# 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 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1472123'
_audit_update_record             
;
2016-04-04 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H9 N3 O2'
_chemical_formula_sum            'C6 H9 N3 O2'
_chemical_formula_weight         155.16

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      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   9.025(4)
_cell_length_b                   9.025(4)
_cell_length_c                   10.200(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     830.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1077
_cell_measurement_theta_min      3.8
_cell_measurement_theta_max      23.2

_exptl_crystal_description       ?plate?
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?



_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'RU200 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       ?245
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1164
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         3.766
_diffrn_reflns_theta_max         23.238
_diffrn_reflns_theta_full        23.238
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             1164
_reflns_number_gt                1076
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.978

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       MAR
_computing_cell_refinement       MAR
_computing_data_reduction        MARHKL
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;



_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²+0.0714P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.11(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 488 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 Data were merged prior to refinement, chiral space group with
 non-chiral molecules.
;
_refine_ls_abs_structure_Flack   -0.1(9)
_chemical_absolute_configuration .
_refine_ls_number_reflns         1164
_refine_ls_number_parameters     147
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0854
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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_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 0.8795(4) 1.3333(3) 1.0829(5) 0.0981(10) Uani 1 1 d . . . . .
N2 N 0.7764(3) 1.4036(3) 1.0051(4) 0.0924(10) Uani 1 1 d . . . . .
C3 C 0.6926(4) 1.3012(3) 0.9563(5) 0.0810(10) Uani 1 1 d . . . . .
H3 H 0.6146 1.3187 0.8987 0.097 Uiso 1 1 calc R U . . .
N4 N 0.7324(3) 1.1663(3) 0.9992(4) 0.0692(7) Uani 1 1 d . . . . .
C5 C 0.8506(4) 1.1928(4) 1.0762(5) 0.0876(11) Uani 1 1 d . . . . .
H5 H 0.9046 1.1197 1.1192 0.105 Uiso 1 1 calc R U . . .
C6 C 0.6695(3) 1.0242(3) 0.9628(4) 0.0711(8) Uani 1 1 d . . . . .
H6A H 0.5643 1.0346 0.9455 0.085 Uiso 1 1 calc R U . A 1
H6B H 0.6822 0.9536 1.0337 0.085 Uiso 1 1 calc R U . A 1
C7 C 0.749(2) 0.9696(17) 0.840(2) 0.077(6) Uani 0.58(3) 1 d D . P B 1
O8 O 0.8502(16) 1.024(2) 0.7835(19) 0.116(6) Uani 0.58(3) 1 d D . P B 1
O9 O 0.6923(12) 0.8377(14) 0.8088(11) 0.086(3) Uani 0.58(3) 1 d D . P B 1
C10 C 0.765(2) 0.7586(19) 0.701(2) 0.136(7) Uani 0.58(3) 1 d D . P B 1
H10A H 0.7702 0.8215 0.6239 0.163 Uiso 0.58(3) 1 calc R U P B 1
H10B H 0.8647 0.7307 0.7258 0.163 Uiso 0.58(3) 1 calc R U P B 1
C11 C 0.6772(17) 0.6269(17) 0.673(3) 0.152(6) Uani 0.58(3) 1 d D . P B 1
H11A H 0.7223 0.5728 0.6021 0.227 Uiso 0.58(3) 1 calc R U P B 1
H11B H 0.6729 0.5653 0.7493 0.227 Uiso 0.58(3) 1 calc R U P B 1
H11C H 0.5787 0.6557 0.6479 0.227 Uiso 0.58(3) 1 calc R U P B 1
C7B C 0.760(2) 0.9404(17) 0.863(2) 0.045(4) Uani 0.42(3) 1 d D . P B 2
O8B O 0.8550(11) 0.9975(19) 0.8004(17) 0.063(3) Uani 0.42(3) 1 d D . P B 2
O9B O 0.7091(13) 0.8021(12) 0.8569(13) 0.069(3) Uani 0.42(3) 1 d D . P B 2
C10B C 0.7801(16) 0.7040(16) 0.7617(14) 0.094(5) Uani 0.42(3) 1 d D . P B 2
H10C H 0.8817 0.7353 0.7473 0.113 Uiso 0.42(3) 1 calc R U P B 2
H10D H 0.7816 0.6034 0.7952 0.113 Uiso 0.42(3) 1 calc R U P B 2
C11B C 0.698(4) 0.709(4) 0.6389(15) 0.172(11) Uani 0.42(3) 1 d D . P B 2
H11D H 0.7446 0.6448 0.5762 0.258 Uiso 0.42(3) 1 calc R U P B 2
H11E H 0.5982 0.6772 0.6537 0.258 Uiso 0.42(3) 1 calc R U P B 2
H11F H 0.6980 0.8087 0.6059 0.258 Uiso 0.42(3) 1 calc R U P B 2


