# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

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

data_111
_database_code_depnum_ccdc_archive 'CCDC 2142244'
loop_
_audit_author_name
_audit_author_address
'lipeng long'
;xia men university
China
;
_audit_update_record             
;
2022-01-15 deposited with the CCDC.	2022-10-03 downloaded from the CCDC.
;
_audit_creation_date             2022-01-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_chemical_formula_moiety         'C17 H13 N3'
_chemical_formula_sum            'C17 H13 N3'
_chemical_formula_weight         259.31
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

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

_symmetry_Int_Tables_number      33
_cell_length_a                   9.1611(17)
_cell_length_b                   28.828(6)
_cell_length_c                   5.3391(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1410.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7235
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.07
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.2214
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544.1925
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            17796
_diffrn_reflns_theta_full        24.9965
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.83
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.9791
_diffrn_measured_fraction_theta_max 0.9791
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.978
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              33
_reflns_limit_k_min              -33
_reflns_limit_l_max              6
_reflns_limit_l_min              -6
_reflns_number_gt                2168
_reflns_number_total             2437
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.4680
_refine_diff_density_min         -0.4569
_refine_diff_density_rms         0.1216
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -1(7)
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             7.2069
_refine_ls_goodness_of_fit_ref   1.0359
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    24
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2437
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1316
_refine_ls_R_factor_gt           0.1207
_refine_ls_restrained_S_all      1.0359
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0975P)²+10.5159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3122
_refine_ls_wR_factor_ref         0.3193
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C003(H003), C005(H005)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00J(H00J)
2.c Idealised Me refined as rotating group:
 C00K(H00c,H00i,H00k)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
N001 N -0.2139(7) -0.5547(2) -0.7536(12) 0.0372(15) Uani 1.000000 .
C002 C -0.1752(8) -0.5842(2) -0.5791(14) 0.0284(15) Uani 1.000000 .
C003 C -0.4088(9) -0.5648(2) -0.3044(13) 0.0331(17) Uani 1.000000 .
N004 N -0.3768(8) -0.4775(2) -0.3841(15) 0.0452(18) Uani 1.000000 .
C005 C -0.4531(9) -0.5993(2) -0.4981(13) 0.0341(17) Uani 1.000000 .
C006 C -0.5527(10) -0.6374(3) -0.4371(15) 0.040(2) Uani 1.000000 .
C007 C -0.3906(8) -0.5156(3) -0.3599(15) 0.0342(17) Uani 1.000000 .
N008 N -0.2316(10) -0.6632(3) -0.0884(17) 0.071(3) Uani 1.000000 .
C009 C -0.2969(8) -0.5996(2) -0.4049(14) 0.0298(16) Uani 1.000000 .
C00A C -0.0330(9) -0.5999(3) -0.5544(17) 0.049(2) Uani 1.000000 .
C00B C 0.0322(11) -0.5533(3) -0.8964(18) 0.054(2) Uani 1.000000 .
C00C C -0.2595(10) -0.6358(3) -0.2248(19) 0.049(2) Uani 1.000000 .
C00D C -0.1111(10) -0.5400(3) -0.9084(16) 0.047(2) Uani 1.000000 .
C00E C -0.5455(11) -0.6775(3) -0.5767(19) 0.057(3) Uani 1.000000 .
C00F C 0.0708(9) -0.5837(4) -0.718(2) 0.059(3) Uani 1.000000 .
C00G C -0.6569(10) -0.6342(3) -0.2473(19) 0.056(2) Uani 1.000000 .
C00H C -0.7360(12) -0.7109(4) -0.3315(19) 0.064(3) Uani 1.000000 .
C00I C -0.6389(13) -0.7154(3) -0.522(2) 0.068(3) Uani 1.000000 .
C00J C -0.7459(11) -0.6713(4) -0.194(2) 0.067(3) Uani 1.000000 .
C00K C -0.624(2) -0.7593(4) -0.667(3) 0.119(6) Uani 1.000000 .
H00G H -0.6663(10) -0.6068(3) -0.1566(19) 0.067(3) Uiso 1.000000 R
H00J H -0.8129(11) -0.6693(4) -0.064(2) 0.081(4) Uiso 1.000000 R
H00H H -0.7977(12) -0.7355(4) -0.2941(19) 0.077(4) Uiso 1.000000 R
H00E H -0.4791(11) -0.6797(3) -0.7080(19) 0.068(3) Uiso 1.000000 R
H00D H -0.1380(10) -0.5194(3) -1.0340(16) 0.057(3) Uiso 1.000000 R
H00B H 0.1007(11) -0.5415(3) -1.0083(18) 0.065(3) Uiso 1.000000 R
H00F H 0.1670(9) -0.5937(4) -0.705(2) 0.071(3) Uiso 1.000000 R
H00A H -0.0083(9) -0.6210(3) -0.4294(17) 0.059(3) Uiso 1.000000 R
H003 H -0.4444(9) -0.5715(2) -0.1351(13) 0.040(2) Uiso 1.000000 R
H005 H -0.4658(9) -0.5864(2) -0.6665(13) 0.041(2) Uiso 1.000000 R
H00c H -0.562(13) -0.7806(19) -0.577(13) 0.179(9) Uiso 1.000000 GR
H00i H -0.718(3) -0.773(3) -0.69(2) 0.179(9) Uiso 1.000000 GR
H00k H -0.581(15) -0.7527(8) -0.827(11) 0.179(9) Uiso 1.000000 GR


