# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_mo_201210_zwq_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2090962'
loop_
_audit_author_name
_audit_author_address
'Wanqiu Zhao'
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2021-06-19 deposited with the CCDC.	2021-09-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H12 Br N5'
_chemical_formula_weight         318.19

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_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'
'-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                   7.3250(4)
_cell_length_b                   12.3657(5)
_cell_length_c                   27.8190(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2519.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    3.256
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26235
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2221
_reflns_number_gt                2056
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0196P)²+8.5283P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2221
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0856
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.16524(7) 0.71898(3) 0.181134(12) 0.04347(15) Uani 1 1 d . . .
N5 N 0.1550(4) 0.4493(2) 0.06398(9) 0.0210(5) Uani 1 1 d . . .
N2 N 0.3297(4) 0.6248(2) -0.04914(9) 0.0255(6) Uani 1 1 d . . .
C3 C 0.0546(5) 0.5796(3) 0.18356(11) 0.0246(7) Uani 1 1 d . . .
N1 N 0.3795(4) 0.4692(2) -0.09325(9) 0.0275(6) Uani 1 1 d . . .
C5 C 0.3237(4) 0.5126(2) -0.05146(11) 0.0216(6) Uani 1 1 d . . .
N3 N 0.2684(4) 0.4461(2) -0.01689(8) 0.0211(5) Uani 1 1 d . . .
N4 N 0.2130(4) 0.6074(2) 0.02779(9) 0.0215(6) Uani 1 1 d . . .
C8 C 0.1190(4) 0.5357(2) 0.09523(11) 0.0202(6) Uani 1 1 d . . .
C9 C 0.2116(4) 0.4946(2) 0.02402(11) 0.0197(6) Uani 1 1 d . . .
C10 C 0.1521(4) 0.6328(3) 0.07361(11) 0.0234(7) Uani 1 1 d . . .
H10 H 0.1367 0.7028 0.0871 0.028 Uiso 1 1 calc R . .
C11 C 0.2740(5) 0.6679(2) -0.00971(11) 0.0256(7) Uani 1 1 d . . .
H11 H 0.2755 0.7445 -0.0067 0.031 Uiso 1 1 calc R . .
C12 C 0.0538(4) 0.5100(2) 0.14409(11) 0.0201(6) Uani 1 1 d . . .
C13 C 0.3681(5) 0.3527(3) -0.10038(12) 0.0340(8) Uani 1 1 d . . .
H13A H 0.4505 0.3162 -0.0778 0.051 Uiso 1 1 calc R . .
H13B H 0.4038 0.3350 -0.1334 0.051 Uiso 1 1 calc R . .
H13C H 0.2426 0.3285 -0.0947 0.051 Uiso 1 1 calc R . .
C14 C -0.0126(4) 0.4055(3) 0.15250(11) 0.0256(7) Uani 1 1 d . . .
H14 H -0.0123 0.3548 0.1269 0.031 Uiso 1 1 calc R . .
C15 C -0.0787(5) 0.3738(3) 0.19696(12) 0.0296(7) Uani 1 1 d . . .
H15 H -0.1217 0.3020 0.2015 0.036 Uiso 1 1 calc R . .
C16 C -0.0151(5) 0.5496(3) 0.22803(12) 0.0307(8) Uani 1 1 d . . .
H16 H -0.0167 0.6000 0.2538 0.037 Uiso 1 1 calc R . .
C17 C -0.0821(5) 0.4464(3) 0.23463(12) 0.0303(8) Uani 1 1 d . . .
H17 H -0.1303 0.4255 0.2649 0.036 Uiso 1 1 calc R . .
C18 C 0.4528(5) 0.5335(3) -0.13267(12) 0.0334(8) Uani 1 1 d . . .
H18A H 0.4499 0.6103 -0.1239 0.050 Uiso 1 1 calc R . .
H18B H 0.3788 0.5220 -0.1616 0.050 Uiso 1 1 calc R . .