_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 C5 1.296(5) . ?
N1 N2 1.378(4) . ?
N2 C3 1.294(4) . ?
C3 N4 1.342(4) . ?
C3 H3 0.9300 . ?
N4 C5 1.346(4) . ?
N4 C6 1.452(4) . ?
C5 H5 0.9300 . ?
C6 C7B 1.507(14) . ?
C6 C7 1.523(16) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 O8 1.189(10) . ?
C7 O9 1.335(9) . ?
O9 C10 1.466(10) . ?
C10 C11 1.456(14) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C7B O8B 1.188(10) . ?
C7B O9B 1.331(10) . ?
O9B C10B 1.462(11) . ?
C10B C11B 1.455(15) . ?
C10B H10C 0.9700 . ?
C10B H10D 0.9700 . ?
C11B H11D 0.9600 . ?
C11B H11E 0.9600 . ?
C11B H11F 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
C5 N1 N2 106.5(3) . . ?
C3 N2 N1 106.7(3) . . ?
N2 C3 N4 111.5(3) . . ?
N2 C3 H3 124.3 . . ?
N4 C3 H3 124.3 . . ?
C3 N4 C5 104.0(3) . . ?
C3 N4 C6 127.8(3) . . ?
C5 N4 C6 128.1(3) . . ?
N1 C5 N4 111.3(3) . . ?
N1 C5 H5 124.3 . . ?
N4 C5 H5 124.3 . . ?
N4 C6 C7B 113.9(5) . . ?
N4 C6 C7 108.1(6) . . ?
N4 C6 H6A 110.1 . . ?
C7 C6 H6A 110.1 . . ?
N4 C6 H6B 110.1 . . ?
C7 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
O8 C7 O9 123.2(14) . . ?
O8 C7 C6 128.9(13) . . ?
O9 C7 C6 107.8(10) . . ?
C7 O9 C10 116.4(9) . . ?
C11 C10 O9 107.7(11) . . ?
C11 C10 H10A 110.2 . . ?
O9 C10 H10A 110.2 . . ?
C11 C10 H10B 110.2 . . ?
O9 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O8B C7B O9B 129.0(13) . . ?
O8B C7B C6 122.4(11) . . ?
O9B C7B C6 108.5(8) . . ?
C7B O9B C10B 116.6(9) . . ?
C11B C10B O9B 109.3(10) . . ?
C11B C10B H10C 109.8 . . ?
O9B C10B H10C 109.8 . . ?
C11B C10B H10D 109.8 . . ?
O9B C10B H10D 109.8 . . ?
H10C C10B H10D 108.3 . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 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
C5 N1 N2 C3 -0.2(4) . . . . ?
N1 N2 C3 N4 1.1(4) . . . . ?
N2 C3 N4 C5 -1.6(4) . . . . ?
N2 C3 N4 C6 -177.3(3) . . . . ?
N2 N1 C5 N4 -0.8(5) . . . . ?
C3 N4 C5 N1 1.4(4) . . . . ?
C6 N4 C5 N1 177.2(3) . . . . ?
C3 N4 C6 C7B 100.4(12) . . . . ?
C5 N4 C6 C7B -74.4(12) . . . . ?
C3 N4 C6 C7 87.0(10) . . . . ?
C5 N4 C6 C7 -87.7(10) . . . . ?
N4 C6 C7 O8 3(3) . . . . ?
N4 C6 C7 O9 179.0(11) . . . . ?
O8 C7 O9 C10 2(3) . . . . ?
C6 C7 O9 C10 -173.9(11) . . . . ?
C7 O9 C10 C11 -174(2) . . . . ?
N4 C6 C7B O8B -15(3) . . . . ?
N4 C6 C7B O9B 167.6(12) . . . . ?
O8B C7B O9B C10B 1(3) . . . . ?
C6 C7B O9B C10B 178.2(13) . . . . ?
C7B O9B C10B C11B -92(3) . . . . ?

