# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_av39m
_database_code_depnum_ccdc_archive 'CCDC 1052135'
_audit_update_record             
;
2015-03-04 deposited with the CCDC.
2015-06-19 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-methyl-3-nitropyrazolo[1,5-a]quinoline 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N3 O2'
_chemical_formula_sum            'C12 H9 N3 O2'
_chemical_formula_weight         227.22

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           Orthorhombic
_symmetry_space_group_name_H-M   'P b c a'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.4947(11)
_cell_length_b                   13.0618(18)
_cell_length_c                   21.098(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2065.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3157
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      25.12

_exptl_crystal_description       Needle
_exptl_crystal_colour            'Pale Yellow'
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9520
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
; 
Sheldrick,G.M.,(2003),University of gottingen,Germany 
;

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18250
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         24.97
_reflns_number_total             1809
_reflns_number_gt                1709
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0339P)²+2.2998P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1809
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0840
_refine_ls_wR_factor_ref         0.1637
_refine_ls_wR_factor_gt          0.1622
_refine_ls_goodness_of_fit_ref   1.399
_refine_ls_restrained_S_all      1.399
_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
C1 C 0.1239(4) 0.0723(2) 0.38892(15) 0.0382(8) Uani 1 1 d . . .
C2 C 0.0488(4) 0.1705(2) 0.38655(15) 0.0385(8) Uani 1 1 d . . .
C3 C -0.0058(6) 0.2399(3) 0.43932(17) 0.0599(11) Uani 1 1 d . . .
H3A H -0.0666 0.2984 0.4222 0.090 Uiso 1 1 calc R . .
H3B H 0.0982 0.2620 0.4621 0.090 Uiso 1 1 calc R . .
H3C H -0.0841 0.2038 0.4676 0.090 Uiso 1 1 calc R . .
C4 C 0.1478(4) 0.0401(2) 0.32659(15) 0.0362(7) Uani 1 1 d . . .
C5 C 0.2172(4) -0.0479(2) 0.29532(17) 0.0425(8) Uani 1 1 d . . .
H5 H 0.2613 -0.1029 0.3186 0.051 Uiso 1 1 calc R . .
C6 C 0.2180(5) -0.0501(3) 0.23142(17) 0.0458(9) Uani 1 1 d . . .
H6 H 0.2628 -0.1076 0.2108 0.055 Uiso 1 1 calc R . .
C7 C 0.1523(4) 0.0327(2) 0.19475(15) 0.0384(8) Uani 1 1 d . . .
C8 C 0.0841(4) 0.1201(2) 0.22505(14) 0.0345(7) Uani 1 1 d . . .
C9 C 0.0175(4) 0.2032(3) 0.19172(16) 0.0413(8) Uani 1 1 d . . .
H9 H -0.0274 0.2600 0.2129 0.050 Uiso 1 1 calc R . .
C10 C 0.0194(5) 0.1995(3) 0.12659(17) 0.0515(10) Uani 1 1 d . . .
H10 H -0.0242 0.2547 0.1034 0.062 Uiso 1 1 calc R . .
C11 C 0.0856(5) 0.1142(3) 0.09505(17) 0.0549(10) Uani 1 1 d . . .
H11 H 0.0848 0.1125 0.0510 0.066 Uiso 1 1 calc R . .
C12 C 0.1515(5) 0.0333(3) 0.12802(16) 0.0495(9) Uani 1 1 d . . .
H12 H 0.1969 -0.0227 0.1061 0.059 Uiso 1 1 calc R . .
N1 N 0.1769(4) 0.0180(3) 0.44356(15) 0.0548(9) Uani 1 1 d . . .
N2 N 0.0241(4) 0.19918(19) 0.32710(12) 0.0383(7) Uani 1 1 d . . .
N3 N 0.0856(3) 0.11870(18) 0.29141(11) 0.0323(6) Uani 1 1 d . . .
O1 O 0.1755(4) 0.0622(3) 0.49491(13) 0.0790(10) Uani 1 1 d . . .
O2 O 0.2234(5) -0.0722(2) 0.43706(14) 0.0783(10) Uani 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
C1 C4 1.392(4) . ?
C1 C2 1.401(4) . ?
C1 N1 1.411(4) . ?
C2 N2 1.322(4) . ?
C2 C3 1.493(5) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 N3 1.349(4) . ?
C4 C5 1.425(5) . ?
C5 C6 1.349(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.419(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.405(4) . ?
C7 C12 1.408(5) . ?
