# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_d8v17148
_database_code_depnum_ccdc_archive 'CCDC 1916325'
loop_
_audit_author_name
_audit_author_address
'zhang jichuan'
;Shanghai institute of Organnic Chemistry,Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-05-15 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_audit_creation_date             2017-06-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/8
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C3 H6 N6 O)'
_chemical_formula_sum            'C6 H12 N12 O2'
_chemical_formula_weight         284.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   3.6422(9)
_cell_length_b                   21.241(4)
_cell_length_c                   15.081(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.902(8)
_cell_angle_gamma                90
_cell_volume                     1160.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3309
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.03
_cell_measurement_theta_min      2.879
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.40
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1573 before and 0.0836 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1922 before and 0.0689 after correction.
 The Ratio of minimum to maximum transmission is 0.41.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 18610 reflections, Rint = 0.1005
 (7302 with I > 3sig(I), Rint = 0.0759)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1041
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3547
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.579
_diffrn_reflns_theta_min         1.918
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2265
_reflns_number_total             3547
_reflns_special_details          
;
 _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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       0.026(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/8 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1461
_refine_ls_R_factor_gt           0.0918
_refine_ls_restrained_S_all      1.039
_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)+(0.1553P)²+0.6257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2307
_refine_ls_wR_factor_ref         0.2745
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.588(4)
 0.412(4)
2. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
3.a Rotating group:
 N3(H3A,H3B), N4(H4A,H4B), N6(H6A,H6B), N10(H10A,H10B)
3.b X=CH2 refined with riding coordinates:
 N9(H9A,H9B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.6651(9) 0.60485(12) 0.86889(16) 0.0300(7) Uani 1 1 d . . . . .
N1 N 0.5953(10) 0.59691(15) 0.77798(19) 0.0265(7) Uani 1 1 d . . . . .
N2 N 0.5558(10) 0.55096(15) 0.91441(19) 0.0278(8) Uani 1 1 d . . . . .
N3 N 0.3043(11) 0.45345(15) 0.8682(2) 0.0303(8) Uani 1 1 d . . . . .
H3A H 0.2282 0.4528 0.9219 0.036 Uiso 1 1 d GR . . . .
H3B H 0.1197 0.4433 0.8282 0.036 Uiso 1 1 d GR . . . .
N4 N 0.3895(9) 0.55448(15) 0.6043(2) 0.0263(7) Uani 1 1 d . . . . .
H4A H 0.5244 0.5874 0.6231 0.032 Uiso 1 1 d GR . . . .
H4B H 0.5091 0.5329 0.5661 0.032 Uiso 1 1 d GR . . . .
N5 N 0.1921(10) 0.46201(15) 0.67337(19) 0.0239(7) Uani 1 1 d . . . . .
N6 N 0.0888(10) 0.43936(15) 0.5861(2) 0.0273(7) Uani 1 1 d . . . . .
H6A H 0.0682 0.3980 0.5874 0.033 Uiso 1 1 d GR . . . .
H6B H -0.1248 0.4559 0.5653 0.033 Uiso 1 1 d GR . . . .
C1 C 0.4260(11) 0.51207(17) 0.8519(2) 0.0232(8) Uani 1 1 d . . . . .
C2 C 0.4484(10) 0.54128(16) 0.7659(2) 0.0208(7) Uani 1 1 d . . . . .
C3 C 0.3328(11) 0.51718(17) 0.6766(2) 0.0215(7) Uani 1 1 d . . . . .
O2 O 0.7496(9) 0.69403(13) 0.49757(16) 0.0330(7) Uani 1 1 d . . . . .
N7 N 0.7868(10) 0.69463(14) 0.58995(18) 0.0237(7) Uani 1 1 d . . . . .
N8 N 0.8855(11) 0.75039(16) 0.46416(19) 0.0306(8) Uani 1 1 d . . . . .
N9 N 1.1454(10) 0.84243(16) 0.5326(2) 0.0292(8) Uani 1 1 d . . . . .
H9A H 1.1709 0.8610 0.4815 0.035 Uiso 1 1 calc R . . . .
H9B H 1.2153 0.8619 0.5831 0.035 Uiso 1 1 calc R . . . .
N10 N 0.9747(10) 0.72395(15) 0.76984(19) 0.0260(7) Uani 1 1 d . . . . .
H10A H 0.9228 0.7431 0.8192 0.031 Uiso 1 1 d GR . . . .
H10B H 0.7865 0.6994 0.7506 0.031 Uiso 1 1 d GR . . . .
N11 N 1.1828(9) 0.82163(15) 0.71758(18) 0.0230(7) Uani 1 1 d . . . . .
N12 N 1.2834(13) 0.83771(18) 0.8067(2) 0.0281(8) Uani 1 1 d . . . . .
H12A H 1.458(13) 0.877(2) 0.802(3) 0.033(12) Uiso 1 1 d . . . . .
H12B H 1.364(17) 0.818(2) 0.826(3) 0.033(18) Uiso 1 1 d . . . . .
C4 C 0.9992(11) 0.78415(18) 0.5338(2) 0.0223(8) Uani 1 1 d . . . . .
C5 C 0.9359(10) 0.74877(16) 0.6133(2) 0.0178(7) Uani 1 1 d . . . . .
