# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_m6
_database_code_depnum_ccdc_archive 'CCDC 1056644'
_audit_update_record             
;
2015-03-27 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;
_audit_creation_date             2015-03-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C4 H3 N5 O6'
_chemical_formula_sum            'C4 H3 N5 O6'
_chemical_formula_weight         217.11
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   11.9211(5)
_cell_length_b                   8.3391(4)
_cell_length_c                   8.4760(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     842.61(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.711
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2187
_diffrn_reflns_point_group_measured_fraction_full 0.732
_diffrn_reflns_point_group_measured_fraction_max 0.617
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.846
_diffrn_reflns_theta_min         3.418
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.315
_reflns_Friedel_fraction_full    0.425
_reflns_Friedel_fraction_max     0.316
_reflns_number_gt                1105
_reflns_number_total             1365
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 253 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.8(10)
_refine_ls_extinction_coef       0.043(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1365
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0343P)²+0.0398P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0912
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6413(2) 0.2445(3) 0.5355(3) 0.0451(6) Uani 1 1 d . . . . .
N2 N 0.7241(2) 0.3352(3) 0.4796(3) 0.0482(7) Uani 1 1 d . . . . .
N3 N 0.7800(2) 0.6114(4) 0.4966(4) 0.0519(7) Uani 1 1 d . . . . .
O4 O 0.4482(2) 0.1292(3) 0.6830(4) 0.0708(8) Uani 1 1 d . . . . .
C5 C 0.7060(2) 0.4803(3) 0.5356(4) 0.0379(7) Uani 1 1 d . . . . .
C6 C 0.6100(2) 0.4856(3) 0.6293(4) 0.0401(7) Uani 1 1 d . . . . .
C7 C 0.5703(2) 0.3318(4) 0.6252(4) 0.0402(7) Uani 1 1 d . . . . .
O8 O 0.7663(2) 0.7341(3) 0.5703(5) 0.0864(11) Uani 1 1 d . . . . .
N9 N 0.5614(3) 0.6241(4) 0.7082(5) 0.0627(9) Uani 1 1 d . . . . .
N10 N 0.4669(2) 0.2723(4) 0.6905(4) 0.0522(7) Uani 1 1 d . . . . .
O11 O 0.8494(2) 0.5909(4) 0.3948(4) 0.0736(8) Uani 1 1 d . . . . .
O12 O 0.4051(3) 0.3730(4) 0.7464(4) 0.0877(11) Uani 1 1 d . . . . .
O13 O 0.5186(2) 0.7273(4) 0.6264(6) 0.1088(15) Uani 1 1 d . . . . .
O14 O 0.5703(3) 0.6250(4) 0.8511(4) 0.0983(12) Uani 1 1 d . . . . .
C15 C 0.6380(4) 0.0738(4) 0.4925(6) 0.0776(14) Uani 1 1 d . . . . .
H15A H 0.5705 0.0520 0.4344 0.116 Uiso 1 1 calc GR . . . .
H15B H 0.6393 0.0096 0.5865 0.116 Uiso 1 1 calc GR . . . .
H15C H 0.7019 0.0483 0.4284 0.116 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.331(3) . ?
N1 C7 1.351(4) . ?
N1 C15 1.470(4) . ?
N2 C5 1.318(4) . ?
N3 C5 1.443(4) . ?
N3 O8 1.210(4) . ?
N3 O11 1.207(4) . ?
O4 N10 1.216(3) . ?
C5 C6 1.394(4) . ?
C6 C7 1.368(4) . ?
C6 N9 1.455(4) . ?
C7 N10 1.439(4) . ?
N9 O13 1.217(5) . ?
N9 O14 1.216(5) . ?
N10 O12 1.213(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C7 111.0(2) . . ?
N2 N1 C15 118.8(3) . . ?
C7 N1 C15 130.1(3) . . ?
C5 N2 N1 105.8(2) . . ?
O8 N3 C5 116.1(3) . . ?
O11 N3 C5 118.4(3) . . ?
O11 N3 O8 125.5(3) . . ?
N2 C5 N3 120.9(3) . . ?