C8 C9 1.386(4) . ?
C8 N3 1.400(4) . ?
C9 C10 1.375(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.389(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.358(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
N1 O1 1.228(4) . ?
N1 O2 1.236(4) . ?
N2 N3 1.373(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
C4 C1 C2 107.1(3) . . ?
C4 C1 N1 125.7(3) . . ?
C2 C1 N1 127.1(3) . . ?
N2 C2 C1 110.5(3) . . ?
N2 C2 C3 119.8(3) . . ?
C1 C2 C3 129.7(3) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N3 C4 C1 104.2(3) . . ?
N3 C4 C5 119.0(3) . . ?
C1 C4 C5 136.7(3) . . ?
C6 C5 C4 118.8(3) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C7 121.8(3) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C12 116.7(3) . . ?
C8 C7 C6 119.9(3) . . ?
C12 C7 C6 123.4(3) . . ?
C9 C8 N3 121.4(3) . . ?
C9 C8 C7 122.4(3) . . ?
N3 C8 C7 116.2(3) . . ?
C10 C9 C8 118.4(3) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C10 C11 120.7(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
O1 N1 O2 123.3(3) . . ?
O1 N1 C1 118.8(3) . . ?
O2 N1 C1 117.9(3) . . ?
C2 N2 N3 104.8(3) . . ?
C4 N3 N2 113.4(2) . . ?
C4 N3 C8 124.3(3) . . ?
N2 N3 C8 122.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C1 C2 N2 0.7(4) . . . . ?
N1 C1 C2 N2 176.9(3) . . . . ?
C4 C1 C2 C3 179.2(3) . . . . ?
N1 C1 C2 C3 -4.6(6) . . . . ?
C2 C1 C4 N3 -0.5(3) . . . . ?
N1 C1 C4 N3 -176.7(3) . . . . ?
C2 C1 C4 C5 179.0(4) . . . . ?
N1 C1 C4 C5 2.7(6) . . . . ?
N3 C4 C5 C6 -0.3(5) . . . . ?
C1 C4 C5 C6 -179.7(4) . . . . ?
C4 C5 C6 C7 0.2(5) . . . . ?
C5 C6 C7 C8 0.0(5) . . . . ?
C5 C6 C7 C12 179.8(3) . . . . ?
C12 C7 C8 C9 0.5(5) . . . . ?
C6 C7 C8 C9 -179.7(3) . . . . ?
C12 C7 C8 N3 -180.0(3) . . . . ?
C6 C7 C8 N3 -0.2(4) . . . . ?
N3 C8 C9 C10 -179.8(3) . . . . ?
C7 C8 C9 C10 -0.3(5) . . . . ?
C8 C9 C10 C11 0.4(5) . . . . ?
C9 C10 C11 C12 -0.7(6) . . . . ?
C10 C11 C12 C7 0.9(6) . . . . ?
C8 C7 C12 C11 -0.8(5) . . . . ?
C6 C7 C12 C11 179.4(3) . . . . ?
C4 C1 N1 O1 167.8(3) . . . . ?
C2 C1 N1 O1 -7.7(5) . . . . ?
C4 C1 N1 O2 -11.9(5) . . . . ?
C2 C1 N1 O2 172.6(3) . . . . ?
C1 C2 N2 N3 -0.6(3) . . . . ?
C3 C2 N2 N3 -179.3(3) . . . . ?
C1 C4 N3 N2 0.2(3) . . . . ?
C5 C4 N3 N2 -179.4(3) . . . . ?
C1 C4 N3 C8 179.7(3) . . . . ?
C5 C4 N3 C8 0.1(5) . . . . ?
C2 N2 N3 C4 0.2(3) . . . . ?
C2 N2 N3 C8 -179.3(3) . . . . ?
C9 C8 N3 C4 179.7(3) . . . . ?
C7 C8 N3 C4 0.2(4) . . . . ?
C9 C8 N3 N2 -0.9(4) . . . . ?
C7 C8 N3 N2 179.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.045
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_ay93m
_database_code_depnum_ccdc_archive 'CCDC 1057420'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2015-06-19 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 '2,10-dimethyl-3-nitro-10H-pyrazolo[1',5':1,6]pyrido[2,3-b]indole' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 N4 O2'
_chemical_formula_sum            'C15 H12 N4 O2'
_chemical_formula_weight         280.29

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           Triclinic
_symmetry_space_group_name_H-M   'P -1   '
_symmetry_space_group_name_Hall  ' -P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1508(10)
_cell_length_b                   9.6154(14)
_cell_length_c                   10.0654(14)
_cell_angle_alpha                82.965(2)
_cell_angle_beta                 70.019(2)
_cell_angle_gamma                87.230(2)
_cell_volume                     645.50(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2280
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      26.60

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9582
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
; 
Sheldrick,G.M.,(2003),University of gottingen,Germany 
;