H18C H 0.5791 0.5116 -0.1391 0.050 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
Br1 C3 1.906(3) . ?
N5 C9 1.313(4) . ?
N5 C8 1.402(4) . ?
N2 C11 1.286(4) . ?
N2 C5 1.390(4) . ?
C3 C16 1.389(5) . ?
C3 C12 1.394(4) . ?
N1 C5 1.344(4) . ?
N1 C13 1.457(4) . ?
N1 C18 1.457(4) . ?
C5 N3 1.328(4) . ?
N3 C9 1.352(4) . ?
N4 C11 1.359(4) . ?
N4 C10 1.386(4) . ?
N4 C9 1.398(4) . ?
C8 C10 1.365(4) . ?
C8 C12 1.475(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C14 1.400(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.385(5) . ?
C14 H14 0.9500 . ?
C15 C17 1.381(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
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
C9 N5 C8 105.0(2) . . ?
C11 N2 C5 116.3(3) . . ?
C16 C3 C12 122.4(3) . . ?
C16 C3 Br1 115.4(2) . . ?
C12 C3 Br1 122.1(2) . . ?
C5 N1 C13 119.7(3) . . ?
C5 N1 C18 123.0(3) . . ?
C13 N1 C18 117.3(3) . . ?
N3 C5 N1 118.2(3) . . ?
N3 C5 N2 126.4(3) . . ?
N1 C5 N2 115.4(3) . . ?
C5 N3 C9 115.4(3) . . ?
C11 N4 C10 133.4(3) . . ?
C11 N4 C9 119.6(3) . . ?
C10 N4 C9 107.0(2) . . ?
C10 C8 N5 111.3(3) . . ?
C10 C8 C12 130.7(3) . . ?
N5 C8 C12 117.9(3) . . ?
N5 C9 N3 128.3(3) . . ?
N5 C9 N4 111.4(3) . . ?
N3 C9 N4 120.3(3) . . ?
C8 C10 N4 105.2(3) . . ?
C8 C10 H10 127.4 . . ?
N4 C10 H10 127.4 . . ?
N2 C11 N4 122.0(3) . . ?
N2 C11 H11 119.0 . . ?
N4 C11 H11 119.0 . . ?
C3 C12 C14 116.0(3) . . ?
C3 C12 C8 126.3(3) . . ?
C14 C12 C8 117.7(3) . . ?
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 . . ?
C15 C14 C12 122.2(3) . . ?
C15 C14 H14 118.9 . . ?
C12 C14 H14 118.9 . . ?
C17 C15 C14 120.0(3) . . ?
C17 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C3 119.7(3) . . ?
C17 C16 H16 120.1 . . ?
C3 C16 H16 120.1 . . ?
C16 C17 C15 119.7(3) . . ?
C16 C17 H17 120.2 . . ?
C15 C17 H17 120.2 . . ?
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
C13 N1 C5 N3 3.5(5) . . . . ?
C18 N1 C5 N3 -176.4(3) . . . . ?
C13 N1 C5 N2 -176.3(3) . . . . ?
C18 N1 C5 N2 3.8(5) . . . . ?
C11 N2 C5 N3 -0.9(5) . . . . ?
C11 N2 C5 N1 178.9(3) . . . . ?
N1 C5 N3 C9 -179.1(3) . . . . ?
N2 C5 N3 C9 0.6(5) . . . . ?
C9 N5 C8 C10 0.8(4) . . . . ?
C9 N5 C8 C12 -179.4(3) . . . . ?
C8 N5 C9 N3 178.0(3) . . . . ?
C8 N5 C9 N4 -0.4(3) . . . . ?
C5 N3 C9 N5 -178.1(3) . . . . ?
C5 N3 C9 N4 0.3(4) . . . . ?
C11 N4 C9 N5 177.7(3) . . . . ?
C10 N4 C9 N5 -0.1(4) . . . . ?
C11 N4 C9 N3 -0.9(5) . . . . ?
