# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_dm16178
_database_code_depnum_ccdc_archive 'CCDC 1905201'
loop_
_audit_author_name
_audit_author_address
'Xiaowei Guo'
;Northeast Agricultural University
China
;
_audit_update_record             
;
2019-03-24 deposited with the CCDC.	2019-07-18 downloaded from the CCDC.
;
_audit_creation_date             2016-04-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H13 N5 O4'
_chemical_formula_sum            'C9 H13 N5 O4'
_chemical_formula_weight         255.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.3117(2)
_cell_length_b                   17.2043(4)
_cell_length_c                   8.3018(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.2310(10)
_cell_angle_gamma                90
_cell_volume                     1155.62(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6074
_cell_measurement_temperature    130
_cell_measurement_theta_max      69.315
_cell_measurement_theta_min      5.141
_shelx_estimated_absorpt_T_max   0.825
_shelx_estimated_absorpt_T_min   0.788
_exptl_absorpt_coefficient_mu    1.003
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0961 before and 0.0445 after correction.
The Ratio of minimum to maximum transmission is 0.6682.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8428
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.354
_diffrn_reflns_theta_min         5.142
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2029
_reflns_number_total             2084
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.748
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0088(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.674
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2084
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      0.674
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0930P)²+3.1499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1260
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.11186(18) 0.31122(8) 0.28057(18) 0.0266(4) Uani 1 1 d . . . . .
O2 O 0.48459(17) 0.13409(9) 0.1988(2) 0.0304(4) Uani 1 1 d . . . . .
O3 O 0.29865(18) -0.10340(8) 0.16592(18) 0.0289(4) Uani 1 1 d . . . . .
O4 O 0.1602(2) 0.10291(9) 0.45214(18) 0.0314(4) Uani 1 1 d . . . . .
N1 N 0.04372(19) 0.12721(9) 0.0825(2) 0.0197(4) Uani 1 1 d . . . . .
H1 H -0.0370 0.0948 0.0706 0.024 Uiso 1 1 d R . . . .
N2 N 0.01300(19) 0.19842(9) 0.1557(2) 0.0208(4) Uani 1 1 d . . . . .
N3 N 0.29369(19) 0.22875(9) 0.1993(2) 0.0214(4) Uani 1 1 d . . . . .
N4 N 0.23746(19) 0.02414(9) 0.0886(2) 0.0205(4) Uani 1 1 d . . . . .
N5 N 0.2235(2) -0.01302(10) 0.3420(2) 0.0242(4) Uani 1 1 d . . . . .
C1 C -0.1509(2) 0.20676(12) 0.1886(3) 0.0273(5) Uani 1 1 d . . . . .
H1A H -0.2345 0.1906 0.0909 0.041 Uiso 1 1 calc GR . . . .
H1B H -0.1692 0.2612 0.2141 0.041 Uiso 1 1 calc GR . . . .
H1C H -0.1591 0.1741 0.2831 0.041 Uiso 1 1 calc GR . . . .
C2 C 0.1336(2) 0.24972(11) 0.2154(2) 0.0201(4) Uani 1 1 d . . . . .
C3 C 0.4211(3) 0.28941(12) 0.2329(3) 0.0284(5) Uani 1 1 d . . . . .
H3A H 0.3719 0.3394 0.1919 0.043 Uiso 1 1 calc GR . . . .
H3B H 0.5093 0.2764 0.1769 0.043 Uiso 1 1 calc GR . . . .
H3C H 0.4672 0.2929 0.3524 0.043 Uiso 1 1 calc GR . . . .
C4 C 0.3426(2) 0.15342(11) 0.1894(2) 0.0206(4) Uani 1 1 d . . . . .
C5 C 0.2016(2) 0.09406(11) 0.1688(2) 0.0193(4) Uani 1 1 d . . . . .
C6 C 0.1909(2) 0.06423(11) 0.3409(2) 0.0219(4) Uani 1 1 d . . . . .
C7 C 0.2578(2) -0.03792(11) 0.1918(2) 0.0208(4) Uani 1 1 d . . . . .
C8 C 0.2249(3) -0.06543(14) 0.4800(3) 0.0383(6) Uani 1 1 d . . . . .
H8A H 0.2440 -0.0356 0.5832 0.057 Uiso 1 1 calc GR . . . .
H8B H 0.3134 -0.1038 0.4869 0.057 Uiso 1 1 calc GR . . . .
H8C H 0.1183 -0.0922 0.4629 0.057 Uiso 1 1 calc GR . . . .
C9 C 0.2723(3) 0.02084(12) -0.0754(3) 0.0264(5) Uani 1 1 d . . . . .
H9A H 0.3648 0.0556 -0.0794 0.040 Uiso 1 1 calc GR . . . .
H9B H 0.1743 0.0373 -0.1582 0.040 Uiso 1 1 calc GR . . . .
H9C H 0.3014 -0.0325 -0.0989 0.040 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.220(2) . ?
O2 C4 1.211(2) . ?
O3 C7 1.210(2) . ?
O4 C6 1.212(2) . ?
N1 H1 0.8600 . ?
N1 N2 1.416(2) . ?
N1 C5 1.460(2) . ?
N2 C1 1.456(2) . ?
N2 C2 1.342(2) . ?
N3 C2 1.414(2) . ?
