24955(8) 0.57783(5) 0.40879(15) 0.0304(3) Uani 1 1 d . . . . .
H00W H 0.1901 0.5665 0.4011 0.036 Uiso 1 1 calc R . . . .
C00X C -0.09744(9) 0.32207(5) 0.15127(16) 0.0341(3) Uani 1 1 d . . . . .
H00X H -0.0759 0.3134 0.2502 0.041 Uiso 1 1 calc R . . . .
C00Y C -0.14566(9) 0.36494(5) -0.05587(14) 0.0301(3) Uani 1 1 d . . . . .
H00Y H -0.1627 0.3923 -0.1211 0.036 Uiso 1 1 calc R . . . .
C00Z C 0.56303(9) 0.74468(6) 0.66635(15) 0.0358(3) Uani 1 1 d . . . . .
C010 C 0.20344(9) 0.47009(6) 0.08634(15) 0.0341(3) Uani 1 1 d . . . . .
H010 H 0.2424 0.4980 0.1032 0.041 Uiso 1 1 calc R . . . .
C011 C 0.42620(9) 0.61192(5) 0.43106(16) 0.0333(3) Uani 1 1 d . . . . .
H011 H 0.4857 0.6231 0.4392 0.040 Uiso 1 1 calc R . . . .
C012 C 0.40799(9) 0.55896(5) 0.42467(16) 0.0342(3) Uani 1 1 d . . . . .
H012 H 0.4549 0.5351 0.4274 0.041 Uiso 1 1 calc R . . . .
C013 C -0.15885(9) 0.49211(5) 0.30660(15) 0.0324(3) Uani 1 1 d . . . . .
H013 H -0.2065 0.5076 0.3527 0.039 Uiso 1 1 calc R . . . .
C014 C 0.17195(10) 0.38357(6) -0.01272(16) 0.0368(3) Uani 1 1 d . . . . .
H014 H 0.1926 0.3541 -0.0610 0.044 Uiso 1 1 calc R . . . .
C015 C -0.11831(9) 0.28938(5) 0.03317(18) 0.0370(3) Uani 1 1 d . . . . .
H015 H -0.1130 0.2534 0.0389 0.044 Uiso 1 1 calc R . . . .
C016 C 0.57730(9) 0.83972(6) 0.65443(16) 0.0390(3) Uani 1 1 d . . . . .
H016 H 0.5576 0.8717 0.6160 0.047 Uiso 1 1 calc R . . . .
C017 C 0.38785(10) 0.90299(6) 0.53345(17) 0.0399(3) Uani 1 1 d . . . . .
H017 H 0.3518 0.8962 0.6137 0.048 Uiso 1 1 calc R . . . .
C018 C 0.23039(9) 0.42576(6) 0.01447(17) 0.0383(3) Uani 1 1 d . . . . .
H018 H 0.2887 0.4237 -0.0168 0.046 Uiso 1 1 calc R . . . .
N019 N 0.47387(14) 0.94346(6) 0.36979(19) 0.0704(5) Uani 1 1 d . . . . .
C01A C -0.11611(10) 0.73612(6) 0.67163(17) 0.0393(3) Uani 1 1 d . . . . .
H01I H -0.1772 0.7304 0.6331 0.059 Uiso 1 1 calc GR . . . .
H01J H -0.1072 0.7724 0.6935 0.059 Uiso 1 1 calc GR . . . .
H01K H -0.1040 0.7163 0.7636 0.059 Uiso 1 1 calc GR . . . .
C01B C 0.63817(10) 0.74153(7) 0.77192(17) 0.0447(4) Uani 1 1 d . . . . .
H01B H 0.6585 0.7097 0.8110 0.054 Uiso 1 1 calc R . . . .
C01C C 0.65121(10) 0.83524(7) 0.75771(17) 0.0473(4) Uani 1 1 d . . . . .
H01C H 0.6822 0.8651 0.7896 0.057 Uiso 1 1 calc R . . . .
C01D C 0.68057(10) 0.78730(8) 0.81540(18) 0.0502(4) Uani 1 1 d . . . . .