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6234
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2269
_reflns_number_gt                1968
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0580P)²+0.2701P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2269
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1411
_refine_ls_wR_factor_gt          0.1339
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.155
_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
C1 C 0.5263(3) 0.2704(2) 0.1971(2) 0.0374(5) Uani 1 1 d . . .
C2 C 0.4741(3) 0.3652(2) 0.2997(2) 0.0395(5) Uani 1 1 d . . .
C3 C 0.5184(4) 0.5175(2) 0.2814(3) 0.0594(7) Uani 1 1 d . . .
H3A H 0.4693 0.5529 0.3724 0.089 Uiso 1 1 calc R . .
H3B H 0.4548 0.5667 0.2194 0.089 Uiso 1 1 calc R . .
H3C H 0.6596 0.5311 0.2408 0.089 Uiso 1 1 calc R . .
C4 C 0.4490(3) 0.1396(2) 0.2660(2) 0.0354(5) Uani 1 1 d . . .
C5 C 0.4471(3) 0.0044(2) 0.2281(2) 0.0427(6) Uani 1 1 d . . .
H5 H 0.5102 -0.0135 0.1343 0.051 Uiso 1 1 calc R . .
C6 C 0.3525(3) -0.1006(2) 0.3291(2) 0.0446(6) Uani 1 1 d . . .
H6 H 0.3517 -0.1907 0.3045 0.054 Uiso 1 1 calc R . .
C7 C 0.2563(3) -0.0731(2) 0.4702(2) 0.0385(5) Uani 1 1 d . . .
C8 C 0.2574(3) 0.0615(2) 0.5065(2) 0.0366(5) Uani 1 1 d . . .
C9 C 0.1175(4) 0.1914(3) 0.7252(3) 0.0612(7) Uani 1 1 d . . .
H9A H 0.2044 0.1878 0.7801 0.092 Uiso 1 1 calc R . .
H9B H -0.0184 0.1907 0.7877 0.092 Uiso 1 1 calc R . .
H9C H 0.1419 0.2756 0.6600 0.092 Uiso 1 1 calc R . .
C10 C 0.0836(3) -0.0646(3) 0.7054(2) 0.0455(6) Uani 1 1 d . . .
C11 C 0.1434(3) -0.1552(2) 0.5996(3) 0.0434(6) Uani 1 1 d . . .
C12 C 0.0888(4) -0.2960(3) 0.6347(3) 0.0564(7) Uani 1 1 d . . .
H12 H 0.1267 -0.3579 0.5659 0.068 Uiso 1 1 calc R . .
C13 C -0.0222(4) -0.3412(3) 0.7730(3) 0.0673(8) Uani 1 1 d . . .
H13 H -0.0598 -0.4346 0.7977 0.081 Uiso 1 1 calc R . .
C14 C -0.0789(4) -0.2502(3) 0.8761(3) 0.0705(9) Uani 1 1 d . . .
H14 H -0.1528 -0.2842 0.9690 0.085 Uiso 1 1 calc R . .
C15 C -0.0292(4) -0.1109(3) 0.8455(3) 0.0595(7) Uani 1 1 d . . .
H15 H -0.0691 -0.0500 0.9153 0.071 Uiso 1 1 calc R . .
N1 N 0.6321(3) 0.2987(2) 0.0512(2) 0.0473(5) Uani 1 1 d . . .
N2 N 0.3700(3) 0.30306(18) 0.42618(19) 0.0403(5) Uani 1 1 d . . .
N3 N 0.3550(3) 0.16574(17) 0.40452(18) 0.0344(4) Uani 1 1 d . . .
N4 N 0.1546(3) 0.0702(2) 0.64596(19) 0.0432(5) Uani 1 1 d . . .
O1 O 0.7014(3) 0.4162(2) 0.0034(2) 0.0720(6) Uani 1 1 d . . .
O2 O 0.6520(3) 0.2037(2) -0.02439(19) 0.0702(6) Uani 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
C1 C4 1.401(3) . ?
C1 N1 1.402(3) . ?
C1 C2 1.404(3) . ?
C2 N2 1.320(3) . ?
C2 C3 1.489(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 N3 1.374(3) . ?
C4 C5 1.401(3) . ?
C5 C6 1.363(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.403(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.388(3) . ?
C7 C11 1.436(3) . ?
C8 N4 1.355(3) . ?
C8 N3 1.368(3) . ?
C9 N4 1.455(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.393(3) . ?
C10 C11 1.398(3) . ?
C10 N4 1.401(3) . ?
C11 C12 1.397(3) . ?
C12 C13 1.373(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.373(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
N1 O1 1.229(2) . ?
N1 O2 1.232(3) . ?
N2 N3 1.379(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
C4 C1 N1 125.0(2) . . ?
C4 C1 C2 107.52(18) . . ?
N1 C1 C2 127.48(19) . . ?
N2 C2 C1 111.09(18) . . ?
N2 C2 C3 119.9(2) . . ?
C1 C2 C3 129.0(2) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N3 C4 C5 119.97(19) . . ?
N3 C4 C1 103.20(17) . . ?
C5 C4 C1 136.8(2) . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 119.8(2) . . ?
C8 C7 C11 105.4(2) . . ?
C6 C7 C11 134.8(2) . . ?
N4 C8 N3 128.3(2) . . ?
N4 C8 C7 112.13(19) . . ?
N3 C8 C7 119.6(2) . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 121.8(2) . . ?
C15 C10 N4 128.9(2) . . ?
C11 C10 N4 109.29(19) . . ?
C12 C11 C10 119.4(2) . . ?
C12 C11 C7 133.9(2) . . ?
C10 C11 C7 106.8(2) . . ?
C13 C12 C11 118.6(3) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C14 121.2(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 121.9(3) . . ?
C15 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
C14 C15 C10 117.1(3) . . ?
C14 C15 H15 121.4 . . ?
C10 C15 H15 121.4 . . ?
O1 N1 O2 122.5(2) . . ?
O1 N1 C1 119.3(2) . . ?
O2 N1 C1 118.20(19) . . ?
C2 N2 N3 104.68(17) . . ?
C8 N3 C4 120.84(18) . . ?
C8 N3 N2 125.65(18) . . ?
C4 N3 N2 113.51(17) . . ?
C8 N4 C10 106.44(19) . . ?
C8 N4 C9 129.39(19) . . ?
C10 N4 C9 124.16(19) . . ?

