# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_P1
_database_code_depnum_ccdc_archive 'CCDC 2007820'
loop_
_audit_author_name
_audit_author_address
'Xiao Ma'
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2020-06-03 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;
_audit_creation_date             2019-05-17
_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        ?
_chemical_formula_moiety         'C20 H14 N4'
_chemical_formula_sum            'C20 H14 N4'
_chemical_formula_weight         310.35
_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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.9973(5)
_cell_length_b                   11.3955(5)
_cell_length_c                   12.0267(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1507.18(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3659
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.8220
_cell_measurement_theta_min      2.5650
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.786
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6735
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.786
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.903
_diffrn_reflns_theta_min         2.574
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.786
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1580
_reflns_number_total             1877
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (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         0.315
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1877
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.097
_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)+(0.0471P)²+0.4650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1043
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11)
;
_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 0.500000 -0.02241(11) 0.750000 0.0190(3) Uani 1 2 d S T P . .
N2 N 0.500000 0.60272(11) 0.750000 0.0151(3) Uani 1 2 d S T P . .
N3 N 0.30990(9) 0.55488(8) 0.51103(8) 0.0177(2) Uani 1 1 d . . . . .
C1 C 0.41245(10) 0.04009(10) 0.69959(9) 0.0180(2) Uani 1 1 d . . . . .
H1 H 0.348907 -0.001603 0.663498 0.022 Uiso 1 1 calc R . . . .
C2 C 0.40895(10) 0.16181(9) 0.69690(9) 0.0160(2) Uani 1 1 d . . . . .
H2 H 0.344991 0.201209 0.659148 0.019 Uiso 1 1 calc R . . . .
C3 C 0.500000 0.22575(12) 0.750000 0.0140(3) Uani 1 2 d S T P . .
C4 C 0.500000 0.35657(13) 0.750000 0.0144(3) Uani 1 2 d S T P . .
C5 C 0.44227(10) 0.41961(9) 0.66559(9) 0.0144(2) Uani 1 1 d . . . . .
H5 H 0.402014 0.379724 0.606794 0.017 Uiso 1 1 calc R . . . .
C6 C 0.44452(9) 0.54211(9) 0.66879(9) 0.0144(2) Uani 1 1 d . . . . .
C7 C 0.38384(10) 0.61326(9) 0.58102(9) 0.0143(2) Uani 1 1 d . . . . .
C8 C 0.40114(10) 0.73489(9) 0.57487(9) 0.0171(2) Uani 1 1 d . . . . .
H8 H 0.455321 0.773558 0.624293 0.021 Uiso 1 1 calc R . . . .
C9 C 0.33749(11) 0.79755(10) 0.49514(9) 0.0193(3) Uani 1 1 d . . . . .
H9 H 0.348084 0.879995 0.488605 0.023 Uiso 1 1 calc R . . . .
C10 C 0.25816(11) 0.73872(10) 0.42496(9) 0.0200(3) Uani 1 1 d . . . . .
H10 H 0.211450 0.780054 0.371280 0.024 Uiso 1 1 calc R . . . .
C11 C 0.24894(11) 0.61799(10) 0.43535(9) 0.0204(3) Uani 1 1 d . . . . .
H11 H 0.196253 0.577533 0.385867 0.024 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 1.3422(13) 3_656 ?
N1 C1 1.3423(13) . ?
N2 C6 1.3428(12) . ?
N2 C6 1.3428(12) 3_656 ?
N3 C7 1.3463(14) . ?
N3 C11 1.3398(14) . ?
C1 H1 0.9500 . ?
C1 C2 1.3880(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.3933(13) . ?
C3 C4 1.4908(19) . ?
C4 C5 1.3963(13) . ?
C4 C5 1.3963(13) 3_656 ?
C5 H5 0.9500 . ?
C5 C6 1.3968(14) . ?
C6 C7 1.4889(15) . ?
C7 C8 1.4010(15) . ?
C8 H8 0.9500 . ?
C8 C9 1.3854(15) . ?
C9 H9 0.9500 . ?
C9 C10 1.3866(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.3851(17) . ?
C11 H11 0.9500 . ?

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 C1 115.91(13) 3_656 . ?
C6 N2 C6 118.10(12) 3_656 . ?
C11 N3 C7 117.50(10) . . ?
N1 C1 H1 117.9 . . ?
