# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 2224156'
loop_
_audit_author_name
_audit_author_address
'Keke Han'
;Nanchang University
China
;
_audit_update_record             
;
2022-12-03 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_audit_creation_date             2022-12-03
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H7 N3'
_chemical_formula_sum            'C10 H7 N3'
_chemical_formula_weight         169.19
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.096(6)
_cell_length_b                   5.6801(19)
_cell_length_c                   16.380(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.239(5)
_cell_angle_gamma                90.00
_cell_volume                     1638.9(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2717
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      3.03
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6700
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1104 before and 0.0317 after correction.
The Ratio of minimum to maximum transmission is 0.8986.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             704
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4570
_diffrn_reflns_theta_full        27.34
_diffrn_reflns_theta_max         27.34
_diffrn_reflns_theta_min         2.55
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1501
_reflns_number_total             1821
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     53
_refine_ls_number_reflns         1821
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0890
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1065P)²+3.7669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2191
_refine_ls_wR_factor_ref         0.2311
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N001(H001), C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C),
 C00D(H00D)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N001 N 0.29640(13) 0.4352(4) 0.43019(14) 0.0425(6) Uiso 1 1 d . . .
H001 H 0.3095 0.3047 0.4561 0.051 Uiso 1 1 calc R . .
N002 N 0.16904(13) 0.4646(4) 0.45108(15) 0.0441(6) Uiso 1 1 d . . .
N003 N 0.09836(15) 0.8033(5) 0.38648(16) 0.0534(7) Uiso 1 1 d . . .
C004 C 0.30065(14) 0.7735(4) 0.35423(15) 0.0362(6) Uiso 1 1 d . . .
C005 C 0.22732(14) 0.5427(5) 0.42034(15) 0.0365(6) Uiso 1 1 d . . .
C006 C 0.34216(14) 0.5733(5) 0.39096(16) 0.0376(6) Uiso 1 1 d . . .
C007 C 0.22597(14) 0.7533(4) 0.37308(15) 0.0365(6) Uiso 1 1 d . . .
C008 C 0.41754(16) 0.5374(5) 0.38622(18) 0.0457(7) Uiso 1 1 d . . .
H008 H 0.4446 0.4063 0.4106 0.055 Uiso 1 1 calc R . .
C009 C 0.33576(16) 0.9404(5) 0.31298(18) 0.0459(7) Uiso 1 1 d . . .
H009 H 0.3095 1.0737 0.2893 0.055 Uiso 1 1 calc R . .
C00A C 0.10758(17) 0.6042(5) 0.43128(19) 0.0488(7) Uiso 1 1 d . . .
H00A H 0.0659 0.5561 0.4514 0.059 Uiso 1 1 calc R . .
C00B C 0.15832(16) 0.8777(5) 0.35736(18) 0.0459(7) Uiso 1 1 d . . .
H00B H 0.1541 1.0156 0.3260 0.055 Uiso 1 1 calc R . .
C00C C 0.45035(18) 0.7041(6) 0.34390(18) 0.0504(7) Uiso 1 1 d . . .
H00C H 0.5002 0.6826 0.3393 0.060 Uiso 1 1 calc R . .
C00D C 0.41067(18) 0.9039(6) 0.3080(2) 0.0522(8) Uiso 1 1 d . . .
H00D H 0.4345 1.0134 0.2805 0.063 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
N001 H001 0.8600 . ?
N001 C005 1.367(3) . ?
N001 C006 1.399(3) . ?
N002 C005 1.344(3) . ?
N002 C00A 1.344(4) . ?
N003 C00A 1.337(4) . ?
N003 C00B 1.349(4) . ?
C004 C006 1.419(4) . ?
C004 C007 1.458(4) . ?
C004 C009 1.398(4) . ?
C005 C007 1.422(4) . ?
C006 C008 1.399(4) . ?
C007 C00B 1.386(4) . ?
C008 H008 0.9300 . ?
C008 C00C 1.385(4) . ?
C009 H009 0.9300 . ?
C009 C00D 1.392(4) . ?