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 C002 1.312(9) . ?
N001 C00D 1.323(11) . ?
C002 C009 1.518(10) . ?
C002 C00A 1.385(11) . ?
C003 C005 1.492(10) . ?
C003 C007 1.456(10) . ?
C003 C009 1.531(10) . ?
N004 C007 1.115(9) . ?
C005 C006 1.464(11) . ?
C005 C009 1.515(11) . ?
C006 C00E 1.377(12) . ?
C006 C00G 1.395(12) . ?
N008 C00C 1.103(12) . ?
C009 C00C 1.461(12) . ?
C00A C00F 1.372(13) . ?
C00B C00D 1.368(13) . ?
C00B C00F 1.344(14) . ?
C00E C00I 1.420(13) . ?
C00G C00J 1.374(13) . ?
C00H C00I 1.356(16) . ?
C00H C00J 1.361(15) . ?
C00I C00K 1.492(16) . ?

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
C00D N001 C002 117.3(7) . . ?
C009 C002 N001 115.2(6) . . ?
C00A C002 N001 122.3(7) . . ?
C00A C002 C009 122.5(7) . . ?
C007 C003 C005 122.6(6) . . ?
C009 C003 C005 60.1(5) . . ?
C009 C003 C007 119.3(6) . . ?
C006 C005 C003 121.0(6) . . ?
C009 C005 C003 61.2(5) . . ?
C009 C005 C006 120.8(6) . . ?
C00E C006 C005 118.6(8) . . ?
C00G C006 C005 122.6(8) . . ?
C00G C006 C00E 118.8(8) . . ?
N004 C007 C003 174.9(9) . . ?
C003 C009 C002 121.0(6) . . ?
C005 C009 C002 119.4(6) . . ?
C005 C009 C003 58.6(5) . . ?
C00C C009 C002 116.1(7) . . ?
C00C C009 C003 113.3(6) . . ?
C00C C009 C005 116.2(6) . . ?
C00F C00A C002 118.7(8) . . ?
C00F C00B C00D 117.8(9) . . ?
C009 C00C N008 179.8(10) . . ?
C00B C00D N001 124.4(9) . . ?
C00I C00E C006 120.4(10) . . ?
C00B C00F C00A 119.5(9) . . ?
C00J C00G C006 120.4(10) . . ?
C00J C00H C00I 122.0(9) . . ?
C00H C00I C00E 118.4(10) . . ?
C00K C00I C00E 119.3(11) . . ?
C00K C00I C00H 122.2(10) . . ?
C00H C00J C00G 120.1(10) . . ?

