# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_shrv362
_database_code_depnum_ccdc_archive 'CCDC 1463784'
_audit_update_record             
;
2016-03-11 deposited with the CCDC.
2016-06-03 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         'C2 H4 N6 O2'
_chemical_formula_sum            'C2 H4 N6 O2'
_chemical_formula_weight         144.11


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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'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                   12.8179(10)
_cell_length_b                   4.8463(3)
_cell_length_c                   18.2472(12)
_cell_angle_alpha                90
_cell_angle_beta                 100.494(3)
_cell_angle_gamma                90
_cell_volume                     1114.55(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2541
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      27.36

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.049
_exptl_absorpt_coefficient_mu    0.149
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6906
_exptl_absorpt_correction_T_max  0.7456

_diffrn_ambient_temperature      150(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  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5450
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.233
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1285
_reflns_number_gt                1128
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_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)+(0.0382P)²+0.8217P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1285
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0738
_refine_ls_wR_factor_gt          0.0699
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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
O1 O 0.22177(6) 1.19288(17) 0.29627(5) 0.0225(2) Uani 1 1 d . . . . .
O2 O 0.39458(6) 1.16920(18) 0.30939(5) 0.0239(2) Uani 1 1 d . . . . .
N3 N 0.30806(7) 1.09004(19) 0.32350(5) 0.0168(2) Uani 1 1 d . . . . .
C4 C 0.31259(8) 0.8703(2) 0.37350(6) 0.0152(2) Uani 1 1 d . . . . .
C5 C 0.39998(9) 0.7432(2) 0.41670(6) 0.0163(2) Uani 1 1 d . . . . .
N6 N 0.50438(8) 0.7894(2) 0.42177(6) 0.0211(2) Uani 1 1 d . . . . .
H6A H 0.5477(11) 0.720(3) 0.4599(8) 0.025 Uiso 1 1 d . U . . .
H6B H 0.5274(11) 0.934(3) 0.4009(8) 0.025 Uiso 1 1 d . U . . .
N7 N 0.36146(7) 0.5397(2) 0.45616(5) 0.0188(2) Uani 1 1 d . . . . .
N8 N 0.25628(7) 0.5358(2) 0.43867(5) 0.0185(2) Uani 1 1 d . . . . .
N9 N 0.22586(7) 0.73382(19) 0.38987(5) 0.0157(2) Uani 1 1 d . . . . .
N10 N 0.11777(7) 0.7565(2) 0.36001(6) 0.0196(2) Uani 1 1 d . . . . .
H10A H 0.0968(11) 0.922(3) 0.3703(8) 0.024 Uiso 1 1 d . U . . .
H10B H 0.1112(11) 0.740(3) 0.3096(8) 0.024 Uiso 1 1 d . U . . .

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
O1 0.0223(4) 0.0193(4) 0.0238(4) 0.0045(3) -0.0008(3) 0.0032(3)
O2 0.0211(4) 0.0264(5) 0.0236(4) 0.0074(3) 0.0025(3) -0.0068(3)
N3 0.0197(5) 0.0152(5) 0.0146(4) -0.0003(3) 0.0006(3) -0.0015(4)
C4 0.0168(5) 0.0149(5) 0.0140(5) 0.0003(4) 0.0029(4) -0.0009(4)
C5 0.0194(5) 0.0155(5) 0.0138(5) 0.0003(4) 0.0021(4) -0.0002(4)
N6 0.0174(5) 0.0228(5) 0.0220(5) 0.0073(4) 0.0006(4) -0.0015(4)
N7 0.0190(5) 0.0190(5) 0.0180(4) 0.0031(4) 0.0024(3) -0.0004(4)
N8 0.0204(5) 0.0186(5) 0.0165(4) 0.0027(4) 0.0030(3) 0.0003(4)
N9 0.0168(4) 0.0157(4) 0.0145(4) 0.0011(3) 0.0027(3) -0.0009(3)
N10 0.0144(5) 0.0235(5) 0.0205(5) 0.0012(4) 0.0017(4) 0.0005(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
O1 N3 1.2322(12) . ?
O2 N3 1.2440(12) . ?
N3 C4 1.3966(14) . ?
C4 N9 1.3724(14) . ?
C4 C5 1.3907(15) . ?
C5 N6 1.3433(15) . ?
C5 N7 1.3653(14) . ?
N6 H6A 0.874(15) . ?
N6 H6B 0.876(16) . ?
N7 N8 1.3277(13) . ?
N8 N9 1.3188(13) . ?
N9 N10 1.3977(13) . ?
N10 H10A 0.878(16) . ?
N10 H10B 0.911(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
O1 N3 O2 124.08(9) . . ?
O1 N3 C4 119.96(9) . . ?
O2 N3 C4 115.97(9) . . ?
N9 C4 C5 105.30(9) . . ?
N9 C4 N3 124.80(9) . . ?
C5 C4 N3 129.90(10) . . ?
N6 C5 N7 122.38(10) . . ?
N6 C5 C4 130.90(10) . . ?
N7 C5 C4 106.71(9) . . ?
C5 N6 H6A 118.1(9) . . ?
C5 N6 H6B 121.0(9) . . ?
H6A N6 H6B 116.0(13) . . ?
N8 N7 C5 109.42(9) . . ?
N9 N8 N7 108.31(9) . . ?
N8 N9 C4 110.25(9) . . ?
N8 N9 N10 118.08(9) . . ?
C4 N9 N10 131.44(9) . . ?
N9 N10 H10A 108.0(9) . . ?
N9 N10 H10B 106.8(9) . . ?
H10A N10 H10B 108.8(13) . . ?