N1 C1 C2 124.10(10) . . ?
C2 C1 H1 117.9 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.47(10) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C2 116.94(13) 3_656 . ?
C2 C3 C4 121.53(7) . . ?
C2 C3 C4 121.53(7) 3_656 . ?
C5 C4 C3 120.96(7) 3_656 . ?
C5 C4 C3 120.96(7) . . ?
C5 C4 C5 118.08(13) . 3_656 ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.08(10) . . ?
C6 C5 H5 120.5 . . ?
N2 C6 C5 122.83(10) . . ?
N2 C6 C7 116.06(9) . . ?
C5 C6 C7 121.11(9) . . ?
N3 C7 C6 116.42(9) . . ?
N3 C7 C8 122.54(10) . . ?
C8 C7 C6 121.02(10) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 C7 118.54(10) . . ?
C9 C8 H8 120.7 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.34(10) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.12(10) . . ?
C11 C10 H10 120.9 . . ?
N3 C11 C10 123.91(11) . . ?
N3 C11 H11 118.0 . . ?
C10 C11 H11 118.0 . . ?

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
N1 C1 C2 C3 -0.68(16) . . . . ?
N2 C6 C7 N3 -168.35(8) . . . . ?
N2 C6 C7 C8 9.89(14) . . . . ?
N3 C7 C8 C9 1.45(16) . . . . ?
C1 N1 C1 C2 0.34(8) 3_656 . . . ?
C1 C2 C3 C2 0.31(7) . . . 3_656 ?
C1 C2 C3 C4 -179.69(7) . . . . ?
C2 C3 C4 C5 -25.45(7) 3_656 . . 3_656 ?
C2 C3 C4 C5 154.55(7) . . . 3_656 ?
C2 C3 C4 C5 154.55(7) 3_656 . . . ?
C2 C3 C4 C5 -25.45(7) . . . . ?
C3 C4 C5 C6 -179.97(7) . . . . ?
C4 C5 C6 N2 -0.05(14) . . . . ?
C4 C5 C6 C7 -179.73(8) . . . . ?
C5 C4 C5 C6 0.03(7) 3_656 . . . ?
C5 C6 C7 N3 11.35(15) . . . . ?
C5 C6 C7 C8 -170.41(10) . . . . ?
C6 N2 C6 C5 0.03(7) 3_656 . . . ?
C6 N2 C6 C7 179.72(10) 3_656 . . . ?
C6 C7 C8 C9 -176.68(10) . . . . ?
C7 N3 C11 C10 0.31(16) . . . . ?
C7 C8 C9 C10 0.64(16) . . . . ?
C8 C9 C10 C11 -2.12(16) . . . . ?
C9 C10 C11 N3 1.70(17) . . . . ?
C11 N3 C7 C6 176.30(9) . . . . ?
C11 N3 C7 C8 -1.91(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_P3
_database_code_depnum_ccdc_archive 'CCDC 2007822'
loop_
_audit_author_name
_audit_author_address
'Xiao Ma'
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2020-06-03 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;
_audit_creation_date             2019-05-17
_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        ?
