# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_exp_110
_database_code_depnum_ccdc_archive 'CCDC 1562138'
_audit_update_record             
;
2017-07-14 deposited with the CCDC.
2018-04-24 downloaded from the CCDC.
;
_audit_creation_date             2014-03-26
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H12 Br N3'
_chemical_formula_sum            'C21 H12 Br N3'
_chemical_formula_weight         386.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         C10H10N3O
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'
Br Br -0.2901 2.4595 '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                   18.8659(10)
_cell_length_b                   10.1158(4)
_cell_length_c                   8.8637(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.138(6)
_cell_angle_gamma                90.00
_cell_volume                     1670.12(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3444
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.9740
_cell_measurement_theta_min      2.2050
_exptl_absorpt_coefficient_mu    2.469
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14628
_diffrn_reflns_theta_min         2.0132
_diffrn_reflns_theta_max         30.8290
_diffrn_measured_fraction_theta_max 0.8950
_diffrn_reflns_theta_full        28.2205
_diffrn_measured_fraction_theta_full 0.9998
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 15.9555

_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -24.00   15.00   1.0000   64.3600
omega____ theta____ kappa____ phi______ frames
    -      -20.6362  -99.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.00   13.00   1.0000   64.3600
omega____ theta____ kappa____ phi______ frames
    -      -20.6362  -99.0000  -90.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega   42.00   95.00   1.0000   64.3600
omega____ theta____ kappa____ phi______ frames
    -       23.1362  178.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
  4 omega    3.00   90.00   1.0000   64.3600
omega____ theta____ kappa____ phi______ frames
    -       23.1362   57.0000   30.0000 87

#__ type_ start__ end____ width___ exp.time_
  5 omega   -2.00   87.00   1.0000   64.3600
omega____ theta____ kappa____ phi______ frames
    -       23.1362   38.0000  -60.0000 89

#__ type_ start__ end____ width___ exp.time_
  6 omega  -49.00   49.00   1.0000   64.3600
omega____ theta____ kappa____ phi______ frames
    -       23.1362  -38.0000  120.0000 98
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0038798000
_diffrn_orient_matrix_UB_12      -0.0515084000
_diffrn_orient_matrix_UB_13      0.0524009000
_diffrn_orient_matrix_UB_21      -0.0216292000
_diffrn_orient_matrix_UB_22      -0.0358067000
_diffrn_orient_matrix_UB_23      -0.0589145000
_diffrn_orient_matrix_UB_31      0.0310955000
_diffrn_orient_matrix_UB_32      -0.0313678000
_diffrn_orient_matrix_UB_33      -0.0187017000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3352
_reflns_number_total             4697
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         1.180
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4697
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0473
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0754P)²+0.0920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1341
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Br1 Br 0.989507(17) 0.78955(3) 0.49721(4) 0.03919(13) Uani 1 1 d . . .
N2 N 0.64835(12) 0.3715(2) 0.0173(2) 0.0239(4) Uani 1 1 d . . .
N1 N 0.60759(13) 0.0609(2) -0.1380(3) 0.0296(5) Uani 1 1 d . . .
C18 C 0.91891(15) 0.6629(3) 0.4134(3) 0.0271(6) Uani 1 1 d . . .
N3 N 0.68677(15) 0.6967(2) 0.0400(3) 0.0357(6) Uani 1 1 d . . .
C6 C 0.59130(14) 0.1673(2) -0.0594(3) 0.0232(5) Uani 1 1 d . . .
C17 C 0.93992(15) 0.5581(3) 0.3293(3) 0.0281(6) Uani 1 1 d . . .
H17 H 0.9878 0.5467 0.3188 0.034 Uiso 1 1 calc R . .
C8 C 0.70894(15) 0.1761(2) 0.1321(3) 0.0227(5) Uani 1 1 d . . .
C19 C 0.84908(16) 0.6792(2) 0.4366(3) 0.0273(6) Uani 1 1 d . . .
H19 H 0.8368 0.7480 0.4969 0.033 Uiso 1 1 calc R . .
C15 C 0.81550(15) 0.4869(2) 0.2776(3) 0.0239(5) Uani 1 1 d . . .
