# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_0392DH
_database_code_depnum_ccdc_archive 'CCDC 2494028'
loop_
_audit_author_name
_audit_author_address
'Manuela Weber'
;Freie Universitaet Berlin
Germany
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 N4'
_chemical_formula_weight         236.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.0059(3)
_cell_length_b                   7.6326(3)
_cell_length_c                   19.6494(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.704(3)
_cell_angle_gamma                90
_cell_volume                     1192.48(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7671
_cell_measurement_theta_min      4.53
_cell_measurement_theta_max      66.94
_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   0.4106
_exptl_transmission_factor_max   0.8892
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.657
_shelx_estimated_absorpt_T_min   0.722
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9833
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.531
_diffrn_reflns_theta_max         66.978
_diffrn_reflns_theta_full        66.979
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             2076
_reflns_number_gt                1809
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+1.8105P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2076
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1425
_refine_ls_wR_factor_gt          0.1355
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4854(2) 0.6464(2) 0.13101(9) 0.0194(4) Uani 1 1 d . . . . .
N2 N 0.2448(2) 0.7629(2) 0.14501(9) 0.0190(4) Uani 1 1 d . . . . .
N3 N 0.9930(2) 0.9003(3) 0.33260(10) 0.0263(5) Uani 1 1 d . . . . .
N4 N 0.8336(3) 0.6910(3) 0.52488(10) 0.0311(5) Uani 1 1 d . . . . .
C1 C 0.2955(3) 0.5960(3) 0.28874(11) 0.0193(5) Uani 1 1 d . . . . .
H1 H 0.188960 0.565303 0.265363 0.023 Uiso 1 1 calc R U . . .
C2 C 0.3309(3) 0.5692(3) 0.35893(11) 0.0202(5) Uani 1 1 d . . . . .
H2 H 0.247538 0.519484 0.383699 0.024 Uiso 1 1 calc R U . . .
C3 C 0.4860(3) 0.6139(3) 0.39325(11) 0.0194(5) Uani 1 1 d . . . . .
H3 H 0.507748 0.591807 0.441041 0.023 Uiso 1 1 calc R U . . .
C4 C 0.6121(3) 0.6914(3) 0.35897(11) 0.0188(5) Uani 1 1 d . . . . .
C5 C 0.5770(3) 0.7144(3) 0.28766(10) 0.0182(5) Uani 1 1 d . . . . .
H5 H 0.661159 0.761370 0.262584 0.022 Uiso 1 1 calc R U . . .
C6 C 0.4206(3) 0.6693(3) 0.25322(10) 0.0178(5) Uani 1 1 d . . . . .
C7 C 0.3860(3) 0.6933(3) 0.17872(11) 0.0177(5) Uani 1 1 d . . . . .
C8 C 0.4043(3) 0.6864(3) 0.06672(11) 0.0228(5) Uani 1 1 d . . . . .
H8 H 0.446482 0.666750 0.024152 0.027 Uiso 1 1 calc R U . . .
C9 C 0.2549(3) 0.7582(3) 0.07550(11) 0.0218(5) Uani 1 1 d . . . . .
H9 H 0.171995 0.798111 0.040399 0.026 Uiso 1 1 calc R U . . .
C10 C 0.7723(3) 0.7434(3) 0.39537(11) 0.0197(5) Uani 1 1 d . . . . .
C11 C 0.8944(3) 0.8296(3) 0.36174(11) 0.0201(5) Uani 1 1 d . . . . .
C12 C 0.8074(3) 0.7163(3) 0.46654(11) 0.0220(5) Uani 1 1 d . . . . .
C13 C 0.6515(3) 0.5634(3) 0.14223(11) 0.0224(5) Uani 1 1 d . . . . .
H13A H 0.662143 0.477724 0.105839 0.034 Uiso 1 1 calc R U . . .
H13B H 0.664338 0.503938 0.186744 0.034 Uiso 1 1 calc R U . . .
H13C H 0.738984 0.652978 0.141620 0.034 Uiso 1 1 calc R U . . .
C14 C 0.1028(3) 0.8385(3) 0.17552(11) 0.0226(5) Uani 1 1 d . . . . .
H14A H 0.058324 0.939031 0.148126 0.034 Uiso 1 1 calc R U . . .
H14B H 0.140600 0.877049 0.222361 0.034 Uiso 1 1 calc R U . . .
H14C H 0.014366 0.750034 0.176485 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.347(3) . ?
N1 C8 1.385(3) . ?
N1 C13 1.466(3) . ?
N2 C7 1.351(3) . ?
N2 C9 1.378(3) . ?
N2 C14 1.464(3) . ?
N3 C11 1.161(3) . ?
N4 C12 1.157(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.402(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.408(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.408(3) . ?
C4 C10 1.449(3) . ?
C5 C6 1.395(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.469(3) . ?
C8 C9 1.344(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.406(3) . ?
C10 C12 1.409(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C8 108.89(18) . . ?
