# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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. 
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data_22019513kno2nh_0m
_database_code_depnum_ccdc_archive 'CCDC 2062975'
loop_
_audit_author_name
_audit_author_address
'yu wang'
;Northwest University
China
;
_audit_update_record             
;
2021-02-14 deposited with the CCDC.	2021-09-22 downloaded from the CCDC.
;
_audit_creation_date             2021-01-19
_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         'C4 H2 K2 N10 O5'
_chemical_formula_sum            'C4 H2 K2 N10 O5'
_chemical_formula_weight         348.36
_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'
K K 0.2009 0.2494 '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                   12.1233(4)
_cell_length_b                   8.2762(3)
_cell_length_c                   11.5289(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.0760(10)
_cell_angle_gamma                90
_cell_volume                     1142.27(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5821
_cell_measurement_temperature    298.0
_cell_measurement_theta_max      27.122
_cell_measurement_theta_min      2.992
_shelx_estimated_absorpt_T_max   0.917
_shelx_estimated_absorpt_T_min   0.579
_exptl_absorpt_coefficient_mu    0.877
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0946 before and 0.0669 after correction. The Ratio of minimum to maximum transmission is 0.9127. 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    2.026
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.0536
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11250
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.144
_diffrn_reflns_theta_min         2.992
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2162
_reflns_number_total             2527
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2527
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      5.248
_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)+(0.0560P)²+2.1583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1109
_refine_ls_wR_factor_ref         0.1196
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 O3-N2
 2.9 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
;
_atom_sites_solution_hydrogens   geom
_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
K1 K 0.93215(5) 0.53476(7) 0.15214(5) 0.01332(17) Uani 1 1 d . . . . .
K2 K 0.65627(5) 0.51623(7) 0.93847(5) 0.01512(18) Uani 1 1 d . . . . .
O1 O 0.48789(16) 0.3025(2) 0.54472(17) 0.0166(4) Uani 1 1 d . . . . .
O2 O 0.95339(16) 0.7287(2) 0.33132(17) 0.0157(4) Uani 1 1 d . . . . .
O3 O 0.87460(16) 0.9194(2) 0.41677(18) 0.0149(4) Uani 1 1 d D . . . .
O4 O 0.43809(17) 0.4872(2) 0.85040(18) 0.0184(5) Uani 1 1 d . . . . .
O5 O 0.28068(16) 0.3561(3) 0.82404(18) 0.0192(4) Uani 1 1 d . . . . .
N1 N 0.9002(2) 0.4244(3) 0.3731(2) 0.0149(5) Uani 1 1 d . . . . .
N2 N 0.8851(2) 0.2695(3) 0.4028(2) 0.0152(5) Uani 1 1 d D . . . .
N3 N 0.83693(19) 0.2555(3) 0.4947(2) 0.0134(5) Uani 1 1 d . . . . .
N4 N 0.81943(19) 0.4092(3) 0.5280(2) 0.0126(5) Uani 1 1 d . . . . .
N5 N 0.84619(19) 0.6741(3) 0.4712(2) 0.0121(5) Uani 1 1 d . . . . .
N6 N 0.89245(19) 0.7712(3) 0.4033(2) 0.0116(5) Uani 1 1 d . . . . .
N7 N 0.59771(19) 0.3278(3) 0.5186(2) 0.0152(5) Uani 1 1 d . . . . .
N8 N 0.58690(19) 0.4144(3) 0.7037(2) 0.0139(5) Uani 1 1 d . . . . .
N9 N 0.38889(19) 0.3258(3) 0.6908(2) 0.0168(5) Uani 1 1 d . . . . .
N10 N 0.37161(19) 0.3917(3) 0.7909(2) 0.0155(5) Uani 1 1 d . . . . .
C1 C 0.8585(2) 0.5125(3) 0.4530(2) 0.0122(5) Uani 1 1 d . . . . .
C2 C 0.7687(2) 0.4451(3) 0.6309(2) 0.0145(6) Uani 1 1 d . . . . .
H2A H 0.773348 0.562750 0.646427 0.017 Uiso 1 1 calc R . . . .
H2B H 0.810667 0.389010 0.699883 0.017 Uiso 1 1 calc R . . . .
C3 C 0.6481(2) 0.3930(3) 0.6149(2) 0.0124(5) Uani 1 1 d . . . . .