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
O1 N3 C4 N9 7.49(16) . . . . ?
O2 N3 C4 N9 -172.44(10) . . . . ?
O1 N3 C4 C5 -172.25(11) . . . . ?
O2 N3 C4 C5 7.83(17) . . . . ?
N9 C4 C5 N6 178.53(11) . . . . ?
N3 C4 C5 N6 -1.7(2) . . . . ?
N9 C4 C5 N7 0.02(12) . . . . ?
N3 C4 C5 N7 179.79(10) . . . . ?
N6 C5 N7 N8 -178.11(10) . . . . ?
C4 C5 N7 N8 0.55(12) . . . . ?
C5 N7 N8 N9 -0.93(12) . . . . ?
N7 N8 N9 C4 0.96(12) . . . . ?
N7 N8 N9 N10 176.07(9) . . . . ?
C5 C4 N9 N8 -0.60(12) . . . . ?
N3 C4 N9 N8 179.62(10) . . . . ?
C5 C4 N9 N10 -174.85(10) . . . . ?
N3 C4 N9 N10 5.36(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6A N7 0.874(15) 2.154(16) 3.0113(14) 166.7(13) 5_666
N6 H6B O2 0.876(16) 2.439(14) 2.9193(13) 115.1(11) .
N6 H6B N10 0.876(16) 2.156(16) 3.0173(14) 167.5(13) 3
N10 H10A N6 0.878(16) 2.420(16) 3.2633(15) 161.2(13) 3_455
N10 H10B O2 0.911(15) 2.186(15) 3.0952(13) 174.9(13) 4_545

_refine_diff_density_max         0.315
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.039



# start Validation Reply Form
_vrf_PLAT015_shrv362             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
# end Validation Reply Form



####################################################################### 
# 
# 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_shrv258
_database_code_depnum_ccdc_archive 'CCDC 1463785'
_audit_update_record             
;
2016-03-11 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;

_audit_creation_date             2014-02-18
_audit_creation_method           'from SHELXTL CIF, local template and enCIFer'
_chemical_name_systematic        
; 
 2,4-dinitro-1H-imidazole-1,5-diamine 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H4 N6 O4'
_chemical_formula_sum            'C3 H4 N6 O4'
_chemical_formula_weight         188.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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

_cell_length_a                   12.7338(4)
_cell_length_b                   9.9770(3)
_cell_length_c                   5.1360(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     652.50(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1058
_cell_measurement_theta_min      4.43
_cell_measurement_theta_max      68.18

_exptl_crystal_description       wedge
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.915
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    1.549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.7897
_exptl_absorpt_correction_T_max  0.9697

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_measurement_device       'Bruker PLATINUM 135 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3278
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         5.63
_diffrn_reflns_theta_max         68.18
_reflns_number_total             1058
_reflns_number_gt                1057
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker PROTEUM v2009.7-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker PROTEUM v2009.7-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.66A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_refinement  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2008/4 (Bruker, 2008)'

