# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1018893'
_audit_update_record             
;
2014-08-11 deposited with the CCDC.
2015-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H9 N9 O'
_chemical_formula_weight         175.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   8.5361(4)
_cell_length_b                   6.5988(3)
_cell_length_c                   13.2935(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.3740(10)
_cell_angle_gamma                90.00
_cell_volume                     728.49(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5898
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         28.68
_reflns_number_total             1862
_reflns_number_gt                1523
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0666P)²+0.0907P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1862
_refine_ls_number_parameters     129
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.1092
_refine_ls_wR_factor_gt          0.1008
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.036
_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 0.83071(12) 0.90573(16) 0.91484(8) 0.0274(2) Uani 1 1 d . . .
N3 N 0.03395(12) 0.24442(16) 0.73341(7) 0.0354(3) Uani 1 1 d . . .
H2 H 1.011(2) 0.552(4) 0.8963(16) 0.091(7) Uiso 1 1 d D . .
H3 H 0.120(2) -0.173(3) 0.6807(12) 0.052(5) Uiso 1 1 d . . .
H4 H -0.030(2) -0.131(3) 0.6125(14) 0.055(5) Uiso 1 1 d . . .
H5 H 0.866(3) 0.531(4) 0.8101(18) 0.092(7) Uiso 1 1 d . . .
H10 H 0.937(2) 0.840(3) 0.8081(12) 0.059(5) Uiso 1 1 d D . .
N1 N 0.76457(12) 0.82258(15) 0.98504(7) 0.0320(2) Uani 1 1 d . . .
H1A H 0.7645 0.6930 0.9919 0.038 Uiso 1 1 calc R . .
H1B H 0.7215 0.8979 1.0241 0.038 Uiso 1 1 calc R . .
N2 N 0.07422(11) 0.10686(14) 0.66805(7) 0.0285(2) Uani 1 1 d . . .
C2 C 0.14889(12) 0.20131(17) 0.60069(8) 0.0278(2) Uani 1 1 d . . .
N4 N 0.03345(15) -0.09575(15) 0.67458(8) 0.0358(3) Uani 1 1 d . . .
N5 N 0.15349(13) 0.39879(15) 0.62583(8) 0.0363(3) Uani 1 1 d . . .
N6 N 0.90629(17) 0.58057(17) 0.87003(10) 0.0450(3) Uani 1 1 d D . .
N7 N 0.83169(13) 1.10566(15) 0.90139(8) 0.0380(3) Uani 1 1 d . . .
H7A H 0.7884 1.1839 0.9390 0.046 Uiso 1 1 calc R . .
H7B H 0.8756 1.1565 0.8550 0.046 Uiso 1 1 calc R . .
N8 N 0.08197(14) 0.41741(17) 0.70672(8) 0.0404(3) Uani 1 1 d . . .
N9 N 0.89754(13) 0.79112(16) 0.85420(8) 0.0389(3) Uani 1 1 d D . .
O1 O 0.20125(11) 0.11499(13) 0.53034(7) 0.0376(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0284(5) 0.0289(5) 0.0271(5) 0.0000(4) 0.0111(4) 0.0001(4)
N3 0.0426(5) 0.0382(6) 0.0307(5) -0.0040(4) 0.0193(4) 0.0008(4)
N1 0.0424(5) 0.0270(5) 0.0340(5) -0.0010(4) 0.0236(4) 0.0006(4)
N2 0.0347(5) 0.0294(5) 0.0257(5) 0.0008(3) 0.0157(4) -0.0013(3)
C2 0.0306(5) 0.0306(5) 0.0253(5) 0.0019(4) 0.0130(4) -0.0025(4)
N4 0.0487(6) 0.0300(5) 0.0334(5) 0.0019(4) 0.0193(5) -0.0067(4)
N5 0.0484(6) 0.0298(5) 0.0373(5) -0.0027(4) 0.0234(4) -0.0037(4)
N6 0.0659(8) 0.0289(5) 0.0503(7) -0.0036(5) 0.0344(6) 0.0053(5)
N7 0.0501(6) 0.0269(5) 0.0452(6) 0.0021(4) 0.0276(5) 0.0008(4)
N8 0.0526(6) 0.0358(5) 0.0396(6) -0.0060(4) 0.0248(5) -0.0011(5)
N9 0.0566(6) 0.0320(5) 0.0385(6) 0.0006(4) 0.0324(5) 0.0021(4)
O1 0.0530(5) 0.0332(5) 0.0356(5) -0.0040(3) 0.0287(4) -0.0031(4)

_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 N1 1.3169(13) . ?
C1 N9 1.3266(14) . ?
C1 N7 1.3317(14) . ?
N3 N8 1.2900(15) . ?
N3 N2 1.3546(13) . ?
N2 C2 1.3640(13) . ?
N2 N4 1.3892(13) . ?
C2 O1 1.2618(13) . ?
C2 N5 1.3436(14) . ?
N5 N8 1.3594(14) . ?
N6 N9 1.4046(15) . ?