C4 C 0.4894(2) 0.3557(3) 0.6561(2) 0.0137(5) 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
K1 K2 3.8313(8) 1_554 ?
K1 O2 2.596(2) . ?
K1 O2 2.880(2) 2_745 ?
K1 O3 2.720(2) 4_575 ?
K1 O3 2.760(2) 2_745 ?
K1 O5 2.788(2) 3_666 ?
K1 N1 2.790(2) . ?
K1 N2 3.087(2) 2_755 ?
K1 N3 3.120(2) 4_565 ?
K1 N5 3.249(2) 4_575 ?
K1 N6 3.181(2) 2_745 ?
K1 N6 3.256(2) 4_575 ?
K2 O1 2.968(2) 2_656 ?
K2 O3 2.750(2) 4_576 ?
K2 O4 2.690(2) . ?
K2 O4 2.848(2) 3_667 ?
K2 O5 2.922(2) 3_667 ?
K2 N3 3.135(2) 4_566 ?
K2 N5 3.426(2) 4_576 ?
K2 N7 3.110(2) 4_566 ?
K2 N8 2.833(2) . ?
K2 N9 2.971(2) 2_656 ?
K2 N10 3.280(2) 3_667 ?
K2 C4 3.405(3) 2_656 ?
O1 N7 1.426(3) . ?
O1 C4 1.355(3) . ?
O2 N6 1.246(3) . ?
O3 N6 1.259(3) . ?
O4 N10 1.253(3) . ?
O5 N10 1.257(3) . ?
N1 N2 1.347(3) . ?
N1 C1 1.335(4) . ?
N2 N3 1.293(3) . ?
N3 N4 1.355(3) . ?
N4 C1 1.354(3) . ?
N4 C2 1.450(3) . ?
N5 N6 1.308(3) . ?
N5 C1 1.366(3) . ?
N7 C3 1.296(4) . ?
N8 C3 1.368(3) . ?
N8 C4 1.315(4) . ?
N9 N10 1.322(3) . ?
N9 C4 1.364(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.508(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
O2 K1 K2 120.22(5) . 1_554 ?
O2 K1 K2 111.71(4) 2_745 1_554 ?
O2 K1 O2 120.31(3) . 2_745 ?
O2 K1 O3 117.43(6) . 2_745 ?
O2 K1 O3 133.25(6) . 4_575 ?
O2 K1 O5 72.46(6) . 3_666 ?
O2 K1 N1 59.10(7) . . ?
O2 K1 N2 77.88(6) . 2_755 ?
O2 K1 N2 102.31(6) 2_745 2_755 ?
O2 K1 N3 156.89(6) . 4_565 ?
O2 K1 N3 59.44(6) 2_745 4_565 ?
O2 K1 N5 91.95(6) . 4_575 ?
O2 K1 N5 142.85(6) 2_745 4_575 ?
O2 K1 N6 126.74(6) . 2_745 ?
O2 K1 N6 23.05(5) 2_745 2_745 ?
O2 K1 N6 112.24(6) . 4_575 ?
O2 K1 N6 119.65(6) 2_745 4_575 ?
O3 K1 K2 119.71(5) 2_745 1_554 ?
O3 K1 K2 45.86(4) 4_575 1_554 ?
O3 K1 O2 44.99(5) 2_745 2_745 ?
O3 K1 O2 103.53(6) 4_575 2_745 ?
O3 K1 O3 81.78(6) 4_575 2_745 ?
O3 K1 O5 168.87(7) 2_745 3_666 ?
O3 K1 O5 87.55(6) 4_575 3_666 ?
O3 K1 N1 154.94(7) 4_575 . ?
O3 K1 N1 113.33(7) 2_745 . ?
O3 K1 N2 59.29(6) 2_745 2_755 ?
O3 K1 N2 77.69(6) 4_575 2_755 ?
O3 K1 N3 60.93(6) 4_575 4_565 ?
O3 K1 N3 79.58(6) 2_745 4_565 ?
O3 K1 N5 105.82(6) 2_745 4_575 ?
O3 K1 N5 41.41(5) 4_575 4_575 ?
O3 K1 N6 88.26(6) 4_575 2_745 ?
O3 K1 N6 23.10(6) 2_745 2_745 ?