C6 C 1.0319(10) 0.76717(16) 0.7059(2) 0.0181(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.379(4) . ?
O1 N2 1.413(4) . ?
N1 C2 1.302(5) . ?
N2 C1 1.305(5) . ?
N3 H3A 0.8825 . ?
N3 H3B 0.8822 . ?
N3 C1 1.353(5) . ?
N4 H4A 0.8841 . ?
N4 H4B 0.8844 . ?
N4 C3 1.381(5) . ?
N5 N6 1.415(4) . ?
N5 C3 1.278(5) . ?
N6 H6A 0.8818 . ?
N6 H6B 0.8817 . ?
C1 C2 1.448(5) . ?
C2 C3 1.462(5) . ?
O2 N7 1.386(3) . ?
O2 N8 1.408(4) . ?
N7 C5 1.304(5) . ?
N8 C4 1.304(5) . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
N9 C4 1.348(5) . ?
N10 H10A 0.8858 . ?
N10 H10B 0.8857 . ?
N10 C6 1.363(4) . ?
N11 N12 1.399(4) . ?
N11 C6 1.285(5) . ?
N12 H12A 1.06(5) . ?
N12 H12B 0.57(5) . ?
C4 C5 1.453(4) . ?
C5 C6 1.458(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
N1 O1 N2 110.6(3) . . ?
C2 N1 O1 106.3(3) . . ?
C1 N2 O1 105.1(3) . . ?
H3A N3 H3B 109.5 . . ?
C1 N3 H3A 108.7 . . ?
C1 N3 H3B 110.0 . . ?
H4A N4 H4B 108.9 . . ?
C3 N4 H4A 108.8 . . ?
C3 N4 H4B 109.9 . . ?
C3 N5 N6 114.5(3) . . ?
N5 N6 H6A 109.5 . . ?
N5 N6 H6B 109.6 . . ?
H6A N6 H6B 109.3 . . ?
N2 C1 N3 123.6(3) . . ?
N2 C1 C2 109.1(3) . . ?
N3 C1 C2 127.3(3) . . ?
N1 C2 C1 108.9(3) . . ?
N1 C2 C3 121.5(3) . . ?
C1 C2 C3 129.7(3) . . ?
N4 C3 C2 118.3(3) . . ?
N5 C3 N4 126.0(3) . . ?
N5 C3 C2 115.6(3) . . ?
N7 O2 N8 110.5(2) . . ?
C5 N7 O2 105.9(3) . . ?
C4 N8 O2 105.9(3) . . ?
H9A N9 H9B 120.0 . . ?
C4 N9 H9A 120.0 . . ?
C4 N9 H9B 120.0 . . ?
H10A N10 H10B 108.7 . . ?
C6 N10 H10A 110.3 . . ?
C6 N10 H10B 109.5 . . ?
C6 N11 N12 114.7(3) . . ?
N11 N12 H12A 103(2) . . ?
N11 N12 H12B 113(5) . . ?
H12A N12 H12B 110(7) . . ?
N8 C4 N9 126.0(3) . . ?
N8 C4 C5 108.4(3) . . ?
N9 C4 C5 125.6(3) . . ?
N7 C5 C4 109.3(3) . . ?
N7 C5 C6 123.2(3) . . ?
C4 C5 C6 127.5(3) . . ?
N10 C6 C5 117.3(3) . . ?
N11 C6 N10 127.1(3) . . ?
N11 C6 C5 115.5(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.588(4)
2 0.412(4)

####################################################################### 
# 
# 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_cd17168
_database_code_depnum_ccdc_archive 'CCDC 1916326'
loop_
_audit_author_name
_audit_author_address
'zhang jichuan'
;Shanghai institute of Organnic Chemistry,Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-05-15 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H7 N10 O2'
_chemical_formula_weight         227.20

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   14.685(10)
_cell_length_b                   7.065(5)
_cell_length_c                   8.601(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.627(15)
_cell_angle_gamma                90
_cell_volume                     890.5(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    828
_cell_measurement_theta_min      5.559
_cell_measurement_theta_max      45.858

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.140
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3520
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4615
_diffrn_reflns_av_unetI/netI     0.1437
_diffrn_reflns_av_R_equivalents  0.1706
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.780
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             1565
_reflns_number_gt                1150
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0502P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1565
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0744
_refine_ls_wR_factor_ref         0.1776
_refine_ls_wR_factor_gt          0.1648
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.93490(18) 0.9953(4) 0.3078(3) 0.0285(7) Uani 1 1 d . . . . .
N2 N 0.9673(2) 0.9603(4) 0.1701(3) 0.0362(8) Uani 1 1 d . . . . .
N3 N 1.0559(2) 0.9290(4) 0.1949(3) 0.0387(8) Uani 1 1 d . . . . .
N4 N 1.07981(19) 0.9461(4) 0.3482(2) 0.0339(7) Uani 1 1 d . . . . .
N5 N 0.6497(2) 0.6483(5) 0.7766(3) 0.0447(8) Uani 1 1 d . . . . .
N6 N 0.5542(2) 0.8017(5) 0.5998(3) 0.0501(9) Uani 1 1 d . . . . .