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
N1 C1 N9 120.54(10) . . ?
N1 C1 N7 121.67(10) . . ?
N9 C1 N7 117.79(10) . . ?
N8 N3 N2 105.82(9) . . ?
N3 N2 C2 109.95(9) . . ?
N3 N2 N4 120.03(9) . . ?
C2 N2 N4 129.98(9) . . ?
O1 C2 N5 128.84(10) . . ?
O1 C2 N2 125.43(11) . . ?
N5 C2 N2 105.73(9) . . ?
C2 N5 N8 106.96(9) . . ?
N3 N8 N5 111.53(9) . . ?
C1 N9 N6 119.22(10) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        28.68
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_140507g
_database_code_depnum_ccdc_archive 'CCDC 1018898'
_audit_update_record             
;
2014-08-11 deposited with the CCDC.
2015-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H3 N5 O'
_chemical_formula_weight         101.08

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   Pbca

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

_cell_length_a                   9.8873(7)
_cell_length_b                   5.5314(3)
_cell_length_c                   13.6734(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     747.81(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1079
_cell_measurement_theta_min      2.962
_cell_measurement_theta_max      25.636

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    0.154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9452
_exptl_absorpt_correction_T_max  0.9758
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            4355
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0477
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         28.61
_reflns_number_total             954
_reflns_number_gt                608
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0427P)²+0.2398P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         954
_refine_ls_number_parameters     64
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.0928
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
N1 N 0.96247(14) 0.9395(3) 0.65764(10) 0.0285(4) Uani 1 1 d . . .
N2 N 1.08195(15) 1.0555(3) 0.65180(12) 0.0358(4) Uani 1 1 d . . .
N3 N 1.15469(16) 0.9438(3) 0.58978(12) 0.0404(5) Uani 1 1 d . . .
N4 N 1.08236(15) 0.7556(3) 0.55565(12) 0.0341(4) Uani 1 1 d . . .
H4 H 1.1108 0.6560 0.5119 0.041 Uiso 1 1 calc R . .
N5 N 0.86560(16) 1.0191(3) 0.72299(11) 0.0346(4) Uani 1 1 d . . .
H5B H 0.8528 0.9066 0.7686 0.052 Uiso 1 1 d R . .
H5C H 0.7884 1.0449 0.6912 0.052 Uiso 1 1 d R . .
O1 O 0.86817(13) 0.5970(3) 0.58754(9) 0.0403(4) Uani 1 1 d . . .
C1 C 0.96010(17) 0.7427(3) 0.59848(12) 0.0287(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0272(8) 0.0300(9) 0.0282(8) -0.0044(7) 0.0004(6) -0.0003(6)
N2 0.0314(9) 0.0367(10) 0.0392(9) -0.0070(8) -0.0002(7) -0.0055(7)
N3 0.0339(9) 0.0426(11) 0.0447(10) -0.0079(8) 0.0033(7) -0.0053(8)
N4 0.0323(9) 0.0358(10) 0.0343(8) -0.0096(8) 0.0035(7) -0.0016(7)
N5 0.0319(9) 0.0402(10) 0.0317(8) -0.0042(7) 0.0028(7) 0.0054(7)
O1 0.0358(8) 0.0437(9) 0.0413(8) -0.0136(7) 0.0069(6) -0.0122(7)
C1 0.0284(9) 0.0309(10) 0.0269(9) -0.0017(8) -0.0012(7) 0.0006(8)

_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 1.347(2) . ?
N1 C1 1.357(2) . ?
N1 N5 1.3818(19) . ?
N2 N3 1.272(2) . ?
N3 N4 1.347(2) . ?
N4 C1 1.345(2) . ?
N4 H4 0.8600 . ?
N5 H5B 0.8900 . ?
N5 H5C 0.8900 . ?
O1 C1 1.224(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
N2 N1 C1 111.23(14) . . ?
N2 N1 N5 119.65(14) . . ?
C1 N1 N5 129.00(15) . . ?
N3 N2 N1 107.70(15) . . ?
N2 N3 N4 107.84(15) . . ?
C1 N4 N3 111.56(16) . . ?
C1 N4 H4 124.2 . . ?
N3 N4 H4 124.2 . . ?
N1 N5 H5B 109.2 . . ?
N1 N5 H5C 109.2 . . ?
H5B N5 H5C 109.5 . . ?
O1 C1 N4 130.49(17) . . ?
O1 C1 N1 127.88(17) . . ?
N4 C1 N1 101.63(15) . . ?

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
C1 N1 N2 N3 1.4(2) . . . . ?
N5 N1 N2 N3 177.65(15) . . . . ?
N1 N2 N3 N4 -0.1(2) . . . . ?
N2 N3 N4 C1 -1.3(2) . . . . ?
N3 N4 C1 O1 -179.03(19) . . . . ?
N3 N4 C1 N1 2.0(2) . . . . ?
N2 N1 C1 O1 178.95(18) . . . . ?
N5 N1 C1 O1 3.2(3) . . . . ?
N2 N1 C1 N4 -2.05(19) . . . . ?
N5 N1 C1 N4 -177.84(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.61
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_140604d
_database_code_depnum_ccdc_archive 'CCDC 1018899'
_audit_update_record             
;
2014-08-11 deposited with the CCDC.
2015-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H6 N6 O'
_chemical_formula_weight         118.12

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   10.6535(7)
_cell_length_b                   6.5711(5)
_cell_length_c                   6.9431(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.531(2)
_cell_angle_gamma                90.00
_cell_volume                     476.24(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    595
_cell_measurement_theta_min      3.672
_cell_measurement_theta_max      23.065