C7 C 0.65211(14) 0.2413(3) 0.0328(3) 0.0229(5) Uani 1 1 d . . .
C20 C 0.79716(15) 0.5909(2) 0.3683(3) 0.0255(5) Uani 1 1 d . . .
H20 H 0.7498 0.6010 0.3831 0.031 Uiso 1 1 calc R . .
C14 C 0.75953(14) 0.3966(3) 0.1983(3) 0.0244(5) Uani 1 1 d . . .
C13 C 0.76327(15) 0.2561(3) 0.2185(3) 0.0240(5) Uani 1 1 d . . .
C21 C 0.70200(14) 0.4452(3) 0.0981(3) 0.0248(5) Uani 1 1 d . . .
C16 C 0.88769(15) 0.4710(3) 0.2616(3) 0.0272(6) Uani 1 1 d . . .
H16 H 0.9008 0.4007 0.2044 0.033 Uiso 1 1 calc R . .
C4 C 0.46578(16) 0.1449(3) -0.1524(3) 0.0322(6) Uani 1 1 d . . .
H4 H 0.4186 0.1732 -0.1573 0.039 Uiso 1 1 calc R . .
C5 C 0.52130(16) 0.2120(3) -0.0631(3) 0.0296(6) Uani 1 1 d . . .
H5 H 0.5119 0.2857 -0.0066 0.036 Uiso 1 1 calc R . .
C1 C 0.69397(14) 0.5864(3) 0.0665(3) 0.0276(6) Uani 1 1 d . . .
C9 C 0.71230(16) 0.0372(3) 0.1528(3) 0.0270(6) Uani 1 1 d . . .
H9 H 0.6767 -0.0160 0.0993 0.032 Uiso 1 1 calc R . .
C11 C 0.82022(16) 0.0585(3) 0.3363(3) 0.0323(6) Uani 1 1 d . . .
H11 H 0.8572 0.0185 0.4024 0.039 Uiso 1 1 calc R . .
C12 C 0.81780(16) 0.1943(3) 0.3234(3) 0.0289(6) Uani 1 1 d . . .
H12 H 0.8521 0.2456 0.3838 0.035 Uiso 1 1 calc R . .
C2 C 0.55309(18) -0.0018(3) -0.2241(4) 0.0332(7) Uani 1 1 d . . .
H2 H 0.5638 -0.0745 -0.2806 0.040 Uiso 1 1 calc R . .
C10 C 0.76719(17) -0.0196(3) 0.2502(3) 0.0311(6) Uani 1 1 d . . .
H10 H 0.7694 -0.1111 0.2596 0.037 Uiso 1 1 calc R . .
C3 C 0.48156(17) 0.0349(3) -0.2346(3) 0.0336(6) Uani 1 1 d . . .
H3 H 0.4454 -0.0127 -0.2947 0.040 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 C18 1.911(3) . ?
N2 C7 1.326(3) . ?
N2 C21 1.365(3) . ?
N1 C6 1.344(3) . ?
N1 C2 1.339(4) . ?
C18 C17 1.390(4) . ?
C18 C19 1.375(4) . ?
N3 C1 1.144(3) . ?
C6 C7 1.499(4) . ?
C6 C5 1.391(4) . ?
C17 C16 1.385(4) . ?
C8 C7 1.435(4) . ?
C8 C13 1.429(4) . ?
C8 C9 1.418(3) . ?
C19 C20 1.391(4) . ?
C15 C20 1.400(3) . ?
C15 C14 1.486(4) . ?
C15 C16 1.401(4) . ?
C14 C13 1.433(4) . ?
C14 C21 1.379(4) . ?
C13 C12 1.418(4) . ?
C21 C1 1.458(4) . ?
C4 C5 1.387(4) . ?
C4 C3 1.388(4) . ?
C9 C10 1.365(4) . ?
C11 C12 1.378(4) . ?
C11 C10 1.402(4) . ?
C2 C3 1.388(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N2 C21 117.7(2) . . ?
C2 N1 C6 117.2(2) . . ?
C17 C18 Br1 118.6(2) . . ?
C19 C18 Br1 119.2(2) . . ?