O3 K1 N6 86.06(6) 2_745 4_575 ?
O3 K1 N6 22.06(6) 4_575 4_575 ?
O5 K1 K2 49.36(4) 3_666 1_554 ?
O5 K1 O2 136.23(6) 3_666 2_745 ?
O5 K1 N1 75.64(7) 3_666 . ?
O5 K1 N2 121.46(6) 3_666 2_755 ?
O5 K1 N3 92.49(6) 3_666 4_565 ?
O5 K1 N5 67.35(6) 3_666 4_575 ?
O5 K1 N6 154.22(6) 3_666 2_745 ?
O5 K1 N6 85.21(6) 3_666 4_575 ?
N1 K1 K2 109.93(5) . 1_554 ?
N1 K1 O2 77.68(6) . 2_745 ?
N1 K1 N2 126.94(7) . 2_755 ?
N1 K1 N3 100.78(7) . 4_565 ?
N1 K1 N5 138.77(6) . 4_575 ?
N1 K1 N6 98.79(6) . 2_745 ?
N1 K1 N6 160.59(7) . 4_575 ?
N2 K1 K2 118.38(5) 2_755 1_554 ?
N2 K1 N3 125.23(6) 2_755 4_565 ?
N2 K1 N5 64.50(6) 2_755 4_575 ?
N2 K1 N6 61.32(6) 2_755 4_575 ?
N2 K1 N6 82.30(6) 2_755 2_745 ?
N3 K1 K2 52.40(4) 4_565 1_554 ?
N3 K1 N5 98.38(6) 4_565 4_575 ?
N3 K1 N6 82.97(6) 4_565 4_575 ?
N3 K1 N6 63.44(6) 4_565 2_745 ?
N5 K1 K2 57.17(4) 4_575 1_554 ?
N5 K1 N6 23.20(5) 4_575 4_575 ?
N6 K1 K2 112.76(5) 2_745 1_554 ?
N6 K1 K2 57.35(4) 4_575 1_554 ?
N6 K1 N5 122.43(6) 2_745 4_575 ?
N6 K1 N6 99.88(5) 2_745 4_575 ?
O1 K2 N3 163.42(6) 2_656 4_566 ?
O1 K2 N5 77.78(5) 2_656 4_576 ?
O1 K2 N7 123.15(6) 2_656 4_566 ?
O1 K2 N9 44.01(6) 2_656 2_656 ?
O1 K2 N10 66.58(6) 2_656 3_667 ?
O1 K2 C4 23.28(6) 2_656 2_656 ?
O3 K2 O1 115.87(6) 4_576 2_656 ?
O3 K2 O4 127.00(6) 4_576 3_667 ?
O3 K2 O5 84.37(6) 4_576 3_667 ?
O3 K2 N3 60.45(6) 4_576 4_566 ?
O3 K2 N5 39.21(5) 4_576 4_576 ?
O3 K2 N7 118.21(6) 4_576 4_566 ?
O3 K2 N8 96.65(6) 4_576 . ?
O3 K2 N9 83.74(6) 4_576 2_656 ?
O3 K2 N10 106.66(6) 4_576 3_667 ?
O3 K2 C4 105.60(6) 4_576 2_656 ?
O4 K2 O1 68.41(6) 3_667 2_656 ?
O4 K2 O1 62.75(6) . 2_656 ?
O4 K2 O3 152.39(6) . 4_576 ?
O4 K2 O4 79.52(7) . 3_667 ?
O4 K2 O5 44.25(6) 3_667 3_667 ?
O4 K2 O5 118.84(6) . 3_667 ?
O4 K2 N3 100.24(6) 3_667 4_566 ?
O4 K2 N3 128.84(6) . 4_566 ?
O4 K2 N5 105.47(6) 3_667 4_576 ?
O4 K2 N5 135.41(6) . 4_576 ?
O4 K2 N7 76.90(6) . 4_566 ?
O4 K2 N7 66.15(6) 3_667 4_566 ?
O4 K2 N8 59.12(6) . . ?
O4 K2 N9 78.19(7) . 2_656 ?
O4 K2 N9 111.73(6) 3_667 2_656 ?
O4 K2 N10 22.17(6) 3_667 3_667 ?
O4 K2 N10 97.87(6) . 3_667 ?