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             248
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9517
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            838
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0726
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.66
_diffrn_reflns_theta_max         25.02
_reflns_number_total             838
_reflns_number_gt                560
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1242P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         838
_refine_ls_number_parameters     74
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0681
_refine_ls_wR_factor_ref         0.2048
_refine_ls_wR_factor_gt          0.1810
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
N1 N 0.8210(3) 0.6287(4) 0.8308(5) 0.0275(8) Uani 1 1 d . . .
N2 N 0.9113(3) 0.7745(4) 0.8517(6) 0.0386(10) Uani 1 1 d . . .
N3 N 0.8505(3) 0.9438(5) 0.8517(6) 0.0471(11) Uani 1 1 d . . .
N4 N 0.7224(3) 0.9126(5) 0.8315(5) 0.0365(9) Uani 1 1 d . . .
N5 N 0.8462(3) 0.4212(4) 0.8187(6) 0.0481(11) Uani 1 1 d . . .
H5A H 0.8901 0.4003 0.7242 0.072 Uiso 1 1 d R . .
H5B H 0.8922 0.3795 0.9332 0.072 Uiso 1 1 d R . .
N6 N 0.3945(3) 0.7545(5) 0.4740(4) 0.0359(9) Uani 1 1 d . . .
H6A H 0.4582 0.7805 0.4098 0.043 Uiso 1 1 d R . .
H6B H 0.3878 0.8613 0.5526 0.043 Uiso 1 1 d R . .
H6D H 0.4122 0.6409 0.5467 0.043 Uiso 1 1 d R . .
H6C H 0.3204 0.7387 0.3866 0.043 Uiso 1 1 d R . .
O1 O 0.6000(2) 0.6135(4) 0.7986(4) 0.0347(8) Uani 1 1 d . . .
C1 C 0.7038(3) 0.7117(5) 0.8190(5) 0.0235(9) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0181(16) 0.0200(15) 0.044(2) 0.0002(13) 0.0057(14) -0.0006(11)
N2 0.0239(18) 0.0305(18) 0.062(3) -0.0018(16) 0.0085(16) -0.0067(14)
N3 0.038(2) 0.031(2) 0.071(3) -0.0034(18) 0.008(2) -0.0048(16)
N4 0.034(2) 0.0262(17) 0.048(2) 0.0001(15) 0.0045(17) 0.0048(13)
N5 0.0277(19) 0.0242(18) 0.091(3) -0.0023(17) 0.0091(19) 0.0058(13)
N6 0.042(2) 0.0332(18) 0.033(2) 0.0010(14) 0.0091(16) -0.0008(14)
O1 0.0187(14) 0.0343(15) 0.0502(18) 0.0039(12) 0.0046(13) 0.0017(11)
C1 0.0200(19) 0.0241(19) 0.025(2) 0.0010(15) 0.0022(15) 0.0039(14)

_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 1.345(4) . ?
N1 C1 1.349(4) . ?
N1 N5 1.396(4) . ?
N2 N3 1.288(4) . ?
N3 N4 1.359(4) . ?
N4 C1 1.335(4) . ?
N5 H5A 0.8900 . ?
N5 H5B 0.8900 . ?
N6 H6A 0.9000 . ?
N6 H6B 0.9000 . ?
N6 H6D 0.9000 . ?
N6 H6C 0.9001 . ?
O1 C1 1.264(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
N2 N1 C1 110.6(3) . . ?
N2 N1 N5 124.1(3) . . ?
C1 N1 N5 125.3(3) . . ?
N3 N2 N1 105.4(3) . . ?
N2 N3 N4 111.4(3) . . ?
C1 N4 N3 106.7(3) . . ?
N1 N5 H5A 109.3 . . ?
N1 N5 H5B 109.0 . . ?
H5A N5 H5B 109.5 . . ?
H6A N6 H6B 108.1 . . ?
H6A N6 H6D 109.9 . . ?
H6B N6 H6D 109.9 . . ?
H6A N6 H6C 109.5 . . ?
H6B N6 H6C 109.5 . . ?
H6D N6 H6C 109.9 . . ?
O1 C1 N4 128.8(3) . . ?
O1 C1 N1 125.4(3) . . ?
N4 C1 N1 105.8(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
C1 N1 N2 N3 -0.3(4) . . . . ?
N5 N1 N2 N3 178.3(4) . . . . ?
N1 N2 N3 N4 0.0(5) . . . . ?
N2 N3 N4 C1 0.2(5) . . . . ?
N3 N4 C1 O1 -179.8(4) . . . . ?
N3 N4 C1 N1 -0.4(4) . . . . ?
N2 N1 C1 O1 179.9(3) . . . . ?
N5 N1 C1 O1 1.3(6) . . . . ?
N2 N1 C1 N4 0.5(4) . . . . ?
N5 N1 C1 N4 -178.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.089
####################################################################### 
# 
# 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_140623d
_database_code_depnum_ccdc_archive 'CCDC 1018904'
_audit_update_record             
;
2014-08-11 deposited with the CCDC.
2015-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H8 N8 O'
_chemical_formula_weight         160.16

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   12.7785(11)
_cell_length_b                   6.4100(6)
_cell_length_c                   16.5787(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.3030(10)
_cell_angle_gamma                90.00
_cell_volume                     1355.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1198
_cell_measurement_theta_min      2.461
_cell_measurement_theta_max      27.731