C19 C18 C17 122.2(3) . . ?
N1 C6 C7 117.7(2) . . ?
N1 C6 C5 122.9(2) . . ?
C5 C6 C7 119.5(2) . . ?
C16 C17 C18 118.3(2) . . ?
C13 C8 C7 118.1(2) . . ?
C9 C8 C7 123.2(2) . . ?
C9 C8 C13 118.6(3) . . ?
C18 C19 C20 118.9(2) . . ?
C20 C15 C14 120.8(2) . . ?
C20 C15 C16 118.5(2) . . ?
C16 C15 C14 120.7(2) . . ?
N2 C7 C6 114.6(2) . . ?
N2 C7 C8 122.9(2) . . ?
C8 C7 C6 122.6(2) . . ?
C19 C20 C15 120.7(2) . . ?
C13 C14 C15 122.3(2) . . ?
C21 C14 C15 120.8(2) . . ?
C21 C14 C13 116.9(2) . . ?
C8 C13 C14 118.5(2) . . ?
C12 C13 C8 119.1(2) . . ?
C12 C13 C14 122.4(2) . . ?
N2 C21 C14 125.8(2) . . ?
N2 C21 C1 112.8(2) . . ?
C14 C21 C1 121.3(2) . . ?
C17 C16 C15 121.3(2) . . ?
C5 C4 C3 119.2(3) . . ?
C4 C5 C6 118.8(3) . . ?
N3 C1 C21 178.9(3) . . ?
C10 C9 C8 120.9(3) . . ?
C12 C11 C10 120.4(3) . . ?
C11 C12 C13 120.3(3) . . ?
N1 C2 C3 124.2(3) . . ?
C9 C10 C11 120.7(3) . . ?
C4 C3 C2 117.8(3) . . ?
####################################################################### 
# 
# 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_exp_204
_database_code_depnum_ccdc_archive 'CCDC 1562139'
_audit_update_record             
;
2017-07-14 deposited with the CCDC.
2018-04-24 downloaded from the CCDC.
;
_audit_creation_date             2014-09-02
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C28 H22 N4 O2'
_chemical_formula_sum            'C28 H22 N4 O2'
_chemical_formula_weight         446.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         C28H22N4O2
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   9.2421(5)
_cell_length_b                   17.3468(11)
_cell_length_c                   28.1793(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4517.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2631
_cell_measurement_temperature    295
_cell_measurement_theta_max      26.6460
_cell_measurement_theta_min      2.3480
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull brownish orange'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_av_unetI/netI     0.1600
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            16469
_diffrn_reflns_theta_full        30.95
_diffrn_reflns_theta_max         30.95
_diffrn_reflns_theta_min         2.35
_diffrn_ambient_temperature      294
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.8726
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -85.00   -9.00   1.0000  200.5800
omega____ theta____ kappa____ phi______ frames
    -      -20.6362  -77.0000   30.0000 76

#__ type_ start__ end____ width___ exp.time_
  2 omega  -95.00  -69.00   1.0000  200.5800
omega____ theta____ kappa____ phi______ frames
    -      -20.6362 -178.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00   20.00   1.0000  200.5800
omega____ theta____ kappa____ phi______ frames
    -      -20.6362  -99.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
  4 omega   51.00   87.00   1.0000  200.5800
omega____ theta____ kappa____ phi______ frames
    -       23.1362   57.0000   90.0000 36
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0085292000
_diffrn_orient_matrix_UB_12      0.0404318000
_diffrn_orient_matrix_UB_13      0.0025476000
_diffrn_orient_matrix_UB_21      0.0760249000
_diffrn_orient_matrix_UB_22      0.0041381000
_diffrn_orient_matrix_UB_23      0.0023360000
_diffrn_orient_matrix_UB_31      0.0062386000
_diffrn_orient_matrix_UB_32      0.0045038000
_diffrn_orient_matrix_UB_33      -0.0249280000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2149
_reflns_number_total             6245
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.932
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         6245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2187
_refine_ls_R_factor_gt           0.0624
_refine_ls_restrained_S_all      0.932
_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)+(0.0289P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1520
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
N1 N 0.1634(2) 0.45242(15) 0.48483(7) 0.0446(6) Uani 1 1 d . . .