_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)+(0.0657P)²+0.1043P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_number_reflns         1058
_refine_ls_number_parameters     124
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.064
_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 0.41104(12) 0.27177(16) 0.0880(4) 0.0187(4) Uani 1 1 d . . .
C2 C 0.36405(13) 0.38799(18) 0.1789(4) 0.0179(4) Uani 1 1 d . . .
N3 N 0.28095(12) 0.42268(14) 0.0444(3) 0.0191(4) Uani 1 1 d . . .
C4 C 0.27322(14) 0.32627(17) -0.1408(5) 0.0197(4) Uani 1 1 d . . .
C5 C 0.35390(13) 0.23053(17) -0.1213(4) 0.0172(4) Uani 1 1 d . . .
N6 N 0.49873(13) 0.19826(17) 0.1753(3) 0.0229(4) Uani 1 1 d D . .
H6A H 0.5501(12) 0.2526(19) 0.170(6) 0.027 Uiso 1 1 d D . .
H6B H 0.479(2) 0.171(2) 0.324(2) 0.027 Uiso 1 1 d D . .
N7 N 0.40098(12) 0.46164(16) 0.3970(3) 0.0197(4) Uani 1 1 d . . .
O8 O 0.47701(11) 0.41610(13) 0.5165(3) 0.0256(3) Uani 1 1 d . . .
O9 O 0.35540(12) 0.56578(14) 0.4541(3) 0.0281(4) Uani 1 1 d . . .
N10 N 0.19449(12) 0.32930(15) -0.3323(3) 0.0213(4) Uani 1 1 d . . .
O11 O 0.12612(11) 0.41762(14) -0.3219(4) 0.0292(4) Uani 1 1 d . . .
O12 O 0.19883(12) 0.24306(14) -0.5053(3) 0.0274(4) Uani 1 1 d . . .
N13 N 0.38021(13) 0.12408(16) -0.2659(4) 0.0223(4) Uani 1 1 d . . .
H13A H 0.4367 0.0773 -0.2272 0.027 Uiso 1 1 calc R . .
H13B H 0.3410 0.1009 -0.3997 0.027 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 0.0155(7) 0.0201(8) 0.0204(8) 0.0021(6) -0.0025(7) -0.0003(6)
C2 0.0166(8) 0.0178(8) 0.0192(10) 0.0017(7) 0.0022(7) -0.0013(7)
N3 0.0153(7) 0.0221(8) 0.0200(9) 0.0016(7) 0.0013(7) -0.0014(6)
C4 0.0157(9) 0.0224(10) 0.0211(9) 0.0031(8) 0.0001(9) -0.0020(7)
C5 0.0154(9) 0.0179(9) 0.0182(10) 0.0033(7) 0.0002(9) -0.0028(6)
N6 0.0170(9) 0.0246(8) 0.0271(10) 0.0013(7) -0.0039(7) 0.0018(7)
N7 0.0186(8) 0.0196(8) 0.0210(8) 0.0020(6) 0.0011(7) -0.0031(6)
O8 0.0246(7) 0.0274(7) 0.0249(8) 0.0001(6) -0.0041(7) -0.0004(6)
O9 0.0321(8) 0.0238(7) 0.0285(9) -0.0051(6) 0.0004(6) 0.0047(6)
N10 0.0170(8) 0.0240(8) 0.0228(9) 0.0072(7) -0.0029(7) -0.0042(6)
O11 0.0186(6) 0.0352(9) 0.0337(9) 0.0068(7) -0.0015(6) 0.0063(6)
O12 0.0274(8) 0.0307(7) 0.0239(7) 0.0002(6) -0.0072(6) -0.0034(6)
N13 0.0201(7) 0.0234(8) 0.0234(10) -0.0024(8) -0.0041(7) 0.0010(7)

_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 1.362(3) . ?
N1 C2 1.386(3) . ?
N1 N6 1.409(2) . ?
C2 N3 1.310(3) . ?
C2 N7 1.420(3) . ?
N3 C4 1.356(3) . ?
C4 N10 1.405(3) . ?
C4 C5 1.406(2) . ?
C5 N13 1.339(3) . ?
N6 H6A 0.8500(11) . ?
N6 H6B 0.8501(11) . ?
N7 O9 1.226(2) . ?
N7 O8 1.233(2) . ?
N10 O12 1.238(2) . ?
N10 O11 1.240(2) . ?
N13 H13A 0.8800 . ?
N13 H13B 0.8800 . ?

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 C2 106.73(16) . . ?
C5 N1 N6 121.15(16) . . ?
C2 N1 N6 132.12(18) . . ?
N3 C2 N1 113.10(19) . . ?
N3 C2 N7 123.14(17) . . ?
N1 C2 N7 123.76(17) . . ?
C2 N3 C4 103.94(15) . . ?
N3 C4 N10 121.84(16) . . ?
N3 C4 C5 112.26(17) . . ?
N10 C4 C5 125.86(18) . . ?
N13 C5 N1 122.96(17) . . ?
N13 C5 C4 133.02(19) . . ?
N1 C5 C4 103.96(16) . . ?
N1 N6 H6A 105.5(17) . . ?
N1 N6 H6B 102.7(18) . . ?
H6A N6 H6B 118(3) . . ?
O9 N7 O8 124.41(18) . . ?
O9 N7 C2 118.08(16) . . ?
O8 N7 C2 117.51(16) . . ?
O12 N10 O11 123.79(17) . . ?
O12 N10 C4 117.11(16) . . ?
O11 N10 C4 119.09(17) . . ?
C5 N13 H13A 120.0 . . ?
C5 N13 H13B 120.0 . . ?
H13A N13 H13B 120.0 . . ?