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9469
_exptl_absorpt_correction_T_max  0.9601
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            3139
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1201
_reflns_number_gt                887
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0649P)²+0.1875P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1201
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1169
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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
N1 N 0.12491(12) 0.1271(3) 0.40069(9) 0.0318(4) Uani 1 1 d . . .
N2 N 0.10477(13) -0.0005(3) 0.33691(9) 0.0410(5) Uani 1 1 d . . .
N3 N 0.09534(15) -0.1845(3) 0.36705(10) 0.0469(5) Uani 1 1 d . . .
N4 N 0.11000(13) -0.1822(3) 0.44902(10) 0.0419(5) Uani 1 1 d . . .
N5 N 0.14156(13) 0.3389(3) 0.38696(10) 0.0401(5) Uani 1 1 d . . .
H5A H 0.2023 0.3767 0.4116 0.060 Uiso 1 1 d R . .
H5B H 0.0898 0.4120 0.4070 0.060 Uiso 1 1 d R . .
N6 N 0.11117(14) 0.5209(3) 0.58094(10) 0.0445(5) Uani 1 1 d . . .
H6A H 0.1104 0.6079 0.5414 0.053 Uiso 1 1 calc R . .
H6B H 0.1039 0.3896 0.5715 0.053 Uiso 1 1 calc R . .
N7 N 0.13456(13) 0.7898(3) 0.67026(10) 0.0448(5) Uani 1 1 d . . .
H7A H 0.1338 0.8767 0.6307 0.054 Uiso 1 1 calc R . .
H7B H 0.1426 0.8341 0.7192 0.054 Uiso 1 1 calc R . .
N8 N 0.12413(14) 0.4551(3) 0.71638(10) 0.0538(6) Uani 1 1 d . . .
H8A H 0.1318 0.4992 0.7654 0.065 Uiso 1 1 calc R . .
H8B H 0.1169 0.3239 0.7069 0.065 Uiso 1 1 calc R . .
O1 O 0.14737(11) 0.0904(2) 0.54036(7) 0.0408(4) Uani 1 1 d . . .
C1 C 0.12890(13) 0.0168(3) 0.47019(11) 0.0308(5) Uani 1 1 d . . .
C2 C 0.12345(14) 0.5887(4) 0.65589(11) 0.0352(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0424(9) 0.0280(9) 0.0246(8) -0.0003(7) -0.0024(6) -0.0013(7)
N2 0.0549(11) 0.0386(11) 0.0290(9) -0.0054(8) -0.0013(7) -0.0027(8)
N3 0.0693(12) 0.0367(11) 0.0345(10) -0.0059(8) 0.0026(8) -0.0062(9)
N4 0.0602(11) 0.0315(10) 0.0340(10) -0.0008(8) 0.0020(8) -0.0042(8)
N5 0.0525(10) 0.0302(10) 0.0367(10) 0.0039(8) -0.0055(7) -0.0026(8)
N6 0.0759(13) 0.0314(10) 0.0262(9) -0.0008(8) 0.0036(8) -0.0061(9)
N7 0.0640(12) 0.0430(12) 0.0272(8) -0.0056(8) -0.0004(8) -0.0027(9)
N8 0.0789(15) 0.0532(13) 0.0291(10) 0.0090(9) 0.0004(9) -0.0056(10)
O1 0.0568(9) 0.0370(9) 0.0279(8) -0.0018(6) -0.0040(6) -0.0028(7)
C1 0.0322(10) 0.0315(11) 0.0286(10) -0.0002(9) -0.0001(8) -0.0011(8)
C2 0.0344(11) 0.0383(13) 0.0329(11) 0.0011(9) 0.0027(8) -0.0017(8)

_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 1.350(2) . ?
N1 C1 1.350(2) . ?
N1 N5 1.395(2) . ?
N2 N3 1.289(2) . ?
N3 N4 1.361(2) . ?
N4 C1 1.341(3) . ?
N5 H5A 0.8900 . ?
N5 H5B 0.8900 . ?
N6 C2 1.317(2) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 C2 1.316(3) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N8 C2 1.318(3) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
O1 C1 1.265(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
N2 N1 C1 110.33(16) . . ?
N2 N1 N5 119.07(14) . . ?
C1 N1 N5 130.56(16) . . ?
N3 N2 N1 105.58(15) . . ?
N2 N3 N4 111.47(16) . . ?
C1 N4 N3 106.52(16) . . ?
N1 N5 H5A 109.1 . . ?
N1 N5 H5B 109.1 . . ?
H5A N5 H5B 109.5 . . ?
C2 N6 H6A 120.0 . . ?
C2 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
C2 N7 H7A 120.0 . . ?
C2 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C2 N8 H8A 120.0 . . ?
C2 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
O1 C1 N4 128.07(17) . . ?
O1 C1 N1 125.84(18) . . ?
N4 C1 N1 106.09(16) . . ?
N7 C2 N6 119.97(19) . . ?
N7 C2 N8 120.15(19) . . ?
N6 C2 N8 119.9(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
C1 N1 N2 N3 0.8(2) . . . . ?
N5 N1 N2 N3 178.56(16) . . . . ?
N1 N2 N3 N4 -0.7(2) . . . . ?
N2 N3 N4 C1 0.4(2) . . . . ?
N3 N4 C1 O1 -179.66(18) . . . . ?
N3 N4 C1 N1 0.1(2) . . . . ?
N2 N1 C1 O1 179.21(17) . . . . ?
N5 N1 C1 O1 1.8(3) . . . . ?
N2 N1 C1 N4 -0.5(2) . . . . ?
N5 N1 C1 N4 -177.97(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_140626g
_database_code_depnum_ccdc_archive 'CCDC 1018905'
_audit_update_record             
;
2014-08-11 deposited with the CCDC.
2015-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H8 N10 O'
_chemical_formula_weight         200.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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

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

_cell_length_a                   6.0700(6)
_cell_length_b                   7.1682(7)
_cell_length_c                   10.6018(9)
_cell_angle_alpha                76.8520(10)
_cell_angle_beta                 88.343(2)
_cell_angle_gamma                65.4060(10)
_cell_volume                     407.32(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    500
_cell_measurement_theta_min      3.217
_cell_measurement_theta_max      21.839

