# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_a
_database_code_depnum_ccdc_archive 'CCDC 1936735'
loop_
_audit_author_name
_audit_author_address
'kangcai wang'
;CAEP
China
;
_audit_update_record             
;
2019-06-27 deposited with the CCDC.	2019-11-27 downloaded from the CCDC.
;
_audit_creation_date             2017-03-25
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.14 svn.r3398 for OlexSys, GUI svn.r5328)
;
_chemical_formula_moiety         'C3 H2 K N5 O5'
_chemical_formula_sum            'C3 H2 K N5 O5'
_chemical_formula_weight         227.18
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
K 0.21174 0.26561 8.21860 7.43980 1.05190 0.86590 12.79490 0.77480 213.18700
41.68410 1.42279994488
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   10.2767(11)
_cell_length_b                   7.5626(8)
_cell_length_c                   9.6783(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.057(2)
_cell_angle_gamma                90
_cell_volume                     735.59(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3030
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.503
_cell_measurement_theta_min      3.372
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0522 before and 0.0363 after correction. The Ratio of minimum to maximum transmission is 0.9050. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear orangish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.0512
_exptl_crystal_description       block
_exptl_crystal_F_000             457.1186
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5030
_diffrn_reflns_theta_full        27.5029
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.03
_diffrn_ambient_temperature      173
_diffrn_measured_fraction_theta_full 0.9782
_diffrn_measured_fraction_theta_max 0.9782
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                1527
_reflns_number_total             1658
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.4383
_refine_diff_density_min         -0.3301
_refine_diff_density_rms         0.0760
_refine_ls_d_res_high            0.7695
_refine_ls_d_res_low             10.0500
_refine_ls_goodness_of_fit_ref   1.0023
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     135
_refine_ls_number_reflns         1658
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0279
_refine_ls_restrained_S_all      1.0023
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1151
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
K1 K 0.40549(3) 0.39993(5) 0.80938(3) 0.01989(18) Uani 1.000000 .
O5 O 0.14968(10) 0.63294(15) 0.16693(10) 0.0173(3) Uani 1.000000 .
O4 O 0.44434(11) 0.72675(16) 0.39895(11) 0.0233(3) Uani 1.000000 .
O3 O 0.40449(11) 0.63730(16) 0.59910(11) 0.0232(3) Uani 1.000000 .
O1 O 0.19382(11) 0.43791(19) 0.58414(11) 0.0266(3) Uani 1.000000 .
O2 O 0.09679(12) 0.3617(2) 0.37219(12) 0.0310(3) Uani 1.000000 .
N2 N 0.37867(11) 0.63322(17) 0.46782(12) 0.0157(3) Uani 1.000000 .
N1 N 0.18807(12) 0.43989(19) 0.45522(12) 0.0195(3) Uani 1.000000 .
N4 N 0.25043(13) 0.49357(19) 0.01631(12) 0.0212(3) Uani 1.000000 .
N3 N 0.31428(12) 0.4490(2) 0.15620(12) 0.0209(3) Uani 1.000000 .
N5 N 0.06383(14) 0.6802(2) -0.06937(14) 0.0233(3) Uani 1.000000 .
C2 C 0.25363(13) 0.5323(2) 0.23890(14) 0.0164(3) Uani 1.000000 .
C3 C 0.15432(14) 0.5999(2) 0.03026(14) 0.0165(3) Uani 1.000000 .
C1 C 0.27917(13) 0.5288(2) 0.39205(14) 0.0172(3) Uani 1.000000 .
H5a H 0.006(2) 0.744(4) -0.044(2) 0.037(6) Uiso 1.000000 .
H5b H 0.0533(19) 0.640(3) -0.158(2) 0.027(5) Uiso 1.000000 .


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 O4 2.9437(11) 3_666 ?
K1 O4 3.2008(12) 2_646 ?
K1 O4 2.9558(13) 4_576 ?
K1 O3 2.7121(12) . ?
K1 O3 2.7965(11) 2_646 ?
K1 O1 2.7541(12) . ?
K1 N2 3.4118(13) 2_646 ?
K1 N4 2.8957(13) 1_556 ?
K1 N3 3.0757(15) 4_566 ?
K1 N3 3.0510(14) 3_666 ?
O5 C2 1.3763(17) . ?
O5 C3 1.3567(16) . ?
O4 N2 1.2601(16) . ?
O3 N2 1.2430(15) . ?
