# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1570942'
_audit_update_record             
;
2017-09-05 deposited with the CCDC.	2019-02-19 downloaded from the CCDC.
;
#=====================================================================

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 N4'
_chemical_formula_sum            'C15 H10 N4'
_chemical_formula_weight         246.27

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.7067(3)
_cell_length_b                   7.2919(3)
_cell_length_c                   15.0345(9)
_cell_angle_alpha                101.367(4)
_cell_angle_beta                 96.548(4)
_cell_angle_gamma                90.231(4)
_cell_volume                     609.13(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    294.8(5)
_cell_measurement_reflns_used    4129
_cell_measurement_theta_min      6.0500
_cell_measurement_theta_max      74.4550

_exptl_crystal_description       flake
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.672
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      294.8(5)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova (Cu) X-ray Source'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.3503
_diffrn_reflns_number            7486
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         6.046
_diffrn_reflns_theta_max         66.596
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             2145
_reflns_number_gt                1930
_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       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0704P)²+0.1024P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2145
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.1106
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.001
_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 0.10035(18) 0.77918(16) 0.03980(7) 0.0442(3) Uani 1 1 d . . . . .
N2 N 0.06504(18) 0.69980(16) -0.04651(7) 0.0447(3) Uani 1 1 d . . . . .
N3 N -0.17181(17) 0.68747(14) -0.07083(7) 0.0362(3) Uani 1 1 d . . . . .
C5 C -0.2647(2) 0.60065(16) -0.16121(8) 0.0351(3) Uani 1 1 d . . . . .
N4 N -0.6069(4) 0.2636(2) -0.49896(10) 0.0898(6) Uani 1 1 d . . . . .
C6 C -0.1346(2) 0.60987(17) -0.23292(9) 0.0396(3) Uani 1 1 d . . . . .
H6A H 0.0104 0.6737 -0.2220 0.048 Uiso 1 1 calc R U . . .
C7 C -0.2224(2) 0.52356(18) -0.32045(9) 0.0444(3) Uani 1 1 d . . . . .
H7A H -0.1361 0.5282 -0.3689 0.053 Uiso 1 1 calc R U . . .
C10 C -0.1291(2) 0.90755(15) 0.16750(8) 0.0352(3) Uani 1 1 d . . . . .
C15 C 0.0581(2) 0.89898(17) 0.23472(9) 0.0407(3) Uani 1 1 d . . . . .
H15A H 0.1951 0.8392 0.2185 0.049 Uiso 1 1 calc R U . . .
C12 C -0.3475(2) 1.07681(18) 0.28397(10) 0.0471(3) Uani 1 1 d . . . . .
H12A H -0.4838 1.1372 0.3006 0.056 Uiso 1 1 calc R U . . .
C3 C -0.5701(2) 0.42282(17) -0.26395(9) 0.0424(3) Uani 1 1 d . . . . .
H3A H -0.7163 0.3606 -0.2748 0.051 Uiso 1 1 calc R U . . .
C8 C -0.2860(2) 0.76025(16) 0.00147(8) 0.0368(3) Uani 1 1 d . . . . .
H8A H -0.4481 0.7684 0.0029 0.044 Uiso 1 1 calc R U . . .
C11 C -0.3327(2) 0.99772(17) 0.19360(9) 0.0415(3) Uani 1 1 d . . . . .
H11A H -0.4595 1.0046 0.1498 0.050 Uiso 1 1 calc R U . . .
C4 C -0.4823(2) 0.50821(17) -0.17634(9) 0.0405(3) Uani 1 1 d . . . . .
H4A H -0.5684 0.5038 -0.1278 0.049 Uiso 1 1 calc R U . . .
C2 C -0.4403(2) 0.42946(17) -0.33627(9) 0.0419(3) Uani 1 1 d . . . . .
C14 C 0.0421(3) 0.97824(19) 0.32491(9) 0.0472(3) Uani 1 1 d . . . . .
H14A H 0.1684 0.9721 0.3690 0.057 Uiso 1 1 calc R U . . .
C9 C -0.1122(2) 0.81950(16) 0.07211(8) 0.0355(3) Uani 1 1 d . . . . .
C1 C -0.5330(3) 0.3376(2) -0.42738(10) 0.0566(4) Uani 1 1 d . . . . .
C13 C -0.1608(3) 1.06677(19) 0.35000(9) 0.0492(4) Uani 1 1 d . . . . .
H13A H -0.1717 1.1193 0.4109 0.059 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 N2 1.3048(15) . ?
N1 C9 1.3695(16) . ?
N2 N3 1.3572(15) . ?
N3 C8 1.3507(15) . ?
N3 C5 1.4220(15) . ?
C5 C4 1.3847(18) . ?
C5 C6 1.3887(18) . ?
N4 C1 1.137(2) . ?
C6 C7 1.3781(18) . ?
C7 C2 1.3911(19) . ?
C10 C11 1.3945(17) . ?
C10 C15 1.3950(17) . ?
C10 C9 1.4653(17) . ?
C15 C14 1.3786(19) . ?
C12 C11 1.3796(19) . ?
C12 C13 1.384(2) . ?
C3 C4 1.3774(18) . ?
C3 C2 1.3917(19) . ?
C8 C9 1.3686(17) . ?
C2 C1 1.4404(18) . ?
C14 C13 1.382(2) . ?