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
C5 N1 C2 N3 0.6(2) . . . . ?
N6 N1 C2 N3 -178.43(18) . . . . ?
C5 N1 C2 N7 179.93(16) . . . . ?
N6 N1 C2 N7 0.9(3) . . . . ?
N1 C2 N3 C4 -0.1(2) . . . . ?
N7 C2 N3 C4 -179.40(17) . . . . ?
C2 N3 C4 N10 -178.13(18) . . . . ?
C2 N3 C4 C5 -0.5(2) . . . . ?
C2 N1 C5 N13 176.64(17) . . . . ?
N6 N1 C5 N13 -4.2(3) . . . . ?
C2 N1 C5 C4 -0.8(2) . . . . ?
N6 N1 C5 C4 178.34(17) . . . . ?
N3 C4 C5 N13 -176.24(19) . . . . ?
N10 C4 C5 N13 1.3(3) . . . . ?
N3 C4 C5 N1 0.8(2) . . . . ?
N10 C4 C5 N1 178.38(18) . . . . ?
N3 C2 N7 O9 -3.4(3) . . . . ?
N1 C2 N7 O9 177.39(17) . . . . ?
N3 C2 N7 O8 176.59(17) . . . . ?
N1 C2 N7 O8 -2.7(3) . . . . ?
N3 C4 N10 O12 174.34(16) . . . . ?
C5 C4 N10 O12 -3.0(3) . . . . ?
N3 C4 N10 O11 -4.8(3) . . . . ?
C5 C4 N10 O11 177.93(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6A O12 0.8500(11) 2.52(2) 3.087(2) 125(2) 4_556
N13 H13A N6 0.88 2.52 2.821(2) 100.8 .
N13 H13B O12 0.88 2.36 2.873(2) 117.1 .

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        68.18
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.226
_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_shrv309
_database_code_depnum_ccdc_archive 'CCDC 1463786'
_audit_update_record             
;
2016-03-11 deposited with the CCDC.
2016-06-03 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         'C2 H4 N6 O2'
_chemical_formula_sum            'C2 H4 N6 O2'
_chemical_formula_weight         144.11

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   3.5852(3)
_cell_length_b                   16.3937(12)
_cell_length_c                   9.4278(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.448(3)
_cell_angle_gamma                90
_cell_volume                     548.10(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1074
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      22.62

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    0.152
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6697
_exptl_absorpt_correction_T_max  0.7454

_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  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5324
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.184
_diffrn_reflns_theta_max         26.474
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2257
_reflns_number_gt                1497
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.985