C10 N4 C9 N3 -178.7(3) . . . . ?
N5 C8 C10 N4 -0.9(4) . . . . ?
C12 C8 C10 N4 179.4(3) . . . . ?
C11 N4 C10 C8 -176.8(3) . . . . ?
C9 N4 C10 C8 0.6(3) . . . . ?
C5 N2 C11 N4 0.2(5) . . . . ?
C10 N4 C11 N2 177.7(3) . . . . ?
C9 N4 C11 N2 0.6(5) . . . . ?
C16 C3 C12 C14 -3.4(5) . . . . ?
Br1 C3 C12 C14 172.6(2) . . . . ?
C16 C3 C12 C8 177.9(3) . . . . ?
Br1 C3 C12 C8 -6.1(5) . . . . ?
C10 C8 C12 C3 -17.6(5) . . . . ?
N5 C8 C12 C3 162.7(3) . . . . ?
C10 C8 C12 C14 163.7(3) . . . . ?
N5 C8 C12 C14 -16.0(4) . . . . ?
C3 C12 C14 C15 1.9(5) . . . . ?
C8 C12 C14 C15 -179.3(3) . . . . ?
C12 C14 C15 C17 0.6(5) . . . . ?
C12 C3 C16 C17 2.4(5) . . . . ?
Br1 C3 C16 C17 -173.8(3) . . . . ?
C3 C16 C17 C15 0.2(5) . . . . ?
C14 C15 C17 C16 -1.6(5) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.518
_refine_diff_density_min         -1.333
_refine_diff_density_rms         0.080
####################################################################### 
# 
# 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_y
_database_code_depnum_ccdc_archive 'CCDC 2090963'
loop_
_audit_author_name
_audit_author_address
'Wanqiu Zhao'
;Zhejiang University of Technology
China
;
_audit_update_record             
;
2021-06-22 deposited with the CCDC.	2021-09-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 N5 O2'
_chemical_formula_weight         371.40

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_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'
'-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                   11.231(2)
_cell_length_b                   7.9355(16)
_cell_length_c                   39.428(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3514.1(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1552
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            39697
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         27.16
_reflns_number_total             3895
_reflns_number_gt                3331
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0628P)²+0.8258P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0162(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3895
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N5 N 0.12239(9) 0.09740(14) 0.42736(3) 0.0257(3) Uani 1 1 d . . .
N3 N 0.47943(9) 0.04147(14) 0.43033(3) 0.0271(3) Uani 1 1 d . . .
N1 N 0.48813(10) 0.20074(15) 0.47954(3) 0.0306(3) Uani 1 1 d . . .
N2 N 0.30268(9) 0.15618(14) 0.45685(3) 0.0272(3) Uani 1 1 d . . .
C3 C 0.09903(11) 0.01600(15) 0.39768(3) 0.0229(3) Uani 1 1 d . . .
O1 O 0.32798(9) -0.19103(13) 0.34465(2) 0.0345(3) Uani 1 1 d . . .
C5 C 0.22693(11) -0.14754(16) 0.35326(3) 0.0246(3) Uani 1 1 d . . .
N4 N 0.29403(9) -0.00110(13) 0.40550(2) 0.0220(2) Uani 1 1 d . . .
O2 O 0.05436(9) -0.31205(13) 0.34442(2) 0.0350(3) Uani 1 1 d . . .
C8 C 0.61692(12) 0.18018(19) 0.48079(4) 0.0338(3) Uani 1 1 d . . .
H8A H 0.6364 0.0859 0.4950 0.051 Uiso 1 1 calc R . .
H8B H 0.6525 0.2805 0.4899 0.051 Uiso 1 1 calc R . .
H8C H 0.6467 0.1606 0.4583 0.051 Uiso 1 1 calc R . .
C9 C 0.12437(11) -0.21481(15) 0.33153(3) 0.0252(3) Uani 1 1 d . . .
C10 C 0.24029(11) 0.08788(16) 0.43159(3) 0.0236(3) Uani 1 1 d . . .