O1 N1 1.2368(16) . ?
O2 N1 1.2492(17) . ?
N2 C1 1.3760(18) . ?
N1 C1 1.3935(19) . ?
N4 N3 1.4163(16) . ?
N4 C3 1.302(2) . ?
N3 C2 1.279(2) . ?
N5 C3 1.337(2) . ?
N5 H5a 0.84(2) . ?
N5 H5b 0.90(2) . ?
C2 C1 1.4506(18) . ?

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
O3 K1 O4 64.34(3) . 4_576 ?
O3 K1 O4 63.54(3) 2_646 3_666 ?
O3 K1 O4 67.78(3) . 3_666 ?
O3 K1 O4 41.75(3) 2_646 2_646 ?
O3 K1 O4 122.88(3) 2_646 4_576 ?
O3 K1 O4 149.11(3) . 2_646 ?
O1 K1 O4 99.70(4) . 4_576 ?
O1 K1 O4 86.11(3) . 3_666 ?
O1 K1 O4 153.68(4) . 2_646 ?
O1 K1 O3 57.21(4) . . ?
O1 K1 O3 135.12(4) . 2_646 ?
N2 K1 O4 110.44(3) 2_646 4_576 ?
N2 K1 O4 82.87(3) 2_646 3_666 ?
N2 K1 O4 21.67(3) 2_646 2_646 ?
N2 K1 O3 139.96(3) 2_646 . ?
N2 K1 O3 20.14(3) 2_646 2_646 ?
N2 K1 O1 149.73(4) 2_646 . ?
N4 K1 O4 67.90(3) 1_556 4_576 ?
N4 K1 O4 73.96(3) 1_556 2_646 ?
N4 K1 O4 175.09(4) 1_556 3_666 ?
N4 K1 O3 116.15(4) 1_556 . ?
N4 K1 O3 113.79(4) 1_556 2_646 ?
N4 K1 O1 93.68(4) 1_556 . ?
N4 K1 N2 94.96(3) 1_556 2_646 ?
N3 K1 O4 96.68(3) 4_566 2_646 ?
N3 K1 O4 65.08(3) 3_666 3_666 ?
N3 K1 O4 62.69(3) 4_566 3_666 ?
N3 K1 O4 62.86(3) 3_666 4_576 ?
N3 K1 O4 77.68(3) 3_666 2_646 ?
N3 K1 O4 165.87(3) 4_566 4_576 ?
N3 K1 O3 69.55(4) 3_666 2_646 ?
N3 K1 O3 70.46(3) 4_566 2_646 ?
N3 K1 O3 71.92(3) 3_666 . ?
N3 K1 O3 104.67(3) 4_566 . ?
N3 K1 O1 66.24(4) 4_566 . ?
N3 K1 O1 128.23(4) 3_666 . ?
N3 K1 N2 83.68(3) 4_566 2_646 ?
N3 K1 N2 71.22(3) 3_666 2_646 ?
N3 K1 N4 118.44(4) 3_666 1_556 ?
N3 K1 N4 112.76(4) 4_566 1_556 ?
C3 O5 C2 102.12(11) . . ?
N2 O4 K1 88.63(7) . 2_656 ?
N2 O4 K1 129.55(9) . 4_575 ?
N2 O4 K1 126.51(9) . 3_666 ?
N2 O3 K1 109.10(9) . 2_656 ?
N2 O3 K1 135.82(9) . . ?
N1 O1 K1 131.54(9) . . ?
O4 N2 K1 69.70(7) . 2_656 ?
O3 N2 K1 50.76(7) . 2_656 ?
O3 N2 O4 120.21(12) . . ?
C1 N2 K1 171.37(9) . 2_656 ?
C1 N2 O4 117.43(11) . . ?
C1 N2 O3 122.36(12) . . ?
O2 N1 O1 120.97(13) . . ?
C1 N1 O1 123.61(12) . . ?
C1 N1 O2 115.42(12) . . ?
N3 N4 K1 113.01(9) . 1_554 ?
C3 N4 K1 139.60(10) . 1_554 ?
C3 N4 N3 104.94(12) . . ?
N4 N3 K1 104.69(8) . 3_666 ?
N4 N3 K1 134.31(10) . 4_565 ?
C2 N3 K1 108.64(10) . 3_666 ?
C2 N3 K1 105.10(10) . 4_565 ?
C2 N3 N4 106.98(12) . . ?