O4 K2 C4 61.54(7) . 2_656 ?
O4 K2 C4 91.37(6) 3_667 2_656 ?
O5 K2 O1 73.74(6) 3_667 2_656 ?
O5 K2 N3 89.69(6) 3_667 4_566 ?
O5 K2 N5 63.53(6) 3_667 4_576 ?
O5 K2 N7 95.21(6) 3_667 4_566 ?
O5 K2 N9 99.13(7) 3_667 2_656 ?
O5 K2 N10 22.45(5) 3_667 3_667 ?
O5 K2 C4 92.73(6) 3_667 2_656 ?
N3 K2 N5 94.50(6) 4_566 4_576 ?
N3 K2 N10 98.24(6) 4_566 3_667 ?
N3 K2 C4 165.55(7) 4_566 2_656 ?
N7 K2 N3 57.76(6) 4_566 4_566 ?
N7 K2 N5 146.41(6) 4_566 4_576 ?
N7 K2 N10 82.37(6) 4_566 3_667 ?
N7 K2 C4 136.00(7) 4_566 2_656 ?
N8 K2 O1 102.17(6) . 2_656 ?
N8 K2 O4 135.63(6) . 3_667 ?
N8 K2 O5 175.76(7) . 3_667 ?
N8 K2 N3 94.39(7) . 4_566 ?
N8 K2 N5 114.90(6) . 4_576 ?
N8 K2 N7 87.95(7) . 4_566 ?
N8 K2 N9 76.93(7) . 2_656 ?
N8 K2 N10 156.66(7) . 3_667 ?
N8 K2 C4 83.03(7) . 2_656 ?
N9 K2 N3 142.17(6) 2_656 4_566 ?
N9 K2 N5 58.52(6) 2_656 4_576 ?
N9 K2 N7 154.94(7) 2_656 4_566 ?
N9 K2 N10 103.80(6) 2_656 3_667 ?
N9 K2 C4 23.45(6) 2_656 2_656 ?
N10 K2 N5 83.68(6) 3_667 4_576 ?
N10 K2 C4 89.26(6) 3_667 2_656 ?
C4 K2 N5 73.96(6) 2_656 4_576 ?
N7 O1 K2 135.24(15) . 2_646 ?
C4 O1 K2 96.75(15) . 2_646 ?
C4 O1 N7 106.2(2) . . ?
K1 O2 K1 125.64(7) . 2_755 ?
N6 O2 K1 135.23(16) . . ?
N6 O2 K1 92.14(14) . 2_755 ?
K1 O3 K1 98.22(6) 4_576 2_755 ?
K1 O3 K2 88.93(6) 4_576 4_575 ?
K2 O3 K1 146.30(8) 4_575 2_755 ?
N6 O3 K1 103.70(15) . 4_576 ?
N6 O3 K1 97.54(15) . 2_755 ?
N6 O3 K2 112.75(15) . 4_575 ?
K2 O4 K2 100.48(7) . 3_667 ?
N10 O4 K2 140.57(17) . . ?
N10 O4 K2 98.70(15) . 3_667 ?
K1 O5 K2 84.26(6) 3_666 3_667 ?
N10 O5 K1 145.43(17) . 3_666 ?
N10 O5 K2 95.03(15) . 3_667 ?
N2 N1 K1 125.97(17) . . ?
C1 N1 K1 125.00(17) . . ?
C1 N1 N2 105.3(2) . . ?
N1 N2 K1 114.61(16) . 2_745 ?
N3 N2 K1 122.92(17) . 2_745 ?
N3 N2 N1 113.0(2) . . ?
K1 N3 K2 75.54(5) 4_566 4_565 ?
N2 N3 K1 111.84(16) . 4_566 ?
N2 N3 K2 106.59(16) . 4_565 ?
N2 N3 N4 105.1(2) . . ?
N4 N3 K1 128.16(16) . 4_566 ?
N4 N3 K2 126.62(16) . 4_565 ?
N3 N4 C2 122.0(2) . . ?
C1 N4 N3 109.0(2) . . ?
C1 N4 C2 129.0(2) . . ?
K1 N5 K2 70.00(5) 4_576 4_575 ?
N6 N5 K1 78.72(14) . 4_576 ?
N6 N5 K2 79.56(14) . 4_575 ?