N2 C5 C6 111.7(3) . . ?
C6 C5 N3 127.5(3) . . ?
C5 C6 N9 127.9(3) . . ?
C7 C6 C5 103.9(3) . . ?
C7 C6 N9 128.2(3) . . ?
N1 C7 C6 107.6(3) . . ?
N1 C7 N10 124.5(3) . . ?
C6 C7 N10 127.6(3) . . ?
O13 N9 C6 117.8(4) . . ?
O14 N9 C6 115.3(4) . . ?
O14 N9 O13 126.9(4) . . ?
O4 N10 C7 118.4(3) . . ?
O12 N10 O4 126.0(3) . . ?
O12 N10 C7 115.5(3) . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
N1 N2 C5 N3 -179.2(3) . . . . ?
N1 N2 C5 C6 -0.2(3) . . . . ?
N1 C7 N10 O4 10.2(5) . . . . ?
N1 C7 N10 O12 -168.7(3) . . . . ?
N2 N1 C7 C6 -0.9(4) . . . . ?
N2 N1 C7 N10 174.0(3) . . . . ?
N2 C5 C6 C7 -0.4(4) . . . . ?
N2 C5 C6 N9 -178.4(3) . . . . ?
N3 C5 C6 C7 178.6(3) . . . . ?
N3 C5 C6 N9 0.6(5) . . . . ?
C5 C6 C7 N1 0.7(3) . . . . ?
C5 C6 C7 N10 -173.9(3) . . . . ?
C5 C6 N9 O13 69.5(4) . . . . ?
C5 C6 N9 O14 -109.1(4) . . . . ?
C6 C7 N10 O4 -176.0(3) . . . . ?
C6 C7 N10 O12 5.1(5) . . . . ?
C7 N1 N2 C5 0.6(3) . . . . ?
C7 C6 N9 O13 -108.0(4) . . . . ?
C7 C6 N9 O14 73.3(5) . . . . ?
O8 N3 C5 N2 -170.0(3) . . . . ?
O8 N3 C5 C6 11.1(5) . . . . ?
N9 C6 C7 N1 178.8(3) . . . . ?
N9 C6 C7 N10 4.1(6) . . . . ?
O11 N3 C5 N2 10.1(4) . . . . ?
O11 N3 C5 C6 -168.8(3) . . . . ?
C15 N1 N2 C5 179.7(3) . . . . ?
C15 N1 C7 C6 -179.8(4) . . . . ?
C15 N1 C7 N10 -5.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c1
_database_code_depnum_ccdc_archive 'CCDC 1056638'
_audit_update_record             
;
2015-03-27 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;
_audit_creation_date             2015-03-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.12.26 svn.r3119 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C4 H3 N5 O6, C6 H6 N12 O12'
_chemical_formula_sum            'C10 H9 N17 O18'
_chemical_formula_weight         655.34
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.3515(3)
_cell_length_b                   11.4299(7)
_cell_length_c                   11.9398(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.663(4)
_cell_angle_gamma                90
_cell_volume                     1126.73(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.932
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.881
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10491
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.052
_diffrn_reflns_theta_min         3.452
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.881
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.828
_reflns_number_gt                3869
_reflns_number_total             5168
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 1357 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.8(10)
_refine_ls_extinction_coef       0.0144(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         5168
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0337P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0855
_refine_ls_wR_factor_ref         0.0996
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C23(H23), C37(H37), C1(H1), C5(H5), C7(H7)
2.b Idealised Me refined as rotating group:
 C40(H40A,H40B,H40C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2164(4) 0.5387(4) 0.4808(3) 0.0347(8) Uani 1 1 d . . . . .
N0AA N -0.0685(3) 0.5385(4) 0.6648(3) 0.0329(8) Uani 1 1 d . . . . .
O3 O 0.1410(4) 0.5467(4) 0.3859(2) 0.0536(9) Uani 1 1 d . . . . .
O0AA O 0.3645(3) 0.5318(4) 0.5025(2) 0.0494(9) Uani 1 1 d . . . . .
N1AA N -0.0297(3) 0.5412(4) 0.5605(3) 0.0318(8) Uani 1 1 d . . . . .