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
N2 N1 C9 109.50(10) . . ?
N1 N2 N3 107.16(10) . . ?
C8 N3 N2 110.30(10) . . ?
C8 N3 C5 129.65(10) . . ?
N2 N3 C5 120.01(10) . . ?
C4 C5 C6 121.10(12) . . ?
C4 C5 N3 119.66(11) . . ?
C6 C5 N3 119.24(11) . . ?
C7 C6 C5 119.42(12) . . ?
C6 C7 C2 119.90(12) . . ?
C11 C10 C15 118.52(11) . . ?
C11 C10 C9 121.22(11) . . ?
C15 C10 C9 120.24(11) . . ?
C14 C15 C10 120.67(12) . . ?
C11 C12 C13 120.37(13) . . ?
C4 C3 C2 120.10(12) . . ?
N3 C8 C9 105.34(10) . . ?
C12 C11 C10 120.51(12) . . ?
C3 C4 C5 119.34(12) . . ?
C7 C2 C3 120.14(12) . . ?
C7 C2 C1 120.37(13) . . ?
C3 C2 C1 119.49(13) . . ?
C15 C14 C13 120.29(13) . . ?
C8 C9 N1 107.70(11) . . ?
C8 C9 C10 130.24(11) . . ?
N1 C9 C10 122.05(11) . . ?
N4 C1 C2 179.30(17) . . ?
C14 C13 C12 119.63(13) . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.032

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_2_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1857195'
loop_
_audit_author_name
_audit_author_address
'ning-ning zhang'
;Fujian Institute of Research on the Structure of Matter
China
;
_audit_update_record             
;
2018-07-21 deposited with the CCDC.	2019-02-19 downloaded from the CCDC.
;
#===================================================================== 

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 N3 O'
_chemical_formula_sum            'C15 H13 N3 O'
_chemical_formula_weight         251.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.6371(5)
_cell_length_b                   7.4472(6)
_cell_length_c                   15.0753(10)
_cell_angle_alpha                93.055(6)
_cell_angle_beta                 96.810(6)
_cell_angle_gamma                90.542(7)
_cell_volume                     627.43(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2798
_cell_measurement_theta_min      3.6550
_cell_measurement_theta_max      24.5230

_exptl_crystal_description       flake
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.96568
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  
;
Rigaku Pilatus 200K
;
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            8616
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.641
_diffrn_reflns_theta_max         28.878
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2861
_reflns_number_gt                1904
_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       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0625P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.029(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2861
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1306
_refine_ls_wR_factor_gt          0.1174
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.094
_refine_ls_shift/su_mean         0.015