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             208
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9805
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            2105
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0780
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         25.01
_reflns_number_total             1427
_reflns_number_gt                873
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0987P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1427
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0817
_refine_ls_wR_factor_ref         0.2065
_refine_ls_wR_factor_gt          0.1930
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
N1 N 0.0691(6) 0.2306(5) 0.4749(3) 0.0355(9) Uani 1 1 d . . .
N2 N -0.1566(6) 0.2958(6) 0.5112(3) 0.0444(10) Uani 1 1 d . . .
N3 N -0.2866(6) 0.2951(6) 0.4168(3) 0.0470(10) Uani 1 1 d . . .
N4 N -0.1487(6) 0.2309(6) 0.3184(3) 0.0451(10) Uani 1 1 d . . .
N5 N 0.2571(6) 0.2122(6) 0.5574(3) 0.0464(10) Uani 1 1 d . . .
H5A H 0.3385 0.2811 0.5131 0.070 Uiso 1 1 d R . .
H5B H 0.3572 0.0765 0.5860 0.070 Uiso 1 1 d R . .
N6 N 0.1764(6) 0.2645(6) 0.9558(3) 0.0427(9) Uani 1 1 d . . .
N7 N 0.3470(6) 0.2428(5) 1.0496(3) 0.0400(9) Uani 1 1 d . . .
H7 H 0.3253 0.2260 1.1312 0.048 Uiso 1 1 calc R . .
N8 N 0.5050(6) 0.2778(5) 0.8699(3) 0.0353(9) Uani 1 1 d . . .
N9 N 0.6776(6) 0.2932(6) 0.7830(3) 0.0482(10) Uani 1 1 d . . .
H9A H 0.6099 0.4134 0.7224 0.072 Uiso 1 1 d R . .
H9B H 0.7279 0.1846 0.7456 0.072 Uiso 1 1 d R . .
N10 N 0.7373(6) 0.2408(6) 1.0559(3) 0.0432(10) Uani 1 1 d . . .
H10A H 0.7486 0.2266 1.1385 0.052 Uiso 1 1 calc R . .
H10B H 0.8541 0.2484 1.0103 0.052 Uiso 1 1 calc R . .
O1 O 0.2716(5) 0.1217(5) 0.2974(3) 0.0490(9) Uani 1 1 d . . .
C1 C 0.0808(7) 0.1874(6) 0.3558(3) 0.0362(10) Uani 1 1 d . . .
C2 C 0.5442(7) 0.2509(6) 1.0001(3) 0.0326(9) Uani 1 1 d . . .
C3 C 0.2798(7) 0.2841(7) 0.8498(4) 0.0398(10) Uani 1 1 d . . .
H3 H 0.2103 0.3007 0.7687 0.048 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0378(19) 0.047(2) 0.0210(17) -0.0085(15) -0.0008(14) -0.0162(17)
N2 0.041(2) 0.056(3) 0.031(2) -0.0100(17) 0.0010(16) -0.0155(19)
N3 0.040(2) 0.051(3) 0.044(2) -0.0061(18) -0.0047(17) -0.0145(18)
N4 0.044(2) 0.053(3) 0.035(2) -0.0106(17) -0.0064(16) -0.0175(19)
N5 0.047(2) 0.062(3) 0.0298(19) -0.0117(17) -0.0058(16) -0.0220(19)
N6 0.043(2) 0.052(2) 0.0324(19) -0.0109(17) -0.0059(16) -0.0190(18)
N7 0.047(2) 0.051(2) 0.0255(18) -0.0099(16) 0.0012(15) -0.0225(18)
N8 0.039(2) 0.041(2) 0.0269(17) -0.0101(15) 0.0011(15) -0.0174(17)
N9 0.050(2) 0.062(3) 0.0285(19) -0.0088(17) 0.0092(17) -0.022(2)
N10 0.041(2) 0.063(3) 0.0302(19) -0.0115(17) 0.0001(16) -0.0255(19)
O1 0.0468(18) 0.067(2) 0.0267(15) -0.0127(14) 0.0030(13) -0.0168(16)
C1 0.047(3) 0.039(3) 0.0181(19) -0.0019(17) -0.0007(17) -0.016(2)
C2 0.038(2) 0.036(3) 0.023(2) -0.0066(17) 0.0033(17) -0.0150(19)
C3 0.041(2) 0.045(3) 0.031(2) -0.0090(19) -0.0099(19) -0.015(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 N2 1.327(4) . ?
N1 C1 1.359(5) . ?
N1 N5 1.402(4) . ?
N2 N3 1.294(4) . ?
N3 N4 1.360(4) . ?
N4 C1 1.345(5) . ?
N5 H5A 0.8900 . ?
N5 H5B 0.8900 . ?
N6 C3 1.279(5) . ?
N6 N7 1.393(4) . ?
N7 C2 1.311(5) . ?
N7 H7 0.8600 . ?
N8 C2 1.363(5) . ?
N8 C3 1.370(5) . ?
N8 N9 1.398(4) . ?
N9 H9A 0.8900 . ?
N9 H9B 0.8900 . ?
N10 C2 1.296(5) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
O1 C1 1.258(4) . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C1 111.1(3) . . ?
N2 N1 N5 120.1(3) . . ?
C1 N1 N5 128.9(3) . . ?
N3 N2 N1 105.8(3) . . ?
N2 N3 N4 111.4(3) . . ?
C1 N4 N3 106.5(3) . . ?
N1 N5 H5A 108.9 . . ?
N1 N5 H5B 109.4 . . ?
H5A N5 H5B 109.5 . . ?
C3 N6 N7 103.4(3) . . ?
C2 N7 N6 112.8(3) . . ?
C2 N7 H7 123.6 . . ?
N6 N7 H7 123.6 . . ?
C2 N8 C3 107.0(3) . . ?
C2 N8 N9 121.9(3) . . ?
C3 N8 N9 131.1(3) . . ?
N8 N9 H9A 109.1 . . ?
N8 N9 H9B 109.1 . . ?
H9A N9 H9B 109.5 . . ?
C2 N10 H10A 120.0 . . ?
C2 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
O1 C1 N4 129.7(4) . . ?
O1 C1 N1 125.1(4) . . ?
N4 C1 N1 105.3(3) . . ?
N10 C2 N7 130.3(3) . . ?
N10 C2 N8 124.9(3) . . ?
N7 C2 N8 104.8(3) . . ?
N6 C3 N8 112.1(4) . . ?
N6 C3 H3 124.0 . . ?
N8 C3 H3 124.0 . . ?