_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       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2014/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_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)+(0.0451P)²+0.1361P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2257
_refine_ls_number_parameters     206
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1114
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.043
_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
N1A N 0.1813(13) 0.6480(3) -0.0617(4) 0.0342(11) Uani 1 1 d . . . . .
C2A C 0.1534(17) 0.7301(4) -0.0782(5) 0.0322(14) Uani 1 1 d . . . . .
C3A C 0.0329(18) 0.7600(3) 0.0451(6) 0.0324(13) Uani 1 1 d . . . . .
N4A N -0.0137(14) 0.6981(3) 0.1375(5) 0.0350(11) Uani 1 1 d . . . . .
N5A N 0.0754(14) 0.6356(3) 0.0668(5) 0.0339(11) Uani 1 1 d . . . . .
N6A N 0.2314(18) 0.7679(3) -0.1949(6) 0.0456(14) Uani 1 1 d D . . . .
N7A N -0.0463(15) 0.8405(3) 0.0792(5) 0.0411(13) Uani 1 1 d . . . . .
O8A O 0.0112(17) 0.8938(3) -0.0073(5) 0.0589(13) Uani 1 1 d . . . . .
O9A O -0.1685(14) 0.8544(3) 0.1945(5) 0.0541(13) Uani 1 1 d . . . . .
N10A N 0.1058(18) 0.5583(3) 0.1254(5) 0.0501(15) Uani 1 1 d D . . . .
N1B N 0.5802(13) 0.6435(3) 0.6129(4) 0.0330(11) Uani 1 1 d . . . . .
C2B C 0.5502(15) 0.5612(3) 0.6174(5) 0.0291(13) Uani 1 1 d . . . . .
C3B C 0.6500(17) 0.5308(3) 0.4887(6) 0.0326(13) Uani 1 1 d . . . . .
N4B N 0.7474(13) 0.5927(3) 0.4076(4) 0.0334(11) Uani 1 1 d . . . . .
N5B N 0.6935(14) 0.6557(3) 0.4858(4) 0.0321(11) Uani 1 1 d . . . . .
N6B N 0.4424(16) 0.5231(3) 0.7303(6) 0.0430(13) Uani 1 1 d D . . . .
N7B N 0.6629(15) 0.4502(3) 0.4420(5) 0.0385(12) Uani 1 1 d . . . . .
O8B O 0.7763(16) 0.4355(3) 0.3276(5) 0.0559(13) Uani 1 1 d . . . . .
O9B O 0.5589(14) 0.3974(2) 0.5212(6) 0.0544(13) Uani 1 1 d . . . . .
N10B N 0.8014(18) 0.7339(3) 0.4506(5) 0.0442(14) Uani 1 1 d D . . . .
H6A H 0.186(19) 0.8201(12) -0.197(7) 0.053 Uiso 1 1 d D U . . .
H6B H 0.344(17) 0.734(3) -0.245(6) 0.053 Uiso 1 1 d D U . . .
H10A H -0.069(14) 0.552(4) 0.180(6) 0.053 Uiso 1 1 d D U . . .
H10B H 0.054(18) 0.515(2) 0.070(5) 0.053 Uiso 1 1 d D U . . .
H6C H 0.390(17) 0.4718(13) 0.726(7) 0.053 Uiso 1 1 d D U . . .
H6D H 0.372(17) 0.556(3) 0.795(5) 0.053 Uiso 1 1 d D U . . .
H10C H 0.664(15) 0.761(3) 0.503(6) 0.053 Uiso 1 1 d D U . . .
H10D H 0.774(19) 0.738(4) 0.3581(18) 0.053 Uiso 1 1 d D U . . .

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
N1A 0.050(3) 0.030(3) 0.026(2) 0.000(2) 0.016(2) -0.002(2)
C2A 0.042(4) 0.027(3) 0.028(3) 0.001(2) 0.008(3) -0.001(3)
C3A 0.044(4) 0.024(3) 0.031(3) 0.001(2) 0.014(3) 0.002(3)
N4A 0.052(3) 0.021(2) 0.033(2) -0.004(2) 0.012(2) 0.000(2)
N5A 0.052(3) 0.022(3) 0.028(2) -0.002(2) 0.010(2) 0.002(2)
N6A 0.079(4) 0.026(3) 0.038(3) 0.003(2) 0.030(3) 0.002(3)
N7A 0.054(4) 0.029(3) 0.041(3) -0.005(2) 0.012(3) 0.001(2)
O8A 0.101(4) 0.025(3) 0.054(3) 0.011(2) 0.026(3) 0.006(2)
O9A 0.084(4) 0.039(3) 0.045(3) -0.010(2) 0.028(2) 0.010(2)
N10A 0.088(5) 0.025(3) 0.043(3) 0.005(2) 0.027(3) 0.003(3)
N1B 0.047(3) 0.023(3) 0.032(2) -0.001(2) 0.015(2) 0.003(2)
C2B 0.032(3) 0.026(3) 0.030(3) -0.001(2) 0.006(2) 0.004(3)
C3B 0.042(4) 0.025(3) 0.032(3) 0.001(3) 0.009(3) 0.002(3)
N4B 0.047(3) 0.024(2) 0.031(2) 0.000(2) 0.011(2) 0.003(2)
N5B 0.044(3) 0.024(3) 0.030(2) 0.004(2) 0.013(2) 0.001(2)
N6B 0.065(4) 0.029(3) 0.040(3) 0.005(2) 0.025(3) 0.000(3)
N7B 0.050(3) 0.025(3) 0.042(3) -0.002(2) 0.011(2) 0.003(2)
O8B 0.092(4) 0.035(3) 0.046(3) -0.009(2) 0.027(3) 0.007(2)
O9B 0.074(4) 0.026(3) 0.067(3) 0.004(2) 0.023(3) -0.004(2)
N10B 0.082(4) 0.022(3) 0.034(3) 0.002(2) 0.024(3) -0.002(3)