N7 N 0.6034(2) 1.1132(5) 0.6450(3) 0.0542(9) Uani 1 1 d . . . . .
H7A H 0.5675 1.1572 0.5707 0.065 Uiso 1 1 calc R U . . .
H7B H 0.6384 1.1886 0.6997 0.065 Uiso 1 1 calc R U . . .
N8 N 0.72213(19) 1.0925(4) 0.9162(3) 0.0378(8) Uani 1 1 d . . . . .
N9 N 0.7916(3) 1.1763(6) 1.0213(4) 0.0518(10) Uani 1 1 d . . . . .
N10 N 0.7926(2) 0.7949(5) 0.9710(3) 0.0420(8) Uani 1 1 d . . . . .
O1 O 0.84794(15) 1.0334(3) 0.3210(2) 0.0349(7) Uani 1 1 d . . . . .
O2 O 0.58220(17) 0.6252(4) 0.6603(2) 0.0512(8) Uani 1 1 d . . . . .
C1 C 1.0040(2) 0.9849(4) 0.4175(3) 0.0284(8) Uani 1 1 d . . . . .
C2 C 0.6046(2) 0.9269(6) 0.6757(3) 0.0372(9) Uani 1 1 d . . . . .
C3 C 0.6639(2) 0.8288(6) 0.7868(3) 0.0327(8) Uani 1 1 d . . . . .
C4 C 0.7323(2) 0.9125(5) 0.8995(3) 0.0317(8) Uani 1 1 d . . . . .
H10B H 0.806(3) 0.678(6) 0.931(4) 0.046(11) Uiso 1 1 d . . . . .
H10A H 0.841(4) 0.844(8) 1.029(5) 0.093(16) Uiso 1 1 d . . . . .
H9A H 0.834(5) 1.231(9) 0.970(7) 0.14(3) Uiso 1 1 d . . . . .
H9B H 0.800(3) 1.121(7) 1.104(5) 0.061(13) Uiso 1 1 d . . . . .
H9C H 0.762(5) 1.285(9) 1.031(6) 0.11(3) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 O1 1.317(4) . ?
N1 N2 1.328(3) . ?
N1 C1 1.343(4) . ?
N2 N3 1.324(4) . ?
N3 N4 1.348(3) . ?
N4 C1 1.324(4) . ?
N5 C3 1.294(5) . ?
N5 O2 1.372(4) . ?
N5 O1 5.716(4) . ?
N6 C2 1.302(5) . ?
N6 O2 1.403(4) . ?
N7 C2 1.342(5) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N8 C4 1.290(5) . ?
N8 N9 1.446(4) . ?
N9 H9A 0.88(6) . ?
N9 H9B 0.82(5) . ?
N9 H9C 0.89(7) . ?
N10 C4 1.335(4) . ?
N10 H10B 0.92(4) . ?
N10 H10A 0.92(6) . ?
C1 C1 1.447(5) 3_776 ?
C2 C3 1.430(5) . ?
C3 C4 1.475(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
O1 N1 N2 121.3(2) . . ?
O1 N1 C1 130.1(2) . . ?
N2 N1 C1 108.6(2) . . ?
N3 N2 N1 106.9(2) . . ?
N2 N3 N4 109.6(2) . . ?
C1 N4 N3 106.5(3) . . ?
C3 N5 O2 105.8(3) . . ?
C3 N5 O1 59.38(17) . . ?
O2 N5 O1 86.14(17) . . ?
C2 N6 O2 105.9(3) . . ?
C2 N7 H7A 120.0 . . ?
C2 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C4 N8 N9 113.0(3) . . ?
N8 N9 H9A 111(4) . . ?
N8 N9 H9B 114(3) . . ?
H9A N9 H9B 126(5) . . ?
N8 N9 H9C 95(4) . . ?
H9A N9 H9C 92(5) . . ?
H9B N9 H9C 112(5) . . ?
C4 N10 H10B 123(2) . . ?
C4 N10 H10A 119(4) . . ?
H10B N10 H10A 111(4) . . ?
N1 O1 N5 120.04(16) . . ?
N5 O2 N6 110.2(2) . . ?
N4 C1 N1 108.3(2) . . ?
N4 C1 C1 126.5(4) . 3_776 ?
N1 C1 C1 125.2(4) . 3_776 ?
N6 C2 N7 124.6(3) . . ?
N6 C2 C3 107.9(4) . . ?
N7 C2 C3 127.3(3) . . ?
N5 C3 C2 110.1(3) . . ?
N5 C3 C4 122.7(3) . . ?
C2 C3 C4 127.2(4) . . ?
N8 C4 N10 129.8(3) . . ?
N8 C4 C3 113.0(3) . . ?
N10 C4 C3 117.2(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
O1 N1 N2 N3 179.5(3) . . . . ?
C1 N1 N2 N3 -0.2(4) . . . . ?
N1 N2 N3 N4 -0.6(4) . . . . ?
N2 N3 N4 C1 1.2(4) . . . . ?
N2 N1 O1 N5 131.4(2) . . . . ?
C1 N1 O1 N5 -48.9(4) . . . . ?
C3 N5 O2 N6 -0.7(3) . . . . ?
O1 N5 O2 N6 -57.4(2) . . . . ?