N6 N5 C1 116.2(2) . . ?
C1 N5 K1 142.47(18) . 4_576 ?
C1 N5 K2 143.47(17) . 4_575 ?
K1 N6 K1 80.11(5) 2_755 4_576 ?
K1 N6 K2 69.76(5) 4_576 4_575 ?
K1 N6 K2 105.57(6) 2_755 4_575 ?
O2 N6 K1 134.87(16) . 4_576 ?
O2 N6 K1 64.81(13) . 2_755 ?
O2 N6 K2 144.63(17) . 4_575 ?
O2 N6 O3 119.3(2) . . ?
O2 N6 N5 125.5(2) . . ?
O3 N6 K1 54.24(13) . 4_576 ?
O3 N6 K1 59.36(13) . 2_755 ?
O3 N6 K2 47.52(12) . 4_575 ?
O3 N6 N5 115.2(2) . . ?
N5 N6 K1 154.79(17) . 2_755 ?
N5 N6 K1 78.08(14) . 4_576 ?
N5 N6 K2 78.47(14) . 4_575 ?
O1 N7 K2 101.11(14) . 4_565 ?
C3 N7 K2 122.46(18) . 4_565 ?
C3 N7 O1 102.1(2) . . ?
C3 N8 K2 129.78(18) . . ?
C4 N8 K2 128.34(18) . . ?
C4 N8 C3 101.4(2) . . ?
N10 N9 K2 138.71(18) . 2_646 ?
N10 N9 C4 116.9(2) . . ?
C4 N9 K2 96.40(16) . 2_646 ?
O4 N10 K2 59.13(14) . 3_667 ?
O4 N10 O5 120.0(2) . . ?
O4 N10 N9 124.1(2) . . ?
O5 N10 K2 62.53(14) . 3_667 ?
O5 N10 N9 115.8(2) . . ?
N9 N10 K2 168.46(18) . 3_667 ?
N1 C1 N4 107.7(2) . . ?
N1 C1 N5 134.7(3) . . ?
N4 C1 N5 117.6(2) . . ?
N4 C2 H2A 109.3 . . ?
N4 C2 H2B 109.3 . . ?
N4 C2 C3 111.7(2) . . ?
H2A C2 H2B 107.9 . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
N7 C3 N8 117.2(2) . . ?
N7 C3 C2 122.7(2) . . ?
N8 C3 C2 120.1(2) . . ?
O1 C4 K2 59.97(13) . 2_646 ?
O1 C4 N9 109.9(2) . . ?
N8 C4 K2 145.59(19) . 2_646 ?
N8 C4 O1 113.1(2) . . ?
N8 C4 N9 136.9(3) . . ?
N9 C4 K2 60.14(14) . 2_646 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2062976'
loop_
_audit_author_name
_audit_author_address
'yu wang'
;Northwest University
China
;
_audit_update_record             
;
2021-02-14 deposited with the CCDC.	2021-09-22 downloaded from the CCDC.
;
_audit_creation_date             2021-01-19
_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         'C4 H2 N10 O5, 2(H4 N)'
_chemical_formula_sum            'C4 H10 N12 O5'
_chemical_formula_weight         306.24
_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 0.0033 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                   12.6801(5)
_cell_length_b                   8.2805(3)
_cell_length_c                   11.6650(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.819(2)
_cell_angle_gamma                90
_cell_volume                     1213.41(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3472
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.84
_cell_measurement_theta_min      2.95
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 13610 reflections, Rint = 0.0533
 (8022 with I > 3sig(I), Rint = 0.0435)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   0.3
_exptl_transmission_factor_min   0.2
_diffrn_reflns_av_R_equivalents  0.1
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            2783
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         2.946
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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                2160
_reflns_number_total             2783
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2783
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+0.9136P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1061
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 N12-H12D
 0.9 with sigma of 0.02
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_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
O4 O 0.86859(11) 0.93753(16) 0.41141(12) 0.0176(3) Uani 1 1 d . . . . .
O5 O 0.94141(11) 0.73901(16) 0.32874(12) 0.0187(3) Uani 1 1 d . . . . .
O3 O 0.43740(11) 0.47964(19) 0.83858(13) 0.0252(4) Uani 1 1 d . . . . .
O2 O 0.28614(11) 0.35450(19) 0.79657(14) 0.0264(4) Uani 1 1 d . . . . .