C00A H00A 0.9300 . ?
C00B H00B 0.9300 . ?
C00C H00C 0.9300 . ?
C00C C00D 1.399(4) . ?
C00D H00D 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
C005 N001 H001 125.8 . . ?
C005 N001 C006 108.4(2) . . ?
C006 N001 H001 125.8 . . ?
C005 N002 C00A 113.1(2) . . ?
C00A N003 C00B 116.7(3) . . ?
C006 C004 C007 105.9(2) . . ?
C009 C004 C006 119.6(2) . . ?
C009 C004 C007 134.6(2) . . ?
N001 C005 C007 110.0(2) . . ?
N002 C005 N001 125.7(2) . . ?
N002 C005 C007 124.4(2) . . ?
N001 C006 C004 109.4(2) . . ?
C008 C006 N001 129.1(2) . . ?
C008 C006 C004 121.4(2) . . ?
C005 C007 C004 106.3(2) . . ?
C00B C007 C004 138.0(2) . . ?
C00B C007 C005 115.7(2) . . ?
C006 C008 H008 121.2 . . ?
C00C C008 C006 117.6(3) . . ?
C00C C008 H008 121.2 . . ?
C004 C009 H009 120.5 . . ?
C00D C009 C004 118.9(3) . . ?
C00D C009 H009 120.5 . . ?
N002 C00A H00A 115.7 . . ?
N003 C00A N002 128.6(3) . . ?
N003 C00A H00A 115.7 . . ?
N003 C00B C007 121.5(3) . . ?
N003 C00B H00B 119.3 . . ?
C007 C00B H00B 119.3 . . ?
C008 C00C H00C 119.1 . . ?
C008 C00C C00D 121.9(3) . . ?
C00D C00C H00C 119.1 . . ?
C009 C00D C00C 120.6(3) . . ?
C009 C00D H00D 119.7 . . ?
C00C C00D H00D 119.7 . . ?

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
N001 C005 C007 C004 -0.7(3) . . . . ?
N001 C005 C007 C00B 178.9(2) . . . . ?
N001 C006 C008 C00C -179.3(3) . . . . ?
N002 C005 C007 C004 178.7(2) . . . . ?
N002 C005 C007 C00B -1.7(4) . . . . ?
C004 C006 C008 C00C -0.3(4) . . . . ?
C004 C007 C00B N003 -179.6(3) . . . . ?
C004 C009 C00D C00C -0.3(4) . . . . ?
C005 N001 C006 C004 -0.7(3) . . . . ?
C005 N001 C006 C008 178.4(3) . . . . ?
C005 N002 C00A N003 0.0(4) . . . . ?
C005 C007 C00B N003 0.9(4) . . . . ?
C006 N001 C005 N002 -178.5(2) . . . . ?
C006 N001 C005 C007 0.8(3) . . . . ?
C006 C004 C007 C005 0.3(3) . . . . ?
C006 C004 C007 C00B -179.2(3) . . . . ?
C006 C004 C009 C00D 0.9(4) . . . . ?
C006 C008 C00C C00D 1.0(4) . . . . ?
C007 C004 C006 N001 0.2(3) . . . . ?
C007 C004 C006 C008 -178.9(2) . . . . ?
C007 C004 C009 C00D 178.6(3) . . . . ?
C008 C00C C00D C009 -0.7(5) . . . . ?
C009 C004 C006 N001 178.5(2) . . . . ?
C009 C004 C006 C008 -0.6(4) . . . . ?
C009 C004 C007 C005 -177.7(3) . . . . ?
C009 C004 C007 C00B 2.8(6) . . . . ?
C00A N002 C005 N001 -179.5(2) . . . . ?
C00A N002 C005 C007 1.2(4) . . . . ?
C00A N003 C00B C007 0.1(4) . . . . ?
C00B N003 C00A N002 -0.6(5) . . . . ?