_chemical_formula_moiety         'C20 H14 N4'
_chemical_formula_sum            'C20 H14 N4'
_chemical_formula_weight         310.35
_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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.4088(8)
_cell_length_b                   11.2036(5)
_cell_length_c                   7.9268(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1457.24(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4080
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.3030
_cell_measurement_theta_min      2.1970
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.805
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8436
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.805
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.617
_diffrn_reflns_theta_min         2.201
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.805
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1509
_reflns_number_total             1815
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (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         0.186
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         1815
_refine_ls_number_restraints     213
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0455P)²+0.3665P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0993
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C7) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(N1) \\sim
Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3. Rigid body (RIGU) restrains
 C17, N2, C6, C10, C5, C7, C9, C11, C4, N1, C8, N3, C12, C3, C1, C16, C15, C13,
  C2, C20, C14, N4, C18, C19
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Others
 Fixed Sof: N2(0.5) C4(0.5) H4(0.5) C6(0.5) N3(0.5) C9(0.5) H9(0.5) C10(0.5)
 C5(0.5) C11(0.5) C15(0.5) H15(0.5) C2(0.5) H2(0.5) C12(0.5) H12(0.5) C14(0.5)
 H14(0.5) C13(0.5) H13(0.5) C3(0.5) H3(0.5) C7(0.5) H7(0.5) C20(0.5) H20(0.5)
 C8(0.5) C16(0.5) N4(0.5) C17(0.5) H17(0.5) C19(0.5) H19(0.5) C18(0.5) H18(0.5)
 N1(0.5) C1(0.5) H1(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C15(H15), C2(H2), C12(H12), C14(H14), C13(H13), C3(H3),
 C7(H7), C20(H20), C17(H17), C19(H19), C18(H18), C1(H1)
;
_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
N2 N 0.4421(3) 0.3450(6) 0.6772(7) 0.0194(10) Uani 0.5 1 d . U P A -1
C4 C 0.5721(4) 0.5905(7) 0.8239(9) 0.0261(11) Uani 0.5 1 d . U P A -1
H4 H 0.615304 0.547839 0.870148 0.031 Uiso 0.5 1 calc R . P A -1
C6 C 0.4958(8) 0.40212(13) 0.745(2) 0.0174(6) Uani 0.5 1 d . U P A -1
N3 N 0.3854(7) 0.0459(7) 0.5396(15) 0.0266(13) Uani 0.5 1 d . U P A -1
C9 C 0.5050(9) 0.16021(14) 0.757(2) 0.0172(8) Uani 0.5 1 d . U P A -1
H9 H 0.508881 0.077436 0.760297 0.021 Uiso 0.5 1 calc R . P A -1
C10 C 0.4330(6) 0.2215(8) 0.6603(16) 0.0176(10) Uani 0.5 1 d . U P A -1
C5 C 0.5050(7) 0.53593(14) 0.756(3) 0.0178(6) Uani 0.5 1 d . U P A -1
C11 C 0.3787(6) 0.1575(9) 0.5777(17) 0.0203(11) Uani 0.5 1 d . U P A -1
C15 C 0.3300(6) -0.0377(8) 0.4481(15) 0.0365(15) Uani 0.5 1 d . U P A -1
H15 H 0.342608 -0.117066 0.425555 0.044 Uiso 0.5 1 calc R . P A -1
C2 C 0.5074(8) 0.77842(17) 0.758(2) 0.0232(12) Uani 0.5 1 d . U P A -1
H2 H 0.510350 0.861283 0.761608 0.028 Uiso 0.5 1 calc R . P A -1
C12 C 0.2935(4) 0.2032(6) 0.5238(12) 0.0235(11) Uani 0.5 1 d . U P A -1
H12 H 0.278749 0.280965 0.551123 0.028 Uiso 0.5 1 calc R . P A -1
C14 C 0.2585(4) 0.0158(5) 0.4011(12) 0.0258(11) Uani 0.5 1 d . U P A -1
H14 H 0.220898 -0.029619 0.341335 0.031 Uiso 0.5 1 calc R . P A -1
C13 C 0.2388(4) 0.1328(5) 0.4368(10) 0.0271(11) Uani 0.5 1 d . U P A -1
H13 H 0.188932 0.163982 0.402452 0.032 Uiso 0.5 1 calc R . P A -1
C3 C 0.5708(8) 0.7093(7) 0.818(2) 0.0257(12) Uani 0.5 1 d . U P A -1
H3 H 0.616511 0.749194 0.858618 0.031 Uiso 0.5 1 calc R . P A -1
C7 C 0.5653(4) 0.3440(7) 0.8412(8) 0.0171(9) Uani 0.5 1 d . U P A -1
H7 H 0.606797 0.383244 0.898725 0.021 Uiso 0.5 1 calc R . P A -1
C20 C 0.6123(9) 0.0342(8) 0.9718(18) 0.0279(13) Uani 0.5 1 d . U P A -1
H20 H 0.563867 -0.004251 0.944136 0.033 Uiso 0.5 1 calc R . P A -1
C8 C 0.5555(6) 0.2212(8) 0.8271(17) 0.0192(11) Uani 0.5 1 d . U P A -1
C16 C 0.6316(6) 0.1577(9) 0.9291(17) 0.0197(11) Uani 0.5 1 d . U P A -1
N4 N 0.6715(5) -0.0139(6) 1.0529(11) 0.0280(10) Uani 0.5 1 d . U P A -1
C17 C 0.6908(4) 0.2227(7) 0.9709(12) 0.0235(10) Uani 0.5 1 d . U P A -1
H17 H 0.693698 0.303199 0.942803 0.028 Uiso 0.5 1 calc R . P A -1
C19 C 0.7412(5) 0.0475(5) 1.1022(13) 0.0280(11) Uani 0.5 1 d . U P A -1
H19 H 0.781481 0.008228 1.163308 0.034 Uiso 0.5 1 calc R . P A -1
C18 C 0.7510(4) 0.1656(5) 1.0615(11) 0.0258(10) Uani 0.5 1 d . U P A -1
H18 H 0.797627 0.206588 1.094520 0.031 Uiso 0.5 1 calc R . P A -1
N1 N 0.4377(3) 0.5959(5) 0.6924(6) 0.0176(8) Uani 0.5 1 d . U P A -1
C1 C 0.4396(8) 0.7219(6) 0.693(2) 0.0251(14) Uani 0.5 1 d . U P A -1
H1 H 0.396172 0.765782 0.649921 0.030 Uiso 0.5 1 calc R . P A -1


_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
N2 C6 1.214(12) . ?