O1 O 0.50694(11) 0.31520(18) 0.53658(13) 0.0218(3) Uani 1 1 d . . . . .
N8 N 0.88609(12) 0.78677(19) 0.40204(14) 0.0140(3) Uani 1 1 d . . . . .
N6 N 0.58792(13) 0.4272(2) 0.69829(15) 0.0184(4) Uani 1 1 d . . . . .
N3 N 0.84715(13) 0.2758(2) 0.51138(15) 0.0178(4) Uani 1 1 d . . . . .
N5 N 0.61409(13) 0.3439(2) 0.51863(15) 0.0202(4) Uani 1 1 d . . . . .
N2 N 0.89392(13) 0.2851(2) 0.41953(15) 0.0183(4) Uani 1 1 d . . . . .
N10 N 0.37581(13) 0.3922(2) 0.77173(15) 0.0204(4) Uani 1 1 d . . . . .
N9 N 0.39953(13) 0.3371(2) 0.67128(15) 0.0212(4) Uani 1 1 d . . . . .
N4 N 0.82484(12) 0.42894(19) 0.54017(14) 0.0146(4) Uani 1 1 d . . . . .
N7 N 0.84463(13) 0.69351(19) 0.47634(14) 0.0144(4) Uani 1 1 d . . . . .
N1 N 0.90389(13) 0.44191(19) 0.38694(14) 0.0158(4) Uani 1 1 d . . . . .
C1 C 0.85995(14) 0.5309(2) 0.46301(17) 0.0136(4) Uani 1 1 d . . . . .
C4 C 0.49852(16) 0.3672(2) 0.64520(18) 0.0178(4) Uani 1 1 d . . . . .
C3 C 0.65509(16) 0.4087(2) 0.61576(17) 0.0173(4) Uani 1 1 d . . . . .
C2 C 0.76886(16) 0.4630(3) 0.63857(18) 0.0179(4) Uani 1 1 d . . . . .
H1 H 0.8037(17) 0.408(3) 0.708(2) 0.019(6) Uiso 1 1 d . . . . .
H2 H 0.7723(16) 0.578(3) 0.6531(19) 0.016(5) Uiso 1 1 d . . . . .
N12 N 0.92615(15) 0.5269(2) 0.15271(16) 0.0161(4) Uani 1 1 d . . . . .
H7 H 0.923(2) 0.505(3) 0.231(3) 0.035(7) Uiso 1 1 d . . . . .
H9 H 0.996(2) 0.541(3) 0.139(2) 0.035(7) Uiso 1 1 d . . . . .
H8 H 0.900(2) 0.437(4) 0.110(3) 0.043(8) Uiso 1 1 d . . . . .
H10 H 0.889(2) 0.612(3) 0.132(2) 0.035(7) Uiso 1 1 d . . . . .
N11 N 0.65302(16) 0.9796(3) 0.44229(19) 0.0247(4) Uani 1 1 d D . . . .
H5 H 0.625(2) 0.989(4) 0.509(3) 0.051(9) Uiso 1 1 d . . . . .
H3 H 0.725(3) 0.996(4) 0.445(3) 0.053(9) Uiso 1 1 d . . . . .
H6 H 0.619(2) 1.033(3) 0.388(3) 0.044(9) Uiso 1 1 d . . . . .
H4 H 0.653(3) 0.870(3) 0.426(4) 0.117(17) Uiso 1 1 d 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
O4 N8 1.275(2) . ?
O5 N8 1.242(2) . ?
O3 N10 1.255(2) . ?
O2 N10 1.251(2) . ?
O1 N5 1.423(2) . ?
O1 C4 1.356(2) . ?
N8 N7 1.322(2) . ?
N6 C4 1.313(3) . ?
N6 C3 1.378(2) . ?
N3 N2 1.295(2) . ?
N3 N4 1.352(2) . ?
N5 C3 1.297(3) . ?
N2 N1 1.364(2) . ?
N10 N9 1.330(2) . ?
N9 C4 1.354(3) . ?
N4 C1 1.353(2) . ?
N4 C2 1.457(2) . ?
N7 C1 1.372(2) . ?
N1 C1 1.332(2) . ?
C3 C2 1.500(3) . ?
C2 H1 0.99(2) . ?