_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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2224160'
loop_
_audit_author_name
_audit_author_address
'Keke Han'
;nanchang University
China
;
_audit_update_record             
;
2022-12-03 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_audit_creation_date             2022-12-03
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H10 N2'
_chemical_formula_sum            'C6.25 H6.25 F6.25 N6.25'
_chemical_formula_weight         287.67
_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'
F F 0.0171 0.0103 '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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.0243(19)
_cell_length_b                   15.100(6)
_cell_length_c                   14.285(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.425(7)
_cell_angle_gamma                90.00
_cell_volume                     1081.8(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1935
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.70
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5689
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0922 before and 0.0641 after correction.
The Ratio of minimum to maximum transmission is 0.7630.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             575
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0865
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4928
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         2.70
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.897
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1217
_reflns_number_total             2255
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2109
_refine_ls_R_factor_gt           0.1310
_refine_ls_restrained_S_all      1.182
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+3.9036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2198
_refine_ls_wR_factor_ref         0.2497
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N001(H001), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N001 N 0.5682(9) 0.5621(3) 0.8952(3) 0.0501(13) Uani 1 1 d . . .
H001 H 0.6183 0.5664 0.9537 0.060 Uiso 1 1 calc R . .
N002 N 0.2366(10) 0.4505(3) 0.9081(3) 0.0540(13) Uani 1 1 d . . .
C003 C 0.6711(11) 0.6097(4) 0.8234(4) 0.0444(14) Uani 1 1 d . . .
C004 C 0.3414(11) 0.5200(4) 0.7588(4) 0.0438(14) Uani 1 1 d . . .
C005 C 0.5373(10) 0.5865(3) 0.7373(4) 0.0414(13) Uani 1 1 d . . .
C006 C 0.3742(11) 0.5070(4) 0.8584(4) 0.0454(14) Uani 1 1 d . . .
C007 C 0.6226(10) 0.6257(3) 0.6532(4) 0.0424(14) Uani 1 1 d . . .
C008 C 0.8346(11) 0.6874(4) 0.6601(4) 0.0469(14) Uani 1 1 d . . .
C009 C 0.5056(11) 0.6055(4) 0.5627(4) 0.0510(15) Uani 1 1 d . . .
H009 H 0.3625 0.5665 0.5566 0.061 Uiso 1 1 calc R . .
C00A C 0.1457(11) 0.4701(4) 0.7125(4) 0.0522(16) Uani 1 1 d . . .
H00A H 0.1116 0.4760 0.6481 0.063 Uiso 1 1 calc R . .
C00B C 0.8769(12) 0.6720(4) 0.8305(5) 0.0546(16) Uani 1 1 d . . .
H00B H 0.9572 0.6877 0.8885 0.065 Uiso 1 1 calc R . .
C00C C 0.6022(13) 0.6432(4) 0.4843(4) 0.0599(18) Uani 1 1 d . . .
H00C H 0.5236 0.6292 0.4255 0.072 Uiso 1 1 calc R . .
C00D C 0.9564(12) 0.7092(4) 0.7496(5) 0.0555(16) Uani 1 1 d . . .
H00D H 1.0949 0.7502 0.7532 0.067 Uiso 1 1 calc R . .
C00E C 0.0013(12) 0.4113(4) 0.7626(5) 0.0578(17) Uani 1 1 d . . .
H00E H -0.1300 0.3766 0.7321 0.069 Uiso 1 1 calc R . .
C00F C 0.9279(13) 0.7240(4) 0.5761(5) 0.0604(18) Uani 1 1 d . . .
H00F H 1.0692 0.7639 0.5797 0.072 Uiso 1 1 calc R . .
C00G C 0.8136(13) 0.7014(5) 0.4909(5) 0.0661(19) Uani 1 1 d . . .
H00G H 0.8783 0.7254 0.4368 0.079 Uiso 1 1 calc R . .
C00H C 0.0520(12) 0.4038(4) 0.8589(5) 0.0622(18) Uani 1 1 d . . .