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 0.3416(2) 0.25306(17) 0.46496(7) 0.0395(3) Uani 1 1 d . . . . .
O1 O 0.0686(2) 0.14732(16) 0.09974(7) 0.0575(4) Uani 1 1 d . . . . .
N2 N 0.6047(2) 0.2973(2) 0.57894(8) 0.0490(4) Uani 1 1 d . . . . .
N3 N 0.5785(2) 0.2739(2) 0.49176(8) 0.0504(4) Uani 1 1 d . . . . .
C5 C 0.0447(3) 0.2919(2) 0.33585(9) 0.0419(4) Uani 1 1 d . . . . .
H5A H -0.0521 0.3531 0.3728 0.050 Uiso 1 1 calc R U . . .
C6 C 0.4050(3) 0.1318(2) 0.31704(10) 0.0439(4) Uani 1 1 d . . . . .
H6A H 0.5496 0.0857 0.3414 0.053 Uiso 1 1 calc R U . . .
C7 C 0.2609(2) 0.2248(2) 0.37173(9) 0.0381(4) Uani 1 1 d . . . . .
C8 C 0.3333(3) 0.1081(2) 0.22720(10) 0.0470(4) Uani 1 1 d . . . . .
H8A H 0.4296 0.0454 0.1906 0.056 Uiso 1 1 calc R U . . .
C9 C 0.1189(3) 0.1766(2) 0.19026(9) 0.0409(4) Uani 1 1 d . . . . .
C10 C 0.3614(2) 0.30802(19) 0.70469(9) 0.0369(4) Uani 1 1 d . . . . .
C11 C -0.0277(3) 0.2678(2) 0.24494(10) 0.0436(4) Uani 1 1 d . . . . .
H11A H -0.1733 0.3122 0.2206 0.052 Uiso 1 1 calc R U . . .
C12 C 0.3848(2) 0.2915(2) 0.60867(9) 0.0378(4) Uani 1 1 d . . . . .
C13 C 0.1626(3) 0.2392(2) 0.73879(10) 0.0441(4) Uani 1 1 d . . . . .
H13A H 0.0374 0.1868 0.7000 0.053 Uiso 1 1 calc R U . . .
C14 C 0.5433(3) 0.3890(2) 0.76433(10) 0.0449(4) Uani 1 1 d . . . . .
H14A H 0.6759 0.4382 0.7427 0.054 Uiso 1 1 calc R U . . .
C15 C 0.2171(3) 0.2639(2) 0.53585(9) 0.0409(4) Uani 1 1 d . . . . .
H15A H 0.0524 0.2547 0.5354 0.049 Uiso 1 1 calc R U . . .
C16 C 0.1498(3) 0.2481(2) 0.82956(10) 0.0510(4) Uani 1 1 d . . . . .
H16A H 0.0159 0.2019 0.8515 0.061 Uiso 1 1 calc R U . . .
C17 C 0.3335(3) 0.3249(2) 0.88811(11) 0.0535(5) Uani 1 1 d . . . . .
H17A H 0.3258 0.3280 0.9495 0.064 Uiso 1 1 calc R U . . .
C18 C 0.5292(3) 0.3971(2) 0.85483(10) 0.0525(4) Uani 1 1 d . . . . .
H18A H 0.6522 0.4516 0.8939 0.063 Uiso 1 1 calc R U . . .
C19 C -0.1604(4) 0.1952(3) 0.05864(11) 0.0710(6) Uani 1 1 d . . . . .
H19A H -0.1713 0.1674 -0.0046 0.106 Uiso 1 1 calc R U . . .
H19B H -0.1832 0.3217 0.0695 0.106 Uiso 1 1 calc R U . . .
H19C H -0.2815 0.1288 0.0833 0.106 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 C15 1.3455(17) . ?
N1 N3 1.3536(16) . ?
N1 C7 1.4289(18) . ?
O1 C9 1.3658(17) . ?
O1 C19 1.422(2) . ?
N2 N3 1.3072(17) . ?
N2 C12 1.3685(18) . ?
C5 C7 1.383(2) . ?
C5 C11 1.384(2) . ?
C6 C8 1.368(2) . ?
C6 C7 1.389(2) . ?
C8 C9 1.384(2) . ?
C9 C11 1.391(2) . ?
C10 C14 1.391(2) . ?
C10 C13 1.392(2) . ?
C10 C12 1.4678(19) . ?
C12 C15 1.3661(19) . ?
C13 C16 1.377(2) . ?
C14 C18 1.374(2) . ?
C16 C17 1.377(2) . ?
C17 C18 1.381(2) . ?

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
C15 N1 N3 110.53(12) . . ?
C15 N1 C7 130.25(12) . . ?
N3 N1 C7 119.21(11) . . ?
C9 O1 C19 118.31(13) . . ?
N3 N2 C12 109.08(11) . . ?
N2 N3 N1 107.19(11) . . ?
C7 C5 C11 119.95(14) . . ?
C8 C6 C7 119.75(14) . . ?
C5 C7 C6 120.25(14) . . ?
C5 C7 N1 120.69(13) . . ?
C6 C7 N1 119.05(13) . . ?
C6 C8 C9 120.59(14) . . ?
O1 C9 C8 115.26(14) . . ?
O1 C9 C11 124.86(14) . . ?
C8 C9 C11 119.88(14) . . ?
C14 C10 C13 118.36(14) . . ?
C14 C10 C12 120.16(13) . . ?
C13 C10 C12 121.46(13) . . ?
C5 C11 C9 119.58(14) . . ?
N2 C12 C15 107.97(12) . . ?
N2 C12 C10 120.79(12) . . ?
C15 C12 C10 131.21(13) . . ?
C16 C13 C10 120.47(14) . . ?
C18 C14 C10 120.75(14) . . ?
N1 C15 C12 105.23(12) . . ?
C13 C16 C17 120.64(15) . . ?
C18 C17 C16 119.33(15) . . ?
C17 C18 C14 120.42(15) . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-2