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
C1 N1 N2 N3 -0.3(4) . . . . ?
N5 N1 N2 N3 -179.6(3) . . . . ?
N1 N2 N3 N4 -0.3(4) . . . . ?
N2 N3 N4 C1 0.7(5) . . . . ?
C3 N6 N7 C2 0.4(4) . . . . ?
N3 N4 C1 O1 179.5(4) . . . . ?
N3 N4 C1 N1 -0.8(4) . . . . ?
N2 N1 C1 O1 -179.6(4) . . . . ?
N5 N1 C1 O1 -0.3(7) . . . . ?
N2 N1 C1 N4 0.7(4) . . . . ?
N5 N1 C1 N4 179.9(4) . . . . ?
N6 N7 C2 N10 178.5(4) . . . . ?
N6 N7 C2 N8 -0.2(4) . . . . ?
C3 N8 C2 N10 -178.9(4) . . . . ?
N9 N8 C2 N10 1.3(6) . . . . ?
C3 N8 C2 N7 0.0(4) . . . . ?
N9 N8 C2 N7 -179.9(3) . . . . ?
N7 N6 C3 N8 -0.4(4) . . . . ?
C2 N8 C3 N6 0.3(5) . . . . ?
N9 N8 C3 N6 -179.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.119
####################################################################### 
# 
# 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_140726b
_database_code_depnum_ccdc_archive 'CCDC 1018919'
_audit_update_record             
;
2014-08-11 deposited with the CCDC.
2015-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H10 N10 O'
_chemical_formula_weight         190.20

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   7.0441(5)
_cell_length_b                   12.0324(11)
_cell_length_c                   10.1093(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.964(2)
_cell_angle_gamma                90.00
_cell_volume                     823.79(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    83.387
_cell_measurement_theta_max      23.301

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9742
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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            4077
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_av_sigmaI/netI    0.0693
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.69
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1452
_reflns_number_gt                866
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0155P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1452
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.0908
_refine_ls_wR_factor_gt          0.0848
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_restrained_S_all      1.185
_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
N1 N 0.4008(3) 0.27227(16) 0.5936(2) 0.0383(5) Uani 1 1 d . . .
N2 N 0.4068(3) 0.38413(17) 0.5821(2) 0.0483(6) Uani 1 1 d . . .
N3 N 0.2308(3) 0.41322(17) 0.5116(2) 0.0540(7) Uani 1 1 d . . .
N4 N 0.1095(3) 0.32254(17) 0.4759(2) 0.0467(6) Uani 1 1 d . . .
N5 N 0.5691(3) 0.21366(16) 0.6645(2) 0.0482(6) Uani 1 1 d . . .
H5B H 0.5967 0.1629 0.6085 0.072 Uiso 1 1 d R . .
H5C H 0.5458 0.1800 0.7369 0.072 Uiso 1 1 d R . .
N6 N 0.2510(3) 0.39866(16) 0.9060(2) 0.0503(7) Uani 1 1 d . . .
H6A H 0.2113 0.4664 0.9035 0.060 Uiso 1 1 calc R . .
H6B H 0.3720 0.3825 0.9464 0.060 Uiso 1 1 calc R . .
N7 N -0.1272(3) 0.45305(17) 0.7801(2) 0.0615(8) Uani 1 1 d . . .
H7B H -0.2246 0.4568 0.8204 0.092 Uiso 1 1 d R . .
H7C H -0.1719 0.4743 0.6927 0.092 Uiso 1 1 d R . .
N8 N -0.0602(3) 0.34248(17) 0.7851(2) 0.0472(6) Uani 1 1 d . . .
H8 H -0.1403 0.2903 0.7476 0.057 Uiso 1 1 calc R . .
N9 N 0.1866(3) 0.21427(17) 0.8519(2) 0.0482(6) Uani 1 1 d . . .
H9 H 0.3081 0.1976 0.8897 0.058 Uiso 1 1 calc R . .
N10 N 0.0480(3) 0.13077(16) 0.7935(2) 0.0503(6) Uani 1 1 d . . .
H10B H 0.0519 0.0779 0.8559 0.075 Uiso 1 1 d R . .
H10C H 0.0783 0.1016 0.7210 0.075 Uiso 1 1 d R . .
O1 O 0.1690(2) 0.13119(14) 0.52029(19) 0.0491(5) Uani 1 1 d . . .
C1 C 0.2184(3) 0.2321(2) 0.5281(3) 0.0372(6) Uani 1 1 d . . .
C2 C 0.1259(3) 0.3192(2) 0.8475(3) 0.0367(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0321(11) 0.0294(13) 0.0469(15) 0.0022(10) -0.0003(10) -0.0027(10)
N2 0.0456(13) 0.0334(15) 0.0585(17) -0.0006(11) 0.0018(12) -0.0035(11)
N3 0.0512(14) 0.0349(14) 0.0687(19) 0.0026(12) 0.0044(13) -0.0013(11)
N4 0.0403(12) 0.0343(13) 0.0588(17) 0.0019(12) 0.0023(11) -0.0004(11)
N5 0.0391(12) 0.0448(14) 0.0532(17) 0.0044(11) 0.0002(11) 0.0029(10)
N6 0.0358(11) 0.0353(14) 0.0696(18) -0.0021(11) -0.0030(11) 0.0031(10)
N7 0.0465(13) 0.0359(15) 0.088(2) 0.0101(12) -0.0048(13) 0.0058(11)
N8 0.0343(12) 0.0310(13) 0.0675(19) 0.0017(11) -0.0008(11) -0.0003(10)
N9 0.0363(12) 0.0360(14) 0.0641(18) -0.0018(11) 0.0002(11) 0.0028(11)
N10 0.0494(13) 0.0346(14) 0.0627(18) -0.0006(11) 0.0083(12) -0.0066(10)
O1 0.0386(10) 0.0322(11) 0.0674(15) 0.0008(9) -0.0008(9) -0.0063(8)
C1 0.0337(14) 0.0374(17) 0.0385(18) -0.0031(13) 0.0065(12) -0.0049(13)
C2 0.0338(14) 0.0352(17) 0.0390(18) 0.0047(12) 0.0064(12) 0.0014(13)