C2 H2 0.97(2) . ?
N12 H7 0.93(3) . ?
N12 H9 0.93(3) . ?
N12 H8 0.93(3) . ?
N12 H10 0.86(3) . ?
N11 H5 0.90(3) . ?
N11 H3 0.92(3) . ?
N11 H6 0.84(3) . ?
N11 H4 0.924(19) . ?

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
C4 O1 N5 106.42(15) . . ?
O4 N8 N7 115.23(15) . . ?
O5 N8 O4 119.46(15) . . ?
O5 N8 N7 125.27(16) . . ?
C4 N6 C3 101.81(17) . . ?
N2 N3 N4 106.51(15) . . ?
C3 N5 O1 102.59(15) . . ?
N3 N2 N1 110.96(15) . . ?
O3 N10 N9 123.31(16) . . ?
O2 N10 O3 120.56(17) . . ?
O2 N10 N9 116.12(17) . . ?
N10 N9 C4 117.54(17) . . ?
N3 N4 C1 108.74(15) . . ?
N3 N4 C2 121.22(16) . . ?
C1 N4 C2 130.01(17) . . ?
N8 N7 C1 115.08(15) . . ?
C1 N1 N2 106.12(16) . . ?
N4 C1 N7 118.19(17) . . ?
N1 C1 N4 107.66(16) . . ?
N1 C1 N7 134.14(18) . . ?
N6 C4 O1 112.83(17) . . ?
N6 C4 N9 136.95(19) . . ?
N9 C4 O1 110.15(17) . . ?
N6 C3 C2 120.93(18) . . ?
N5 C3 N6 116.34(18) . . ?
N5 C3 C2 122.72(18) . . ?
N4 C2 C3 111.23(17) . . ?
N4 C2 H1 110.5(12) . . ?
N4 C2 H2 108.3(12) . . ?
C3 C2 H1 108.6(12) . . ?
C3 C2 H2 110.2(12) . . ?
H1 C2 H2 107.9(18) . . ?
H7 N12 H9 111(2) . . ?
H7 N12 H8 108(2) . . ?
H7 N12 H10 110(2) . . ?
H9 N12 H8 107(2) . . ?
H9 N12 H10 110(2) . . ?
H8 N12 H10 111(2) . . ?
H5 N11 H3 117(3) . . ?
H5 N11 H6 113(3) . . ?
H5 N11 H4 106(3) . . ?
H3 N11 H6 111(3) . . ?
H3 N11 H4 97(3) . . ?
H6 N11 H4 112(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_220195802_0m
_database_code_depnum_ccdc_archive 'CCDC 2062977'
loop_
_audit_author_name
_audit_author_address
'yu wang'
;Northwest University
China
;
_audit_update_record             
;
2021-02-14 deposited with the CCDC.	2021-09-22 downloaded from the CCDC.
;
_audit_creation_date             2021-01-12
_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         'C4 H4 N10 O5'
_chemical_formula_sum            'C4 H4 N10 O5'
_chemical_formula_weight         272.17
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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                   9.4839(5)
_cell_length_b                   9.0436(5)
_cell_length_c                   22.4984(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1929.66(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2222
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.806
_cell_measurement_theta_min      3.241
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1442 before and 0.0698 after correction. The Ratio of minimum to maximum transmission is 0.7735. 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    1.874
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1156
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21618
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         2.809
_diffrn_ambient_temperature      298.0
_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       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1341
_reflns_number_total             2211
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.308
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.142
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0382P)²+1.7225P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1313
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
;
_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
O3 O 0.1447(2) 0.5772(2) 0.72749(9) 0.0294(5) Uani 1 1 d . . . . .
O2 O 0.0238(2) 0.3748(2) 0.73865(9) 0.0329(5) Uani 1 1 d . . . . .
O4 O 0.7300(2) 0.9480(2) 0.45096(8) 0.0331(5) Uani 1 1 d . . . . .
O5 O 0.9144(2) 0.8098(3) 0.46674(10) 0.0353(6) Uani 1 1 d . . . . .
O1 O 0.4192(2) 0.3420(2) 0.63648(9) 0.0259(5) Uani 1 1 d . . . . .
N8 N 0.7935(3) 0.8525(3) 0.47947(10) 0.0265(6) Uani 1 1 d . . . . .