C7 N1 C13 127.53(18) . . ?
C8 N1 C13 123.57(18) . . ?
C7 N2 C9 109.44(18) . . ?
C7 N2 C14 126.86(18) . . ?
C9 N2 C14 123.67(18) . . ?
C2 C1 C6 118.55(19) . . ?
C2 C1 H1 120.7 . . ?
C6 C1 H1 120.7 . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 121.53(19) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 117.24(19) . . ?
C5 C4 C10 121.29(19) . . ?
C3 C4 C10 121.46(19) . . ?
C6 C5 C4 121.04(19) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 120.63(19) . . ?
C5 C6 C7 120.45(19) . . ?
C1 C6 C7 118.89(18) . . ?
N1 C7 N2 106.98(18) . . ?
N1 C7 C6 127.05(19) . . ?
N2 C7 C6 125.95(19) . . ?
C9 C8 N1 107.59(19) . . ?
C9 C8 H8 126.2 . . ?
N1 C8 H8 126.2 . . ?
C8 C9 N2 107.10(18) . . ?
C8 C9 H9 126.4 . . ?
N2 C9 H9 126.4 . . ?
C11 C10 C12 117.78(19) . . ?
C11 C10 C4 121.36(19) . . ?
C12 C10 C4 120.80(19) . . ?
N3 C11 C10 178.5(2) . . ?
N4 C12 C10 178.5(2) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C2 C3 C4 C5 -2.8(3) . . . . ?
C2 C3 C4 C10 177.9(2) . . . . ?
C3 C4 C5 C6 2.8(3) . . . . ?
C10 C4 C5 C6 -177.9(2) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
C4 C5 C6 C7 -179.70(19) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C1 C6 C7 178.20(19) . . . . ?
C8 N1 C7 N2 -0.4(2) . . . . ?
C13 N1 C7 N2 -179.29(19) . . . . ?
C8 N1 C7 C6 177.9(2) . . . . ?
C13 N1 C7 C6 -0.9(3) . . . . ?
C9 N2 C7 N1 0.6(2) . . . . ?
C14 N2 C7 N1 -177.42(19) . . . . ?
C9 N2 C7 C6 -177.8(2) . . . . ?
C14 N2 C7 C6 4.2(3) . . . . ?
C5 C6 C7 N1 46.7(3) . . . . ?
C1 C6 C7 N1 -131.6(2) . . . . ?
C5 C6 C7 N2 -135.3(2) . . . . ?
C1 C6 C7 N2 46.5(3) . . . . ?
C7 N1 C8 C9 0.1(2) . . . . ?
C13 N1 C8 C9 179.0(2) . . . . ?
N1 C8 C9 N2 0.3(2) . . . . ?
C7 N2 C9 C8 -0.5(2) . . . . ?
C14 N2 C9 C8 177.56(19) . . . . ?
C5 C4 C10 C11 4.4(3) . . . . ?
C3 C4 C10 C11 -176.4(2) . . . . ?
C5 C4 C10 C12 -178.6(2) . . . . ?
C3 C4 C10 C12 0.6(3) . . . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.065


#END===============================================
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_0761DH
_database_code_depnum_ccdc_archive 'CCDC 2494031'
loop_
_audit_author_name
_audit_author_address
'Manuela Weber'
;Freie Universitaet Berlin
Germany
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-06-17 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT097_0761DH              
;
PROBLEM: Large Reported Max. (Positive) Residual Density 0.89 eA-3.
RESPONSE: This alert may have been caused by a twin problem. 
Furthermore, the very small crystals  scatter weakly at higher 
diffraction angles.
;
# end Validation Reply Form 

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 N4'
_chemical_formula_weight         286.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.3190(10)
_cell_length_b                   13.967(2)
_cell_length_c                   11.3680(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.300(10)
_cell_angle_gamma                90
_cell_volume                     1427.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1955
_cell_measurement_theta_min      5.13
_cell_measurement_theta_max      66.47
_exptl_crystal_description       platelet
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   0.6027
_exptl_transmission_factor_max   0.8642
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.650
_shelx_estimated_absorpt_T_min   0.903
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6241
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.164
_diffrn_reflns_theta_max         65.082
_diffrn_reflns_theta_full        65.082
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             2353
_reflns_number_gt                1738
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1082P)²+4.2837P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2353
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1209
_refine_ls_R_factor_gt           0.0948
_refine_ls_wR_factor_ref         0.2616
_refine_ls_wR_factor_gt          0.2417
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.1587(4) 0.6381(3) 0.8528(3) 0.0291(9) Uani 1 1 d . . . . .
N2 N 1.2384(4) 0.7136(3) 0.7181(3) 0.0300(9) Uani 1 1 d . . . . .
N3 N 0.1217(5) 0.6194(3) 0.3020(4) 0.0535(12) Uani 1 1 d . . . . .
N4 N 0.3232(5) 0.4321(4) 0.0796(4) 0.0534(13) Uani 1 1 d . . . . .