C2 N6 O2 N5 1.1(3) . . . . ?
N3 N4 C1 N1 -1.3(4) . . . . ?
N3 N4 C1 C1 179.9(4) . . . 3_776 ?
O1 N1 C1 N4 -178.7(3) . . . . ?
N2 N1 C1 N4 0.9(4) . . . . ?
O1 N1 C1 C1 0.1(6) . . . 3_776 ?
N2 N1 C1 C1 179.8(4) . . . 3_776 ?
O2 N6 C2 N7 175.2(3) . . . . ?
O2 N6 C2 C3 -0.9(3) . . . . ?
O2 N5 C3 C2 0.2(3) . . . . ?
O1 N5 C3 C2 75.8(2) . . . . ?
O2 N5 C3 C4 -179.9(2) . . . . ?
O1 N5 C3 C4 -104.3(3) . . . . ?
N6 C2 C3 N5 0.5(4) . . . . ?
N7 C2 C3 N5 -175.5(3) . . . . ?
N6 C2 C3 C4 -179.4(3) . . . . ?
N7 C2 C3 C4 4.6(5) . . . . ?
N9 N8 C4 N10 4.6(5) . . . . ?
N9 N8 C4 C3 -177.3(3) . . . . ?
N5 C3 C4 N8 -165.2(3) . . . . ?
C2 C3 C4 N8 14.6(4) . . . . ?
N5 C3 C4 N10 13.1(4) . . . . ?
C2 C3 C4 N10 -167.1(3) . . . . ?

_refine_diff_density_max         0.315
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.084

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd17170
_database_code_depnum_ccdc_archive 'CCDC 1916327'
loop_
_audit_author_name
_audit_author_address
'zhang jichuan'
;Shanghai institute of Organnic Chemistry,Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-05-15 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H9 N7 O5'
_chemical_formula_weight         223.17

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-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                   6.8490(11)
_cell_length_b                   11.5108(19)
_cell_length_c                   22.982(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1811.8(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3683
_cell_measurement_theta_min      6.926
_cell_measurement_theta_max      55.783

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6714
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9442
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.772
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1683
_reflns_number_gt                1547
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0675P)²+0.4968P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1683
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3174(2) 0.97403(12) 0.18890(6) 0.0316(4) Uani 1 1 d . . . . .
N2 N 0.3386(2) 0.94528(13) 0.28701(6) 0.0316(4) Uani 1 1 d . . . . .
N3 N 0.4660(2) 0.75584(14) 0.28758(7) 0.0321(4) Uani 1 1 d . . . . .
N4 N 0.5027(2) 0.69196(11) 0.16839(6) 0.0265(3) Uani 1 1 d . . . . .
N5 N 0.5502(2) 0.61257(13) 0.12185(6) 0.0275(4) Uani 1 1 d . . . . .
N6 N 0.3969(3) 0.82642(15) 0.09665(7) 0.0345(4) Uani 1 1 d . . . . .
N7 N 0.5569(2) 1.29883(13) 0.05119(6) 0.0323(4) Uani 1 1 d . . . . .
O1 O 0.28777(19) 1.02342(10) 0.24229(5) 0.0359(4) Uani 1 1 d . . . . .
O2 O 0.4530(2) 1.29548(13) 0.00726(5) 0.0439(4) Uani 1 1 d . . . . .
O3 O 0.5779(2) 1.20776(13) 0.08142(6) 0.0476(4) Uani 1 1 d . . . . .
O4 O 0.6388(3) 1.38933(14) 0.06589(7) 0.0583(5) Uani 1 1 d . . . . .
O5 O 0.2729(2) 1.05100(12) 0.05300(7) 0.0394(4) Uani 1 1 d . . . . .
C1 C 0.3983(2) 0.85098(13) 0.26043(7) 0.0246(4) Uani 1 1 d . . . . .
C2 C 0.3842(2) 0.87059(13) 0.19850(7) 0.0242(4) Uani 1 1 d . . . . .
C3 C 0.4329(2) 0.79046(13) 0.15046(7) 0.0240(4) Uani 1 1 d . . . . .
H7 H 0.361(5) 1.099(3) 0.0590(13) 0.074(9) Uiso 1 1 d . . . . .
H8 H 0.240(4) 1.049(2) 0.0200(14) 0.061(8) Uiso 1 1 d . . . . .
H5A H 0.588(3) 0.549(2) 0.1388(8) 0.034(5) Uiso 1 1 d . . . . .
H6A H 0.362(3) 0.898(2) 0.0934(10) 0.045(6) Uiso 1 1 d . . . . .
H5B H 0.648(3) 0.6405(19) 0.1004(10) 0.041(6) Uiso 1 1 d . . . . .
H6B H 0.433(3) 0.7883(19) 0.0717(10) 0.034(6) Uiso 1 1 d . . . . .
H5C H 0.442(3) 0.5951(19) 0.0989(10) 0.040(5) Uiso 1 1 d . . . . .
H3A H 0.450(3) 0.7478(18) 0.3252(11) 0.042(6) Uiso 1 1 d . . . . .
H3B H 0.482(3) 0.6986(19) 0.2680(10) 0.036(6) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag


N1 C2 1.295(2) . ?
N1 O1 1.3675(18) . ?