_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
N1A N5A 1.338(6) . ?
N1A C2A 1.357(7) . ?
C2A N6A 1.327(7) . ?
C2A C3A 1.388(8) . ?
C3A N4A 1.363(7) . ?
C3A N7A 1.398(7) . ?
N4A N5A 1.288(6) . ?
N5A N10A 1.380(6) . ?
N6A H6A 0.871(15) . ?
N6A H6B 0.865(15) . ?
N7A O8A 1.233(6) . ?
N7A O9A 1.252(6) . ?
N10A H10A 0.870(15) . ?
N10A H10B 0.877(15) . ?
N1B N5B 1.336(6) . ?
N1B C2B 1.354(7) . ?
C2B N6B 1.339(7) . ?
C2B C3B 1.406(8) . ?
C3B N4B 1.347(7) . ?
C3B N7B 1.395(7) . ?
N4B N5B 1.300(6) . ?
N5B N10B 1.393(6) . ?
N6B H6C 0.862(15) . ?
N6B H6D 0.877(15) . ?
N7B O8B 1.232(6) . ?
N7B O9B 1.236(6) . ?
N10B H10C 0.872(15) . ?
N10B H10D 0.865(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
N5A N1A C2A 103.3(4) . . ?
N6A C2A N1A 122.5(5) . . ?
N6A C2A C3A 131.3(6) . . ?
N1A C2A C3A 106.3(5) . . ?
N4A C3A C2A 110.8(5) . . ?
N4A C3A N7A 120.6(5) . . ?
C2A C3A N7A 128.6(5) . . ?
N5A N4A C3A 101.5(4) . . ?
N4A N5A N1A 118.1(4) . . ?
N4A N5A N10A 122.3(4) . . ?
N1A N5A N10A 119.1(4) . . ?
C2A N6A H6A 114(4) . . ?
C2A N6A H6B 109(4) . . ?
H6A N6A H6B 136(6) . . ?
O8A N7A O9A 124.0(5) . . ?
O8A N7A C3A 117.3(5) . . ?
O9A N7A C3A 118.7(5) . . ?
N5A N10A H10A 109(4) . . ?
N5A N10A H10B 120(4) . . ?
H10A N10A H10B 98(6) . . ?
N5B N1B C2B 102.3(4) . . ?
N6B C2B N1B 121.5(5) . . ?
N6B C2B C3B 131.3(5) . . ?
N1B C2B C3B 107.2(4) . . ?
N4B C3B N7B 120.7(5) . . ?
N4B C3B C2B 110.0(5) . . ?
N7B C3B C2B 129.2(5) . . ?
N5B N4B C3B 101.8(4) . . ?
N4B N5B N1B 118.7(4) . . ?
N4B N5B N10B 121.8(4) . . ?
N1B N5B N10B 118.9(4) . . ?
C2B N6B H6C 120(4) . . ?
C2B N6B H6D 114(4) . . ?
H6C N6B H6D 123(6) . . ?
O8B N7B O9B 124.0(5) . . ?
O8B N7B C3B 119.5(5) . . ?
O9B N7B C3B 116.5(5) . . ?
N5B N10B H10C 98(4) . . ?
N5B N10B H10D 108(5) . . ?
H10C N10B H10D 123(6) . . ?