C1 C 0.7008(5) 0.6861(4) 0.6259(4) 0.0383(12) Uani 1 1 d . . . . .
H1 H 0.618455 0.709881 0.651617 0.046 Uiso 1 1 calc R U . . .
C2 C 0.6774(5) 0.6381(3) 0.5153(4) 0.0345(11) Uani 1 1 d . . . . .
C3 C 0.7966(5) 0.6072(3) 0.4710(4) 0.0327(11) Uani 1 1 d . . . . .
C4 C 0.9466(5) 0.6232(3) 0.5465(4) 0.0371(11) Uani 1 1 d . . . . .
H4 H 1.029741 0.603498 0.518865 0.044 Uiso 1 1 calc R U . . .
C5 C 0.9678(5) 0.6667(3) 0.6575(4) 0.0325(11) Uani 1 1 d . . . . .
C6 C 0.8406(5) 0.6989(4) 0.6969(4) 0.0381(11) Uani 1 1 d . . . . .
H6 H 0.855571 0.729536 0.773759 0.046 Uiso 1 1 calc R U . . .
C7 C 1.1164(5) 0.6740(3) 0.7404(4) 0.0273(10) Uani 1 1 d . . . . .
C8 C 1.3085(5) 0.6541(3) 0.9025(4) 0.0337(11) Uani 1 1 d . . . . .
H8 H 1.365623 0.634781 0.981024 0.040 Uiso 1 1 calc R U . . .
C9 C 1.3583(5) 0.7021(3) 0.8184(4) 0.0338(11) Uani 1 1 d . . . . .
H9 H 1.457011 0.723946 0.826584 0.041 Uiso 1 1 calc R U . . .
C10 C 0.5286(5) 0.6195(3) 0.4393(4) 0.0385(11) Uani 1 1 d . . . . .
H10 H 0.445823 0.641478 0.465803 0.046 Uiso 1 1 calc R U . . .
C11 C 0.5032(5) 0.5720(3) 0.3322(4) 0.0365(11) Uani 1 1 d . . . . .
C12 C 0.6309(5) 0.5439(3) 0.2897(4) 0.0372(11) Uani 1 1 d . . . . .
H12 H 0.615542 0.512935 0.212917 0.045 Uiso 1 1 calc R U . . .
C13 C 0.7731(5) 0.5611(3) 0.3582(4) 0.0389(12) Uani 1 1 d . . . . .
H13 H 0.855415 0.541854 0.329258 0.047 Uiso 1 1 calc R U . . .
C14 C 0.3553(5) 0.5494(3) 0.2563(4) 0.0334(11) Uani 1 1 d . . . . .
C15 C 0.2254(6) 0.5863(3) 0.2816(4) 0.0361(11) Uani 1 1 d . . . . .
C16 C 0.3376(5) 0.4855(3) 0.1602(4) 0.0349(11) Uani 1 1 d . . . . .
C17 C 1.2414(6) 0.7688(4) 0.6093(4) 0.0448(13) Uani 1 1 d . . . . .
H17A H 1.243098 0.724827 0.542494 0.067 Uiso 1 1 calc R U . . .
H17B H 1.330518 0.809136 0.627054 0.067 Uiso 1 1 calc R U . . .
H17C H 1.152519 0.809239 0.585607 0.067 Uiso 1 1 calc R U . . .
C18 C 1.0643(6) 0.5849(4) 0.9151(5) 0.0468(14) Uani 1 1 d . . . . .
H18A H 0.972704 0.564894 0.855467 0.070 Uiso 1 1 calc R U . . .
H18B H 1.039281 0.625953 0.976726 0.070 Uiso 1 1 calc R U . . .
H18C H 1.117882 0.528169 0.954726 0.070 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.332(5) . ?
N1 C8 1.379(6) . ?
N1 C18 1.469(6) . ?
N2 C7 1.347(6) . ?
N2 C9 1.379(6) . ?
N2 C17 1.464(6) . ?
N3 C15 1.149(6) . ?
N4 C16 1.161(6) . ?
C1 C6 1.352(7) . ?
C1 C2 1.390(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.403(6) . ?
C2 C10 1.451(7) . ?
C3 C13 1.400(6) . ?
C3 C4 1.452(7) . ?
C4 C5 1.367(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.445(7) . ?
C5 C7 1.459(6) . ?
C6 H6 0.9500 . ?
C8 C9 1.347(6) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.352(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.452(7) . ?
C11 C14 1.454(6) . ?
C12 C13 1.370(7) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C16 1.387(7) . ?
C14 C15 1.413(7) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C8 110.1(4) . . ?
C7 N1 C18 126.2(4) . . ?
C8 N1 C18 123.7(4) . . ?
C7 N2 C9 109.7(4) . . ?
C7 N2 C17 125.4(4) . . ?
C9 N2 C17 124.6(4) . . ?
C6 C1 C2 120.0(5) . . ?
C6 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C1 C2 C3 121.5(5) . . ?