N2AA N 0.4690(4) 0.4548(3) 0.2101(3) 0.0299(9) Uani 1 1 d . . . . .
C3AA C 0.1302(4) 0.5359(5) 0.5760(3) 0.0284(8) Uani 1 1 d . . . . .
O9 O 0.1966(3) 0.4389(3) 0.1693(3) 0.0469(9) Uani 1 1 d . . . . .
C10 C 0.1959(4) 0.5300(5) 0.6882(3) 0.0305(9) Uani 1 1 d . . . . .
C11 C 0.6080(4) 0.6047(4) 0.3284(3) 0.0279(9) Uani 1 1 d . . . . .
H11 H 0.5823 0.6275 0.4028 0.033 Uiso 1 1 calc R . . . .
N12 N 0.7917(4) 0.7144(4) 0.0291(3) 0.0381(9) Uani 1 1 d . . . . .
N13 N 0.8347(4) 0.7394(4) 0.3728(3) 0.0372(10) Uani 1 1 d . . . . .
O14 O 0.3784(4) 0.7603(3) 0.3620(3) 0.0521(10) Uani 1 1 d . . . . .
O15 O 0.9426(4) 0.2938(3) 0.3239(3) 0.0536(10) Uani 1 1 d . . . . .
O16 O 0.7696(4) 0.7725(4) 0.4520(3) 0.0519(10) Uani 1 1 d . . . . .
O17 O 0.4222(4) 0.4227(4) 0.7458(4) 0.0696(13) Uani 1 1 d . . . . .
O18 O 0.9544(4) 0.7817(3) 0.3422(3) 0.0542(10) Uani 1 1 d . . . . .
N19 N 0.3167(4) 0.4072(4) 0.2315(4) 0.0373(10) Uani 1 1 d . . . . .
N20 N 0.3598(4) 0.7186(4) 0.2670(4) 0.0413(10) Uani 1 1 d . . . . .
O21 O 0.3265(4) 0.3350(4) 0.3064(3) 0.0502(9) Uani 1 1 d . . . . .
O22 O 0.7168(3) 0.7141(4) -0.0659(3) 0.0501(9) Uani 1 1 d . . . . .
C23 C 0.5927(4) 0.4688(4) 0.3111(3) 0.0294(10) Uani 1 1 d . . . . .
H23 H 0.5592 0.4307 0.3774 0.035 Uiso 1 1 calc R . . . .
O24 O -0.0617(4) 0.5214(5) 0.9013(3) 0.0769(14) Uani 1 1 d . . . . .
N25 N 0.7720(4) 0.6388(3) 0.3163(3) 0.0300(9) Uani 1 1 d . . . . .
O26 O 0.9187(4) 0.7623(4) 0.0619(3) 0.0609(11) Uani 1 1 d . . . . .
O27 O 0.1996(4) 0.5163(4) 0.9212(3) 0.0618(12) Uani 1 1 d . . . . .
N28 N 0.0663(4) 0.5241(4) 0.8654(3) 0.0432(10) Uani 1 1 d . . . . .
N29 N 0.7442(4) 0.4233(4) 0.2879(3) 0.0335(9) Uani 1 1 d . . . . .
N30 N 0.4912(3) 0.6541(4) 0.2375(3) 0.0309(9) Uani 1 1 d . . . . .
N31 N 0.8155(5) 0.3294(4) 0.3493(3) 0.0403(10) Uani 1 1 d . . . . .
O32 O 0.2447(4) 0.7303(4) 0.1933(3) 0.0616(12) Uani 1 1 d . . . . .
N33 N 0.3655(4) 0.5206(5) 0.7392(3) 0.0452(11) Uani 1 1 d . . . . .
O34 O 0.7461(4) 0.2923(4) 0.4234(3) 0.0629(12) Uani 1 1 d . . . . .
O35 O 0.4374(4) 0.6096(4) 0.7672(4) 0.0710(13) Uani 1 1 d . . . . .
C36 C 0.0648(4) 0.5315(5) 0.7444(3) 0.0303(9) Uani 1 1 d . . . . .