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
N5A N1A C2A N6A -179.2(6) . . . . ?
N5A N1A C2A C3A 0.4(6) . . . . ?
N6A C2A C3A N4A 179.7(6) . . . . ?
N1A C2A C3A N4A 0.1(7) . . . . ?
N6A C2A C3A N7A 1.1(11) . . . . ?
N1A C2A C3A N7A -178.5(6) . . . . ?
C2A C3A N4A N5A -0.5(6) . . . . ?
N7A C3A N4A N5A 178.2(6) . . . . ?
C3A N4A N5A N1A 0.8(6) . . . . ?
C3A N4A N5A N10A 173.4(6) . . . . ?
C2A N1A N5A N4A -0.8(7) . . . . ?
C2A N1A N5A N10A -173.6(5) . . . . ?
N4A C3A N7A O8A 178.1(6) . . . . ?
C2A C3A N7A O8A -3.4(10) . . . . ?
N4A C3A N7A O9A -1.5(8) . . . . ?
C2A C3A N7A O9A 176.9(6) . . . . ?
N5B N1B C2B N6B 179.8(5) . . . . ?
N5B N1B C2B C3B -0.2(6) . . . . ?
N6B C2B C3B N4B -178.7(6) . . . . ?
N1B C2B C3B N4B 1.3(7) . . . . ?
N6B C2B C3B N7B 0.3(11) . . . . ?
N1B C2B C3B N7B -179.8(6) . . . . ?
N7B C3B N4B N5B 179.2(5) . . . . ?
C2B C3B N4B N5B -1.8(6) . . . . ?
C3B N4B N5B N1B 1.8(6) . . . . ?
C3B N4B N5B N10B 172.4(6) . . . . ?
C2B N1B N5B N4B -1.1(6) . . . . ?
C2B N1B N5B N10B -172.0(5) . . . . ?
N4B C3B N7B O8B 2.4(9) . . . . ?
C2B C3B N7B O8B -176.5(6) . . . . ?
N4B C3B N7B O9B -178.1(5) . . . . ?
C2B C3B N7B O9B 3.1(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6A H6A O8A 0.871(15) 2.32(5) 2.902(7) 125(5) .
N6A H6A O8B 0.871(15) 2.27(4) 3.017(7) 143(6) 2_655
N6A H6B N1B 0.865(15) 2.248(18) 3.110(7) 174(6) 1_554
N10A H10A N4B 0.870(15) 2.43(4) 3.170(7) 143(6) 1_455
N10A H10A O8B 0.870(15) 2.47(5) 3.121(6) 132(5) 1_455
N10A H10B O8A 0.877(15) 2.08(3) 2.923(6) 160(6) 2_545
N6B H6C O9A 0.862(15) 2.25(3) 3.052(7) 154(6) 2_546
N6B H6C O9B 0.862(15) 2.43(5) 2.925(7) 117(5) .
N6B H6D N1A 0.877(15) 2.202(18) 3.075(7) 174(6) 1_556
N10B H10C O9B 0.872(15) 2.37(5) 3.004(6) 130(5) 2_656
N10B H10D N4A 0.865(15) 2.41(4) 3.173(6) 148(6) 1_655
N10B H10D O9A 0.865(15) 2.49(5) 3.134(6) 132(6) 1_655

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_shrv361
_database_code_depnum_ccdc_archive 'CCDC 1463787'
_audit_update_record             
;
2016-03-11 deposited with the CCDC.
2016-06-03 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         'C2 H4 N6 O2'
_chemical_formula_sum            'C2 H4 N6 O2'
_chemical_formula_weight         144.11

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.0055(7)
_cell_length_b                   6.4742(6)
_cell_length_c                   10.7844(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.2240(10)
_cell_angle_gamma                90
_cell_volume                     555.65(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3832
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.54

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.427
_exptl_crystal_size_mid          0.397
_exptl_crystal_size_min          0.089
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.7151
_exptl_absorpt_correction_T_max  0.7456

_diffrn_ambient_temperature      150(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  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5213
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.018
_diffrn_reflns_theta_max         27.543
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1290
_reflns_number_gt                1214
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_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)+(0.0494P)²+0.1838P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1290
_refine_ls_number_parameters     103
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0869
_refine_ls_wR_factor_gt          0.0855
_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
O1 O 0.27929(10) 0.58988(14) 0.73169(8) 0.0262(2) Uani 1 1 d . . . . .
O2 O 0.26831(10) 0.68650(14) 0.53690(8) 0.0246(2) Uani 1 1 d . . . . .
N3 N 0.34608(11) 0.65791(14) 0.64154(8) 0.0176(2) Uani 1 1 d . . . . .
C4 C 0.51862(12) 0.70044(16) 0.65450(9) 0.0152(2) Uani 1 1 d . . . . .
C5 C 0.61612(12) 0.75321(15) 0.55920(9) 0.0135(2) Uani 1 1 d . . . . .
N6 N 0.58318(12) 0.78814(15) 0.43757(8) 0.0175(2) Uani 1 1 d . . . . .
N7 N 0.77184(11) 0.76131(14) 0.62074(8) 0.0158(2) Uani 1 1 d . . . . .
N8 N 0.91326(11) 0.81585(17) 0.56425(9) 0.0216(2) Uani 1 1 d . . . . .
N9 N 0.77066(12) 0.71783(15) 0.74614(8) 0.0195(2) Uani 1 1 d . . . . .
N10 N 0.61695(11) 0.68039(15) 0.76508(8) 0.0190(2) Uani 1 1 d . . . . .
H6A H 0.665(2) 0.815(2) 0.3960(13) 0.023 Uiso 1 1 d . U . . .
H6B H 0.483(2) 0.783(2) 0.4027(14) 0.023 Uiso 1 1 d . U . . .
H8A H 0.9516(18) 0.931(2) 0.6018(13) 0.023 Uiso 1 1 d . U . . .
H8B H 0.9866(19) 0.715(2) 0.5729(13) 0.023 Uiso 1 1 d . U . . .