H00H H -0.0493 0.3636 0.8910 0.075 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N001 0.056(3) 0.047(3) 0.048(3) 0.001(2) 0.005(2) -0.004(3)
N002 0.050(3) 0.051(3) 0.062(3) 0.005(3) 0.009(3) -0.002(3)
C003 0.041(3) 0.036(3) 0.057(4) 0.001(3) 0.006(3) 0.007(3)
C004 0.038(3) 0.037(3) 0.056(4) 0.001(3) 0.003(3) 0.012(3)
C005 0.037(3) 0.035(3) 0.053(3) 0.003(3) 0.005(3) 0.008(2)
C006 0.038(3) 0.035(3) 0.064(4) 0.004(3) 0.006(3) 0.007(3)
C007 0.032(3) 0.035(3) 0.060(4) 0.000(3) 0.003(3) 0.010(2)
C008 0.037(3) 0.040(3) 0.064(4) 0.001(3) 0.007(3) 0.006(3)
C009 0.042(3) 0.052(4) 0.058(4) 0.006(3) 0.000(3) 0.006(3)
C00A 0.042(3) 0.052(4) 0.062(4) -0.002(3) -0.007(3) 0.002(3)
C00B 0.058(4) 0.044(4) 0.062(4) -0.010(3) 0.004(3) -0.002(3)
C00C 0.061(4) 0.065(5) 0.054(4) 0.011(3) 0.003(3) 0.012(4)
C00D 0.045(4) 0.044(4) 0.078(5) -0.002(3) 0.008(3) -0.002(3)
C00E 0.047(4) 0.052(4) 0.073(5) -0.002(3) -0.006(3) -0.007(3)
C00F 0.047(4) 0.050(4) 0.086(5) 0.010(4) 0.018(4) 0.003(3)
C00G 0.059(4) 0.073(5) 0.068(5) 0.017(4) 0.014(4) 0.016(4)
C00H 0.047(4) 0.055(4) 0.085(5) 0.008(4) 0.006(3) 0.001(3)

_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
N001 H001 0.8600 . ?
N001 C003 1.378(7) . ?
N001 C006 1.362(7) . ?
N002 C006 1.330(7) . ?
N002 C00H 1.332(8) . ?
C003 C005 1.410(8) . ?
C003 C00B 1.397(8) . ?
C004 C005 1.451(8) . ?
C004 C006 1.436(8) . ?
C004 C00A 1.377(8) . ?
C005 C007 1.428(7) . ?
C007 C008 1.414(7) . ?
C007 C009 1.421(8) . ?
C008 C00D 1.423(8) . ?
C008 C00F 1.426(8) . ?
C009 H009 0.9300 . ?
C009 C00C 1.370(8) . ?
C00A H00A 0.9300 . ?
C00A C00E 1.374(8) . ?
C00B H00B 0.9300 . ?
C00B C00D 1.366(8) . ?
C00C H00C 0.9300 . ?
C00C C00G 1.378(9) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00E C00H 1.388(9) . ?
C00F H00F 0.9300 . ?
C00F C00G 1.358(9) . ?
C00G H00G 0.9300 . ?
C00H H00H 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
C003 N001 H001 125.6 . . ?
C006 N001 H001 125.6 . . ?
C006 N001 C003 108.8(5) . . ?
C006 N002 C00H 115.2(6) . . ?
N001 C003 C005 109.8(5) . . ?
N001 C003 C00B 127.3(6) . . ?
C00B C003 C005 122.9(5) . . ?
C006 C004 C005 105.4(5) . . ?
C00A C004 C005 138.7(6) . . ?
C00A C004 C006 115.9(5) . . ?
C003 C005 C004 106.3(5) . . ?
C003 C005 C007 118.7(5) . . ?
C007 C005 C004 134.9(5) . . ?
N001 C006 C004 109.6(5) . . ?
N002 C006 N001 124.7(6) . . ?
N002 C006 C004 125.7(6) . . ?
C008 C007 C005 118.5(5) . . ?
C008 C007 C009 118.3(5) . . ?
C009 C007 C005 123.3(5) . . ?
C007 C008 C00D 119.8(5) . . ?
C007 C008 C00F 118.7(6) . . ?
C00D C008 C00F 121.4(6) . . ?