H5a N5 C3 118.3(15) . . ?
H5b N5 C3 117.5(14) . . ?
H5b N5 H5a 121.8(19) . . ?
N3 C2 O5 112.58(12) . . ?
C1 C2 O5 118.88(13) . . ?
C1 C2 N3 128.52(13) . . ?
N4 C3 O5 113.37(13) . . ?
N5 C3 O5 117.30(13) . . ?
N5 C3 N4 129.33(14) . . ?
N1 C1 N2 122.39(12) . . ?
C2 C1 N2 119.32(13) . . ?
C2 C1 N1 117.55(12) . . ?

_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_mo_2017212ltl-4-3_0ma
_database_code_depnum_ccdc_archive 'CCDC 1936738'
loop_
_audit_author_name
_audit_author_address
'kangcai wang'
;CAEP
China
;
_audit_update_record             
;
2019-11-18 deposited with the CCDC.	2019-11-27 downloaded from the CCDC.
;
_audit_creation_date             2019-10-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C3 H2 N5 O5, H4 N'
_chemical_formula_sum            'C3 H6 N6 O5'
_chemical_formula_weight         206.14
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   10.1650(12)
_cell_length_b                   7.8116(9)
_cell_length_c                   9.9589(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.907(2)
_cell_angle_gamma                90.00
_cell_volume                     770.81(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1118
_cell_measurement_temperature    173
_cell_measurement_theta_max      23.98
_cell_measurement_theta_min      3.32
_exptl_absorpt_coefficient_mu    0.165
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0673 before and 0.0491 after correction. The Ratio of minimum to maximum transmission is 0.9107. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6401
_diffrn_reflns_theta_full        27.17
_diffrn_reflns_theta_max         27.17
_diffrn_reflns_theta_min         2.06
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                1322
_reflns_number_total             1694
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1694
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0696P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1233
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Restrained distances
 N6-H6B = N6-H6D = N6-H6A = N6-H6C
 0.84 with sigma of 0.02
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O5 O 0.64638(13) 0.36384(15) 0.16535(13) 0.0235(3) Uani 1 d . . .
O3 O 0.90314(15) 0.36772(16) 0.58779(13) 0.0311(4) Uani 1 d . . .
O4 O 0.94100(15) 0.27748(17) 0.39400(13) 0.0325(4) Uani 1 d . . .
O1 O 0.69167(15) 0.5671(2) 0.56731(14) 0.0366(4) Uani 1 d . . .
O2 O 0.59650(16) 0.6420(2) 0.35944(15) 0.0428(5) Uani 1 d . . .
N1 N 0.87685(16) 0.36979(18) 0.45999(15) 0.0222(4) Uani 1 d . . .
N2 N 0.68679(17) 0.5628(2) 0.44212(16) 0.0267(4) Uani 1 d . . .
N3 N 0.81004(17) 0.5447(2) 0.15297(16) 0.0282(4) Uani 1 d . . .
N4 N 0.74417(17) 0.4973(2) 0.01786(16) 0.0280(4) Uani 1 d . . .
N5 N 0.55883(19) 0.3109(2) -0.06407(18) 0.0298(4) Uani 1 d . . .
C3 C 0.64891(19) 0.3917(2) 0.03199(18) 0.0217(4) Uani 1 d . . .
C2 C 0.75041(19) 0.4653(2) 0.23485(19) 0.0222(4) Uani 1 d . . .
C1 C 0.77692(19) 0.4724(2) 0.38339(18) 0.0227(4) Uani 1 d . . .
H5A H 0.547(2) 0.345(3) -0.154(3) 0.039(6) Uiso 1 d . . .
H5B H 0.493(3) 0.249(4) -0.038(3) 0.059(8) Uiso 1 d . . .
N6 N 1.10162(17) 0.4049(2) 0.18628(16) 0.0145(3) Uani 1 d . . D
H6A H 1.049(2) 0.479(3) 0.182(3) 0.058(9) Uiso 1 d . . D
H6B H 1.146(2) 0.415(3) 0.133(2) 0.033(7) Uiso 1 d . . D
H6C H 1.060(3) 0.321(3) 0.166(3) 0.066(9) Uiso 1 d . . D
H6D H 1.135(3) 0.407(4) 0.259(2) 0.065(10) Uiso 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
O5 C3 1.352(2) . ?
O5 C2 1.378(2) . ?
O3 N1 1.2408(19) . ?