N2 C10 1.398(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(8) . ?
C4 C3 1.332(9) . ?
C6 C5 1.509(3) . ?
C6 C7 1.519(14) . ?
N3 C11 1.290(13) . ?
N3 C15 1.494(15) . ?
C9 H9 0.9300 . ?
C9 C10 1.567(17) . ?
C9 C8 1.210(17) . ?
C10 C11 1.318(17) . ?
C5 N1 1.387(7) . ?
C11 C12 1.548(13) . ?
C15 H15 0.9300 . ?
C15 C14 1.368(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(6) . ?
C2 C1 1.382(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(5) . ?
C14 H14 0.9300 . ?
C14 C13 1.380(5) . ?
C13 H13 0.9300 . ?
C3 H3 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.389(12) . ?
C20 H20 0.9300 . ?
C20 C16 1.459(13) . ?
C20 N4 1.284(18) . ?
C8 C16 1.648(16) . ?
C16 C17 1.259(14) . ?
N4 C19 1.391(7) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.371(5) . ?
C18 H18 0.9300 . ?
N1 C1 1.412(8) . ?
C1 H1 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N2 C10 130.0(7) . . ?
C5 C4 H4 122.6 . . ?
C3 C4 H4 122.6 . . ?
C3 C4 C5 114.8(8) . . ?
N2 C6 C5 128.4(8) . . ?
N2 C6 C7 122.73(18) . . ?
C5 C6 C7 108.8(7) . . ?
C11 N3 C15 132.0(9) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.6(2) . . ?
N2 C10 C9 107.8(7) . . ?
C11 C10 N2 131.2(8) . . ?
C11 C10 C9 120.9(7) . . ?
C4 C5 C6 123.1(7) . . ?
C4 C5 N1 124.5(2) . . ?
N1 C5 C6 112.4(7) . . ?
N3 C11 C10 125.9(9) . . ?
N3 C11 C12 109.4(8) . . ?
C10 C11 C12 124.5(9) . . ?
N3 C15 H15 123.9 . . ?
C14 C15 N3 112.2(7) . . ?
C14 C15 H15 123.9 . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.60(18) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 C11 122.4(7) . . ?
C13 C12 H12 118.8 . . ?
C15 C14 H14 117.9 . . ?
C15 C14 C13 124.2(7) . . ?
C13 C14 H14 117.9 . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.5(6) . . ?
C14 C13 H13 120.3 . . ?
C4 C3 C2 125.7(9) . . ?
C4 C3 H3 117.1 . . ?
C2 C3 H3 117.1 . . ?
C6 C7 H7 126.3 . . ?
C8 C7 C6 107.3(7) . . ?
C8 C7 H7 126.3 . . ?
C16 C20 H20 124.8 . . ?
N4 C20 H20 124.8 . . ?
N4 C20 C16 110.5(11) . . ?
C9 C8 C7 132.5(9) . . ?
C9 C8 C16 120.0(7) . . ?
C7 C8 C16 107.5(7) . . ?
C20 C16 C8 111.0(9) . . ?
C17 C16 C20 130.9(9) . . ?
C17 C16 C8 117.6(8) . . ?
C20 N4 C19 123.7(7) . . ?
C16 C17 H17 122.5 . . ?
C16 C17 C18 114.9(8) . . ?
C18 C17 H17 122.5 . . ?