C1 C2 C10 121.5(4) . . ?
C3 C2 C10 117.0(4) . . ?
C13 C3 C2 121.5(5) . . ?
C13 C3 C4 120.4(4) . . ?
C2 C3 C4 118.1(4) . . ?
C5 C4 C3 119.7(5) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 119.6(4) . . ?
C4 C5 C7 120.6(4) . . ?
C6 C5 C7 119.6(4) . . ?
C1 C6 C5 121.0(4) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
N1 C7 N2 106.5(4) . . ?
N1 C7 C5 125.7(4) . . ?
N2 C7 C5 127.7(4) . . ?
C9 C8 N1 106.9(4) . . ?
C9 C8 H8 126.5 . . ?
N1 C8 H8 126.5 . . ?
C8 C9 N2 106.8(4) . . ?
C8 C9 H9 126.6 . . ?
N2 C9 H9 126.6 . . ?
C11 C10 C2 122.5(4) . . ?
C11 C10 H10 118.7 . . ?
C2 C10 H10 118.7 . . ?
C10 C11 C12 117.9(4) . . ?
C10 C11 C14 123.6(5) . . ?
C12 C11 C14 118.4(4) . . ?
C13 C12 C11 121.2(4) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C3 119.7(5) . . ?
C12 C13 H13 120.1 . . ?
C3 C13 H13 120.1 . . ?
C16 C14 C15 117.7(4) . . ?
C16 C14 C11 120.2(4) . . ?
C15 C14 C11 121.9(4) . . ?
N3 C15 C14 177.7(5) . . ?
N4 C16 C14 179.8(6) . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -4.0(7) . . . . ?
C6 C1 C2 C10 177.3(5) . . . . ?
C1 C2 C3 C13 -178.3(4) . . . . ?
C10 C2 C3 C13 0.4(6) . . . . ?
C1 C2 C3 C4 2.5(6) . . . . ?
C10 C2 C3 C4 -178.7(4) . . . . ?
C13 C3 C4 C5 -178.7(4) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C3 C4 C5 C6 -1.9(6) . . . . ?
C3 C4 C5 C7 173.3(4) . . . . ?
C2 C1 C6 C5 2.4(7) . . . . ?
C4 C5 C6 C1 0.5(7) . . . . ?
C7 C5 C6 C1 -174.7(4) . . . . ?
C8 N1 C7 N2 -0.5(5) . . . . ?
C18 N1 C7 N2 -177.6(4) . . . . ?
C8 N1 C7 C5 176.9(4) . . . . ?
C18 N1 C7 C5 -0.2(7) . . . . ?
C9 N2 C7 N1 0.0(5) . . . . ?
C17 N2 C7 N1 -174.4(4) . . . . ?
C9 N2 C7 C5 -177.3(4) . . . . ?
C17 N2 C7 C5 8.3(7) . . . . ?
C4 C5 C7 N1 -120.6(5) . . . . ?
C6 C5 C7 N1 54.5(6) . . . . ?
C4 C5 C7 N2 56.2(6) . . . . ?
C6 C5 C7 N2 -128.7(5) . . . . ?
C7 N1 C8 C9 0.8(5) . . . . ?
C18 N1 C8 C9 178.0(4) . . . . ?
N1 C8 C9 N2 -0.8(5) . . . . ?
C7 N2 C9 C8 0.5(5) . . . . ?
C17 N2 C9 C8 175.0(4) . . . . ?
C1 C2 C10 C11 -179.2(4) . . . . ?
C3 C2 C10 C11 2.0(7) . . . . ?
C2 C10 C11 C12 -3.6(7) . . . . ?
C2 C10 C11 C14 177.8(4) . . . . ?
C10 C11 C12 C13 2.8(7) . . . . ?
C14 C11 C12 C13 -178.5(4) . . . . ?
C11 C12 C13 C3 -0.4(7) . . . . ?
C2 C3 C13 C12 -1.2(7) . . . . ?
C4 C3 C13 C12 178.0(4) . . . . ?
C10 C11 C14 C16 -167.8(5) . . . . ?
C12 C11 C14 C16 13.5(7) . . . . ?
C10 C11 C14 C15 8.2(7) . . . . ?
C12 C11 C14 C15 -170.4(4) . . . . ?

_refine_diff_density_max         0.891
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.085


#END===============================================
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_0501DH
_database_code_depnum_ccdc_archive 'CCDC 2494029'
loop_
_audit_author_name
_audit_author_address
'Manuela Weber'
;Freie Universitaet Berlin
Germany
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 N4'
_chemical_formula_weight         236.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.90861(9)
_cell_length_b                   8.59323(6)
_cell_length_c                   10.50182(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1255.176(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8489
_cell_measurement_theta_min      6.05
_cell_measurement_theta_max      68.11
_exptl_crystal_description       chunk
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   0.6873
_exptl_transmission_factor_max   0.9022
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.624
_shelx_estimated_absorpt_T_min   0.780
_shelx_estimated_absorpt_T_max   0.940
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9057
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         6.053
_diffrn_reflns_theta_max         68.105
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             2219
_reflns_number_gt                2176
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_max     0.915
_reflns_Friedel_fraction_full    0.919

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0379P)²+0.3232P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0062(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 971 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(14)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         2219
_refine_ls_number_parameters     166
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0761
_refine_ls_wR_factor_gt          0.0748
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.11213(12) 0.57269(18) 0.36402(17) 0.0184(4) Uani 1 1 d . . . . .