O4 N1 1.2525(19) . ?
O1 N2 1.237(2) . ?
O2 N2 1.251(2) . ?
N1 C1 1.382(2) . ?
N2 C1 1.386(2) . ?
N3 N4 1.412(2) . ?
N3 C2 1.280(2) . ?
N4 C3 1.303(2) . ?
N5 C3 1.327(3) . ?
N5 H5A 0.91(2) . ?
N5 H5B 0.91(3) . ?
C2 C1 1.444(2) . ?
N6 H6A 0.780(17) . ?
N6 H6B 0.769(17) . ?
N6 H6C 0.782(18) . ?
N6 H6D 0.727(18) . ?

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
C3 O5 C2 102.71(14) . . ?
O3 N1 O4 120.84(15) . . ?
O3 N1 C1 122.49(15) . . ?
O4 N1 C1 116.67(15) . . ?
O1 N2 O2 120.54(16) . . ?
O1 N2 C1 123.91(16) . . ?
O2 N2 C1 115.55(15) . . ?
C2 N3 N4 106.78(16) . . ?
C3 N4 N3 105.60(14) . . ?
C3 N5 H5A 118.8(14) . . ?
C3 N5 H5B 118.8(18) . . ?
H5A N5 H5B 120(2) . . ?
N4 C3 O5 112.68(15) . . ?
N4 C3 N5 129.26(17) . . ?
N5 C3 O5 118.05(17) . . ?
O5 C2 C1 118.90(16) . . ?
N3 C2 O5 112.23(16) . . ?
N3 C2 C1 128.86(17) . . ?
N1 C1 N2 122.44(16) . . ?
N1 C1 C2 119.28(16) . . ?
N2 C1 C2 117.53(16) . . ?
H6A N6 H6B 112(3) . . ?
H6A N6 H6C 107(3) . . ?
H6A N6 H6D 102(3) . . ?
H6B N6 H6C 106(3) . . ?
H6B N6 H6D 117(3) . . ?
H6C N6 H6D 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_mo_ltl-4-2-2_0ma
_database_code_depnum_ccdc_archive 'CCDC 1936736'
loop_
_audit_author_name
_audit_author_address
'kangcai wang'
;CAEP
China
;
_audit_update_record             
;
2019-06-27 deposited with the CCDC.	2019-11-27 downloaded from the CCDC.
;
_audit_creation_date             2017-03-30
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.14 svn.r3398 for OlexSys, GUI svn.r5328)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C3 H3 N5 O5'
_chemical_formula_sum            'C3 H3 N5 O5'
_chemical_formula_weight         189.10
_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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   8.2688(10)
_cell_length_b                   6.1121(7)
_cell_length_c                   13.2779(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     671.06(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2027
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.06
_cell_measurement_theta_min      3.07
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0846 before and 0.0410 after correction. The Ratio of minimum to maximum transmission is 0.8906. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3692
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         3.068
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.919
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                1367
_reflns_number_total             1436
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1436
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      1.105
_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)+(0.0475P)²+0.0299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0779
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9(17)
 0.1(17)
2. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
3.a X=CH2 refined with riding coordinates:
 N5(H5A,H5B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.1, Nqual =  -1, Ralpha = 0.035
;
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
O5 O -0.2462(2) 0.1074(3) -0.30930(13) 0.0206(4) Uani 1 1 d . . . . .
O3 O -0.3473(2) -0.2745(3) -0.57766(12) 0.0262(4) Uani 1 1 d . . . . .
N4 N -0.3880(2) 0.0170(3) -0.17989(15) 0.0214(4) Uani 1 1 d . . . . .
O4 O -0.4701(2) -0.0239(3) -0.49016(13) 0.0273(4) Uani 1 1 d . . . . .
O2 O -0.0738(2) -0.3771(3) -0.32979(12) 0.0267(4) Uani 1 1 d . . . . .
N1 N -0.3667(2) -0.1772(3) -0.49748(13) 0.0179(4) Uani 1 1 d . . . . .
N3 N -0.4003(3) -0.1574(3) -0.24563(14) 0.0210(4) Uani 1 1 d . . . . .
O1 O -0.1171(2) -0.4852(4) -0.48266(14) 0.0404(6) Uani 1 1 d . . . . .
N5 N -0.2512(3) 0.3583(3) -0.18085(17) 0.0298(5) Uani 1 1 d . . . . .