C37 C 0.4589(4) 0.5661(4) 0.1491(3) 0.0310(10) Uani 1 1 d . . . . .
H37 H 0.3522 0.5771 0.1034 0.037 Uiso 1 1 calc R . . . .
C40 C -0.2399(4) 0.5433(6) 0.6783(4) 0.0540(14) Uani 1 1 d . . . . .
H40A H -0.2699 0.6229 0.6902 0.081 Uiso 1 1 calc GR . . . .
H40B H -0.2572 0.4967 0.7423 0.081 Uiso 1 1 calc GR . . . .
H40C H -0.3049 0.5135 0.6112 0.081 Uiso 1 1 calc GR . . . .
C1 C 0.8139(4) 0.4736(4) 0.1964(3) 0.0298(10) Uani 1 1 d . . . . .
H1 H 0.9196 0.4388 0.1907 0.036 Uiso 1 1 calc R . . . .
N2 N 0.7047(4) 0.4663(3) 0.0885(3) 0.0317(8) Uani 1 1 d . . . . .
N3 N 0.7154(3) 0.6592(3) 0.1145(3) 0.0291(8) Uani 1 1 d . . . . .
O4 O 0.7312(5) 0.2739(4) 0.0815(4) 0.0674(11) Uani 1 1 d . . . . .
C5 C 0.8269(4) 0.6097(4) 0.2115(3) 0.0290(10) Uani 1 1 d . . . . .
H5 H 0.9382 0.6366 0.2111 0.035 Uiso 1 1 calc R . . . .
N6 N 0.6509(5) 0.3580(4) 0.0466(4) 0.0451(10) Uani 1 1 d . . . . .
C7 C 0.5995(4) 0.5687(4) 0.0732(3) 0.0295(10) Uani 1 1 d . . . . .
H7 H 0.5560 0.5806 -0.0068 0.035 Uiso 1 1 calc R . . . .
O8 O 0.5289(4) 0.3600(4) -0.0245(3) 0.0671(12) 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
N1 O3 1.214(4) . ?
N1 O0AA 1.227(4) . ?
N1 C3AA 1.435(4) . ?
N0AA N1AA 1.333(4) . ?
N0AA C36 1.353(4) . ?
N0AA C40 1.466(4) . ?
N1AA C3AA 1.322(4) . ?
N2AA N19 1.441(4) . ?
N2AA C23 1.474(5) . ?
N2AA C37 1.462(6) . ?
C3AA C10 1.371(5) . ?
O9 N19 1.211(5) . ?
C10 N33 1.459(4) . ?
C10 C36 1.368(5) . ?
C11 H11 0.9800 . ?
C11 C23 1.569(6) . ?
C11 N25 1.452(5) . ?
C11 N30 1.459(5) . ?
N12 O22 1.211(4) . ?
N12 O26 1.205(5) . ?
N12 N3 1.428(5) . ?
N13 O16 1.220(5) . ?
N13 O18 1.215(5) . ?
N13 N25 1.394(5) . ?
O14 N20 1.218(5) . ?
O15 N31 1.217(5) . ?
O17 N33 1.213(6) . ?
N19 O21 1.211(5) . ?
N20 N30 1.409(5) . ?
N20 O32 1.209(5) . ?
C23 H23 0.9800 . ?
C23 N29 1.433(5) . ?
O24 N28 1.211(4) . ?
N25 C5 1.434(5) . ?
O27 N28 1.212(4) . ?
N28 C36 1.445(5) . ?
N29 N31 1.383(5) . ?
N29 C1 1.433(5) . ?
N30 C37 1.455(6) . ?
N31 O34 1.205(5) . ?
N33 O35 1.204(6) . ?
C37 H37 0.9800 . ?
C37 C7 1.587(5) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C1 H1 0.9800 . ?
C1 N2 1.465(5) . ?
C1 C5 1.568(6) . ?
N2 N6 1.385(6) . ?
N2 C7 1.457(6) . ?
N3 C5 1.485(5) . ?
N3 C7 1.452(5) . ?
O4 N6 1.210(6) . ?