C007 C009 H009 119.7 . . ?
C00C C009 C007 120.5(6) . . ?
C00C C009 H009 119.7 . . ?
C004 C00A H00A 120.4 . . ?
C00E C00A C004 119.2(6) . . ?
C00E C00A H00A 120.4 . . ?
C003 C00B H00B 121.0 . . ?
C00D C00B C003 118.0(6) . . ?
C00D C00B H00B 121.0 . . ?
C009 C00C H00C 119.4 . . ?
C009 C00C C00G 121.2(6) . . ?
C00G C00C H00C 119.4 . . ?
C008 C00D H00D 118.9 . . ?
C00B C00D C008 122.2(6) . . ?
C00B C00D H00D 118.9 . . ?
C00A C00E H00E 120.1 . . ?
C00A C00E C00H 119.8(6) . . ?
C00H C00E H00E 120.1 . . ?
C008 C00F H00F 119.5 . . ?
C00G C00F C008 121.0(6) . . ?
C00G C00F H00F 119.5 . . ?
C00C C00G H00G 119.8 . . ?
C00F C00G C00C 120.3(6) . . ?
C00F C00G H00G 119.8 . . ?
N002 C00H C00E 124.1(6) . . ?
N002 C00H H00H 117.9 . . ?
C00E C00H H00H 117.9 . . ?

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
N001 C003 C005 C004 -0.3(6) . . . . ?
N001 C003 C005 C007 -177.2(5) . . . . ?
N001 C003 C00B C00D 177.3(5) . . . . ?
C003 N001 C006 N002 178.7(5) . . . . ?
C003 N001 C006 C004 -1.6(6) . . . . ?
C003 C005 C007 C008 -1.2(7) . . . . ?
C003 C005 C007 C009 178.6(5) . . . . ?
C003 C00B C00D C008 0.9(9) . . . . ?
C004 C005 C007 C008 -176.9(6) . . . . ?
C004 C005 C007 C009 2.8(9) . . . . ?
C004 C00A C00E C00H 0.8(9) . . . . ?
C005 C003 C00B C00D -2.4(9) . . . . ?
C005 C004 C006 N001 1.3(6) . . . . ?
C005 C004 C006 N002 -179.0(5) . . . . ?
C005 C004 C00A C00E 179.2(6) . . . . ?
C005 C007 C008 C00D -0.3(8) . . . . ?
C005 C007 C008 C00F 177.4(5) . . . . ?
C005 C007 C009 C00C -177.8(5) . . . . ?
C006 N001 C003 C005 1.2(6) . . . . ?
C006 N001 C003 C00B -178.6(5) . . . . ?
C006 N002 C00H C00E 0.3(9) . . . . ?
C006 C004 C005 C003 -0.6(6) . . . . ?
C006 C004 C005 C007 175.5(6) . . . . ?
C006 C004 C00A C00E -1.2(8) . . . . ?
C007 C008 C00D C00B 0.4(9) . . . . ?
C007 C008 C00F C00G 1.1(9) . . . . ?
C007 C009 C00C C00G -0.2(9) . . . . ?
C008 C007 C009 C00C 1.9(8) . . . . ?
C008 C00F C00G C00C 0.7(10) . . . . ?
C009 C007 C008 C00D 180.0(5) . . . . ?
C009 C007 C008 C00F -2.3(8) . . . . ?
C009 C00C C00G C00F -1.2(10) . . . . ?
C00A C004 C005 C003 179.0(6) . . . . ?
C00A C004 C005 C007 -4.9(11) . . . . ?
C00A C004 C006 N001 -178.3(5) . . . . ?
C00A C004 C006 N002 1.3(8) . . . . ?
C00A C00E C00H N002 -0.3(10) . . . . ?
C00B C003 C005 C004 179.5(5) . . . . ?
C00B C003 C005 C007 2.6(8) . . . . ?
C00D C008 C00F C00G 178.7(6) . . . . ?
C00F C008 C00D C00B -177.2(6) . . . . ?
C00H N002 C006 N001 178.8(5) . . . . ?