H5A H -0.2830 0.3964 -0.1201 0.036 Uiso 1 1 calc R . . . .
H5B H -0.1889 0.4464 -0.2161 0.036 Uiso 1 1 calc R . . . .
C3 C -0.2963(3) 0.1723(4) -0.21848(17) 0.0206(5) Uani 1 1 d . . . . .
C2 C -0.3152(3) -0.0992(4) -0.32162(17) 0.0177(4) Uani 1 1 d . . . . .
C1 C -0.2806(3) -0.2222(4) -0.41182(16) 0.0192(5) Uani 1 1 d . . . . .
N2 N -0.1527(3) -0.3699(3) -0.41036(15) 0.0217(4) Uani 1 1 d . . . . .
H4 H -0.429(5) 0.022(6) -0.127(3) 0.044(10) 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
O5 C3 1.335(3) . ?
O5 C2 1.395(3) . ?
O3 N1 1.230(2) . ?
N4 N3 1.381(3) . ?
N4 C3 1.319(3) . ?
N4 H4 0.79(4) . ?
O4 N1 1.273(2) . ?
O2 N2 1.254(3) . ?
N1 C1 1.369(3) . ?
N3 C2 1.280(3) . ?
O1 N2 1.227(3) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C3 1.296(3) . ?
C2 C1 1.443(3) . ?
C1 N2 1.391(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O5 C2 104.36(19) . . ?
N3 N4 H4 124(3) . . ?
C3 N4 N3 110.61(19) . . ?
C3 N4 H4 125(3) . . ?
O3 N1 O4 120.65(18) . . ?
O3 N1 C1 123.65(19) . . ?
O4 N1 C1 115.69(19) . . ?
C2 N3 N4 104.1(2) . . ?
H5A N5 H5B 120.0 . . ?
C3 N5 H5A 120.0 . . ?
C3 N5 H5B 120.0 . . ?
N4 C3 O5 108.4(2) . . ?
N5 C3 O5 121.3(2) . . ?
N5 C3 N4 130.3(2) . . ?
O5 C2 C1 119.19(19) . . ?
N3 C2 O5 112.6(2) . . ?
N3 C2 C1 128.2(2) . . ?
N1 C1 C2 118.8(2) . . ?
N1 C1 N2 122.5(2) . . ?
N2 C1 C2 118.52(19) . . ?
O2 N2 C1 115.48(19) . . ?
O1 N2 O2 121.5(2) . . ?
O1 N2 C1 123.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O5 C2 C1 N1 -82.0(3) . . . . ?
O5 C2 C1 N2 93.2(3) . . . . ?
O3 N1 C1 C2 -179.2(2) . . . . ?
O3 N1 C1 N2 5.9(4) . . . . ?
N4 N3 C2 O5 0.1(2) . . . . ?
N4 N3 C2 C1 177.6(2) . . . . ?
O4 N1 C1 C2 1.4(3) . . . . ?
O4 N1 C1 N2 -173.6(2) . . . . ?
N1 C1 N2 O2 172.5(2) . . . . ?
N1 C1 N2 O1 -6.9(4) . . . . ?
N3 N4 C3 O5 0.2(3) . . . . ?
N3 N4 C3 N5 -178.1(3) . . . . ?
N3 C2 C1 N1 100.6(3) . . . . ?
N3 C2 C1 N2 -84.3(3) . . . . ?
C3 O5 C2 N3 0.1(3) . . . . ?
C3 O5 C2 C1 -177.8(2) . . . . ?
C3 N4 N3 C2 -0.1(2) . . . . ?
C2 O5 C3 N4 -0.1(2) . . . . ?
C2 O5 C3 N5 178.3(2) . . . . ?
C2 C1 N2 O2 -2.5(3) . . . . ?
C2 C1 N2 O1 178.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9(17)
2 0.1(17)

####################################################################### 
# 
# 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_zz
_database_code_depnum_ccdc_archive 'CCDC 1936737'
loop_
_audit_author_name
_audit_author_address
'kangcai wang'
;CAEP
China
;
_audit_update_record             
;
2019-11-18 deposited with the CCDC.	2019-11-27 downloaded from the CCDC.