_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 1.353(2) . ?
N1 C1 1.362(3) . ?
N1 N5 1.397(2) . ?
N2 N3 1.296(2) . ?
N3 N4 1.372(2) . ?
N4 C1 1.353(3) . ?
N5 H5B 0.8900 . ?
N5 H5C 0.8900 . ?
N6 C2 1.324(3) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
N7 N8 1.408(3) . ?
N7 H7B 0.8900 . ?
N7 H7C 0.8900 . ?
N8 C2 1.319(3) . ?
N8 H8 0.8600 . ?
N9 C2 1.330(3) . ?
N9 N10 1.412(2) . ?
N9 H9 0.8600 . ?
N10 H10B 0.8900 . ?
N10 H10C 0.8900 . ?
O1 C1 1.259(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 N1 C1 111.0(2) . . ?
N2 N1 N5 120.30(19) . . ?
C1 N1 N5 128.7(2) . . ?
N3 N2 N1 105.56(19) . . ?
N2 N3 N4 111.24(19) . . ?
C1 N4 N3 106.95(18) . . ?
N1 N5 H5B 108.8 . . ?
N1 N5 H5C 109.2 . . ?
H5B N5 H5C 109.5 . . ?
C2 N6 H6A 120.0 . . ?
C2 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
N8 N7 H7B 108.9 . . ?
N8 N7 H7C 109.3 . . ?
H7B N7 H7C 109.5 . . ?
C2 N8 N7 119.8(2) . . ?
C2 N8 H8 120.1 . . ?
N7 N8 H8 120.1 . . ?
C2 N9 N10 118.87(19) . . ?
C2 N9 H9 120.6 . . ?
N10 N9 H9 120.6 . . ?
N9 N10 H10B 109.2 . . ?
N9 N10 H10C 109.3 . . ?
H10B N10 H10C 109.5 . . ?
O1 C1 N4 129.3(2) . . ?
O1 C1 N1 125.5(2) . . ?
N4 C1 N1 105.2(2) . . ?
N8 C2 N6 120.8(2) . . ?
N8 C2 N9 119.0(2) . . ?
N6 C2 N9 120.2(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
C1 N1 N2 N3 0.5(3) . . . . ?
N5 N1 N2 N3 179.9(2) . . . . ?
N1 N2 N3 N4 -0.3(3) . . . . ?
N2 N3 N4 C1 0.1(3) . . . . ?
N3 N4 C1 O1 -179.6(3) . . . . ?
N3 N4 C1 N1 0.2(3) . . . . ?
N2 N1 C1 O1 179.4(2) . . . . ?
N5 N1 C1 O1 0.0(4) . . . . ?
N2 N1 C1 N4 -0.4(3) . . . . ?
N5 N1 C1 N4 -179.8(2) . . . . ?
N7 N8 C2 N6 0.1(4) . . . . ?
N7 N8 C2 N9 179.7(2) . . . . ?
N10 N9 C2 N8 -2.1(3) . . . . ?
N10 N9 C2 N6 177.5(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         0.206
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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 1018921'
_audit_update_record             
;
2014-08-11 deposited with the CCDC.
2015-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H11 N11 O'
_chemical_formula_weight         205.22