N4 C19 H19 119.7 . . ?
C18 C19 N4 120.5(6) . . ?
C18 C19 H19 119.7 . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.1(6) . . ?
C19 C18 H18 120.4 . . ?
C5 N1 C1 117.8(6) . . ?
C2 C1 N1 118.5(7) . . ?
C2 C1 H1 120.8 . . ?
N1 C1 H1 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
N2 C6 C5 C4 -174.2(17) . . . . ?
N2 C6 C5 N1 7(3) . . . . ?
N2 C6 C7 C8 2(2) . . . . ?
N2 C10 C11 N3 163.9(12) . . . . ?
N2 C10 C11 C12 -21(3) . . . . ?
C4 C5 N1 C1 2(2) . . . . ?
C6 N2 C10 C9 3(2) . . . . ?
C6 N2 C10 C11 -174.6(19) . . . . ?
C6 C5 N1 C1 -178.8(15) . . . . ?
C6 C7 C8 C9 0(3) . . . . ?
C6 C7 C8 C16 179.2(12) . . . . ?
N3 C11 C12 C13 -4.6(16) . . . . ?
N3 C15 C14 C13 -1.3(14) . . . . ?
C9 C10 C11 N3 -14(3) . . . . ?
C9 C10 C11 C12 161.3(14) . . . . ?
C9 C8 C16 C20 -20(3) . . . . ?
C9 C8 C16 C17 166.1(17) . . . . ?
C10 N2 C6 C5 177.9(17) . . . . ?
C10 N2 C6 C7 -4(3) . . . . ?
C10 C9 C8 C7 -1(4) . . . . ?
C10 C9 C8 C16 -180.0(9) . . . . ?
C10 C11 C12 C13 179.8(13) . . . . ?
C5 C4 C3 C2 2.9(17) . . . . ?
C5 C6 C7 C8 -179.4(15) . . . . ?
C5 N1 C1 C2 -0.8(16) . . . . ?
C11 N3 C15 C14 -2(2) . . . . ?
C11 C12 C13 C14 2.5(12) . . . . ?
C15 N3 C11 C10 180.0(15) . . . . ?
C15 N3 C11 C12 4(2) . . . . ?
C15 C14 C13 C12 0.7(12) . . . . ?
C3 C4 C5 C6 178.0(18) . . . . ?
C3 C4 C5 N1 -3(2) . . . . ?
C3 C2 C1 N1 0.8(18) . . . . ?
C7 C6 C5 C4 8(3) . . . . ?
C7 C6 C5 N1 -171.3(13) . . . . ?
C7 C8 C16 C20 160.2(10) . . . . ?
C7 C8 C16 C17 -13.2(19) . . . . ?
C20 C16 C17 C18 6(2) . . . . ?
C20 N4 C19 C18 -1.7(15) . . . . ?
C8 C9 C10 N2 0(3) . . . . ?
C8 C9 C10 C11 177.6(12) . . . . ?
C8 C16 C17 C18 177.6(10) . . . . ?
C16 C20 N4 C19 4.3(17) . . . . ?
C16 C17 C18 C19 -1.9(12) . . . . ?
N4 C20 C16 C8 -179.2(12) . . . . ?
N4 C20 C16 C17 -7(2) . . . . ?
N4 C19 C18 C17 0.0(10) . . . . ?
C1 C2 C3 C4 -2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_P2
_database_code_depnum_ccdc_archive 'CCDC 2007821'
loop_
_audit_author_name
_audit_author_address
'Xiao Ma'
;The Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2020-06-03 deposited with the CCDC.	2020-11-30 downloaded from the CCDC.