N2 N 0.0720(2) 0.51132(15) 0.36540(7) 0.0441(6) Uani 1 1 d . . .
O3 O -0.2069(2) 0.23247(14) 0.41440(7) 0.0635(6) Uani 1 1 d . . .
O4 O -0.1246(2) 0.21499(14) 0.50095(7) 0.0632(7) Uani 1 1 d . . .
N5 N 0.0171(2) 0.58451(15) 0.36379(7) 0.0510(7) Uani 1 1 d . . .
N6 N 0.0051(2) 0.60244(15) 0.31868(8) 0.0496(7) Uani 1 1 d . . .
C7 C 0.0504(3) 0.54880(18) 0.23925(9) 0.0422(7) Uani 1 1 d . . .
C8 C 0.0256(3) 0.40496(18) 0.42536(8) 0.0425(7) Uani 1 1 d . . .
C9 C 0.0967(3) 0.48360(18) 0.32061(9) 0.0407(7) Uani 1 1 d . . .
C10 C 0.1590(3) 0.40727(18) 0.31069(9) 0.0426(7) Uani 1 1 d . . .
C11 C 0.0252(3) 0.3296(2) 0.49939(10) 0.0495(8) Uani 1 1 d . . .
C12 C 0.0915(3) 0.47339(18) 0.40983(9) 0.0418(7) Uani 1 1 d . . .
C13 C 0.0710(3) 0.39235(19) 0.47234(9) 0.0431(7) Uani 1 1 d . . .
C14 C 0.0519(3) 0.54246(19) 0.29138(9) 0.0411(7) Uani 1 1 d . . .
C15 C 0.1754(3) 0.50346(19) 0.44593(9) 0.0439(8) Uani 1 1 d . . .
C16 C -0.0679(3) 0.2782(2) 0.47874(10) 0.0489(8) Uani 1 1 d . . .
C17 C -0.0567(3) 0.59188(19) 0.21745(9) 0.0527(8) Uani 1 1 d . . .
H17 H -0.1280 0.6150 0.2359 0.063 Uiso 1 1 calc R . .
C18 C -0.1139(3) 0.2884(2) 0.43083(10) 0.0483(8) Uani 1 1 d . . .
C19 C -0.0681(3) 0.35020(19) 0.40450(9) 0.0462(8) Uani 1 1 d . . .
C20 C 0.2642(3) 0.5684(2) 0.45132(9) 0.0511(8) Uani 1 1 d . . .
H20 H 0.2729 0.6035 0.4266 0.061 Uiso 1 1 calc R . .
C21 C 0.2868(3) 0.3835(2) 0.33180(10) 0.0557(9) Uani 1 1 d . . .
H21 H 0.3335 0.4154 0.3535 0.067 Uiso 1 1 calc R . .
C22 C 0.2371(3) 0.4652(2) 0.52666(9) 0.0557(9) Uani 1 1 d . . .
H22 H 0.2274 0.4311 0.5519 0.067 Uiso 1 1 calc R . .
C23 C 0.1541(3) 0.51439(19) 0.21054(9) 0.0530(9) Uani 1 1 d . . .
H23 H 0.2272 0.4851 0.2243 0.064 Uiso 1 1 calc R . .
C24 C -0.0596(3) 0.6011(2) 0.16877(10) 0.0661(10) Uani 1 1 d . . .
H24 H -0.1315 0.6309 0.1547 0.079 Uiso 1 1 calc R . .
C25 C 0.1503(3) 0.5230(2) 0.16197(10) 0.0644(10) Uani 1 1 d . . .
H25 H 0.2202 0.4993 0.1433 0.077 Uiso 1 1 calc R . .
C26 C 0.0932(3) 0.3587(2) 0.27825(10) 0.0564(9) Uani 1 1 d . . .
H26 H 0.0072 0.3739 0.2639 0.068 Uiso 1 1 calc R . .
C27 C 0.3232(3) 0.5276(2) 0.53057(10) 0.0637(10) Uani 1 1 d . . .
H27 H 0.3737 0.5361 0.5586 0.076 Uiso 1 1 calc R . .