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
C4 C1 C2 N2 -0.2(3) . . . . ?
N1 C1 C2 N2 178.3(2) . . . . ?
C4 C1 C2 C3 -179.4(2) . . . . ?
N1 C1 C2 C3 -0.8(4) . . . . ?
N1 C1 C4 N3 -178.2(2) . . . . ?
C2 C1 C4 N3 0.4(2) . . . . ?
N1 C1 C4 C5 1.6(4) . . . . ?
C2 C1 C4 C5 -179.8(2) . . . . ?
N3 C4 C5 C6 -0.2(3) . . . . ?
C1 C4 C5 C6 180.0(2) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C5 C6 C7 C11 179.0(2) . . . . ?
C6 C7 C8 N4 178.75(19) . . . . ?
C11 C7 C8 N4 -0.4(2) . . . . ?
C6 C7 C8 N3 -1.0(3) . . . . ?
C11 C7 C8 N3 179.86(18) . . . . ?
C15 C10 C11 C12 0.1(3) . . . . ?
N4 C10 C11 C12 -179.9(2) . . . . ?
C15 C10 C11 C7 -179.8(2) . . . . ?
N4 C10 C11 C7 0.2(2) . . . . ?
C8 C7 C11 C12 -179.8(2) . . . . ?
C6 C7 C11 C12 1.2(5) . . . . ?
C8 C7 C11 C10 0.1(2) . . . . ?
C6 C7 C11 C10 -178.9(2) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C7 C11 C12 C13 179.7(2) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C13 C14 C15 0.6(4) . . . . ?
C13 C14 C15 C10 -0.7(4) . . . . ?
C11 C10 C15 C14 0.3(4) . . . . ?
N4 C10 C15 C14 -179.7(2) . . . . ?
C4 C1 N1 O1 -176.5(2) . . . . ?
C2 C1 N1 O1 5.1(4) . . . . ?
C4 C1 N1 O2 3.4(3) . . . . ?
C2 C1 N1 O2 -175.0(2) . . . . ?
C1 C2 N2 N3 0.0(2) . . . . ?
C3 C2 N2 N3 179.2(2) . . . . ?
N4 C8 N3 C4 -178.5(2) . . . . ?
C7 C8 N3 C4 1.2(3) . . . . ?
N4 C8 N3 N2 1.2(3) . . . . ?
C7 C8 N3 N2 -179.13(18) . . . . ?
C5 C4 N3 C8 -0.6(3) . . . . ?
C1 C4 N3 C8 179.29(18) . . . . ?
C5 C4 N3 N2 179.70(18) . . . . ?
C1 C4 N3 N2 -0.4(2) . . . . ?
C2 N2 N3 C8 -179.41(19) . . . . ?
C2 N2 N3 C4 0.3(2) . . . . ?
N3 C8 N4 C10 -179.8(2) . . . . ?
C7 C8 N4 C10 0.5(2) . . . . ?
N3 C8 N4 C9 0.8(4) . . . . ?
C7 C8 N4 C9 -178.9(2) . . . . ?
C15 C10 N4 C8 179.5(2) . . . . ?
C11 C10 N4 C8 -0.5(2) . . . . ?
C15 C10 N4 C9 -1.0(4) . . . . ?
C11 C10 N4 C9 179.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.042
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol:Chloroform (9:1)'