N2 C1 1.311(2) . ?
N2 O1 1.4095(19) . ?
N3 C1 1.343(2) . ?
N3 H3A 0.88(3) . ?
N3 H3B 0.80(2) . ?
N4 C3 1.298(2) . ?
N4 N5 1.4438(19) . ?
N5 H5A 0.86(2) . ?
N5 H5B 0.89(2) . ?
N5 H5C 0.93(2) . ?
N6 C3 1.327(2) . ?
N6 H6A 0.86(3) . ?
N6 H6B 0.76(2) . ?
N7 O4 1.231(2) . ?
N7 O2 1.236(2) . ?
N7 O3 1.266(2) . ?
O5 H7 0.83(4) . ?
O5 H7 0.83(4) . ?
O5 H8 0.79(3) . ?
C1 C2 1.444(2) . ?
C2 C3 1.477(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
C2 N1 O1 106.37(13) . . ?
C1 N2 O1 105.42(12) . . ?
C1 N3 H3A 120.1(14) . . ?
C1 N3 H3B 117.0(15) . . ?
H3A N3 H3B 119(2) . . ?
C3 N4 N5 113.63(13) . . ?
N4 N5 H5A 105.5(13) . . ?
N4 N5 H5B 110.5(14) . . ?
H5A N5 H5B 109(2) . . ?
N4 N5 H5C 112.1(13) . . ?
H5A N5 H5C 108.2(19) . . ?
H5B N5 H5C 111.1(19) . . ?
C3 N6 H6A 115.6(15) . . ?
C3 N6 H6B 117.5(16) . . ?
H6A N6 H6B 125(2) . . ?
O4 N7 O2 120.89(16) . . ?
O4 N7 O3 119.89(16) . . ?
O2 N7 O3 119.22(15) . . ?
N1 O1 N2 110.63(11) . . ?
N7 O3 H7 106.9(8) . . ?
H7 O5 H6A 106(2) . . ?
H7 O5 H7 0(6) . . ?
H6A O5 H7 106(2) . . ?
H7 O5 H8 113(3) . . ?
H6A O5 H8 119(2) . . ?
H7 O5 H8 113(3) . . ?
N2 C1 N3 124.50(15) . . ?
N2 C1 C2 107.99(14) . . ?
N3 C1 C2 127.47(15) . . ?
N1 C2 C1 109.60(14) . . ?
N1 C2 C3 121.79(14) . . ?
C1 C2 C3 128.61(14) . . ?
N4 C3 N6 129.55(15) . . ?
N4 C3 C2 113.05(13) . . ?
N6 C3 C2 117.38(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
C2 N1 O1 N2 -0.31(17) . . . . ?
C1 N2 O1 N1 0.22(17) . . . . ?
O4 N7 O3 H7 162.1(9) . . . . ?
O2 N7 O3 H7 -17.5(9) . . . . ?
O1 N2 C1 N3 177.87(15) . . . . ?
O1 N2 C1 C2 -0.05(16) . . . . ?
O1 N1 C2 C1 0.27(17) . . . . ?
O1 N1 C2 C3 179.75(13) . . . . ?
N2 C1 C2 N1 -0.14(18) . . . . ?
N3 C1 C2 N1 -177.99(16) . . . . ?
N2 C1 C2 C3 -179.57(15) . . . . ?
N3 C1 C2 C3 2.6(3) . . . . ?
N5 N4 C3 N6 1.3(3) . . . . ?
N5 N4 C3 C2 179.75(13) . . . . ?
N1 C2 C3 N4 178.24(14) . . . . ?
C1 C2 C3 N4 -2.4(2) . . . . ?
N1 C2 C3 N6 -3.1(2) . . . . ?
C1 C2 C3 N6 176.28(15) . . . . ?

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
N3 H3B O1 0.80(2) 2.57(2) 3.236(2) 141(2) 3_645
N3 H3B N4 0.80(2) 2.30(2) 2.847(2) 126.4(18) .
N3 H3A O3 0.88(3) 2.20(3) 3.076(2) 174(2) 3_645
N5 H5C O5 0.93(2) 1.88(2) 2.811(2) 177(2) 8_655
N6 H6B O2 0.76(2) 2.20(2) 2.954(2) 171(2) 5_675
N5 H5B O3 0.89(2) 2.08(2) 2.924(2) 158.2(19) 8_755
N6 H6A O5 0.86(3) 2.08(3) 2.900(2) 158(2) .
N5 H5A O4 0.86(2) 2.51(2) 2.937(2) 111.0(15) 1_545
N5 H5A N2 0.86(2) 2.14(2) 2.945(2) 153.9(18) 3_645
O5 H8 O4 0.79(3) 2.21(3) 2.963(2) 159(3) 4_475
O5 H7 O3 0.83(4) 2.01(4) 2.837(2) 174(3) .
O5 H7 O2 0.83(4) 2.63(3) 3.247(2) 132(3) .
O5 H7 N7 0.83(4) 2.67(4) 3.453(2) 158(3) .
N6 H6A O5 0.86(3) 2.08(3) 2.900(2) 158(2) .