_refine_diff_density_max         0.079
_refine_diff_density_min         -0.079
_refine_diff_density_rms         0.021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1472124'
_audit_update_record             
;
2016-04-04 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H7 N3 O2'
_chemical_formula_sum            'C5 H7 N3 O2'
_chemical_formula_weight         141.14

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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.7498(5)
_cell_length_b                   10.7110(4)
_cell_length_c                   12.7361(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1330.04(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
__cell_measurement_reflns_used   4263
_cell_measurement_theta_min      2.4796
_cell_measurement_theta_max      25.6975

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.91659
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?


_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Zr filter'

_diffrn_measurement_device_type  'MAR345 image plate'

_diffrn_measurement_method       '100 images, ΔΦ 2.0°'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9867
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.485
_diffrn_reflns_theta_max         25.753
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2490
_reflns_number_gt                2201
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_max     0.957
_reflns_Friedel_fraction_full    0.992

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0317P)²+0.5234P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 824 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(10)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2490
_refine_ls_number_parameters     231
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.088
_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_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
C1 C 0.4474(4) -0.0303(3) 0.0842(3) 0.0452(8) Uani 1 1 d . . . . .
H1 H 0.5155 -0.0704 0.1255 0.054 Uiso 1 1 calc R U . . .
N2 N 0.3838(3) -0.0829(3) 0.0061(2) 0.0541(8) Uani 1 1 d . . . . .
N3 N 0.2935(3) 0.0067(2) -0.0309(2) 0.0512(8) Uani 1 1 d . . . . .
C4 C 0.3083(4) 0.1066(3) 0.0257(2) 0.0421(8) Uani 1 1 d . . . . .
H4 H 0.2579 0.1817 0.0163 0.050 Uiso 1 1 calc R U . . .
N5 N 0.4046(3) 0.0888(2) 0.09935(18) 0.0338(6) Uani 1 1 d . . . . .
C6 C 0.4434(3) 0.1802(3) 0.1800(2) 0.0375(8) Uani 1 1 d . . . . .
H6 H 0.4086 0.2635 0.1565 0.045 Uiso 1 1 calc R U . . .
C7 C 0.5978(4) 0.1907(4) 0.1914(3) 0.0597(11) Uani 1 1 d . . . . .
H7A H 0.6347 0.1115 0.2175 0.090 Uiso 1 1 calc R U . . .
H7B H 0.6197 0.2576 0.2412 0.090 Uiso 1 1 calc R U . . .
H7C H 0.6386 0.2099 0.1230 0.090 Uiso 1 1 calc R U . . .
C8 C 0.3772(4) 0.1517(3) 0.2857(3) 0.0382(8) Uani 1 1 d . . . . .
O9 O 0.3688(3) 0.2328(2) 0.3516(2) 0.0567(7) Uani 1 1 d . . . . .
O10 O 0.3354(3) 0.0376(2) 0.2969(2) 0.0618(9) Uani 1 1 d . . . . .
H10 H 0.2922 0.0308 0.3537 0.093 Uiso 1 1 calc R U . . .
C21 C 0.0558(4) 0.5598(4) 0.4244(3) 0.0541(9) Uani 1 1 d . . . . .
H21 H 0.0001 0.6139 0.3834 0.065 Uiso 1 1 calc R U . . .
N22 N 0.1240(3) 0.5945(3) 0.5062(2) 0.0471(8) Uani 1 1 d . . . . .
N23 N 0.1904(3) 0.4895(2) 0.5418(2) 0.0463(7) Uani 1 1 d . . . . .
C24 C 0.1565(5) 0.3976(3) 0.4797(3) 0.0574(10) Uani 1 1 d . . . . .
H24 H 0.1873 0.3140 0.4876 0.069 Uiso 1 1 calc R U . . .
N25 N 0.0734(3) 0.4367(3) 0.4042(2) 0.0536(9) Uani 1 1 d . . . . .
C26 C -0.0072(8) 0.3914(7) 0.3107(5) 0.0389(18) Uani 0.529(10) 1 d D U P A 1
H26 H -0.0822 0.4507 0.2910 0.047 Uiso 0.529(10) 1 calc R U P A 1
C27 C -0.0621(10) 0.2633(8) 0.3384(7) 0.058(2) Uani 0.529(10) 1 d D . P A 1
H27A H 0.0146 0.2071 0.3538 0.087 Uiso 0.529(10) 1 calc R U P A 1
H27B H -0.1149 0.2302 0.2791 0.087 Uiso 0.529(10) 1 calc R U P A 1
H27C H -0.1216 0.2696 0.4002 0.087 Uiso 0.529(10) 1 calc R U P A 1
C28 C 0.101(2) 0.3780(14) 0.2224(13) 0.060(6) Uani 0.529(10) 1 d D U P A 1
O29 O 0.096(3) 0.293(2) 0.1611(18) 0.064(5) Uani 0.529(10) 1 d D U P A 1
O30 O 0.177(3) 0.4801(13) 0.2092(17) 0.051(3) Uani 0.529(10) 1 d D U P A 1
H30 H 0.2281 0.4707 0.1568 0.077 Uiso 0.529(10) 1 calc R U P A 1
C26B C 0.0490(8) 0.3342(8) 0.3243(5) 0.035(2) Uani 0.471(10) 1 d D U P A 2
H26B H 0.0838 0.2516 0.3493 0.043 Uiso 0.471(10) 1 calc R U P A 2
C27B C -0.1054(8) 0.3348(12) 0.3117(9) 0.063(3) Uani 0.471(10) 1 d D . P A 2
H27D H -0.1316 0.2764 0.2559 0.095 Uiso 0.471(10) 1 calc R U P A 2
H27E H -0.1361 0.4191 0.2931 0.095 Uiso 0.471(10) 1 calc R U P A 2
H27F H -0.1484 0.3093 0.3778 0.095 Uiso 0.471(10) 1 calc R U P A 2
C28B C 0.110(2) 0.3702(18) 0.2149(12) 0.059(7) Uani 0.471(10) 1 d D U P A 2
O29B O 0.126(3) 0.291(2) 0.1494(18) 0.058(4) Uani 0.471(10) 1 d D U P A 2
O30B O 0.147(3) 0.4887(18) 0.208(2) 0.082(9) Uani 0.471(10) 1 d D U P A 2
H30B H 0.2032 0.4975 0.1590 0.123 Uiso 0.471(10) 1 calc R U P A 2