;
_audit_creation_date             2019-10-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C3 H4 N6 O5'
_chemical_formula_sum            'C3 H4 N6 O5'
_chemical_formula_weight         204.12
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   18.330(3)
_cell_length_b                   6.1101(8)
_cell_length_c                   13.6007(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.342(2)
_cell_angle_gamma                90.00
_cell_volume                     1454.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3125
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.30
_cell_measurement_theta_min      2.33
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0555 before and 0.0451 after correction. The Ratio of minimum to maximum transmission is 0.8755. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.865
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10362
_diffrn_reflns_theta_full        27.46
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_min         1.16
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2710
_reflns_number_total             3301
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         3301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0683P)²+0.0344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1098
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O10 O 0.14396(6) 0.75552(17) 0.73019(7) 0.0208(2) Uani 1 d . . .
O5 O 0.35268(6) 0.23710(17) 0.61734(7) 0.0214(2) Uani 1 d . . .
O9 O 0.23114(6) 0.28959(19) 0.80288(9) 0.0285(3) Uani 1 d . . .
O7 O -0.00291(6) 0.5196(2) 0.78601(9) 0.0322(3) Uani 1 d . . .
O6 O 0.05067(7) 0.30880(19) 0.91606(9) 0.0308(3) Uani 1 d . . .
O4 O 0.50903(6) 0.4655(2) 0.79404(9) 0.0331(3) Uani 1 d . . .
O2 O 0.27295(6) 0.6840(2) 0.63041(9) 0.0323(3) Uani 1 d . . .
O3 O 0.45738(7) 0.67829(19) 0.88247(8) 0.0329(3) Uani 1 d . . .
O1 O 0.31520(7) 0.7898(2) 0.79079(9) 0.0354(3) Uani 1 d . . .
O8 O 0.19222(7) 0.1958(2) 0.93332(9) 0.0373(3) Uani 1 d . . .
N10 N 0.10193(7) 0.67835(19) 0.56916(9) 0.0193(3) Uani 1 d . . .
N4 N 0.39227(7) 0.3199(2) 0.48858(9) 0.0207(3) Uani 1 d . . .
N1 N 0.45441(7) 0.5736(2) 0.80369(9) 0.0230(3) Uani 1 d . . .
N11 N 0.15434(8) 1.0304(2) 0.61867(11) 0.0239(3) Uani 1 d . . .
N3 N 0.41083(7) 0.4972(2) 0.55438(9) 0.0221(3) Uani 1 d . . .
N8 N 0.05234(7) 0.4116(2) 0.83807(9) 0.0229(3) Uani 1 d . . .
N7 N 0.18180(7) 0.2932(2) 0.85050(9) 0.0231(3) Uani 1 d . . .
N9 N 0.08892(7) 0.4929(2) 0.61989(9) 0.0219(3) Uani 1 d . . .
N2 N 0.32415(7) 0.6869(2) 0.71670(10) 0.0237(3) Uani 1 d . . .
N5 N 0.33557(8) -0.0288(2) 0.49270(10) 0.0266(3) Uani 1 d . . .
N6 N 0.41135(9) 0.3036(2) 0.39785(10) 0.0281(3) Uani 1 d . . .
N12 N 0.08577(10) 0.6952(2) 0.46351(10) 0.0304(3) Uani 1 d . . .
C3 C 0.35929(8) 0.1646(2) 0.52813(11) 0.0200(3) Uani 1 d . . .
C2 C 0.38687(8) 0.4442(2) 0.62989(11) 0.0197(3) Uani 1 d . . .
C6 C 0.13437(8) 0.8332(2) 0.63551(11) 0.0189(3) Uani 1 d . . .
C5 C 0.11481(8) 0.5434(2) 0.71510(11) 0.0196(3) Uani 1 d . . .
C1 C 0.38827(8) 0.5699(2) 0.72042(10) 0.0210(3) Uani 1 d . . .
C4 C 0.11689(8) 0.4128(2) 0.80445(11) 0.0217(3) Uani 1 d . . .
H11A H 0.1374(11) 1.082(3) 0.5552(16) 0.039(5) Uiso 1 d . . .
H6A H 0.4632(13) 0.319(3) 0.4166(17) 0.048(6) Uiso 1 d . . .
H11B H 0.1784(12) 1.114(4) 0.6724(18) 0.049(6) Uiso 1 d . . .
H5A H 0.3145(12) -0.119(4) 0.5316(18) 0.054(6) Uiso 1 d . . .
H5B H 0.3437(13) -0.074(4) 0.4355(19) 0.058(7) Uiso 1 d . . .
H12A H 0.0340(16) 0.684(4) 0.439(2) 0.069(8) Uiso 1 d . . .