C00H N002 C006 C004 -0.9(8) . . . . ?

_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_1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2224157'
loop_
_audit_author_name
_audit_author_address
'Keke Han'
;nanchang University
China
;
_audit_update_record             
;
2022-12-03 deposited with the CCDC.	2023-05-15 downloaded from the CCDC.
;
_audit_creation_date             2022-12-03
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H9 N3'
_chemical_formula_sum            'C14 H9 N3'
_chemical_formula_weight         219.24
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   9.977(3)
_cell_length_b                   5.2487(13)
_cell_length_c                   20.047(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.257(4)
_cell_angle_gamma                90.00
_cell_volume                     1043.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1777
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.74
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6098
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0972 before and 0.0415 after correction.
The Ratio of minimum to maximum transmission is 0.8179.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             456
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5882
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         2.04
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1577
_reflns_number_total             2359
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.167
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0807P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1581
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N001(H001), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N001 N 0.43574(15) 0.7401(3) 0.44258(7) 0.0350(4) Uani 1 1 d . . .
H001 H 0.4995 0.8497 0.4413 0.042 Uiso 1 1 calc R . .
N002 N 0.35878(17) 0.8678(3) 0.54639(8) 0.0386(4) Uani 1 1 d . . .
N003 N 0.45899(16) 0.5373(3) 0.33768(8) 0.0392(4) Uani 1 1 d . . .
C004 C 0.35378(18) 0.7165(3) 0.49245(9) 0.0312(5) Uani 1 1 d . . .
C005 C 0.26253(18) 0.5104(3) 0.47739(9) 0.0314(5) Uani 1 1 d . . .
C006 C 0.23874(18) 0.2173(4) 0.36898(9) 0.0333(5) Uani 1 1 d . . .
C007 C 0.29276(18) 0.4104(3) 0.41383(9) 0.0306(5) Uani 1 1 d . . .
C008 C 0.39872(19) 0.5583(4) 0.39462(9) 0.0314(5) Uani 1 1 d . . .
C009 C 0.2985(2) 0.1959(4) 0.30819(10) 0.0363(5) Uani 1 1 d . . .
C00A C 0.1318(2) 0.0507(4) 0.37987(11) 0.0407(5) Uani 1 1 d . . .
H00A H 0.0920 0.0599 0.4197 0.049 Uiso 1 1 calc R . .
C00B C 0.1716(2) 0.4623(4) 0.52377(10) 0.0393(5) Uani 1 1 d . . .
H00B H 0.1102 0.3289 0.5175 0.047 Uiso 1 1 calc R . .
C00C C 0.4070(2) 0.3583(4) 0.29623(10) 0.0412(5) Uani 1 1 d . . .
H00C H 0.4445 0.3371 0.2561 0.049 Uiso 1 1 calc R . .
C00D C 0.2491(2) 0.0116(4) 0.25992(11) 0.0458(6) Uani 1 1 d . . .
H00D H 0.2880 -0.0032 0.2200 0.055 Uiso 1 1 calc R . .
C00E C 0.1752(2) 0.6189(4) 0.57956(10) 0.0454(6) Uani 1 1 d . . .
H00E H 0.1148 0.5923 0.6111 0.054 Uiso 1 1 calc R . .
C00F C 0.2682(2) 0.8146(4) 0.58867(10) 0.0446(6) Uani 1 1 d . . .
H00F H 0.2676 0.9156 0.6267 0.054 Uiso 1 1 calc R . .
C00G C 0.0867(2) -0.1241(4) 0.33185(12) 0.0491(6) Uani 1 1 d . . .
H00G H 0.0159 -0.2318 0.3394 0.059 Uiso 1 1 calc R . .
C00H C 0.1450(2) -0.1439(4) 0.27165(12) 0.0523(6) Uani 1 1 d . . .