N6 H6B O2 0.76(2) 2.20(2) 2.954(2) 171(2) 5_675
N5 H5B O2 0.89(2) 2.67(2) 3.151(2) 114.8(16) 5_675
N5 H5B O3 0.89(2) 2.08(2) 2.924(2) 158.2(19) 8_755
N5 H5A O4 0.86(2) 2.51(2) 2.937(2) 111.0(15) 1_545
N5 H5A N2 0.86(2) 2.14(2) 2.945(2) 153.9(18) 3_645
O5 H8 O4 0.79(3) 2.21(3) 2.963(2) 159(3) 4_475
O5 H7 N7 0.83(4) 2.67(4) 3.453(2) 158(3) .
O5 H7 O2 0.83(4) 2.63(3) 3.247(2) 132(3) .
O5 H7 O3 0.83(4) 2.01(4) 2.837(2) 174(3) .
N5 H5C O5 0.93(2) 1.88(2) 2.811(2) 177(2) 8_655
N3 H3B O1 0.80(2) 2.57(2) 3.236(2) 141(2) 3_645
N3 H3B N4 0.80(2) 2.30(2) 2.847(2) 126.4(18) .
N3 H3A O3 0.88(3) 2.20(3) 3.076(2) 174(2) 3_645
N5 H5C O5 0.93(2) 1.88(2) 2.811(2) 177(2) 8_655
N3 H3B N4 0.80(2) 2.30(2) 2.847(2) 126.4(18) .
N3 H3A O3 0.88(3) 2.20(3) 3.076(2) 174(2) 3_645
N3 H3B N4 0.80(2) 2.30(2) 2.847(2) 126.4(18) .
N3 H3B O1 0.80(2) 2.57(2) 3.236(2) 141(2) 3_645
N5 H5C O5 0.93(2) 1.88(2) 2.811(2) 177(2) 8_655
O5 H7 O3 0.83(4) 2.01(4) 2.837(2) 174(3) .
O5 H8 N7 0.79(3) 2.71(3) 3.303(2) 134(2) 4_475
O5 H8 O4 0.79(3) 2.21(3) 2.963(2) 159(3) 4_475
N3 H3A O3 0.88(3) 2.20(3) 3.076(2) 174(2) 3_645
N3 H3B N4 0.80(2) 2.30(2) 2.847(2) 126.4(18) .
N3 H3B O1 0.80(2) 2.57(2) 3.236(2) 141(2) 3_645
N5 H5C O5 0.93(2) 1.88(2) 2.811(2) 177(2) 8_655
O5 H7 O3 0.83(4) 2.01(4) 2.837(2) 174(3) .
O5 H7 O2 0.83(4) 2.63(3) 3.247(2) 132(3) .
O5 H7 N7 0.83(4) 2.67(4) 3.453(2) 158(3) .
O5 H8 O4 0.79(3) 2.21(3) 2.963(2) 159(3) 4_475
N5 H5A N2 0.86(2) 2.14(2) 2.945(2) 153.9(18) 3_645
N5 H5A O4 0.86(2) 2.51(2) 2.937(2) 111.0(15) 1_545
N5 H5B O3 0.89(2) 2.08(2) 2.924(2) 158.2(19) 8_755
N6 H6B O2 0.76(2) 2.20(2) 2.954(2) 171(2) 5_675
N6 H6A O5 0.86(3) 2.08(3) 2.900(2) 158(2) .

_refine_diff_density_max         0.301
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.079

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_d8v17149_0m
_database_code_depnum_ccdc_archive 'CCDC 1916328'
loop_
_audit_author_name
_audit_author_address
'zhang jichuan'
;Shanghai institute of Organnic Chemistry,Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-05-15 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_audit_creation_date             2019-02-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C3 H7 N6 O), C3 N8 O3'
_chemical_formula_sum            'C9 H14 N20 O5'
_chemical_formula_weight         482.40
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   6.8147(6)
_cell_length_b                   14.3240(11)
_cell_length_c                   10.2906(8)
_cell_angle_alpha                90
_cell_angle_beta                 103.859(3)
_cell_angle_gamma                90
_cell_volume                     975.26(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3279
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.10
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1327 before and 0.0712 after correction.
The Ratio of minimum to maximum transmission is 0.8567.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_unetI/netI     0.0767
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12732
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.672
_diffrn_reflns_theta_min         2.485
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.860
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.866
_reflns_number_gt                3102
_reflns_number_total             4700
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.585
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 1040 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4700
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1157
_refine_ls_R_factor_gt           0.0695
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0616P)²+1.1637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1771
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups, All N(H,H,H) groups
2.a Rotating group:
 N3(H3A,H3B)
2.b X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N9(H9A,H9B), N10(H10A,H10B)
2.c Idealised Me refined as rotating group:
 N6(H6A,H6B,H6C), N12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 -0.9768(8) -1.0573(3) -0.7396(5) 0.0342(12) Uani 1 1 d . . . . .
N1 N -0.8497(9) -1.0201(4) -0.6245(6) 0.0348(14) Uani 1 1 d . . . . .
N2 N -1.0746(8) -0.9887(4) -0.8208(6) 0.0297(13) Uani 1 1 d . . . . .
N3 N -0.7662(10) -0.8662(4) -0.5467(7) 0.0397(16) Uani 1 1 d . . . . .