C28 C 0.0444(3) 0.5662(2) 0.14110(10) 0.0667(10) Uani 1 1 d . . .
H28 H 0.0424 0.5720 0.1083 0.080 Uiso 1 1 calc R . .
C29 C -0.2528(3) 0.2394(2) 0.36623(10) 0.0756(11) Uani 1 1 d . . .
H29A H -0.1698 0.2391 0.3458 0.113 Uiso 1 1 calc R . .
H29B H -0.3048 0.2868 0.3622 0.113 Uiso 1 1 calc R . .
H29C H -0.3148 0.1968 0.3583 0.113 Uiso 1 1 calc R . .
C30 C 0.3450(3) 0.3124(2) 0.32070(11) 0.0649(10) Uani 1 1 d . . .
H30 H 0.4298 0.2963 0.3355 0.078 Uiso 1 1 calc R . .
C31 C 0.3377(3) 0.5803(2) 0.49244(11) 0.0615(9) Uani 1 1 d . . .
H31 H 0.3976 0.6231 0.4956 0.074 Uiso 1 1 calc R . .
C32 C 0.1524(4) 0.2881(2) 0.26676(12) 0.0692(10) Uani 1 1 d . . .
H32 H 0.1070 0.2562 0.2448 0.083 Uiso 1 1 calc R . .
C33 C -0.1060(3) 0.2100(2) 0.55122(10) 0.0726(11) Uani 1 1 d . . .
H33A H -0.0047 0.2077 0.5586 0.109 Uiso 1 1 calc R . .
H33B H -0.1530 0.1644 0.5628 0.109 Uiso 1 1 calc R . .
H33C H -0.1479 0.2546 0.5660 0.109 Uiso 1 1 calc R . .
C34 C 0.2788(3) 0.2653(2) 0.28801(12) 0.0673(10) Uani 1 1 d . . .
H34 H 0.3197 0.2179 0.2803 0.081 Uiso 1 1 calc R . .
H19 H -0.102(2) 0.3569(15) 0.3719(8) 0.040(7) Uiso 1 1 d . . .
H11 H 0.058(2) 0.3225(15) 0.5304(8) 0.038(7) 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 C13 1.392(4) . ?
N1 C15 1.413(3) . ?
N1 C22 1.379(3) . ?
N2 N5 1.368(3) . ?
N2 C9 1.370(3) . ?
N2 C12 1.426(3) . ?
O3 C18 1.376(3) . ?
O3 C29 1.427(3) . ?
O4 C16 1.367(3) . ?
O4 C33 1.430(3) . ?
N5 N6 1.313(3) . ?
N6 C14 1.364(3) . ?
C7 C14 1.473(3) . ?
C7 C17 1.384(4) . ?
C7 C23 1.389(3) . ?
C8 C12 1.404(4) . ?
C8 C13 1.406(3) . ?
C8 C19 1.413(4) . ?
C9 C10 1.471(4) . ?
C9 C14 1.376(4) . ?
C10 C21 1.385(4) . ?
C10 C26 1.384(4) . ?
C11 C13 1.394(4) . ?
C11 C16 1.369(4) . ?
C12 C15 1.382(3) . ?
C15 C20 1.402(4) . ?
C16 C18 1.426(4) . ?
C17 C24 1.381(3) . ?
C18 C19 1.371(4) . ?
C20 C31 1.359(3) . ?
C21 C30 1.381(4) . ?
C22 C27 1.348(4) . ?
C23 C25 1.377(3) . ?
C24 C28 1.378(4) . ?
C25 C28 1.366(4) . ?
C26 C32 1.380(4) . ?
C27 C31 1.418(4) . ?
C30 C34 1.376(4) . ?
C32 C34 1.370(4) . ?

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
C13 N1 C15 108.7(2) . . ?
C22 N1 C13 129.7(3) . . ?
C22 N1 C15 121.5(3) . . ?
N5 N2 C9 110.9(2) . . ?
N5 N2 C12 120.3(2) . . ?
C9 N2 C12 128.8(3) . . ?
C18 O3 C29 116.5(2) . . ?
C16 O4 C33 117.1(2) . . ?