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
O1 0.0262(4) 0.0325(5) 0.0227(4) -0.0019(3) 0.0147(3) -0.0057(3)
O2 0.0147(4) 0.0372(5) 0.0214(4) 0.0015(3) -0.0005(3) 0.0017(3)
N3 0.0159(4) 0.0206(4) 0.0171(4) -0.0020(3) 0.0058(3) 0.0004(3)
C4 0.0149(5) 0.0182(5) 0.0128(5) 0.0003(3) 0.0024(4) 0.0002(4)
C5 0.0127(4) 0.0143(5) 0.0137(5) -0.0017(3) 0.0016(4) 0.0009(3)
N6 0.0143(4) 0.0273(5) 0.0108(4) 0.0005(3) 0.0020(3) -0.0004(3)
N7 0.0134(4) 0.0214(4) 0.0124(4) -0.0012(3) 0.0007(3) -0.0008(3)
N8 0.0123(4) 0.0322(5) 0.0209(5) -0.0055(4) 0.0045(3) -0.0037(4)
N9 0.0199(5) 0.0252(5) 0.0128(4) 0.0011(3) -0.0014(3) -0.0003(3)
N10 0.0200(4) 0.0227(5) 0.0140(4) 0.0016(3) 0.0006(3) -0.0011(3)

_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
O1 N3 1.2401(12) . ?
O2 N3 1.2422(12) . ?
N3 C4 1.4005(13) . ?
C4 N10 1.3620(13) . ?
C4 C5 1.3986(13) . ?
C5 N6 1.3291(13) . ?
C5 N7 1.3483(12) . ?
N6 H6A 0.850(16) . ?
N6 H6B 0.851(16) . ?
N7 N9 1.3824(12) . ?
N7 N8 1.3882(12) . ?
N8 H8A 0.889(16) . ?
N8 H8B 0.876(16) . ?
N9 N10 1.2919(13) . ?

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 N3 O2 123.30(9) . . ?
O1 N3 C4 119.74(9) . . ?
O2 N3 C4 116.94(9) . . ?
N10 C4 C5 110.55(9) . . ?
N10 C4 N3 122.60(9) . . ?
C5 C4 N3 126.70(9) . . ?
N6 C5 N7 123.58(9) . . ?
N6 C5 C4 134.43(9) . . ?
N7 C5 C4 101.99(8) . . ?
C5 N6 H6A 118.3(10) . . ?
C5 N6 H6B 120.4(10) . . ?
H6A N6 H6B 121.3(14) . . ?
C5 N7 N9 111.69(8) . . ?
C5 N7 N8 123.26(9) . . ?
N9 N7 N8 124.99(8) . . ?
N7 N8 H8A 105.8(9) . . ?
N7 N8 H8B 109.4(10) . . ?
H8A N8 H8B 112.6(13) . . ?
N10 N9 N7 107.48(8) . . ?
N9 N10 C4 108.29(8) . . ?

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
O1 N3 C4 N10 -3.52(16) . . . . ?
O2 N3 C4 N10 178.29(10) . . . . ?
O1 N3 C4 C5 171.67(10) . . . . ?
O2 N3 C4 C5 -6.53(16) . . . . ?
N10 C4 C5 N6 179.33(11) . . . . ?
N3 C4 C5 N6 3.7(2) . . . . ?
N10 C4 C5 N7 0.11(12) . . . . ?
N3 C4 C5 N7 -175.56(10) . . . . ?
N6 C5 N7 N9 -179.73(9) . . . . ?
C4 C5 N7 N9 -0.40(11) . . . . ?
N6 C5 N7 N8 2.88(16) . . . . ?
C4 C5 N7 N8 -177.79(9) . . . . ?
C5 N7 N9 N10 0.57(12) . . . . ?
N8 N7 N9 N10 177.91(10) . . . . ?
N7 N9 N10 C4 -0.47(12) . . . . ?
C5 C4 N10 N9 0.23(13) . . . . ?
N3 C4 N10 N9 176.11(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N6 H6A O1 0.850(16) 2.170(16) 2.9620(12) 154.9(13) 4_675
N6 H6B O2 0.851(16) 2.442(16) 2.9189(13) 116.1(12) .
N6 H6A N8 0.850(16) 2.542(14) 2.8458(13) 102.2(11) .
N6 H6B N9 0.851(16) 2.261(16) 3.0664(13) 158.0(14) 4_575
N8 H8A N10 0.889(16) 2.266(15) 3.0188(14) 142.4(13) 2_656
N8 H8B O2 0.876(16) 2.337(15) 3.0082(12) 133.5(13) 1_655

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.085