C5 H5 0.9800 . ?
N6 O8 1.223(5) . ?
C7 H7 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
O3 N1 O0AA 124.5(3) . . ?
O3 N1 C3AA 119.3(3) . . ?
O0AA N1 C3AA 116.2(3) . . ?
N1AA N0AA C36 111.6(3) . . ?
N1AA N0AA C40 118.7(3) . . ?
C36 N0AA C40 129.7(3) . . ?
C3AA N1AA N0AA 104.5(3) . . ?
N19 N2AA C23 115.2(3) . . ?
N19 N2AA C37 115.5(3) . . ?
C37 N2AA C23 107.1(3) . . ?
N1AA C3AA N1 120.3(3) . . ?
N1AA C3AA C10 112.7(3) . . ?
C10 C3AA N1 126.9(3) . . ?
C3AA C10 N33 129.2(3) . . ?
C36 C10 C3AA 104.3(3) . . ?
C36 C10 N33 126.5(3) . . ?
C23 C11 H11 110.9 . . ?
N25 C11 H11 110.9 . . ?
N25 C11 C23 108.2(3) . . ?
N25 C11 N30 111.0(3) . . ?
N30 C11 H11 110.9 . . ?
N30 C11 C23 104.7(3) . . ?
O22 N12 N3 116.4(3) . . ?
O26 N12 O22 127.7(4) . . ?
O26 N12 N3 115.7(4) . . ?
O16 N13 N25 116.9(4) . . ?
O18 N13 O16 126.3(4) . . ?
O18 N13 N25 116.6(4) . . ?
O9 N19 N2AA 116.8(4) . . ?
O9 N19 O21 127.9(4) . . ?
O21 N19 N2AA 115.2(4) . . ?
O14 N20 N30 116.2(3) . . ?
O32 N20 O14 127.6(4) . . ?
O32 N20 N30 116.1(4) . . ?
N2AA C23 C11 104.4(3) . . ?
N2AA C23 H23 111.2 . . ?
C11 C23 H23 111.2 . . ?
N29 C23 N2AA 109.5(3) . . ?
N29 C23 C11 109.1(4) . . ?
N29 C23 H23 111.2 . . ?
N13 N25 C11 117.7(3) . . ?
N13 N25 C5 117.9(4) . . ?
C5 N25 C11 117.0(3) . . ?
O24 N28 O27 126.1(4) . . ?
O24 N28 C36 118.8(3) . . ?
O27 N28 C36 115.0(3) . . ?
C23 N29 C1 118.2(4) . . ?
N31 N29 C23 120.1(4) . . ?
N31 N29 C1 121.6(3) . . ?
N20 N30 C11 118.4(3) . . ?
N20 N30 C37 118.5(3) . . ?
C37 N30 C11 107.6(3) . . ?
O15 N31 N29 116.7(4) . . ?
O34 N31 O15 126.9(4) . . ?
O34 N31 N29 116.4(4) . . ?
O17 N33 C10 116.1(5) . . ?
O35 N33 C10 117.8(5) . . ?
O35 N33 O17 126.0(4) . . ?
N0AA C36 C10 106.9(3) . . ?
N0AA C36 N28 126.0(3) . . ?
C10 C36 N28 127.1(3) . . ?
N2AA C37 H37 111.6 . . ?
N2AA C37 C7 108.0(3) . . ?
N30 C37 N2AA 104.4(3) . . ?
N30 C37 H37 111.6 . . ?
N30 C37 C7 109.2(3) . . ?
C7 C37 H37 111.6 . . ?
N0AA C40 H40A 109.5 . . ?
N0AA C40 H40B 109.5 . . ?
N0AA C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
N29 C1 H1 111.3 . . ?
N29 C1 N2 112.2(3) . . ?
N29 C1 C5 109.8(4) . . ?
N2 C1 H1 111.3 . . ?
N2 C1 C5 100.4(3) . . ?
C5 C1 H1 111.3 . . ?
N6 N2 C1 119.6(4) . . ?
N6 N2 C7 121.1(3) . . ?
C7 N2 C1 110.3(3) . . ?