_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 N2 1.301(4) . ?
C1 N5 1.356(4) . ?
C1 H1 0.9500 . ?
N2 N3 1.384(4) . ?
N3 C4 1.299(4) . ?
C4 N5 1.341(4) . ?
C4 H4 0.9500 . ?
N5 C6 1.468(4) . ?
C6 C7 1.516(5) . ?
C6 C8 1.524(5) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O9 1.211(4) . ?
C8 O10 1.297(4) . ?
O10 H10 0.8400 . ?
C21 N22 1.291(5) . ?
C21 N25 1.354(5) . ?
C21 H21 0.9500 . ?
N22 N23 1.374(4) . ?
N23 C24 1.306(4) . ?
C24 N25 1.325(5) . ?
C24 H24 0.9500 . ?
N25 C26 1.507(7) . ?
N25 C26B 1.516(7) . ?
C26 C27 1.515(9) . ?
C26 C28 1.550(10) . ?
C26 H26 1.0000 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 O29 1.205(9) . ?
C28 O30 1.329(9) . ?
O30 H30 0.8400 . ?
C26B C27B 1.514(9) . ?
C26B C28B 1.562(10) . ?
C26B H26B 1.0000 . ?
C27B H27D 0.9800 . ?
C27B H27E 0.9800 . ?
C27B H27F 0.9800 . ?
C28B O29B 1.202(10) . ?
C28B O30B 1.323(11) . ?
O30B H30B 0.8400 . ?