N7 N 0.7212(2) 0.7967(3) 0.52670(10) 0.0223(5) Uani 1 1 d . . . . .
N9 N 0.2131(2) 0.3619(2) 0.68417(10) 0.0221(5) Uani 1 1 d . . . . .
N10 N 0.1247(3) 0.4443(3) 0.71831(10) 0.0247(6) Uani 1 1 d . . . . .
N4 N 0.7406(2) 0.6463(2) 0.61031(10) 0.0214(5) Uani 1 1 d . . . . .
N3 N 0.8346(3) 0.5545(3) 0.63762(11) 0.0255(6) Uani 1 1 d . . . . .
N2 N 0.9440(3) 0.5472(3) 0.60474(11) 0.0264(6) Uani 1 1 d . . . . .
N1 N 0.9221(3) 0.6348(3) 0.55620(11) 0.0234(6) Uani 1 1 d . . . . .
H1 H 0.983(5) 0.655(5) 0.5299(19) 0.072(14) Uiso 1 1 d . . . . .
N6 N 0.3827(2) 0.5646(3) 0.66914(10) 0.0188(5) Uani 1 1 d . . . . .
H6 H 0.337(4) 0.644(4) 0.6812(16) 0.051(11) Uiso 1 1 d . . . . .
N5 N 0.5411(2) 0.4283(3) 0.62204(11) 0.0257(6) Uani 1 1 d . . . . .
C3 C 0.5124(3) 0.5577(3) 0.64237(12) 0.0201(6) Uani 1 1 d . . . . .
C4 C 0.3283(3) 0.4287(3) 0.66555(12) 0.0204(6) Uani 1 1 d . . . . .
C1 C 0.7945(3) 0.7002(3) 0.55914(12) 0.0218(6) Uani 1 1 d . . . . .
C2 C 0.6091(3) 0.6867(3) 0.63901(13) 0.0221(6) Uani 1 1 d . . . . .
H2A H 0.563238 0.767305 0.616340 0.027 Uiso 1 1 calc R . . . .
H2B H 0.628705 0.723586 0.679609 0.027 Uiso 1 1 calc R . . . .


_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
O3 N10 1.234(3) . ?
O2 N10 1.233(3) . ?
O4 N8 1.233(3) . ?
O5 N8 1.244(3) . ?
O1 N5 1.432(3) . ?
O1 C4 1.337(3) . ?
N8 N7 1.362(3) . ?
N7 C1 1.334(4) . ?
N9 N10 1.360(3) . ?
N9 C4 1.317(4) . ?
N4 N3 1.364(3) . ?
N4 C1 1.351(4) . ?
N4 C2 1.451(4) . ?
N3 N2 1.276(3) . ?
N2 N1 1.365(3) . ?
N1 C1 1.349(4) . ?
N6 C3 1.372(4) . ?
N6 C4 1.335(3) . ?
N5 C3 1.285(3) . ?
C3 C2 1.486(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
C4 O1 N5 108.2(2) . . ?
O4 N8 O5 123.2(2) . . ?
O4 N8 N7 114.8(2) . . ?
O5 N8 N7 121.9(2) . . ?
C1 N7 N8 114.0(2) . . ?
C4 N9 N10 116.1(2) . . ?
O3 N10 N9 122.3(2) . . ?
O2 N10 O3 123.6(2) . . ?
O2 N10 N9 114.1(2) . . ?
N3 N4 C2 121.0(2) . . ?
C1 N4 N3 110.9(2) . . ?
C1 N4 C2 127.8(2) . . ?
N2 N3 N4 107.6(2) . . ?
N3 N2 N1 108.0(2) . . ?
C1 N1 N2 110.6(2) . . ?
C4 N6 C3 106.1(2) . . ?
C3 N5 O1 104.1(2) . . ?
N6 C3 C2 122.7(2) . . ?
N5 C3 N6 112.8(2) . . ?
N5 C3 C2 124.5(3) . . ?
N9 C4 O1 115.0(2) . . ?
N9 C4 N6 136.4(3) . . ?
N6 C4 O1 108.7(2) . . ?
N7 C1 N4 120.4(3) . . ?
N7 C1 N1 136.7(3) . . ?
N1 C1 N4 102.9(2) . . ?
N4 C2 C3 110.8(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