;
_audit_creation_date             2019-05-29
_audit_creation_method           
;
Olex2 1.2-beta
(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         'C20 H14 N4'
_chemical_formula_sum            'C20 H14 N4'
_chemical_formula_weight         310.35
_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 0.0030 0.0020 '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 0.0060 0.0030 '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                   8.3024(6)
_cell_length_b                   16.0020(10)
_cell_length_c                   11.5519(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.915(6)
_cell_angle_gamma                90
_cell_volume                     1529.08(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5404
_cell_measurement_temperature    299.3(6)
_cell_measurement_theta_max      30.5380
_cell_measurement_theta_min      2.1680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            light
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.1570
_diffrn_reflns_Laue_measured_fraction_full 0.932
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17756
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_min         2.462
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.3(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.932
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  28.00   0.50    4.00    --    6.28  37.00 -60.00   50
  2  ω     51.00  80.00   0.50    4.00    --    6.28  37.00 -60.00   58
  3  ω    -12.00  30.00   0.50    4.00    --   -3.93  86.00 120.00   84
  4  ω    -39.00  23.00   0.50    4.00    --   -3.93 -86.00   2.00  124
  5  ω     -5.00  39.00   0.50    4.00    --    6.28 -99.00 -60.00   88
  6  ω    -79.00   9.00   0.50    4.00    --   -3.93 -19.00  60.00  176
  7  ω     -3.00  23.00   0.50    4.00    --    6.28  86.00 120.00   52
  8  ω     37.00  63.00   0.50    4.00    --    6.28  37.00  60.00   52
  9  ω     25.00  70.00   0.50    4.00    --    6.28  77.00 150.00   90
 10  ω      0.00  26.00   0.50    4.00    --    6.28 -99.00-180.00   52
 11  ω    -15.00  10.00   0.50    4.00    --    6.28  87.00 121.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0393840000
_diffrn_orient_matrix_UB_12      -0.0182229000
_diffrn_orient_matrix_UB_13      0.0507941000
_diffrn_orient_matrix_UB_21      0.0206281000
_diffrn_orient_matrix_UB_22      -0.0352626000
_diffrn_orient_matrix_UB_23      -0.0328413000
_diffrn_orient_matrix_UB_31      0.0733328000
_diffrn_orient_matrix_UB_32      0.0197080000
_diffrn_orient_matrix_UB_33      -0.0118479000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1117
_reflns_number_total             2647
_reflns_odcompleteness_completeness 99.97
_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 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (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         0.282
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2647
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1563
_refine_ls_R_factor_gt           0.0975
_refine_ls_restrained_S_all      1.018
_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)+(0.0207P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2125
_refine_ls_wR_factor_ref         0.2338
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
C17 \\sim C18: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01
N4 \\sim C16 \\sim C17 \\sim C18: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
C16 \\sim N4: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(N4) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3. Rigid body (RIGU) restrains
 C17, C18
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C16, N4
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Others
 Fixed U11: N2(0.06005) N3(0.076705) N4(0.074445)
 Fixed U12: N2(0.00946) N3(-0.019975) N4(-0.007805)
 Fixed U13: N2(-0.005545) N3(0.002173) N4(-0.001295)
 Fixed U22: N2(0.05559) N3(0.0703) N4(0.07231)
 Fixed U23: N2(0.00332) N3(-0.01597) N4(-0.00273)
 Fixed U33: N2(0.05829) N3(0.06775) N4(0.07528)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20)
;
_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 0.8004(4) 0.5671(2) 0.5936(3) 0.0745(10) Uani 1 1 d . . . . .
N2 N 0.6678(4) 0.43538(19) 0.3445(3) 0.058 Uani 1 1 d . . . . .
N3 N 0.5569(5) 0.3809(2) 0.0377(3) 0.072 Uani 1 1 d . . . . .
N4 N 0.9506(5) 0.6060(2) 0.0585(3) 0.074 Uani 1 1 d . U . . .
C1 C 0.7968(6) 0.5689(3) 0.7088(5) 0.0852(14) Uani 1 1 d . . . . .
H1 H 0.833919 0.616550 0.748759 0.102 Uiso 1 1 calc R . . . .
C2 C 0.7407(6) 0.5034(3) 0.7712(5) 0.0909(16) Uani 1 1 d . . . . .
H2 H 0.737270 0.506813 0.851291 0.109 Uiso 1 1 calc R . . . .
C3 C 0.6905(7) 0.4334(3) 0.7116(5) 0.0886(15) Uani 1 1 d . . . . .
H3 H 0.654736 0.387302 0.751154 0.106 Uiso 1 1 calc R . . . .
C4 C 0.6928(6) 0.4312(2) 0.5939(4) 0.0689(12) Uani 1 1 d . . . . .
H4 H 0.657337 0.383683 0.552965 0.083 Uiso 1 1 calc R . . . .
C5 C 0.7462(4) 0.4977(2) 0.5365(4) 0.0556(10) Uani 1 1 d . . . . .
C6 C 0.7484(4) 0.4974(2) 0.4095(4) 0.0536(10) Uani 1 1 d . . . . .