_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_cjl20201209sy_0m
_database_code_depnum_ccdc_archive 'CCDC 2141258'
loop_
_audit_author_name
_audit_author_address
'lipeng long'
;xia men university
China
;
_audit_update_record             
;
2022-01-17 deposited with the CCDC.	2022-10-03 downloaded from the CCDC.
;
_audit_creation_date             2022-01-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 N3'
_chemical_formula_sum            'C16 H11 N3'
_chemical_formula_weight         245.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.3594(9)
_cell_length_b                   12.4742(12)
_cell_length_c                   11.0555(12)
_cell_angle_alpha                90
_cell_angle_beta                 95.258(4)
_cell_angle_gamma                90
_cell_volume                     1285.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6571
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.547
_cell_measurement_theta_min      2.990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16661
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         27.578
_diffrn_reflns_theta_min         3.182
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1967
_reflns_number_total             2862
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2862
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0629
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+0.4479P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1408
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.17608(18) 0.74214(14) 0.04356(17) 0.0568(5) Uani 1 1 d . . . . .
C2 C 0.58969(18) 0.86292(14) -0.01832(16) 0.0373(4) Uani 1 1 d . . . . .
C8 C 0.41428(19) 0.69874(14) 0.00339(15) 0.0373(4) Uani 1 1 d . . . . .
C4 C 0.25667(19) 0.67775(15) -0.01673(16) 0.0405(4) Uani 1 1 d . . . . .
C5 C 0.46401(19) 0.81268(14) 0.03222(16) 0.0389(4) Uani 1 1 d . . . . .
H5 H 0.384341 0.862777 0.038329 0.047 Uiso 1 1 calc R U . . .
C6 C 0.6911(2) 0.91776(16) 0.05767(18) 0.0466(5) Uani 1 1 d . . . . .
H6 H 0.685654 0.916549 0.141238 0.056 Uiso 1 1 calc R U . . .
C7 C 0.7098(2) 0.92242(17) -0.18856(19) 0.0519(5) Uani 1 1 d . . . . .
H7 H 0.716335 0.923618 -0.271979 0.062 Uiso 1 1 calc R U . . .
C3 C 0.6004(2) 0.86624(17) -0.14199(18) 0.0467(5) Uani 1 1 d . . . . .
N2 N 0.5766(2) 0.57865(17) -0.11637(18) 0.0685(6) Uani 1 1 d . . . . .
C10 C 0.6136(2) 0.68934(17) 0.17871(18) 0.0502(5) Uani 1 1 d . . . . .
C11 C 0.4760(2) 0.73035(15) 0.13225(16) 0.0414(4) Uani 1 1 d . . . . .
H11 H 0.405439 0.737100 0.192032 0.050 Uiso 1 1 calc R U . . .
C12 C 0.5060(2) 0.63188(16) -0.06362(17) 0.0439(5) Uani 1 1 d . . . . .
C13 C 0.8089(2) 0.97648(18) -0.1127(2) 0.0542(6) Uani 1 1 d . . . . .
H13 H 0.882084 1.014710 -0.144472 0.065 Uiso 1 1 calc R U . . .
C14 C 0.7998(2) 0.97406(17) 0.0100(2) 0.0544(6) Uani 1 1 d . . . . .
H14 H 0.867208 1.010544 0.061606 0.065 Uiso 1 1 calc R U . . .
N3 N 0.7222(2) 0.65697(19) 0.21636(19) 0.0759(6) Uani 1 1 d . . . . .
C16 C 0.2015(2) 0.59761(18) -0.09329(18) 0.0536(5) Uani 1 1 d . . . . .
H16 H 0.261744 0.552026 -0.131612 0.064 Uiso 1 1 calc R U . . .
C17 C 0.0341(2) 0.7295(2) 0.0249(3) 0.0725(7) Uani 1 1 d . . . . .
H17 H -0.024175 0.774093 0.066581 0.087 Uiso 1 1 calc R U . . .
C18 C -0.0303(3) 0.6544(3) -0.0523(3) 0.0803(9) Uani 1 1 d . . . . .
H18 H -0.129758 0.649401 -0.064326 0.096 Uiso 1 1 calc R U . . .
C19 C 0.0553(3) 0.5870(2) -0.1113(2) 0.0748(8) Uani 1 1 d . . . . .
H19 H 0.014652 0.534402 -0.163222 0.090 Uiso 1 1 calc R U . . .
H3 H 0.529(2) 0.8331(18) -0.1944(19) 0.060(6) Uiso 1 1 d . . . . .