N2 N 0.15771(11) 0.79736(18) 0.29480(16) 0.0173(4) Uani 1 1 d . . . . .
N3 N 0.66246(12) 0.3756(2) 0.57746(19) 0.0246(4) Uani 1 1 d . . . . .
N4 N 0.61106(13) 0.8381(2) 0.7485(2) 0.0275(4) Uani 1 1 d . . . . .
C1 C 0.31469(14) 0.7760(2) 0.50443(19) 0.0183(4) Uani 1 1 d . . . . .
H1 H 0.277824 0.867717 0.517489 0.022 Uiso 1 1 calc R U . . .
C6 C 0.27861(14) 0.6568(2) 0.42740(17) 0.0170(4) Uani 1 1 d . . . . .
C7 C 0.18531(15) 0.6744(2) 0.36387(19) 0.0175(4) Uani 1 1 d . . . . .
C8 C 0.03710(14) 0.6331(2) 0.2934(2) 0.0208(4) Uani 1 1 d . . . . .
H8 H -0.023070 0.584478 0.277546 0.025 Uiso 1 1 calc R U . . .
C9 C 0.06538(15) 0.7737(2) 0.2515(2) 0.0200(4) Uani 1 1 d . . . . .
H9 H 0.028522 0.843726 0.201272 0.024 Uiso 1 1 calc R U . . .
C10 C 0.55417(14) 0.6159(2) 0.60359(19) 0.0178(4) Uani 1 1 d . . . . .
C11 C 0.61380(13) 0.4840(2) 0.58920(19) 0.0182(4) Uani 1 1 d . . . . .
C12 C 0.58738(14) 0.7360(2) 0.6834(2) 0.0196(4) Uani 1 1 d . . . . .
C13 C 0.10825(16) 0.4246(2) 0.4340(2) 0.0262(5) Uani 1 1 d . . . . .
H13A H 0.041349 0.400612 0.455688 0.039 Uiso 1 1 calc R U . . .
H13B H 0.146253 0.433361 0.512260 0.039 Uiso 1 1 calc R U . . .
H13C H 0.134571 0.341280 0.380711 0.039 Uiso 1 1 calc R U . . .
C14 C 0.21734(15) 0.9332(2) 0.2634(2) 0.0228(4) Uani 1 1 d . . . . .
H14A H 0.196008 0.977486 0.182168 0.034 Uiso 1 1 calc R U . . .
H14B H 0.284740 0.901043 0.256321 0.034 Uiso 1 1 calc R U . . .
H14C H 0.211049 1.011507 0.330660 0.034 Uiso 1 1 calc R U . . .
C2 C 0.40369(14) 0.7611(2) 0.56164(19) 0.0178(4) Uani 1 1 d . . . . .
H2 H 0.426707 0.842720 0.614535 0.021 Uiso 1 1 calc R U . . .
C3 C 0.46113(14) 0.6279(2) 0.54342(18) 0.0169(4) Uani 1 1 d . . . . .
C4 C 0.42360(14) 0.5087(2) 0.46549(19) 0.0177(4) Uani 1 1 d . . . . .
H4 H 0.460546 0.417376 0.451070 0.021 Uiso 1 1 calc R U . . .
C5 C 0.33409(14) 0.5226(2) 0.40991(19) 0.0175(4) Uani 1 1 d . . . . .
H5 H 0.309817 0.439948 0.359115 0.021 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.342(3) . ?
N1 C8 1.381(3) . ?
N1 C13 1.470(2) . ?
N2 C7 1.338(3) . ?
N2 C9 1.378(3) . ?
N2 C14 1.469(2) . ?
N3 C11 1.158(3) . ?
N4 C12 1.160(3) . ?
C1 C2 1.382(3) . ?
C1 C6 1.399(3) . ?
C1 H1 0.9500 . ?
C6 C5 1.400(3) . ?
C6 C7 1.467(3) . ?
C8 C9 1.345(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C12 1.407(3) . ?
C10 C11 1.412(3) . ?
C10 C3 1.444(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C2 C3 1.409(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.412(3) . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 H5 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
C7 N1 C8 109.13(16) . . ?
C7 N1 C13 126.32(16) . . ?
C8 N1 C13 124.45(17) . . ?
C7 N2 C9 109.28(16) . . ?
C7 N2 C14 125.95(16) . . ?
C9 N2 C14 124.69(17) . . ?