C7 C 0.8299(5) 0.5574(2) 0.3524(3) 0.0549(10) Uani 1 1 d . . . . .
H7 H 0.885591 0.599292 0.394901 0.066 Uiso 1 1 calc R . . . .
C8 C 0.8303(5) 0.5565(2) 0.2339(3) 0.0527(9) Uani 1 1 d . . . . .
C9 C 0.7506(4) 0.4957(2) 0.1716(3) 0.0477(9) Uani 1 1 d . . . . .
H9 H 0.751270 0.494942 0.091116 0.057 Uiso 1 1 calc R . . . .
C10 C 0.6694(4) 0.4357(2) 0.2261(3) 0.0532(9) Uani 1 1 d . . . . .
C11 C 0.5780(4) 0.3727(2) 0.1567(3) 0.0532(9) Uani 1 1 d . . . . .
C12 C 0.5128(5) 0.3069(2) 0.2094(4) 0.0623(11) Uani 1 1 d . . . . .
H12 H 0.528633 0.300909 0.289622 0.075 Uiso 1 1 calc R . . . .
C13 C 0.4260(6) 0.2509(3) 0.1461(5) 0.0843(15) Uani 1 1 d . . . . .
H13 H 0.379550 0.206681 0.183464 0.101 Uiso 1 1 calc R . . . .
C14 C 0.4031(6) 0.2565(3) 0.0284(5) 0.0787(14) Uani 1 1 d . . . . .
H14 H 0.344201 0.216088 -0.014930 0.094 Uiso 1 1 calc R . . . .
C15 C 0.4688(7) 0.3229(3) -0.0242(4) 0.0863(15) Uani 1 1 d . . . . .
H15 H 0.452580 0.328379 -0.104494 0.104 Uiso 1 1 calc R . . . .
C16 C 0.9195(5) 0.6223(3) 0.1693(4) 0.0606(10) Uani 1 1 d . U . . .
C17 C 0.9692(5) 0.6908(2) 0.2283(4) 0.0664(11) Uani 1 1 d . U . . .
H17 H 0.948034 0.698489 0.305387 0.080 Uiso 1 1 calc R . . . .
C18 C 1.0517(6) 0.7486(3) 0.1714(5) 0.0856(14) Uani 1 1 d . U . . .
H18 H 1.087864 0.796789 0.210450 0.103 Uiso 1 1 calc R . . . .
C19 C 1.0831(6) 0.7381(3) 0.0581(5) 0.0844(15) Uani 1 1 d . . . . .
H19 H 1.137265 0.778955 0.019221 0.101 Uiso 1 1 calc R . . . .
C20 C 1.0324(6) 0.6654(3) 0.0034(4) 0.0840(15) Uani 1 1 d . . . . .
H20 H 1.054531 0.656630 -0.073248 0.101 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 1.334(6) . ?
N1 C5 1.350(5) . ?
N2 C6 1.382(5) . ?
N2 C10 1.369(5) . ?
N3 C11 1.377(5) . ?
N3 C15 1.348(6) . ?
N4 C16 1.352(5) . ?
N4 C20 1.358(6) . ?
C1 C2 1.375(7) . ?
C2 C3 1.361(7) . ?
C3 C4 1.362(6) . ?
C4 C5 1.348(5) . ?
C5 C6 1.468(6) . ?
C6 C7 1.376(5) . ?
C7 C8 1.369(5) . ?
C8 C9 1.349(5) . ?
C8 C16 1.520(5) . ?
C9 C10 1.359(5) . ?
C10 C11 1.460(5) . ?
C11 C12 1.352(5) . ?
C12 C13 1.329(6) . ?
C13 C14 1.360(6) . ?
C14 C15 1.361(6) . ?
C16 C17 1.338(5) . ?
C17 C18 1.354(6) . ?
C18 C19 1.367(7) . ?
C19 C20 1.373(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 118.0(4) . . ?
C10 N2 C6 119.6(3) . . ?
C15 N3 C11 118.7(4) . . ?
C16 N4 C20 116.9(4) . . ?
N1 C1 C2 122.9(5) . . ?
C3 C2 C1 117.7(5) . . ?
C2 C3 C4 119.8(5) . . ?
C5 C4 C3 120.3(4) . . ?
N1 C5 C6 117.3(3) . . ?
C4 C5 N1 121.3(4) . . ?