_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 C4 1.323(2) . ?
N1 C17 1.335(3) . ?
C2 C5 1.486(2) . ?
C2 C6 1.388(3) . ?
C2 C3 1.381(3) . ?
C8 C4 1.495(3) . ?
C8 C5 1.520(2) . ?
C8 C11 1.539(2) . ?
C8 C12 1.448(3) . ?
C4 C16 1.379(3) . ?
C5 H5 0.9800 . ?
C5 C11 1.506(2) . ?
C6 H6 0.9300 . ?
C6 C14 1.380(3) . ?
C7 H7 0.9300 . ?
C7 C3 1.378(3) . ?
C7 C13 1.370(3) . ?
C3 H3 0.94(2) . ?
N2 C12 1.135(2) . ?
C10 C11 1.436(3) . ?
C10 N3 1.136(3) . ?
C11 H11 0.9800 . ?
C13 H13 0.9300 . ?
C13 C14 1.367(3) . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?
C16 C19 1.371(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.369(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.368(4) . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C17 117.1(2) . . ?
C6 C2 C5 120.05(16) . . ?
C3 C2 C5 121.12(16) . . ?
C3 C2 C6 118.47(18) . . ?
C4 C8 C5 118.29(15) . . ?
C4 C8 C11 117.68(15) . . ?
C5 C8 C11 58.97(11) . . ?
C12 C8 C4 116.49(16) . . ?
C12 C8 C5 117.46(16) . . ?
C12 C8 C11 115.55(15) . . ?
N1 C4 C8 114.78(17) . . ?
N1 C4 C16 123.39(18) . . ?
C16 C4 C8 121.82(18) . . ?
C2 C5 C8 123.58(15) . . ?
C2 C5 H5 113.0 . . ?
C2 C5 C11 123.73(15) . . ?
C8 C5 H5 113.0 . . ?
C11 C5 C8 61.13(12) . . ?
C11 C5 H5 113.0 . . ?
C2 C6 H6 119.8 . . ?
C14 C6 C2 120.43(18) . . ?
C14 C6 H6 119.8 . . ?
C3 C7 H7 119.8 . . ?
C13 C7 H7 119.8 . . ?
C13 C7 C3 120.37(19) . . ?
C2 C3 H3 118.9(13) . . ?
C7 C3 C2 120.60(19) . . ?
C7 C3 H3 120.4(13) . . ?
N3 C10 C11 179.5(2) . . ?
C8 C11 H11 115.3 . . ?
C5 C11 C8 59.90(11) . . ?
C5 C11 H11 115.3 . . ?
C10 C11 C8 119.22(16) . . ?
C10 C11 C5 120.64(17) . . ?
C10 C11 H11 115.3 . . ?
N2 C12 C8 179.2(2) . . ?
C7 C13 H13 120.1 . . ?
C14 C13 C7 119.78(19) . . ?
C14 C13 H13 120.1 . . ?
C6 C14 H14 119.8 . . ?
C13 C14 C6 120.34(19) . . ?
C13 C14 H14 119.8 . . ?
C4 C16 H16 120.9 . . ?
C19 C16 C4 118.1(2) . . ?
C19 C16 H16 120.9 . . ?
N1 C17 H17 118.2 . . ?
N1 C17 C18 123.5(3) . . ?
C18 C17 H17 118.2 . . ?
C17 C18 H18 120.8 . . ?
C19 C18 C17 118.3(2) . . ?
C19 C18 H18 120.8 . . ?
C16 C19 H19 120.3 . . ?
C18 C19 C16 119.5(3) . . ?
C18 C19 H19 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C4 C16 C19 2.6(3) . . . . ?
N1 C17 C18 C19 1.6(4) . . . . ?
C2 C5 C11 C8 -113.04(19) . . . . ?
C2 C5 C11 C10 -4.8(3) . . . . ?
C2 C6 C14 C13 0.0(3) . . . . ?
C8 C4 C16 C19 -176.88(18) . . . . ?
C8 C5 C11 C10 108.20(19) . . . . ?
C4 N1 C17 C18 0.0(3) . . . . ?
C4 C8 C5 C2 -139.77(17) . . . . ?
C4 C8 C5 C11 106.96(17) . . . . ?
C4 C8 C11 C5 -108.01(17) . . . . ?
C4 C8 C11 C10 141.46(18) . . . . ?
C4 C16 C19 C18 -0.9(3) . . . . ?
C5 C2 C6 C14 -173.22(18) . . . . ?
C5 C2 C3 C7 173.37(17) . . . . ?
C5 C8 C4 N1 -29.7(2) . . . . ?
C5 C8 C4 C16 149.80(17) . . . . ?
C5 C8 C11 C10 -110.5(2) . . . . ?
C6 C2 C5 C8 -132.76(19) . . . . ?
C6 C2 C5 C11 -57.5(2) . . . . ?
C6 C2 C3 C7 0.3(3) . . . . ?
C7 C13 C14 C6 -0.2(3) . . . . ?
C3 C2 C5 C8 54.2(2) . . . . ?
C3 C2 C5 C11 129.55(19) . . . . ?
C3 C2 C6 C14 0.0(3) . . . . ?
C3 C7 C13 C14 0.5(3) . . . . ?
C11 C8 C4 N1 38.0(2) . . . . ?
C11 C8 C4 C16 -142.46(18) . . . . ?
C11 C8 C5 C2 113.27(19) . . . . ?
C12 C8 C4 N1 -178.34(16) . . . . ?
C12 C8 C4 C16 1.2(3) . . . . ?
C12 C8 C5 C2 8.5(3) . . . . ?
C12 C8 C5 C11 -104.74(18) . . . . ?
C12 C8 C11 C5 108.00(18) . . . . ?
C12 C8 C11 C10 -2.5(2) . . . . ?
C13 C7 C3 C2 -0.5(3) . . . . ?
C17 N1 C4 C8 177.38(18) . . . . ?
C17 N1 C4 C16 -2.2(3) . . . . ?
C17 C18 C19 C16 -1.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