H01D H 0.7303 0.7861 0.8854 0.060 Uiso 1 1 calc R . . . .
C01E C 0.42207(13) 0.94904(6) 0.4955(2) 0.0551(4) Uani 1 1 d . . . . .
H01E H 0.4126 0.9802 0.5458 0.066 Uiso 1 1 calc R . . . .
C01F C 0.36174(11) 0.45235(6) 0.4131(2) 0.0535(4) Uani 1 1 d . . . . .
H01A H 0.4013 0.4588 0.3330 0.080 Uiso 1 1 calc GR . . . .
H01F H 0.3345 0.4188 0.3985 0.080 Uiso 1 1 calc GR . . . .
H01G H 0.3955 0.4534 0.5104 0.080 Uiso 1 1 calc GR . . . .
C01G C 0.46818(14) 0.89460(6) 0.33323(18) 0.0535(5) Uani 1 1 d . . . . .
H01H H 0.4957 0.8798 0.2515 0.064 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
O001 C00K 1.3664(15) . ?
O001 C01F 1.4141(18) . ?
O002 C00D 1.3677(15) . ?
O002 C01A 1.4253(17) . ?
N003 C00A 1.4142(15) . ?
N003 C00C 1.3965(16) . ?
N003 C00G 1.3804(16) . ?
N004 C00F 1.3826(17) . ?
N004 C00M 1.4074(17) . ?
N004 C00N 1.3995(16) . ?
N005 C00A 1.3225(16) . ?
N005 C00B 1.3795(16) . ?
N006 C00G 1.4165(16) . ?
N006 C00X 1.3807(16) . ?
N006 C00Y 1.3619(16) . ?
N007 C00F 1.4118(16) . ?
N007 C017 1.3781(18) . ?
N007 C01G 1.3602(18) . ?
N008 C00M 1.3217(17) . ?
N008 C00Z 1.3819(18) . ?
N009 C00Y 1.3070(17) . ?
N009 C015 1.3742(19) . ?
C00A C00H 1.4353(17) . ?
C00B C00C 1.4008(17) . ?
C00B C010 1.4030(18) . ?
C00C C00U 1.3967(18) . ?
C00D C00L 1.3874(18) . ?
C00D C00Q 1.3923(18) . ?
C00E C00H 1.4780(17) . ?
C00E C00O 1.3990(17) . ?
C00E C00R 1.3958(17) . ?
C00F C00T 1.3457(18) . ?
C00G C00P 1.3444(18) . ?
C00H C013 1.3729(18) . ?
C00I C00J 1.4801(18) . ?
C00I C00M 1.4350(17) . ?
C00I C00V 1.3690(18) . ?
C00J C00S 1.4031(17) . ?
C00J C011 1.3927(19) . ?
C00K C00W 1.3924(18) . ?
C00K C012 1.3876(18) . ?
C00L C00R 1.3885(17) . ?
C00N C00Z 1.400(2) . ?
C00N C016 1.4026(19) . ?
C00O C00Q 1.3789(18) . ?
C00P C013 1.4143(18) . ?
C00S C00W 1.3757(18) . ?
C00T C00V 1.4160(18) . ?
C00U C014 1.3813(19) . ?
C00X C015 1.353(2) . ?
C00Z C01B 1.405(2) . ?
C010 C018 1.376(2) . ?
C011 C012 1.3901(19) . ?
C014 C018 1.402(2) . ?
C016 C01C 1.382(2) . ?
C017 C01E 1.341(2) . ?
N019 C01E 1.394(2) . ?
N019 C01G 1.299(2) . ?
C01B C01D 1.378(2) . ?
C01C C01D 1.392(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00K O001 C01F 118.38(11) . . ?
C00D O002 C01A 117.71(11) . . ?
C00C N003 C00A 106.42(10) . . ?
C00G N003 C00A 121.79(10) . . ?
C00G N003 C00C 131.76(11) . . ?
C00F N004 C00M 121.94(11) . . ?
C00F N004 C00N 131.89(12) . . ?
C00N N004 C00M 106.16(11) . . ?
C00A N005 C00B 105.15(10) . . ?
C00X N006 C00G 128.24(11) . . ?