C11 C 0.20234(11) -0.05106(15) 0.38309(3) 0.0228(3) Uani 1 1 d . . .
C12 C 0.42072(11) 0.13261(16) 0.45505(3) 0.0257(3) Uani 1 1 d . . .
C13 C 0.41461(11) -0.02278(16) 0.40636(3) 0.0249(3) Uani 1 1 d . . .
H13 H 0.4512 -0.0852 0.3893 0.030 Uiso 1 1 calc R . .
C14 C -0.05647(12) 0.06828(18) 0.35301(3) 0.0287(3) Uani 1 1 d . . .
H14 H 0.0025 0.0971 0.3375 0.034 Uiso 1 1 calc R . .
C15 C -0.11491(12) -0.02797(19) 0.40832(4) 0.0320(3) Uani 1 1 d . . .
H15 H -0.0949 -0.0617 0.4302 0.038 Uiso 1 1 calc R . .
C16 C 0.43077(13) 0.2928(2) 0.50717(4) 0.0382(4) Uani 1 1 d . . .
H16A H 0.3845 0.3837 0.4980 0.057 Uiso 1 1 calc R . .
H16B H 0.4905 0.3372 0.5221 0.057 Uiso 1 1 calc R . .
H16C H 0.3796 0.2178 0.5195 0.057 Uiso 1 1 calc R . .
C17 C 0.21302(13) -0.07848(18) 0.27943(4) 0.0348(3) Uani 1 1 d . . .
H17 H 0.2745 -0.0341 0.2925 0.042 Uiso 1 1 calc R . .
C18 C -0.26413(13) 0.0331(2) 0.36654(4) 0.0368(3) Uani 1 1 d . . .
H18 H -0.3437 0.0397 0.3602 0.044 Uiso 1 1 calc R . .
C19 C -0.02552(11) 0.01548(15) 0.38555(3) 0.0240(3) Uani 1 1 d . . .
C20 C 0.12319(12) -0.17309(16) 0.29475(3) 0.0259(3) Uani 1 1 d . . .
C21 C 0.03006(13) -0.23436(19) 0.27499(4) 0.0352(3) Uani 1 1 d . . .
H21 H -0.0312 -0.2951 0.2851 0.042 Uiso 1 1 calc R . .
C22 C -0.23371(13) -0.0215(2) 0.39872(4) 0.0377(3) Uani 1 1 d . . .
H22 H -0.2928 -0.0538 0.4139 0.045 Uiso 1 1 calc R . .
C23 C -0.17542(13) 0.07772(19) 0.34386(4) 0.0348(3) Uani 1 1 d . . .
H23 H -0.1959 0.1145 0.3222 0.042 Uiso 1 1 calc R . .
C24 C 0.02809(16) -0.2054(2) 0.24036(4) 0.0435(4) Uani 1 1 d . . .
H24 H -0.0341 -0.2471 0.2272 0.052 Uiso 1 1 calc R . .
C25 C 0.21041(16) -0.0508(2) 0.24472(4) 0.0443(4) Uani 1 1 d . . .
H25 H 0.2708 0.0110 0.2345 0.053 Uiso 1 1 calc R . .
C26 C 0.11872(16) -0.1144(2) 0.22535(4) 0.0438(4) Uani 1 1 d . . .
H26 H 0.1179 -0.0960 0.2021 0.053 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
N5 C10 1.3368(16) . ?
N5 C3 1.3621(16) . ?
N3 C13 1.2975(16) . ?
N3 C12 1.3812(17) . ?
N1 C12 1.3410(16) . ?
N1 C8 1.4564(17) . ?
N1 C16 1.4610(18) . ?
N2 C10 1.3329(16) . ?
N2 C12 1.3408(17) . ?
C3 C11 1.4002(17) . ?
C3 C19 1.4783(17) . ?
O1 C5 1.2338(16) . ?
C5 C11 1.4301(17) . ?