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 C1 N5 111.7(3) . . ?
N2 C1 H1 124.2 . . ?
N5 C1 H1 124.2 . . ?
C1 N2 N3 105.3(3) . . ?
C4 N3 N2 108.1(3) . . ?
N3 C4 N5 110.4(3) . . ?
N3 C4 H4 124.8 . . ?
N5 C4 H4 124.8 . . ?
C4 N5 C1 104.4(3) . . ?
C4 N5 C6 125.1(3) . . ?
C1 N5 C6 130.4(3) . . ?
N5 C6 C7 111.9(3) . . ?
N5 C6 C8 112.0(2) . . ?
C7 C6 C8 110.5(3) . . ?
N5 C6 H6 107.4 . . ?
C7 C6 H6 107.4 . . ?
C8 C6 H6 107.4 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O9 C8 O10 125.4(3) . . ?
O9 C8 C6 119.8(3) . . ?
O10 C8 C6 114.8(3) . . ?
C8 O10 H10 109.5 . . ?
N22 C21 N25 111.6(4) . . ?
N22 C21 H21 124.2 . . ?
N25 C21 H21 124.2 . . ?
C21 N22 N23 105.9(3) . . ?
C24 N23 N22 107.3(3) . . ?
N23 C24 N25 110.8(3) . . ?
N23 C24 H24 124.6 . . ?
N25 C24 H24 124.6 . . ?
C24 N25 C21 104.4(3) . . ?
C24 N25 C26 142.2(4) . . ?
C21 N25 C26 113.4(4) . . ?
C24 N25 C26B 110.7(4) . . ?
C21 N25 C26B 144.3(5) . . ?
N25 C26 C27 107.0(6) . . ?
N25 C26 C28 104.3(9) . . ?
C27 C26 C28 109.0(8) . . ?
N25 C26 H26 112.0 . . ?
C27 C26 H26 112.0 . . ?
C28 C26 H26 112.0 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O29 C28 O30 124.4(11) . . ?
O29 C28 C26 120.9(11) . . ?
O30 C28 C26 113.2(10) . . ?
C28 O30 H30 109.5 . . ?
C27B C26B N25 103.0(7) . . ?
C27B C26B C28B 106.4(11) . . ?
N25 C26B C28B 111.2(8) . . ?
C27B C26B H26B 112.0 . . ?
N25 C26B H26B 112.0 . . ?
C28B C26B H26B 112.0 . . ?
C26B C27B H27D 109.5 . . ?
C26B C27B H27E 109.5 . . ?
H27D C27B H27E 109.5 . . ?
C26B C27B H27F 109.5 . . ?
H27D C27B H27F 109.5 . . ?
H27E C27B H27F 109.5 . . ?
O29B C28B O30B 126.8(13) . . ?
O29B C28B C26B 119.7(13) . . ?
O30B C28B C26B 113.3(12) . . ?
C28B O30B H30B 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
N5 C1 N2 N3 -0.6(4) . . . . ?
C1 N2 N3 C4 0.3(4) . . . . ?
N2 N3 C4 N5 0.1(4) . . . . ?
N3 C4 N5 C1 -0.4(4) . . . . ?
N3 C4 N5 C6 -177.1(3) . . . . ?
N2 C1 N5 C4 0.7(4) . . . . ?
N2 C1 N5 C6 177.1(3) . . . . ?
C4 N5 C6 C7 -135.1(3) . . . . ?
C1 N5 C6 C7 49.1(4) . . . . ?
C4 N5 C6 C8 100.2(4) . . . . ?
C1 N5 C6 C8 -75.6(4) . . . . ?
N5 C6 C8 O9 -160.8(3) . . . . ?
C7 C6 C8 O9 73.7(4) . . . . ?
N5 C6 C8 O10 20.1(4) . . . . ?
C7 C6 C8 O10 -105.3(4) . . . . ?
N25 C21 N22 N23 0.2(4) . . . . ?
C21 N22 N23 C24 -0.8(4) . . . . ?
N22 N23 C24 N25 1.1(5) . . . . ?
N23 C24 N25 C21 -0.9(4) . . . . ?
N23 C24 N25 C26 -178.2(5) . . . . ?
N23 C24 N25 C26B 172.6(4) . . . . ?
N22 C21 N25 C24 0.4(4) . . . . ?
N22 C21 N25 C26 178.6(4) . . . . ?
N22 C21 N25 C26B -169.2(6) . . . . ?
C24 N25 C26 C27 36.7(10) . . . . ?
C21 N25 C26 C27 -140.5(6) . . . . ?
C24 N25 C26 C28 -78.8(10) . . . . ?
C21 N25 C26 C28 104.1(9) . . . . ?
N25 C26 C28 O29 142(3) . . . . ?
C27 C26 C28 O29 28(3) . . . . ?
N25 C26 C28 O30 -52(3) . . . . ?
C27 C26 C28 O30 -166(2) . . . . ?
C24 N25 C26B C27B 131.8(7) . . . . ?
C21 N25 C26B C27B -59.0(10) . . . . ?
C24 N25 C26B C28B -114.7(11) . . . . ?
C21 N25 C26B C28B 54.5(13) . . . . ?
C27B C26B C28B O29B -85(3) . . . . ?
N25 C26B C28B O29B 164(3) . . . . ?
C27B C26B C28B O30B 100(3) . . . . ?
N25 C26B C28B O30B -12(3) . . . . ?

_refine_diff_density_max         0.159
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.035