N3 C3 1.467(2) . ?
N3 C4 1.366(3) . ?
N4 C5 1.439(2) . ?
N4 C7 1.355(2) . ?
N4 C9 1.456(3) . ?
N5 C6 1.356(3) . ?
N5 C7 1.408(3) . ?
N5 C8 1.456(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.534(3) . ?
C5 C6 1.540(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 H1 113.4 . . ?
N2 N1 C5 110.95(14) . . ?
C5 N1 H1 113.1 . . ?
N1 N2 C1 115.72(15) . . ?
C2 N2 N1 122.32(15) . . ?
C2 N2 C1 121.13(16) . . ?
C2 N3 C3 117.03(16) . . ?
C4 N3 C2 123.16(16) . . ?
C4 N3 C3 118.31(16) . . ?
C5 N4 C9 124.86(16) . . ?
C7 N4 C5 112.07(15) . . ?
C7 N4 C9 122.50(16) . . ?
C6 N5 C7 111.89(16) . . ?
C6 N5 C8 125.32(18) . . ?
C7 N5 C8 122.79(17) . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N2 124.07(17) . . ?
O1 C2 N3 120.05(17) . . ?
N2 C2 N3 115.87(16) . . ?
N3 C3 H3A 109.5 . . ?
N3 C3 H3B 109.5 . . ?
N3 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 N3 123.74(18) . . ?
O2 C4 C5 122.17(17) . . ?
N3 C4 C5 114.07(15) . . ?
N1 C5 C4 111.88(15) . . ?
N1 C5 C6 110.42(15) . . ?
N4 C5 N1 110.96(15) . . ?
N4 C5 C4 111.99(15) . . ?
N4 C5 C6 102.28(15) . . ?
C4 C5 C6 108.87(15) . . ?
O4 C6 N5 127.57(19) . . ?
O4 C6 C5 126.23(18) . . ?
N5 C6 C5 106.20(16) . . ?
O3 C7 N4 128.40(19) . . ?
O3 C7 N5 124.22(18) . . ?
N4 C7 N5 107.38(16) . . ?
N5 C8 H8A 109.5 . . ?
N5 C8 H8B 109.5 . . ?
N5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N4 C9 H9A 109.5 . . ?
N4 C9 H9B 109.5 . . ?
N4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C4 C5 N1 -152.02(18) . . . . ?
O2 C4 C5 N4 -26.7(3) . . . . ?
O2 C4 C5 C6 85.7(2) . . . . ?
N1 N2 C2 O1 -179.30(17) . . . . ?
N1 N2 C2 N3 0.7(3) . . . . ?
N1 C5 C6 O4 -60.8(2) . . . . ?
N1 C5 C6 N5 119.62(16) . . . . ?
N2 N1 C5 N4 -176.59(14) . . . . ?
N2 N1 C5 C4 -50.7(2) . . . . ?
N2 N1 C5 C6 70.73(18) . . . . ?
N3 C4 C5 N1 29.2(2) . . . . ?
N3 C4 C5 N4 154.53(16) . . . . ?
N3 C4 C5 C6 -93.10(19) . . . . ?
N4 C5 C6 O4 -178.92(19) . . . . ?
N4 C5 C6 N5 1.47(19) . . . . ?
C1 N2 C2 O1 -10.2(3) . . . . ?
C1 N2 C2 N3 169.75(17) . . . . ?
C2 N3 C4 O2 -169.31(18) . . . . ?
C2 N3 C4 C5 9.4(3) . . . . ?
C3 N3 C2 O1 -11.7(3) . . . . ?
C3 N3 C2 N2 168.29(17) . . . . ?
C3 N3 C4 O2 -3.7(3) . . . . ?
C3 N3 C4 C5 175.03(17) . . . . ?
C4 N3 C2 O1 154.04(18) . . . . ?
C4 N3 C2 N2 -25.9(3) . . . . ?
C4 C5 C6 O4 62.4(2) . . . . ?
C4 C5 C6 N5 -117.18(17) . . . . ?
C5 N1 N2 C1 -132.25(17) . . . . ?
C5 N1 N2 C2 37.4(2) . . . . ?
C5 N4 C7 O3 -175.07(18) . . . . ?
C5 N4 C7 N5 4.5(2) . . . . ?
C6 N5 C7 O3 176.13(18) . . . . ?
C6 N5 C7 N4 -3.5(2) . . . . ?
C7 N4 C5 N1 -121.49(17) . . . . ?
C7 N4 C5 C4 112.70(17) . . . . ?
C7 N4 C5 C6 -3.72(19) . . . . ?
C7 N5 C6 O4 -178.47(19) . . . . ?
C7 N5 C6 C5 1.1(2) . . . . ?
C8 N5 C6 O4 1.2(3) . . . . ?
C8 N5 C6 C5 -179.25(19) . . . . ?
C8 N5 C7 O3 -3.5(3) . . . . ?
C8 N5 C7 N4 176.87(18) . . . . ?
C9 N4 C5 N1 67.0(2) . . . . ?
C9 N4 C5 C4 -58.8(2) . . . . ?
C9 N4 C5 C6 -175.21(17) . . . . ?
C9 N4 C7 O3 -3.3(3) . . . . ?
C9 N4 C7 N5 176.26(17) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