H3A H -0.635795 -0.873277 -0.540314 0.048 Uiso 1 1 d GR . . . .
H3B H -0.802313 -0.809033 -0.574086 0.048 Uiso 1 1 d GR . . . .
N4 N -1.2195(9) -0.8197(4) -0.9382(6) 0.0317(14) Uani 1 1 d . . . . .
H4A H -1.271906 -0.766773 -0.973812 0.038 Uiso 1 1 calc R . . . .
H4B H -1.248027 -0.872187 -0.983164 0.038 Uiso 1 1 calc R . . . .
N5 N -1.0367(9) -0.7507(4) -0.7341(6) 0.0316(14) Uani 1 1 d . . . . .
N6 N -1.1177(9) -0.6623(4) -0.7881(6) 0.0318(14) Uani 1 1 d . . . . .
H6A H -1.106517 -0.657158 -0.874156 0.038 Uiso 1 1 calc GR . . . .
H6B H -1.047653 -0.615225 -0.738273 0.038 Uiso 1 1 calc GR . . . .
H6C H -1.250238 -0.658597 -0.786002 0.038 Uiso 1 1 calc GR . . . .
C1 C -0.8701(9) -0.9285(5) -0.6359(7) 0.0262(15) Uani 1 1 d . . . . .
C2 C -1.0119(10) -0.9104(4) -0.7593(7) 0.0275(15) Uani 1 1 d . . . . .
C3 C -1.0965(9) -0.8204(4) -0.8157(7) 0.0237(14) Uani 1 1 d . . . . .
O2 O 0.0060(7) -1.0596(3) -0.2585(5) 0.0309(11) Uani 1 1 d . . . . .
N7 N -0.1210(8) -1.0253(4) -0.3769(6) 0.0295(13) Uani 1 1 d . . . . .
N8 N 0.1005(8) -0.9879(4) -0.1790(6) 0.0288(13) Uani 1 1 d . . . . .
N9 N -0.2123(9) -0.8743(4) -0.4563(6) 0.0360(15) Uani 1 1 d . . . . .
H9A H -0.297215 -0.895261 -0.528771 0.043 Uiso 1 1 calc R . . . .
H9B H -0.196137 -0.813767 -0.443114 0.043 Uiso 1 1 calc R . . . .
N10 N 0.2219(9) -0.8144(3) -0.0633(6) 0.0319(14) Uani 1 1 d . . . . .
H10A H 0.265782 -0.760037 -0.028211 0.038 Uiso 1 1 calc R . . . .
H10B H 0.256924 -0.865995 -0.017235 0.038 Uiso 1 1 calc R . . . .
N11 N 0.0338(8) -0.7523(4) -0.2701(6) 0.0279(13) Uani 1 1 d . . . . .
N12 N 0.0895(9) -0.6599(4) -0.2201(6) 0.0329(14) Uani 1 1 d . . . . .
H12A H 0.017476 -0.617051 -0.277573 0.039 Uiso 1 1 calc GR . . . .
H12B H 0.223879 -0.650953 -0.212969 0.039 Uiso 1 1 calc GR . . . .
H12C H 0.062438 -0.653251 -0.138234 0.039 Uiso 1 1 calc GR . . . .
C4 C -0.1075(9) -0.9344(5) -0.3663(7) 0.0275(15) Uani 1 1 d . . . . .
C5 C 0.0349(9) -0.9110(4) -0.2415(7) 0.0225(14) Uani 1 1 d . . . . .
C6 C 0.1028(10) -0.8185(4) -0.1860(7) 0.0250(14) Uani 1 1 d . . . . .
O3 O -0.4161(10) -0.6687(4) -0.4651(8) 0.070(2) Uani 1 1 d . . . . .
O4 O -0.0024(8) -0.4789(4) -0.3230(6) 0.0470(14) Uani 1 1 d . . . . .
O5 O -0.0670(9) -0.3329(4) -0.3708(6) 0.0471(15) Uani 1 1 d . . . . .
N13 N -0.2736(10) -0.6013(4) -0.4212(7) 0.0512(17) Uani 1 1 d . . . . .
N14 N -0.6041(11) -0.6373(5) -0.5281(8) 0.060(2) Uani 1 1 d . . . . .
N15 N -0.3047(8) -0.4305(5) -0.4453(6) 0.0377(14) Uani 1 1 d . . . . .
N16 N -0.1171(9) -0.4162(4) -0.3784(6) 0.0366(14) Uani 1 1 d . . . . .
N17 N -0.7188(10) -0.3898(5) -0.5669(7) 0.0450(16) Uani 1 1 d . . . . .
N18 N -0.9068(10) -0.3509(4) -0.6295(7) 0.0395(15) Uani 1 1 d . . . . .
N19 N -1.0208(10) -0.4214(4) -0.6790(6) 0.0453(15) Uani 1 1 d . . . . .
N20 N -0.9324(10) -0.5016(4) -0.6523(7) 0.0407(16) Uani 1 1 d . . . . .
C7 C -0.3756(11) -0.5244(5) -0.4627(8) 0.0363(17) Uani 1 1 d . . . . .
C8 C -0.5863(11) -0.5424(5) -0.5287(8) 0.0383(18) Uani 1 1 d . . . . .