C5 C9 1.5317(18) . ?
N4 C13 1.3655(16) . ?
N4 C10 1.3862(15) . ?
N4 C11 1.4137(15) . ?
O2 C9 1.2133(16) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C20 1.4875(18) . ?
C13 H13 0.9300 . ?
C14 C23 1.3859(19) . ?
C14 C19 1.3938(18) . ?
C14 H14 0.9300 . ?
C15 C22 1.388(2) . ?
C15 C19 1.3904(19) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C25 1.386(2) . ?
C17 C20 1.3952(19) . ?
C17 H17 0.9300 . ?
C18 C22 1.384(2) . ?
C18 C23 1.385(2) . ?
C18 H18 0.9300 . ?
C20 C21 1.3919(19) . ?
C21 C24 1.385(2) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C26 1.381(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.378(2) . ?
C25 H25 0.9300 . ?
C26 H26 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
C10 N5 C3 105.75(10) . . ?
C13 N3 C12 116.86(11) . . ?
C12 N1 C8 122.68(11) . . ?
C12 N1 C16 119.30(11) . . ?
C8 N1 C16 117.95(11) . . ?
C10 N2 C12 115.06(11) . . ?
N5 C3 C11 111.93(11) . . ?
N5 C3 C19 117.48(11) . . ?
C11 C3 C19 130.56(11) . . ?
O1 C5 C11 123.62(11) . . ?
O1 C5 C9 116.12(11) . . ?
C11 C5 C9 120.09(11) . . ?
C13 N4 C10 118.53(10) . . ?
C13 N4 C11 134.64(11) . . ?
C10 N4 C11 106.83(10) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 C20 122.95(12) . . ?
O2 C9 C5 118.35(12) . . ?
C20 C9 C5 118.33(11) . . ?
N2 C10 N5 126.24(11) . . ?
N2 C10 N4 122.19(11) . . ?
N5 C10 N4 111.56(10) . . ?
C3 C11 N4 103.91(10) . . ?
C3 C11 C5 134.54(11) . . ?
N4 C11 C5 121.56(11) . . ?
N2 C12 N1 117.64(11) . . ?
N2 C12 N3 125.63(11) . . ?
N1 C12 N3 116.72(11) . . ?
N3 C13 N4 121.67(12) . . ?
N3 C13 H13 119.2 . . ?
N4 C13 H13 119.2 . . ?
C23 C14 C19 119.74(13) . . ?
C23 C14 H14 120.1 . . ?
C19 C14 H14 120.1 . . ?
C22 C15 C19 120.60(13) . . ?
C22 C15 H15 119.7 . . ?
C19 C15 H15 119.7 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C25 C17 C20 119.83(14) . . ?
C25 C17 H17 120.1 . . ?
C20 C17 H17 120.1 . . ?
C22 C18 C23 119.64(13) . . ?
C22 C18 H18 120.2 . . ?
C23 C18 H18 120.2 . . ?
C15 C19 C14 119.27(12) . . ?
C15 C19 C3 118.37(12) . . ?
C14 C19 C3 122.20(12) . . ?
C21 C20 C17 119.28(13) . . ?
C21 C20 C9 118.34(12) . . ?
C17 C20 C9 122.37(12) . . ?
C24 C21 C20 120.40(14) . . ?
C24 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C18 C22 C15 119.94(14) . . ?
C18 C22 H22 120.0 . . ?
C15 C22 H22 120.0 . . ?
C18 C23 C14 120.79(13) . . ?
C18 C23 H23 119.6 . . ?
C14 C23 H23 119.6 . . ?
C26 C24 C21 119.82(15) . . ?
C26 C24 H24 120.1 . . ?
C21 C24 H24 120.1 . . ?
C26 C25 C17 120.32(15) . . ?
C26 C25 H25 119.8 . . ?
C17 C25 H25 119.8 . . ?
C25 C26 C24 120.33(14) . . ?
C25 C26 H26 119.8 . . ?