N6 N5 N2 106.5(2) . . ?
N5 N6 C14 109.8(2) . . ?
C17 C7 C14 119.3(2) . . ?
C17 C7 C23 117.9(2) . . ?
C23 C7 C14 122.8(2) . . ?
C12 C8 C13 107.2(2) . . ?
C12 C8 C19 134.8(3) . . ?
C13 C8 C19 118.0(3) . . ?
N2 C9 C10 123.8(3) . . ?
N2 C9 C14 103.9(3) . . ?
C14 C9 C10 132.2(2) . . ?
C21 C10 C9 121.3(3) . . ?
C26 C10 C9 120.1(3) . . ?
C26 C10 C21 118.5(3) . . ?
C16 C11 C13 117.8(3) . . ?
C8 C12 N2 127.5(2) . . ?
C15 C12 N2 122.9(3) . . ?
C15 C12 C8 109.5(2) . . ?
N1 C13 C8 107.7(2) . . ?
N1 C13 C11 129.2(2) . . ?
C11 C13 C8 123.1(3) . . ?
N6 C14 C7 120.2(3) . . ?
N6 C14 C9 108.9(2) . . ?
C9 C14 C7 130.9(3) . . ?
C12 C15 N1 106.9(3) . . ?
C12 C15 C20 135.4(3) . . ?
C20 C15 N1 117.7(2) . . ?
O4 C16 C11 124.7(3) . . ?
O4 C16 C18 114.7(3) . . ?
C11 C16 C18 120.6(3) . . ?
C24 C17 C7 121.1(3) . . ?
O3 C18 C16 114.7(3) . . ?
C19 C18 O3 124.2(2) . . ?
C19 C18 C16 121.1(3) . . ?
C18 C19 C8 119.3(3) . . ?
C31 C20 C15 120.5(3) . . ?
C30 C21 C10 120.0(3) . . ?
C27 C22 N1 119.4(3) . . ?
C25 C23 C7 120.9(3) . . ?
C28 C24 C17 119.9(3) . . ?
C28 C25 C23 120.4(3) . . ?
C32 C26 C10 121.4(3) . . ?
C22 C27 C31 120.8(3) . . ?
C25 C28 C24 119.8(3) . . ?
C34 C30 C21 120.6(3) . . ?
C20 C31 C27 120.0(3) . . ?
C34 C32 C26 119.5(3) . . ?
C32 C34 C30 120.0(3) . . ?
####################################################################### 
# 
# 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_exp_117
_database_code_depnum_ccdc_archive 'CCDC 1562142'
_audit_update_record             
;
2017-07-14 deposited with the CCDC.
2018-04-24 downloaded from the CCDC.
;
_audit_creation_date             2014-04-09
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H13 N5'
_chemical_formula_sum            'C21 H13 N5'
_chemical_formula_weight         335.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         C10H10N4
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                   13.2575(7)
_cell_length_b                   15.3061(7)
_cell_length_c                   7.8541(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.654(5)
_cell_angle_gamma                90.00
_cell_volume                     1575.61(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2041
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      30.0940
_cell_measurement_theta_min      2.6460
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8647
_diffrn_reflns_theta_full        30.77
_diffrn_reflns_theta_max         30.77
_diffrn_reflns_theta_min         2.66
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector_area_resol_mean 15.9555
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.8760
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00    0.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.6360  -99.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -34.00   53.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360  -77.0000  -90.0000 87

#__ type_ start__ end____ width___ exp.time_
  3 omega   -7.00   92.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   77.0000   60.0000 99

#__ type_ start__ end____ width___ exp.time_
  4 omega   44.00   79.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       23.1360   77.0000 -180.0000 35
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0093107000
_diffrn_orient_matrix_UB_12      -0.0447008000
_diffrn_orient_matrix_UB_13      -0.0157431000
_diffrn_orient_matrix_UB_21      -0.0524328000
_diffrn_orient_matrix_UB_22      -0.0093806000
_diffrn_orient_matrix_UB_23      -0.0004506000
_diffrn_orient_matrix_UB_31      -0.0096936000
_diffrn_orient_matrix_UB_32      0.0079031000
_diffrn_orient_matrix_UB_33      -0.0899551000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2828
_reflns_number_total             4303
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      1.002
_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)+(0.0659P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1391
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
N3 N 0.88735(11) 0.09535(9) 0.58175(18) 0.0221(3) Uani 1 1 d . . .