N12 N3 C5 115.5(3) . . ?
N12 N3 C7 114.8(3) . . ?
C7 N3 C5 107.5(3) . . ?
N25 C5 C1 107.8(4) . . ?
N25 C5 N3 110.3(3) . . ?
N25 C5 H5 111.1 . . ?
C1 C5 H5 111.1 . . ?
N3 C5 C1 105.3(3) . . ?
N3 C5 H5 111.1 . . ?
O4 N6 N2 117.0(4) . . ?
O4 N6 O8 127.9(5) . . ?
O8 N6 N2 115.1(5) . . ?
C37 C7 H7 111.2 . . ?
N2 C7 C37 113.4(3) . . ?
N2 C7 H7 111.2 . . ?
N3 C7 C37 109.4(3) . . ?
N3 C7 N2 99.9(3) . . ?
N3 C7 H7 111.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C3AA C10 N33 -2.7(9) . . . . ?
N1 C3AA C10 C36 179.1(5) . . . . ?
N0AA N1AA C3AA N1 -179.0(5) . . . . ?
N0AA N1AA C3AA C10 -0.1(6) . . . . ?
O3 N1 C3AA N1AA 0.5(8) . . . . ?
O3 N1 C3AA C10 -178.3(5) . . . . ?
O0AA N1 C3AA N1AA -179.0(5) . . . . ?
O0AA N1 C3AA C10 2.2(8) . . . . ?
N1AA N0AA C36 C10 0.2(6) . . . . ?
N1AA N0AA C36 N28 -178.4(5) . . . . ?
N1AA C3AA C10 N33 178.4(6) . . . . ?
N1AA C3AA C10 C36 0.2(6) . . . . ?
N2AA C23 N29 N31 -117.3(4) . . . . ?
N2AA C23 N29 C1 59.4(5) . . . . ?
N2AA C37 C7 N2 -3.3(4) . . . . ?
N2AA C37 C7 N3 -113.9(4) . . . . ?
C3AA C10 N33 O17 -83.9(7) . . . . ?
C3AA C10 N33 O35 93.8(6) . . . . ?
C3AA C10 C36 N0AA -0.2(6) . . . . ?
C3AA C10 C36 N28 178.3(5) . . . . ?
C11 C23 N29 N31 129.0(4) . . . . ?
C11 C23 N29 C1 -54.2(5) . . . . ?
C11 N25 C5 C1 -58.5(5) . . . . ?
C11 N25 C5 N3 56.0(5) . . . . ?
C11 N30 C37 N2AA 34.1(3) . . . . ?
C11 N30 C37 C7 -81.2(4) . . . . ?
N12 N3 C5 N25 135.7(4) . . . . ?
N12 N3 C5 C1 -108.3(4) . . . . ?
N12 N3 C7 C37 -147.8(3) . . . . ?
N12 N3 C7 N2 93.0(4) . . . . ?
N13 N25 C5 C1 152.3(3) . . . . ?
N13 N25 C5 N3 -93.2(4) . . . . ?
O14 N20 N30 C11 22.7(6) . . . . ?
O14 N20 N30 C37 155.8(4) . . . . ?
O16 N13 N25 C11 20.3(5) . . . . ?
O16 N13 N25 C5 169.3(4) . . . . ?
O18 N13 N25 C11 -163.6(4) . . . . ?
O18 N13 N25 C5 -14.7(5) . . . . ?
N19 N2AA C23 C11 -110.2(4) . . . . ?
N19 N2AA C23 N29 133.2(4) . . . . ?
N19 N2AA C37 N30 96.4(3) . . . . ?
N19 N2AA C37 C7 -147.4(3) . . . . ?
N20 N30 C37 N2AA -103.6(4) . . . . ?
N20 N30 C37 C7 141.1(4) . . . . ?
O22 N12 N3 C5 152.0(4) . . . . ?
O22 N12 N3 C7 26.0(5) . . . . ?
C23 N2AA N19 O9 148.9(4) . . . . ?
C23 N2AA N19 O21 -34.9(5) . . . . ?
C23 N2AA C37 N30 -33.4(3) . . . . ?