C24 C26 H26 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N5 C3 C11 1.76(14) . . . . ?
C10 N5 C3 C19 -176.56(11) . . . . ?
O1 C5 C9 O2 114.24(14) . . . . ?
C11 C5 C9 O2 -61.19(17) . . . . ?
O1 C5 C9 C20 -59.03(16) . . . . ?
C11 C5 C9 C20 125.55(13) . . . . ?
C12 N2 C10 N5 -178.37(12) . . . . ?
C12 N2 C10 N4 0.12(18) . . . . ?
C3 N5 C10 N2 177.51(12) . . . . ?
C3 N5 C10 N4 -1.12(14) . . . . ?
C13 N4 C10 N2 1.78(18) . . . . ?
C11 N4 C10 N2 -178.58(11) . . . . ?
C13 N4 C10 N5 -179.53(11) . . . . ?
C11 N4 C10 N5 0.11(14) . . . . ?
N5 C3 C11 N4 -1.67(14) . . . . ?
C19 C3 C11 N4 176.37(12) . . . . ?
N5 C3 C11 C5 178.72(13) . . . . ?
C19 C3 C11 C5 -3.2(2) . . . . ?
C13 N4 C11 C3 -179.53(13) . . . . ?
C10 N4 C11 C3 0.92(13) . . . . ?
C13 N4 C11 C5 0.1(2) . . . . ?
C10 N4 C11 C5 -179.41(11) . . . . ?
O1 C5 C11 C3 178.21(13) . . . . ?
C9 C5 C11 C3 -6.7(2) . . . . ?
O1 C5 C11 N4 -1.3(2) . . . . ?
C9 C5 C11 N4 173.73(11) . . . . ?
C10 N2 C12 N1 179.05(12) . . . . ?
C10 N2 C12 N3 -2.06(19) . . . . ?
C8 N1 C12 N2 178.41(12) . . . . ?
C16 N1 C12 N2 1.48(19) . . . . ?
C8 N1 C12 N3 -0.58(19) . . . . ?
C16 N1 C12 N3 -177.51(12) . . . . ?
C13 N3 C12 N2 1.96(19) . . . . ?
C13 N3 C12 N1 -179.14(12) . . . . ?
C12 N3 C13 N4 0.17(18) . . . . ?
C10 N4 C13 N3 -1.91(18) . . . . ?
C11 N4 C13 N3 178.58(12) . . . . ?
C22 C15 C19 C14 1.0(2) . . . . ?
C22 C15 C19 C3 176.47(13) . . . . ?
C23 C14 C19 C15 0.4(2) . . . . ?
C23 C14 C19 C3 -174.94(13) . . . . ?
N5 C3 C19 C15 -48.50(17) . . . . ?
C11 C3 C19 C15 133.55(15) . . . . ?
N5 C3 C19 C14 126.87(13) . . . . ?
C11 C3 C19 C14 -51.1(2) . . . . ?
C25 C17 C20 C21 -1.9(2) . . . . ?
C25 C17 C20 C9 176.69(13) . . . . ?
O2 C9 C20 C21 7.00(19) . . . . ?
C5 C9 C20 C21 179.93(12) . . . . ?
O2 C9 C20 C17 -171.57(13) . . . . ?
C5 C9 C20 C17 1.36(18) . . . . ?
C17 C20 C21 C24 1.6(2) . . . . ?
C9 C20 C21 C24 -176.99(13) . . . . ?
C23 C18 C22 C15 1.3(2) . . . . ?
C19 C15 C22 C18 -1.8(2) . . . . ?
C22 C18 C23 C14 0.0(2) . . . . ?
C19 C14 C23 C18 -0.9(2) . . . . ?
C20 C21 C24 C26 -0.4(2) . . . . ?
C20 C17 C25 C26 0.8(2) . . . . ?
C17 C25 C26 C24 0.4(3) . . . . ?
C21 C24 C26 C25 -0.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.16
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.509
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.138