C00Y N006 C00G 125.00(11) . . ?
C00Y N006 C00X 106.76(11) . . ?
C017 N007 C00F 127.13(12) . . ?
C01G N007 C00F 125.94(12) . . ?
C01G N007 C017 106.89(12) . . ?
C00M N008 C00Z 104.82(12) . . ?
C00Y N009 C015 104.77(11) . . ?
N003 C00A C00H 118.46(11) . . ?
N005 C00A N003 111.93(11) . . ?
N005 C00A C00H 129.61(11) . . ?
N005 C00B C00C 112.04(11) . . ?
N005 C00B C010 128.16(12) . . ?
C00C C00B C010 119.79(12) . . ?
N003 C00C C00B 104.46(10) . . ?
N003 C00C C00U 133.10(12) . . ?
C00U C00C C00B 122.43(12) . . ?
O002 C00D C00L 124.78(12) . . ?
O002 C00D C00Q 115.92(11) . . ?
C00L C00D C00Q 119.30(12) . . ?
C00O C00E C00H 122.49(11) . . ?
C00R C00E C00H 120.12(11) . . ?
C00R C00E C00O 117.27(11) . . ?
N004 C00F N007 117.46(11) . . ?
C00T C00F N004 119.58(12) . . ?
C00T C00F N007 122.96(12) . . ?
N003 C00G N006 117.60(11) . . ?
C00P C00G N003 119.74(11) . . ?
C00P C00G N006 122.61(11) . . ?
C00A C00H C00E 122.21(11) . . ?
C013 C00H C00A 117.25(11) . . ?
C013 C00H C00E 120.50(11) . . ?
C00M C00I C00J 121.01(11) . . ?
C00V C00I C00J 121.09(11) . . ?
C00V C00I C00M 117.89(12) . . ?
C00S C00J C00I 119.57(12) . . ?
C011 C00J C00I 122.84(11) . . ?
C011 C00J C00S 117.53(12) . . ?
O001 C00K C00W 115.55(11) . . ?
O001 C00K C012 124.64(12) . . ?
C012 C00K C00W 119.81(12) . . ?
C00D C00L C00R 119.70(12) . . ?
N004 C00M C00I 118.28(11) . . ?
N008 C00M N004 112.49(11) . . ?
N008 C00M C00I 129.20(13) . . ?
N004 C00N C00Z 104.54(12) . . ?
N004 C00N C016 132.86(14) . . ?
C00Z C00N C016 122.60(13) . . ?
C00Q C00O C00E 121.34(12) . . ?
C00G C00P C013 120.12(12) . . ?
C00O C00Q C00D 120.46(12) . . ?
C00L C00R C00E 121.84(12) . . ?
C00W C00S C00J 121.63(12) . . ?
C00F C00T C00V 120.30(13) . . ?
C014 C00U C00C 116.61(12) . . ?
C00I C00V C00T 121.99(12) . . ?
C00S C00W C00K 119.86(12) . . ?
C015 C00X N006 105.03(12) . . ?
N009 C00Y N006 112.03(12) . . ?
N008 C00Z C00N 111.98(12) . . ?
N008 C00Z C01B 128.26(15) . . ?
C00N C00Z C01B 119.76(14) . . ?
C018 C010 C00B 117.97(13) . . ?
C012 C011 C00J 121.44(12) . . ?
C00K C012 C011 119.73(12) . . ?
C00H C013 C00P 122.54(12) . . ?
C00U C014 C018 121.70(13) . . ?
C00X C015 N009 111.41(12) . . ?
C01C C016 C00N 116.18(15) . . ?
C01E C017 N007 105.95(14) . . ?
C010 C018 C014 121.50(13) . . ?
C01G N019 C01E 105.31(14) . . ?
C01D C01B C00Z 117.54(16) . . ?
C016 C01C C01D 121.88(15) . . ?
C01B C01D C01C 122.04(14) . . ?
C017 C01E N019 110.17(14) . . ?
N019 C01G N007 111.67(15) . . ?

_olex2_date_sample_data_collection 2021-08-11
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.252
_oxdiff_exptl_absorpt_empirical_full_min 0.600