C4 C5 C6 121.4(4) . . ?
N2 C6 C5 119.9(3) . . ?
C7 C6 N2 118.4(4) . . ?
C7 C6 C5 121.7(3) . . ?
C8 C7 C6 121.0(4) . . ?
C7 C8 C16 121.8(3) . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 C16 118.3(4) . . ?
C8 C9 C10 120.1(4) . . ?
N2 C10 C11 119.8(3) . . ?
C9 C10 N2 120.9(3) . . ?
C9 C10 C11 119.3(3) . . ?
N3 C11 C10 119.9(3) . . ?
C12 C11 N3 120.1(4) . . ?
C12 C11 C10 120.0(4) . . ?
C13 C12 C11 119.8(4) . . ?
C12 C13 C14 121.9(4) . . ?
C13 C14 C15 118.0(4) . . ?
N3 C15 C14 121.4(5) . . ?
N4 C16 C8 118.2(4) . . ?
C17 C16 N4 124.4(4) . . ?
C17 C16 C8 117.3(4) . . ?
C16 C17 C18 117.3(4) . . ?
C17 C18 C19 121.8(4) . . ?
C18 C19 C20 117.9(4) . . ?
N4 C20 C19 121.6(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 1.5(8) . . . . ?
N1 C5 C6 N2 -168.0(3) . . . . ?
N1 C5 C6 C7 12.3(5) . . . . ?
N2 C6 C7 C8 0.6(5) . . . . ?
N2 C10 C11 N3 169.1(3) . . . . ?
N2 C10 C11 C12 -10.1(5) . . . . ?
N3 C11 C12 C13 -1.1(6) . . . . ?
N4 C16 C17 C18 2.2(7) . . . . ?
C1 N1 C5 C4 -1.2(6) . . . . ?
C1 N1 C5 C6 179.0(4) . . . . ?
C1 C2 C3 C4 -1.8(7) . . . . ?
C2 C3 C4 C5 0.7(7) . . . . ?
C3 C4 C5 N1 0.9(6) . . . . ?
C3 C4 C5 C6 -179.4(4) . . . . ?
C4 C5 C6 N2 12.2(5) . . . . ?
C4 C5 C6 C7 -167.5(4) . . . . ?
C5 N1 C1 C2 0.0(7) . . . . ?
C5 C6 C7 C8 -179.7(3) . . . . ?
C6 N2 C10 C9 0.6(5) . . . . ?
C6 N2 C10 C11 -177.1(3) . . . . ?
C6 C7 C8 C9 -0.4(5) . . . . ?
C6 C7 C8 C16 180.0(3) . . . . ?
C7 C8 C9 C10 0.3(5) . . . . ?
C7 C8 C16 N4 163.0(4) . . . . ?
C7 C8 C16 C17 -13.7(6) . . . . ?
C8 C9 C10 N2 -0.5(5) . . . . ?
C8 C9 C10 C11 177.3(3) . . . . ?
C8 C16 C17 C18 178.7(4) . . . . ?
C9 C8 C16 N4 -16.7(5) . . . . ?
C9 C8 C16 C17 166.6(4) . . . . ?
C9 C10 C11 N3 -8.7(5) . . . . ?
C9 C10 C11 C12 172.1(4) . . . . ?
C10 N2 C6 C5 179.6(3) . . . . ?
C10 N2 C6 C7 -0.7(5) . . . . ?
C10 C11 C12 C13 178.1(4) . . . . ?
C11 N3 C15 C14 -0.9(7) . . . . ?
C11 C12 C13 C14 1.5(8) . . . . ?
C12 C13 C14 C15 -1.6(8) . . . . ?
C13 C14 C15 N3 1.3(8) . . . . ?
C15 N3 C11 C10 -178.4(4) . . . . ?
C15 N3 C11 C12 0.8(6) . . . . ?
C16 N4 C20 C19 0.9(7) . . . . ?
C16 C8 C9 C10 180.0(3) . . . . ?
C16 C17 C18 C19 0.2(8) . . . . ?
C17 C18 C19 C20 -1.8(8) . . . . ?
C18 C19 C20 N4 1.2(8) . . . . ?
C20 N4 C16 C8 -179.1(4) . . . . ?
C20 N4 C16 C17 -2.7(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 1.833
_oxdiff_exptl_absorpt_empirical_full_min 0.668