C23 N2AA C37 C7 82.8(4) . . . . ?
C23 C11 N25 N13 -153.3(3) . . . . ?
C23 C11 N25 C5 57.5(5) . . . . ?
C23 C11 N30 N20 116.4(4) . . . . ?
C23 C11 N30 C37 -21.3(4) . . . . ?
C23 N29 N31 O15 178.8(4) . . . . ?
C23 N29 N31 O34 -2.2(7) . . . . ?
C23 N29 C1 N2 -57.5(5) . . . . ?
C23 N29 C1 C5 53.3(5) . . . . ?
O24 N28 C36 N0AA 1.5(8) . . . . ?
O24 N28 C36 C10 -176.8(6) . . . . ?
N25 C11 C23 N2AA -117.6(3) . . . . ?
N25 C11 C23 N29 -0.7(5) . . . . ?
N25 C11 N30 N20 -127.1(4) . . . . ?
N25 C11 N30 C37 95.2(4) . . . . ?
O26 N12 N3 C5 -32.6(6) . . . . ?
O26 N12 N3 C7 -158.5(4) . . . . ?
O27 N28 C36 N0AA 178.7(5) . . . . ?
O27 N28 C36 C10 0.3(8) . . . . ?
N29 C1 N2 N6 -58.8(5) . . . . ?
N29 C1 N2 C7 88.6(4) . . . . ?
N29 C1 C5 N25 3.0(4) . . . . ?
N29 C1 C5 N3 -114.7(3) . . . . ?
N30 C11 C23 N2AA 0.8(5) . . . . ?
N30 C11 C23 N29 117.7(3) . . . . ?
N30 C11 N25 N13 92.4(4) . . . . ?
N30 C11 N25 C5 -56.8(5) . . . . ?
N30 C37 C7 N2 109.7(4) . . . . ?
N30 C37 C7 N3 -0.9(5) . . . . ?
N31 N29 C1 N2 119.2(4) . . . . ?
N31 N29 C1 C5 -130.0(4) . . . . ?
O32 N20 N30 C11 -160.4(4) . . . . ?
O32 N20 N30 C37 -27.3(6) . . . . ?
N33 C10 C36 N0AA -178.6(5) . . . . ?
N33 C10 C36 N28 0.0(9) . . . . ?
C36 N0AA N1AA C3AA -0.1(6) . . . . ?
C36 C10 N33 O17 94.0(6) . . . . ?
C36 C10 N33 O35 -88.3(7) . . . . ?
C37 N2AA N19 O9 23.2(5) . . . . ?
C37 N2AA N19 O21 -160.6(4) . . . . ?
C37 N2AA C23 C11 19.8(4) . . . . ?
C37 N2AA C23 N29 -96.9(4) . . . . ?
C40 N0AA N1AA C3AA 179.8(5) . . . . ?
C40 N0AA C36 C10 -179.7(6) . . . . ?
C40 N0AA C36 N28 1.7(9) . . . . ?
C1 N29 N31 O15 2.1(7) . . . . ?
C1 N29 N31 O34 -178.9(4) . . . . ?
C1 N2 N6 O4 -21.5(6) . . . . ?
C1 N2 N6 O8 160.5(4) . . . . ?
C1 N2 C7 C37 -75.0(4) . . . . ?
C1 N2 C7 N3 41.3(3) . . . . ?
N2 C1 C5 N25 121.3(3) . . . . ?
N2 C1 C5 N3 3.6(4) . . . . ?
C5 C1 N2 N6 -175.4(3) . . . . ?
C5 C1 N2 C7 -27.9(4) . . . . ?
C5 N3 C7 C37 82.2(4) . . . . ?
C5 N3 C7 N2 -37.1(3) . . . . ?
N6 N2 C7 C37 72.0(5) . . . . ?
N6 N2 C7 N3 -171.7(4) . . . . ?
C7 N2 N6 O4 -165.5(4) . . . . ?
C7 N2 N6 O8 16.5(6) . . . . ?
C7 N3 C5 N25 -94.7(4) . . . . ?
C7 N3 C5 C1 21.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