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           ?
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   12.8237(6)
_cell_length_b                   6.7049(3)
_cell_length_c                   20.2018(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1736.98(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9748
_exptl_absorpt_correction_T_max  0.9748
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13549
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         28.57
_reflns_number_total             2195
_reflns_number_gt                1654
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0495P)²+0.2720P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2195
_refine_ls_number_parameters     171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0985
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.08796(9) 0.2819(2) 0.61832(6) 0.0300(3) Uani 1 1 d . . .
C2 C 0.74393(9) 0.24562(16) 0.58266(6) 0.0259(3) Uani 1 1 d . . .
H1 H 0.1429(16) -0.063(3) 0.6779(10) 0.067(6) Uiso 1 1 d . . .
H2 H 0.0378(18) -0.037(3) 0.6877(10) 0.070(6) Uiso 1 1 d . . .
H4 H 0.6414(14) 0.234(3) 0.5155(10) 0.052(5) Uiso 1 1 d . . .
H5 H 0.8439(13) 0.087(3) 0.4608(9) 0.053(5) Uiso 1 1 d . . .
H6 H 0.8391(13) 0.307(3) 0.4537(9) 0.056(5) Uiso 1 1 d . . .
H7 H 0.8905(13) 0.229(2) 0.5611(8) 0.041(4) Uiso 1 1 d . . .
H8 H 0.5179(15) 0.182(3) 0.5973(9) 0.061(5) Uiso 1 1 d . . .
H9 H 0.5323(15) 0.392(3) 0.5813(9) 0.059(5) Uiso 1 1 d . . .
H10 H 0.7015(12) 0.289(2) 0.6710(7) 0.032(4) Uiso 1 1 d . . .
H11 H 0.8531(15) 0.181(3) 0.7082(12) 0.073(6) Uiso 1 1 d . . .
H12 H 0.8640(15) 0.390(3) 0.6934(10) 0.062(6) Uiso 1 1 d . . .
N1 N 0.10774(9) 0.20278(18) 0.67886(5) 0.0347(3) Uani 1 1 d . . .
N2 N 0.09702(14) 0.0085(2) 0.70141(7) 0.0525(4) Uani 1 1 d . . .
N3 N 0.13703(10) 0.3476(2) 0.72154(6) 0.0489(3) Uani 1 1 d . . .
N4 N 0.10688(10) 0.47694(18) 0.62378(6) 0.0428(3) Uani 1 1 d . . .
N5 N 0.13650(11) 0.5098(2) 0.68744(7) 0.0532(4) Uani 1 1 d . . .
N6 N 0.80991(9) 0.1981(2) 0.47577(5) 0.0361(3) Uani 1 1 d . . .
N7 N 0.56438(9) 0.2856(2) 0.59879(6) 0.0379(3) Uani 1 1 d . . .
N8 N 0.75520(9) 0.27199(18) 0.64737(5) 0.0355(3) Uani 1 1 d . . .
N9 N 0.64913(8) 0.23955(18) 0.55686(6) 0.0336(3) Uani 1 1 d . . .
N10 N 0.82691(8) 0.22266(18) 0.54437(5) 0.0330(3) Uani 1 1 d . . .
N11 N 0.85611(9) 0.2705(2) 0.67439(6) 0.0416(3) Uani 1 1 d . . .
O1 O 0.05702(7) 0.18279(15) 0.56897(4) 0.0378(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0253(6) 0.0408(7) 0.0239(6) 0.0028(5) 0.0012(4) 0.0036(5)
C2 0.0322(6) 0.0218(5) 0.0237(6) 0.0001(4) -0.0005(4) 0.0004(5)
N1 0.0360(6) 0.0439(6) 0.0241(5) 0.0030(4) -0.0066(4) 0.0006(5)
N2 0.0623(9) 0.0532(9) 0.0420(8) 0.0164(6) -0.0081(7) 0.0004(8)
N3 0.0477(7) 0.0671(9) 0.0319(6) -0.0114(6) -0.0100(5) -0.0003(6)
N4 0.0462(7) 0.0392(7) 0.0429(7) 0.0010(5) -0.0007(5) 0.0015(5)
N5 0.0543(8) 0.0513(8) 0.0540(9) -0.0156(7) -0.0044(6) -0.0024(6)
N6 0.0398(6) 0.0464(7) 0.0221(5) -0.0022(5) 0.0026(4) 0.0006(5)
N7 0.0297(6) 0.0490(7) 0.0351(6) 0.0022(5) 0.0047(5) -0.0005(5)
N8 0.0332(6) 0.0509(7) 0.0225(5) -0.0053(5) -0.0007(4) 0.0036(5)
N9 0.0303(5) 0.0475(7) 0.0231(6) -0.0004(5) 0.0004(4) 0.0001(5)
N10 0.0298(5) 0.0459(7) 0.0232(5) -0.0040(4) -0.0011(4) 0.0027(5)
N11 0.0401(7) 0.0557(8) 0.0290(6) -0.0056(6) -0.0090(5) 0.0018(6)
O1 0.0395(5) 0.0522(6) 0.0217(4) -0.0021(4) -0.0023(4) -0.0029(4)

_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 O1 1.2621(16) . ?
C1 N4 1.3343(18) . ?
C1 N1 1.3572(16) . ?
C2 N9 1.3233(16) . ?
C2 N10 1.3246(15) . ?
C2 N8 1.3270(16) . ?
N1 N3 1.3516(17) . ?
N1 N2 1.3868(18) . ?
N3 N5 1.288(2) . ?
N4 N5 1.3591(19) . ?
N6 N10 1.4124(15) . ?
N7 N9 1.4119(16) . ?
N8 N11 1.4045(16) . ?

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
O1 C1 N4 129.68(12) . . ?
O1 C1 N1 124.37(13) . . ?
N4 C1 N1 105.94(11) . . ?
N9 C2 N10 120.29(11) . . ?
N9 C2 N8 119.48(11) . . ?
N10 C2 N8 120.22(11) . . ?
N3 N1 C1 110.24(12) . . ?
N3 N1 N2 119.52(12) . . ?
C1 N1 N2 130.15(12) . . ?
N5 N3 N1 105.32(12) . . ?
C1 N4 N5 106.74(12) . . ?
N3 N5 N4 111.75(12) . . ?
C2 N8 N11 118.83(11) . . ?
C2 N9 N7 117.65(11) . . ?
C2 N10 N6 117.56(11) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        28.57
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.062