H6B H 0.3895(11) 0.423(4) 0.3585(16) 0.039(5) Uiso 1 d . . .
H12B H 0.1117(12) 0.578(4) 0.4458(17) 0.050(6) Uiso 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
O10 C6 1.3339(17) . ?
O10 C5 1.3938(18) . ?
O5 C3 1.3306(16) . ?
O5 C2 1.3999(18) . ?
O9 N7 1.2597(16) . ?
O7 N8 1.2389(17) . ?
O6 N8 1.2409(16) . ?
O4 N1 1.2387(17) . ?
O2 N2 1.2656(17) . ?
O3 N1 1.2350(16) . ?
O1 N2 1.2395(16) . ?
O8 N7 1.2375(16) . ?
N10 N9 1.3840(17) . ?
N10 N12 1.3818(17) . ?
N10 C6 1.3203(19) . ?
N4 N3 1.3819(17) . ?
N4 N6 1.3828(17) . ?
N4 C3 1.3224(19) . ?
N1 C1 1.3906(18) . ?
N11 C6 1.299(2) . ?
N11 H11A 0.88(2) . ?
N11 H11B 0.89(2) . ?
N3 C2 1.2732(18) . ?
N8 C4 1.3899(18) . ?
N7 C4 1.3776(19) . ?
N9 C5 1.2770(18) . ?
N2 C1 1.3637(19) . ?
N5 C3 1.301(2) . ?
N5 H5A 0.92(2) . ?
N5 H5B 0.88(2) . ?
N6 H6A 0.91(2) . ?
N6 H6B 0.92(2) . ?
N12 H12A 0.91(3) . ?
N12 H12B 0.93(2) . ?
C2 C1 1.4449(19) . ?
C5 C4 1.4445(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
C6 O10 C5 104.73(11) . . ?
C3 O5 C2 104.66(11) . . ?
N12 N10 N9 124.34(12) . . ?
C6 N10 N9 110.83(12) . . ?
C6 N10 N12 124.79(13) . . ?
N3 N4 N6 123.73(12) . . ?
C3 N4 N3 110.69(12) . . ?
C3 N4 N6 125.41(13) . . ?
O4 N1 C1 116.16(12) . . ?
O3 N1 O4 122.68(13) . . ?
O3 N1 C1 121.15(13) . . ?
C6 N11 H11A 118.0(13) . . ?
C6 N11 H11B 118.7(15) . . ?
H11A N11 H11B 122.6(19) . . ?
C2 N3 N4 104.21(12) . . ?
O7 N8 O6 122.26(12) . . ?
O7 N8 C4 116.11(12) . . ?
O6 N8 C4 121.62(13) . . ?
O9 N7 C4 115.51(12) . . ?
O8 N7 O9 121.32(13) . . ?
O8 N7 C4 123.17(13) . . ?
C5 N9 N10 103.92(12) . . ?
O2 N2 C1 114.83(12) . . ?
O1 N2 O2 121.31(13) . . ?
O1 N2 C1 123.87(13) . . ?
C3 N5 H5A 118.7(15) . . ?
C3 N5 H5B 119.2(16) . . ?
H5A N5 H5B 122(2) . . ?
N4 N6 H6A 105.2(14) . . ?
N4 N6 H6B 106.2(12) . . ?
H6A N6 H6B 108.5(18) . . ?
N10 N12 H12A 104.6(16) . . ?
N10 N12 H12B 104.2(13) . . ?
H12A N12 H12B 114(2) . . ?
N4 C3 O5 108.00(12) . . ?
N5 C3 O5 121.93(13) . . ?
N5 C3 N4 130.07(13) . . ?
O5 C2 C1 118.55(12) . . ?
N3 C2 O5 112.40(12) . . ?
N3 C2 C1 129.01(14) . . ?
N10 C6 O10 107.92(12) . . ?
N11 C6 O10 122.48(13) . . ?
N11 C6 N10 129.59(14) . . ?
O10 C5 C4 118.47(12) . . ?
N9 C5 O10 112.60(12) . . ?
N9 C5 C4 128.93(13) . . ?
N1 C1 C2 119.50(12) . . ?
N2 C1 N1 123.65(13) . . ?
N2 C1 C2 116.79(12) . . ?
N8 C4 C5 117.92(13) . . ?
N7 C4 N8 123.51(13) . . ?
N7 C4 C5 118.56(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