C2 C1 C6 120.33(17) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C6 C5 118.80(17) . . ?
C1 C6 C7 120.30(16) . . ?
C5 C6 C7 120.88(17) . . ?
N2 C7 N1 107.31(17) . . ?
N2 C7 C6 125.61(17) . . ?
N1 C7 C6 127.08(17) . . ?
C9 C8 N1 107.00(17) . . ?
C9 C8 H8 126.5 . . ?
N1 C8 H8 126.5 . . ?
C8 C9 N2 107.27(17) . . ?
C8 C9 H9 126.4 . . ?
N2 C9 H9 126.4 . . ?
C12 C10 C11 117.35(17) . . ?
C12 C10 C3 120.14(17) . . ?
C11 C10 C3 122.48(17) . . ?
N3 C11 C10 179.8(2) . . ?
N4 C12 C10 177.1(2) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C1 C2 C3 121.61(18) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C4 117.31(17) . . ?
C2 C3 C10 120.47(17) . . ?
C4 C3 C10 122.22(17) . . ?
C5 C4 C3 121.07(17) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.87(17) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 C6 C5 0.2(3) . . . . ?
C2 C1 C6 C7 -178.31(18) . . . . ?
C9 N2 C7 N1 0.5(2) . . . . ?
C14 N2 C7 N1 -176.40(18) . . . . ?
C9 N2 C7 C6 -179.25(19) . . . . ?
C14 N2 C7 C6 3.8(3) . . . . ?
C8 N1 C7 N2 0.1(2) . . . . ?
C13 N1 C7 N2 -176.30(18) . . . . ?
C8 N1 C7 C6 179.82(19) . . . . ?
C13 N1 C7 C6 3.5(3) . . . . ?
C1 C6 C7 N2 49.5(3) . . . . ?
C5 C6 C7 N2 -129.0(2) . . . . ?
C1 C6 C7 N1 -130.2(2) . . . . ?
C5 C6 C7 N1 51.3(3) . . . . ?
C7 N1 C8 C9 -0.6(2) . . . . ?
C13 N1 C8 C9 175.82(18) . . . . ?
N1 C8 C9 N2 0.9(2) . . . . ?
C7 N2 C9 C8 -0.9(2) . . . . ?
C14 N2 C9 C8 176.06(18) . . . . ?
C6 C1 C2 C3 0.8(3) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C1 C2 C3 C10 179.54(18) . . . . ?
C12 C10 C3 C2 1.4(3) . . . . ?
C11 C10 C3 C2 179.32(19) . . . . ?
C12 C10 C3 C4 -178.21(19) . . . . ?
C11 C10 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C10 C3 C4 C5 179.46(18) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C1 C6 C5 C4 -1.2(3) . . . . ?
C7 C6 C5 C4 177.32(18) . . . . ?

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.035


#END===============================================
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_0751DH
_database_code_depnum_ccdc_archive 'CCDC 2494030'
loop_
_audit_author_name
_audit_author_address
'Manuela Weber'
;Freie Universitaet Berlin
Germany
;
_audit_update_record             
;
2025-10-08 deposited with the CCDC.	2026-06-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 Cl2 N4'
_chemical_formula_weight         371.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.6087(4)
_cell_length_b                   12.6810(8)
_cell_length_c                   18.7415(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1808.29(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    149(2)
_cell_measurement_reflns_used    3337
_cell_measurement_theta_min      4.21
_cell_measurement_theta_max      66.50
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   0.2859
_exptl_transmission_factor_max   0.5913
_exptl_crystal_size_max          0.620
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    3.294
_shelx_estimated_absorpt_T_min   0.235
_shelx_estimated_absorpt_T_max   0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      149(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Photon CMOS Detector, D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11063
_diffrn_reflns_av_unetI/netI     0.0857
_diffrn_reflns_av_R_equivalents  0.0912
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.209
_diffrn_reflns_theta_max         66.730
_diffrn_reflns_theta_full        66.730
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             3052
_reflns_number_gt                2177
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_max     0.927
_reflns_Friedel_fraction_full    0.927

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0552P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0028(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 673 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.078(14)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3052
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1234
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.3302(2) 0.62897(13) 0.43338(9) 0.0560(5) Uani 1 1 d . . . . .
Cl2 Cl 0.6085(3) 0.59706(15) 0.53787(10) 0.0729(7) Uani 1 1 d . . . . .
C19 C 0.4549(10) 0.6874(5) 0.5025(3) 0.0462(17) Uani 1 1 d . . . . .
H19A H 0.517763 0.749815 0.483648 0.055 Uiso 1 1 calc R U . . .
H19B H 0.375112 0.711449 0.540925 0.055 Uiso 1 1 calc R U . . .
N1 N 0.2764(6) 0.1058(3) 0.6795(2) 0.0282(11) Uani 1 1 d . . . . .
N2 N 0.4031(6) 0.2586(3) 0.6777(2) 0.0265(11) Uani 1 1 d . . . . .