C9 C -0.7420(10) -0.4786(5) -0.5814(7) 0.0331(15) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.395(8) . ?
O1 N2 1.357(7) . ?
N1 C1 1.322(9) . ?
N2 C2 1.308(8) . ?
N3 H3A 0.8814 . ?
N3 H3B 0.8814 . ?
N3 C1 1.353(9) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C3 1.336(8) . ?
N5 N6 1.439(7) . ?
N5 C3 1.305(8) . ?
N6 H6A 0.9100 . ?
N6 H6B 0.9100 . ?
N6 H6C 0.9100 . ?
C1 C2 1.423(10) . ?
C2 C3 1.473(9) . ?
O2 N7 1.403(7) . ?
O2 N8 1.374(7) . ?
N7 C4 1.309(9) . ?
N8 C5 1.299(8) . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
N9 C4 1.339(9) . ?
N10 H10A 0.8800 . ?
N10 H10B 0.8800 . ?
N10 C6 1.329(9) . ?
N11 N12 1.437(8) . ?
N11 C6 1.295(8) . ?
N12 H12A 0.9100 . ?
N12 H12B 0.9100 . ?
N12 H12C 0.9100 . ?
C4 C5 1.451(9) . ?
C5 C6 1.473(9) . ?
O3 N13 1.366(8) . ?
O3 N14 1.366(8) . ?
O4 N16 1.236(7) . ?
O5 N16 1.239(7) . ?
N13 C7 1.319(8) . ?
N14 C8 1.365(10) . ?
N15 N16 1.314(8) . ?
N15 C7 1.425(10) . ?
N17 N18 1.404(9) . ?
N17 C9 1.286(9) . ?
N18 N19 1.301(8) . ?
N19 N20 1.296(9) . ?
N20 C9 1.368(10) . ?
C7 C8 1.457(9) . ?
C8 C9 1.407(10) . ?

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 O1 N1 111.1(5) . . ?
C1 N1 O1 105.8(5) . . ?
C2 N2 O1 105.6(5) . . ?
H3A N3 H3B 109.3 . . ?
C1 N3 H3A 109.2 . . ?
C1 N3 H3B 109.6 . . ?
H4A N4 H4B 120.0 . . ?
C3 N4 H4A 120.0 . . ?
C3 N4 H4B 120.0 . . ?
C3 N5 N6 113.1(5) . . ?
N5 N6 H6A 109.5 . . ?
N5 N6 H6B 109.5 . . ?
N5 N6 H6C 109.5 . . ?
H6A N6 H6B 109.5 . . ?
H6A N6 H6C 109.5 . . ?
H6B N6 H6C 109.5 . . ?
N1 C1 N3 124.6(6) . . ?
N1 C1 C2 107.1(6) . . ?
N3 C1 C2 128.2(6) . . ?
N2 C2 C1 110.4(6) . . ?
N2 C2 C3 120.5(6) . . ?
C1 C2 C3 129.0(6) . . ?
N4 C3 C2 118.4(6) . . ?
N5 C3 N4 129.0(6) . . ?
N5 C3 C2 112.6(6) . . ?
N8 O2 N7 111.0(5) . . ?
C4 N7 O2 105.0(5) . . ?
C5 N8 O2 106.4(5) . . ?
H9A N9 H9B 120.0 . . ?
C4 N9 H9A 120.0 . . ?
C4 N9 H9B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
C6 N10 H10A 120.0 . . ?
C6 N10 H10B 120.0 . . ?
C6 N11 N12 114.4(5) . . ?
N11 N12 H12A 109.5 . . ?
N11 N12 H12B 109.5 . . ?
N11 N12 H12C 109.5 . . ?
H12A N12 H12B 109.5 . . ?
H12A N12 H12C 109.5 . . ?
H12B N12 H12C 109.5 . . ?
N7 C4 N9 124.5(6) . . ?
N7 C4 C5 108.8(5) . . ?
N9 C4 C5 126.6(6) . . ?
N8 C5 C4 108.7(5) . . ?
N8 C5 C6 122.1(6) . . ?
C4 C5 C6 129.2(6) . . ?
N10 C6 C5 118.2(6) . . ?
N11 C6 N10 130.1(6) . . ?
N11 C6 C5 111.7(6) . . ?
N14 O3 N13 115.9(6) . . ?
C7 N13 O3 101.8(6) . . ?
C8 N14 O3 104.8(6) . . ?
N16 N15 C7 118.1(6) . . ?
O4 N16 O5 122.4(6) . . ?
O4 N16 N15 123.8(6) . . ?
O5 N16 N15 113.7(6) . . ?
C9 N17 N18 105.4(6) . . ?
N19 N18 N17 105.4(6) . . ?
N20 N19 N18 113.6(6) . . ?
N19 N20 C9 103.5(6) . . ?
N13 C7 N15 127.7(7) . . ?
N13 C7 C8 112.8(7) . . ?
N15 C7 C8 119.5(6) . . ?
N14 C8 C7 104.7(7) . . ?
N14 C8 C9 126.1(7) . . ?
C9 C8 C7 129.2(6) . . ?
N17 C9 N20 112.0(6) . . ?
N17 C9 C8 122.5(7) . . ?
N20 C9 C8 125.5(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