N2 N 0.83044(11) 0.02932(9) 0.51652(19) 0.0226(3) Uani 1 1 d . . .
N1 N 0.75471(11) 0.06171(9) 0.39965(18) 0.0188(3) Uani 1 1 d . . .
C7 C 0.89476(13) 0.25715(11) 0.5614(2) 0.0186(4) Uani 1 1 d . . .
N5 N 0.52869(12) -0.05230(10) 0.19619(19) 0.0262(4) Uani 1 1 d . . .
C4 C 0.84869(13) 0.17191(11) 0.5096(2) 0.0182(4) Uani 1 1 d . . .
C5 C 0.76368(13) 0.15090(10) 0.3913(2) 0.0181(3) Uani 1 1 d . . .
C3 C 0.70031(13) -0.06912(11) 0.2172(2) 0.0195(4) Uani 1 1 d . . .
C21 C 0.60497(12) -0.10538(10) 0.1478(2) 0.0151(3) Uani 1 1 d . . .
C6 C 0.69590(13) 0.20158(11) 0.2728(2) 0.0201(4) Uani 1 1 d . . .
N4 N 0.64144(12) 0.24206(10) 0.1755(2) 0.0258(4) Uani 1 1 d . . .
C12 C 0.98253(13) 0.26028(12) 0.6855(2) 0.0228(4) Uani 1 1 d . . .
C18 C 0.78058(16) -0.18228(12) 0.0743(2) 0.0267(4) Uani 1 1 d . . .
C1 C 0.57366(13) 0.01793(11) 0.2939(2) 0.0202(4) Uani 1 1 d . . .
C2 C 0.67989(13) 0.00679(11) 0.3067(2) 0.0203(4) Uani 1 1 d . . .
C15 C 0.36273(14) -0.00288(13) 0.2215(2) 0.0269(4) Uani 1 1 d . . .
C14 C 0.40576(14) 0.06852(12) 0.3222(2) 0.0257(4) Uani 1 1 d . . .
C9 C 0.89692(14) 0.41484(12) 0.5470(2) 0.0245(4) Uani 1 1 d . . .
C10 C 0.98221(14) 0.41740(13) 0.6726(2) 0.0248(4) Uani 1 1 d . . .
C11 C 1.02533(14) 0.34037(12) 0.7406(2) 0.0262(4) Uani 1 1 d . . .
C8 C 0.85350(14) 0.33536(11) 0.4918(2) 0.0222(4) Uani 1 1 d . . .
C13 C 0.50902(14) 0.07919(12) 0.3597(2) 0.0225(4) Uani 1 1 d . . .
C16 C 0.42319(14) -0.06268(13) 0.1587(2) 0.0248(4) Uani 1 1 d . . .
C20 C 0.59618(16) -0.17964(12) 0.0444(2) 0.0251(4) Uani 1 1 d . . .
C19 C 0.68421(15) -0.21685(12) 0.0073(2) 0.0264(4) Uani 1 1 d . . .
C17 C 0.78981(14) -0.11042(12) 0.1806(2) 0.0238(4) Uani 1 1 d . . .
H9 H 0.8636(16) 0.4718(14) 0.498(3) 0.038(6) Uiso 1 1 d . . .
H12 H 1.0139(15) 0.2037(13) 0.734(3) 0.028(5) Uiso 1 1 d . . .
H15 H 0.2899(15) -0.0120(12) 0.191(2) 0.026(5) Uiso 1 1 d . . .
H13 H 0.5415(14) 0.1271(13) 0.430(2) 0.026(5) Uiso 1 1 d . . .
H16 H 0.3985(16) -0.1124(14) 0.093(3) 0.036(6) Uiso 1 1 d . . .
H17 H 0.8592(15) -0.0847(13) 0.227(3) 0.037(6) Uiso 1 1 d . . .