N3 N 0.1353(7) 0.5208(4) 0.2992(2) 0.0399(13) Uani 1 1 d . . . . .
N4 N 0.3452(8) 0.3188(4) 0.1278(3) 0.0492(15) Uani 1 1 d . . . . .
C1 C 0.3517(8) 0.2378(4) 0.5114(2) 0.0239(12) Uani 1 1 d . . . . .
H1 H 0.299147 0.301839 0.526815 0.029 Uiso 1 1 calc R U . . .
C2 C 0.3883(7) 0.2230(3) 0.4379(3) 0.0231(12) Uani 1 1 d . . . . .
C3 C 0.4629(7) 0.1251(4) 0.4153(3) 0.0254(12) Uani 1 1 d . . . . .
C4 C 0.5028(7) 0.0483(4) 0.4670(3) 0.0276(13) Uani 1 1 d . . . . .
H4 H 0.553754 -0.016623 0.452509 0.033 Uiso 1 1 calc R U . . .
C5 C 0.4693(7) 0.0655(4) 0.5379(3) 0.0276(13) Uani 1 1 d . . . . .
H5 H 0.498791 0.012922 0.572012 0.033 Uiso 1 1 calc R U . . .
C6 C 0.3908(7) 0.1615(4) 0.5607(3) 0.0250(12) Uani 1 1 d . . . . .
C7 C 0.3547(7) 0.1765(3) 0.6363(2) 0.0219(12) Uani 1 1 d . . . . .
C8 C 0.2802(8) 0.1435(4) 0.7490(3) 0.0322(14) Uani 1 1 d . . . . .
H8 H 0.235818 0.108557 0.790011 0.039 Uiso 1 1 calc R U . . .
C9 C 0.3584(8) 0.2387(4) 0.7475(3) 0.0320(14) Uani 1 1 d . . . . .
H9 H 0.378936 0.283610 0.787245 0.038 Uiso 1 1 calc R U . . .
C10 C 0.3450(7) 0.3006(4) 0.3868(3) 0.0260(13) Uani 1 1 d . . . . .
H10 H 0.298030 0.366196 0.402215 0.031 Uiso 1 1 calc R U . . .
C11 C 0.3700(8) 0.2825(4) 0.3142(3) 0.0262(13) Uani 1 1 d . . . . .
C12 C 0.4502(8) 0.1862(4) 0.2933(3) 0.0301(14) Uani 1 1 d . . . . .
H12 H 0.473634 0.174043 0.244156 0.036 Uiso 1 1 calc R U . . .
C13 C 0.4942(8) 0.1108(4) 0.3418(3) 0.0307(14) Uani 1 1 d . . . . .
H13 H 0.547118 0.047250 0.325839 0.037 Uiso 1 1 calc R U . . .
C14 C 0.3126(8) 0.3573(4) 0.2607(3) 0.0283(13) Uani 1 1 d . . . . .
C15 C 0.2147(8) 0.4481(4) 0.2804(3) 0.0298(14) Uani 1 1 d . . . . .
C16 C 0.3301(8) 0.3364(4) 0.1872(3) 0.0333(14) Uani 1 1 d . . . . .
C17 C 0.4868(8) 0.3574(4) 0.6526(3) 0.0306(14) Uani 1 1 d . . . . .
H17A H 0.567098 0.383811 0.689349 0.046 Uiso 1 1 calc R U . . .
H17B H 0.395934 0.410369 0.643091 0.046 Uiso 1 1 calc R U . . .
H17C H 0.552772 0.343429 0.608658 0.046 Uiso 1 1 calc R U . . .
C18 C 0.1943(8) 0.0058(4) 0.6580(3) 0.0350(15) Uani 1 1 d . . . . .
H18A H 0.082684 -0.002958 0.683388 0.053 Uiso 1 1 calc R U . . .
H18B H 0.272971 -0.052815 0.669774 0.053 Uiso 1 1 calc R U . . .
H18C H 0.172497 0.006621 0.606448 0.053 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 C19 1.769(7) . ?
Cl2 C19 1.766(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
N1 C7 1.346(6) . ?
N1 C8 1.387(6) . ?
N1 C18 1.470(6) . ?
N2 C7 1.349(6) . ?
N2 C9 1.376(6) . ?
N2 C17 1.483(6) . ?
N3 C15 1.157(7) . ?
N4 C16 1.142(7) . ?
C1 C6 1.371(6) . ?
C1 C2 1.419(7) . ?
C1 H1 0.9500 . ?
C2 C10 1.412(6) . ?
C2 C3 1.428(7) . ?
C3 C4 1.407(7) . ?
C3 C13 1.410(7) . ?
C4 C5 1.370(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.422(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.455(7) . ?
C8 C9 1.346(8) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.394(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.420(7) . ?
C11 C14 1.447(7) . ?
C12 C13 1.362(7) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C16 1.408(7) . ?
C14 C15 1.420(8) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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
Cl2 C19 Cl1 111.0(3) . . ?