H00H H 0.1126 -0.2634 0.2396 0.063 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N001 0.0355(9) 0.0326(9) 0.0376(9) -0.0009(7) 0.0066(7) -0.0059(7)
N002 0.0445(10) 0.0367(9) 0.0348(9) -0.0026(7) 0.0046(8) -0.0005(8)
N003 0.0391(10) 0.0415(10) 0.0380(9) 0.0002(8) 0.0090(8) 0.0005(8)
C004 0.0332(10) 0.0303(10) 0.0302(10) 0.0031(8) 0.0038(8) 0.0047(8)
C005 0.0318(10) 0.0299(10) 0.0321(10) 0.0049(8) 0.0014(8) 0.0041(8)
C006 0.0330(10) 0.0291(10) 0.0368(11) 0.0030(8) -0.0006(8) 0.0054(8)
C007 0.0301(10) 0.0285(10) 0.0332(11) 0.0024(8) 0.0028(8) 0.0024(8)
C008 0.0322(10) 0.0301(10) 0.0317(10) 0.0009(8) 0.0024(8) 0.0033(8)
C009 0.0383(11) 0.0330(11) 0.0369(11) -0.0027(8) 0.0005(9) 0.0061(9)
C00A 0.0405(12) 0.0352(11) 0.0462(12) 0.0035(9) 0.0037(10) -0.0015(9)
C00B 0.0376(11) 0.0423(12) 0.0386(11) 0.0047(9) 0.0064(9) -0.0021(9)
C00C 0.0423(12) 0.0447(12) 0.0378(11) -0.0038(9) 0.0099(9) 0.0040(10)
C00D 0.0512(14) 0.0434(12) 0.0417(12) -0.0081(10) -0.0001(10) 0.0061(11)
C00E 0.0452(13) 0.0568(14) 0.0367(12) 0.0040(10) 0.0157(10) 0.0003(11)
C00F 0.0531(13) 0.0482(13) 0.0337(12) -0.0027(10) 0.0096(10) 0.0016(11)
C00G 0.0469(13) 0.0384(12) 0.0602(15) 0.0022(11) -0.0027(11) -0.0078(10)
C00H 0.0592(15) 0.0422(13) 0.0522(14) -0.0110(11) -0.0084(12) -0.0032(11)

_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
N001 H001 0.8600 . ?
N001 C004 1.365(2) . ?
N001 C008 1.376(2) . ?
N002 C004 1.338(2) . ?
N002 C00F 1.334(3) . ?
N003 C008 1.352(2) . ?
N003 C00C 1.322(2) . ?
C004 C005 1.425(3) . ?
C005 C007 1.440(3) . ?
C005 C00B 1.391(3) . ?
C006 C007 1.422(3) . ?
C006 C009 1.418(3) . ?
C006 C00A 1.415(3) . ?
C007 C008 1.399(3) . ?
C009 C00C 1.418(3) . ?
C009 C00D 1.419(3) . ?
C00A H00A 0.9300 . ?
C00A C00G 1.370(3) . ?
C00B H00B 0.9300 . ?
C00B C00E 1.385(3) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00D C00H 1.361(3) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.383(3) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00H 1.399(3) . ?
C00H H00H 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
C004 N001 H001 125.9 . . ?
C004 N001 C008 108.19(15) . . ?
C008 N001 H001 125.9 . . ?
C00F N002 C004 114.90(17) . . ?
C00C N003 C008 114.12(17) . . ?
N001 C004 C005 109.50(16) . . ?
N002 C004 N001 124.46(17) . . ?
N002 C004 C005 126.04(18) . . ?
C004 C005 C007 105.87(16) . . ?
C00B C005 C004 116.37(17) . . ?
C00B C005 C007 137.75(18) . . ?
C009 C006 C007 115.70(17) . . ?
C00A C006 C007 125.69(18) . . ?
C00A C006 C009 118.61(18) . . ?
C006 C007 C005 135.89(18) . . ?
C008 C007 C005 106.19(16) . . ?
C008 C007 C006 117.86(17) . . ?
N001 C008 C007 110.24(16) . . ?
N003 C008 N001 122.43(17) . . ?
N003 C008 C007 127.33(17) . . ?
C006 C009 C00D 119.49(19) . . ?