H11 H 1.0900(16) 0.3421(13) 0.830(3) 0.038(6) Uiso 1 1 d . . .
H10 H 1.0122(16) 0.4713(14) 0.716(3) 0.038(6) Uiso 1 1 d . . .
H8 H 0.7901(14) 0.3323(11) 0.396(2) 0.020(5) Uiso 1 1 d . . .
H19 H 0.6808(15) -0.2674(13) -0.058(3) 0.030(5) Uiso 1 1 d . . .
H18 H 0.8390(17) -0.2101(14) 0.046(3) 0.042(6) Uiso 1 1 d . . .
H14 H 0.3609(14) 0.1107(13) 0.375(3) 0.029(5) Uiso 1 1 d . . .
H20 H 0.5253(17) -0.2005(14) 0.004(3) 0.041(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
N3 N2 1.318(2) . ?
N3 C4 1.367(2) . ?
N2 N1 1.3488(19) . ?
N1 C5 1.373(2) . ?
N1 C2 1.416(2) . ?
C7 C4 1.472(2) . ?
C7 C12 1.402(2) . ?
C7 C8 1.393(2) . ?
N5 C21 1.394(2) . ?
N5 C1 1.401(2) . ?
N5 C16 1.394(2) . ?
C4 C5 1.387(2) . ?
C5 C6 1.423(2) . ?
C3 C21 1.412(2) . ?
C3 C2 1.406(2) . ?
C3 C17 1.412(2) . ?
C21 C20 1.392(2) . ?
C6 N4 1.150(2) . ?
C12 C11 1.392(3) . ?
C18 C19 1.410(3) . ?
C18 C17 1.375(3) . ?
C1 C2 1.407(2) . ?
C1 C13 1.419(2) . ?
C15 C14 1.418(3) . ?
C15 C16 1.357(3) . ?
C14 C13 1.366(3) . ?
C9 C10 1.385(3) . ?
C9 C8 1.387(2) . ?
C10 C11 1.382(3) . ?
C20 C19 1.369(3) . ?

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 N3 C4 109.83(14) . . ?
N3 N2 N1 107.86(13) . . ?
N2 N1 C5 109.70(13) . . ?
N2 N1 C2 121.64(13) . . ?
C5 N1 C2 128.66(14) . . ?
C12 C7 C4 119.27(16) . . ?
C8 C7 C4 122.10(16) . . ?
C8 C7 C12 118.63(16) . . ?
C21 N5 C1 109.28(14) . . ?
C21 N5 C16 128.46(15) . . ?
C16 N5 C1 122.25(16) . . ?
N3 C4 C7 122.10(15) . . ?
N3 C4 C5 107.17(14) . . ?
C5 C4 C7 130.73(15) . . ?
N1 C5 C4 105.43(14) . . ?
N1 C5 C6 121.52(15) . . ?
C4 C5 C6 132.99(15) . . ?
C2 C3 C21 106.81(15) . . ?
C2 C3 C17 134.67(16) . . ?
C17 C3 C21 118.46(15) . . ?
N5 C21 C3 108.04(14) . . ?
C20 C21 N5 129.39(16) . . ?
C20 C21 C3 122.51(16) . . ?
N4 C6 C5 179.28(19) . . ?
C11 C12 C7 120.21(17) . . ?
C17 C18 C19 121.33(19) . . ?
N5 C1 C2 106.57(15) . . ?
N5 C1 C13 118.43(16) . . ?
C2 C1 C13 134.96(16) . . ?
C3 C2 N1 125.16(16) . . ?
C3 C2 C1 109.29(15) . . ?
C1 C2 N1 125.52(15) . . ?
C16 C15 C14 120.83(17) . . ?
C13 C14 C15 121.22(18) . . ?
C10 C9 C8 120.21(18) . . ?
C11 C10 C9 119.80(18) . . ?
C10 C11 C12 120.38(17) . . ?
C9 C8 C7 120.74(17) . . ?
C14 C13 C1 118.89(17) . . ?
C15 C16 N5 118.36(18) . . ?
C19 C20 C21 117.70(18) . . ?
C20 C19 C18 121.20(18) . . ?
C18 C17 C3 118.74(17) . . ?