Cl2 C19 H19A 109.4 . . ?
Cl1 C19 H19A 109.4 . . ?
Cl2 C19 H19B 109.4 . . ?
Cl1 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
C7 N1 C8 109.0(4) . . ?
C7 N1 C18 126.7(4) . . ?
C8 N1 C18 124.3(4) . . ?
C7 N2 C9 109.7(4) . . ?
C7 N2 C17 126.0(4) . . ?
C9 N2 C17 124.3(4) . . ?
C6 C1 C2 121.2(5) . . ?
C6 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C10 C2 C1 121.4(4) . . ?
C10 C2 C3 119.9(4) . . ?
C1 C2 C3 118.7(4) . . ?
C4 C3 C13 123.2(4) . . ?
C4 C3 C2 118.9(4) . . ?
C13 C3 C2 117.9(4) . . ?
C5 C4 C3 121.2(5) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 120.4(5) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.5(5) . . ?
C1 C6 C7 121.5(4) . . ?
C5 C6 C7 119.0(4) . . ?
N1 C7 N2 106.8(4) . . ?
N1 C7 C6 125.5(4) . . ?
N2 C7 C6 127.5(4) . . ?
C9 C8 N1 107.4(5) . . ?
C9 C8 H8 126.3 . . ?
N1 C8 H8 126.3 . . ?
C8 C9 N2 107.0(5) . . ?
C8 C9 H9 126.5 . . ?
N2 C9 H9 126.5 . . ?
C11 C10 C2 121.0(4) . . ?
C11 C10 H10 119.5 . . ?
C2 C10 H10 119.5 . . ?
C10 C11 C12 118.0(4) . . ?
C10 C11 C14 121.8(4) . . ?
C12 C11 C14 120.1(4) . . ?
C13 C12 C11 121.7(5) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C3 121.4(5) . . ?
C12 C13 H13 119.3 . . ?
C3 C13 H13 119.3 . . ?
C16 C14 C15 117.2(5) . . ?
C16 C14 C11 121.7(5) . . ?
C15 C14 C11 120.6(4) . . ?
N3 C15 C14 177.4(6) . . ?
N4 C16 C14 179.5(7) . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C10 178.7(5) . . . . ?
C6 C1 C2 C3 1.7(8) . . . . ?
C10 C2 C3 C4 -179.1(5) . . . . ?
C1 C2 C3 C4 -2.0(7) . . . . ?
C10 C2 C3 C13 1.3(8) . . . . ?
C1 C2 C3 C13 178.4(5) . . . . ?
C13 C3 C4 C5 -179.7(6) . . . . ?
C2 C3 C4 C5 0.8(8) . . . . ?
C3 C4 C5 C6 0.9(9) . . . . ?
C2 C1 C6 C5 -0.1(8) . . . . ?
C2 C1 C6 C7 179.6(5) . . . . ?
C4 C5 C6 C1 -1.2(8) . . . . ?
C4 C5 C6 C7 179.1(5) . . . . ?
C8 N1 C7 N2 -1.5(6) . . . . ?
C18 N1 C7 N2 176.8(5) . . . . ?
C8 N1 C7 C6 174.2(5) . . . . ?
C18 N1 C7 C6 -7.5(9) . . . . ?
C9 N2 C7 N1 1.3(6) . . . . ?
C17 N2 C7 N1 -177.0(5) . . . . ?
C9 N2 C7 C6 -174.3(5) . . . . ?
C17 N2 C7 C6 7.4(9) . . . . ?
C1 C6 C7 N1 133.2(6) . . . . ?
C5 C6 C7 N1 -47.1(8) . . . . ?
C1 C6 C7 N2 -52.0(8) . . . . ?
C5 C6 C7 N2 127.7(6) . . . . ?
C7 N1 C8 C9 1.2(6) . . . . ?
C18 N1 C8 C9 -177.2(5) . . . . ?
N1 C8 C9 N2 -0.4(6) . . . . ?
C7 N2 C9 C8 -0.6(7) . . . . ?
C17 N2 C9 C8 177.8(5) . . . . ?
C1 C2 C10 C11 -175.5(5) . . . . ?
C3 C2 C10 C11 1.5(8) . . . . ?
C2 C10 C11 C12 -3.7(8) . . . . ?
C2 C10 C11 C14 174.6(5) . . . . ?
C10 C11 C12 C13 3.1(9) . . . . ?
C14 C11 C12 C13 -175.2(5) . . . . ?
C11 C12 C13 C3 -0.3(9) . . . . ?
C4 C3 C13 C12 178.5(5) . . . . ?
C2 C3 C13 C12 -1.9(8) . . . . ?
C10 C11 C14 C16 -176.7(6) . . . . ?
C12 C11 C14 C16 1.5(9) . . . . ?
C10 C11 C14 C15 -5.4(8) . . . . ?
C12 C11 C14 C15 172.8(5) . . . . ?

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.070


#END===============================================
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