C00C C009 C006 119.87(18) . . ?
C00C C009 C00D 120.6(2) . . ?
C006 C00A H00A 120.0 . . ?
C00G C00A C006 120.1(2) . . ?
C00G C00A H00A 120.0 . . ?
C005 C00B H00B 120.9 . . ?
C00E C00B C005 118.10(19) . . ?
C00E C00B H00B 120.9 . . ?
N003 C00C C009 125.09(19) . . ?
N003 C00C H00C 117.5 . . ?
C009 C00C H00C 117.5 . . ?
C009 C00D H00D 119.8 . . ?
C00H C00D C009 120.4(2) . . ?
C00H C00D H00D 119.8 . . ?
C00B C00E H00E 119.8 . . ?
C00F C00E C00B 120.3(2) . . ?
C00F C00E H00E 119.8 . . ?
N002 C00F C00E 124.25(19) . . ?
N002 C00F H00F 117.9 . . ?
C00E C00F H00F 117.9 . . ?
C00A C00G H00G 119.3 . . ?
C00A C00G C00H 121.4(2) . . ?
C00H C00G H00G 119.3 . . ?
C00D C00H C00G 120.1(2) . . ?
C00D C00H H00H 120.0 . . ?
C00G C00H H00H 120.0 . . ?

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
N001 C004 C005 C007 -0.88(19) . . . . ?
N001 C004 C005 C00B -179.87(15) . . . . ?
N002 C004 C005 C007 178.32(17) . . . . ?
N002 C004 C005 C00B -0.7(3) . . . . ?
C004 N001 C008 N003 178.15(16) . . . . ?
C004 N001 C008 C007 -1.1(2) . . . . ?
C004 N002 C00F C00E 0.4(3) . . . . ?
C004 C005 C007 C006 -176.7(2) . . . . ?
C004 C005 C007 C008 0.21(19) . . . . ?
C004 C005 C00B C00E 1.1(3) . . . . ?
C005 C007 C008 N001 0.5(2) . . . . ?
C005 C007 C008 N003 -178.67(17) . . . . ?
C005 C00B C00E C00F -0.8(3) . . . . ?
C006 C007 C008 N001 178.11(15) . . . . ?
C006 C007 C008 N003 -1.1(3) . . . . ?
C006 C009 C00C N003 -0.9(3) . . . . ?
C006 C009 C00D C00H 0.0(3) . . . . ?
C006 C00A C00G C00H 0.4(3) . . . . ?
C007 C005 C00B C00E -177.5(2) . . . . ?
C007 C006 C009 C00C 1.3(3) . . . . ?
C007 C006 C009 C00D -178.75(16) . . . . ?
C007 C006 C00A C00G 178.46(18) . . . . ?
C008 N001 C004 N002 -178.00(17) . . . . ?
C008 N001 C004 C005 1.2(2) . . . . ?
C008 N003 C00C C009 -0.5(3) . . . . ?
C009 C006 C007 C005 176.23(19) . . . . ?
C009 C006 C007 C008 -0.4(2) . . . . ?
C009 C006 C00A C00G -0.9(3) . . . . ?
C009 C00D C00H C00G -0.5(3) . . . . ?
C00A C006 C007 C005 -3.2(3) . . . . ?
C00A C006 C007 C008 -179.83(16) . . . . ?
C00A C006 C009 C00C -179.24(17) . . . . ?
C00A C006 C009 C00D 0.7(3) . . . . ?
C00A C00G C00H C00D 0.3(3) . . . . ?
C00B C005 C007 C006 1.9(4) . . . . ?
C00B C005 C007 C008 178.9(2) . . . . ?
C00B C00E C00F N002 0.0(3) . . . . ?
C00C N003 C008 N001 -177.56(16) . . . . ?
C00C N003 C008 C007 1.5(3) . . . . ?
C00C C009 C00D C00H 179.95(19) . . . . ?
C00D C009 C00C N003 179.18(18) . . . . ?
C00F N002 C004 N001 179.00(16) . . . . ?
C00F N002 C004 C005 -0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
