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

data_201103c
_database_code_depnum_ccdc_archive 'CCDC 2044151'
loop_
_audit_author_name
_audit_author_address
'Max Hu'
;Beijing insitute of technology
China
;
_audit_update_record             
;
2020-11-13 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H6 Li N7 O4'
_chemical_formula_weight         187.07

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'
Li Li -0.0003 0.0001 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   10.8794(11)
_cell_length_b                   6.6298(7)
_cell_length_c                   12.4870(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.646(5)
_cell_angle_gamma                90.00
_cell_volume                     837.15(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    914
_cell_measurement_theta_min      3.122
_cell_measurement_theta_max      26.981

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9733
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4055
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_av_sigmaI/netI    0.0653
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1467
_reflns_number_gt                901
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0584P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1467
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1487
_refine_ls_wR_factor_gt          0.1340
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Li1 Li 0.6891(6) 0.3400(8) 0.1131(5) 0.0495(14) Uani 1 1 d . . .
N1 N 0.9695(2) 0.4287(4) 0.1777(2) 0.0366(7) Uani 1 1 d . . .
N2 N 0.9847(3) 0.6297(4) 0.1768(2) 0.0476(8) Uani 1 1 d . . .
N3 N 1.0838(3) 0.6613(4) 0.1418(3) 0.0528(8) Uani 1 1 d . . .
N4 N 1.1329(3) 0.4841(4) 0.1209(2) 0.0446(7) Uani 1 1 d . . .
N5 N 1.0673(3) 0.1336(4) 0.1370(3) 0.0484(8) Uani 1 1 d . . .
N6 N 1.1607(3) 0.0783(4) 0.1070(3) 0.0519(8) Uani 1 1 d . . .
N7 N 1.2391(4) 0.0088(5) 0.0818(4) 0.0783(12) Uani 1 1 d . . .
O1 O 0.87782(19) 0.3423(3) 0.21094(19) 0.0442(6) Uani 1 1 d . . .
O2 O 0.6646(2) 0.4900(4) -0.0226(2) 0.0747(9) Uani 1 1 d . . .
H2A H 0.7187 0.4980 -0.0572 0.090 Uiso 1 1 d R . .
H2B H 0.5912 0.5102 -0.0774 0.090 Uiso 1 1 d R . .
O3 O 0.5858(2) 0.4532(3) 0.19961(19) 0.0471(6) Uani 1 1 d . . .
H3A H 0.5947 0.5705 0.2290 0.057 Uiso 1 1 d R . .
H3B H 0.5707 0.3653 0.2428 0.057 Uiso 1 1 d R . .
O4 O 0.6234(2) 0.0615(4) 0.0970(2) 0.0583(7) Uani 1 1 d . . .
H4A H 0.6247 -0.0034 0.1561 0.070 Uiso 1 1 d R . .
H4B H 0.5537 0.0291 0.0406 0.070 Uiso 0.50 1 d PR A 1
H4C H 0.6642 0.0057 0.0585 0.070 Uiso 0.50 1 d PR B 2
C1 C 1.0600(3) 0.3417(4) 0.1438(3) 0.0363(8) 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
Li1 O2 1.897(6) . ?
Li1 O4 1.963(6) . ?
Li1 O1 1.964(6) . ?
Li1 O3 1.971(6) . ?
Li1 H4C 2.3049 . ?
N1 C1 1.338(3) . ?
N1 O1 1.342(3) . ?
N1 N2 1.343(3) . ?
N2 N3 1.320(3) . ?
N3 N4 1.355(3) . ?
N4 C1 1.330(4) . ?
N5 N6 1.259(4) . ?
N5 C1 1.386(4) . ?
N6 N7 1.112(3) . ?
O2 H2A 0.8499 . ?
O2 H2B 0.8499 . ?
O3 H3A 0.8500 . ?
O3 H3B 0.8499 . ?
O4 H4A 0.8499 . ?
O4 H4B 0.8500 . ?
O4 H4C 0.8501 . ?

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 Li1 O4 118.4(3) . . ?
O2 Li1 O1 108.7(3) . . ?
O4 Li1 O1 109.2(3) . . ?
O2 Li1 O3 111.7(3) . . ?
O4 Li1 O3 98.9(2) . . ?
O1 Li1 O3 109.4(3) . . ?
O2 Li1 H4C 106.1 . . ?
O4 Li1 H4C 21.1 . . ?
O1 Li1 H4C 100.0 . . ?
O3 Li1 H4C 120.0 . . ?
C1 N1 O1 129.2(2) . . ?
C1 N1 N2 108.5(2) . . ?
O1 N1 N2 122.3(2) . . ?
N3 N2 N1 106.2(2) . . ?
N2 N3 N4 110.7(2) . . ?
C1 N4 N3 105.4(2) . . ?
N6 N5 C1 112.2(2) . . ?
N7 N6 N5 172.4(3) . . ?
N1 O1 Li1 122.5(2) . . ?
Li1 O2 H2A 126.2 . . ?
Li1 O2 H2B 125.6 . . ?
H2A O2 H2B 101.6 . . ?
Li1 O3 H3A 126.0 . . ?
Li1 O3 H3B 111.7 . . ?
H3A O3 H3B 111.8 . . ?
Li1 O4 H4A 119.9 . . ?
Li1 O4 H4B 120.2 . . ?
H4A O4 H4B 108.3 . . ?
Li1 O4 H4C 102.8 . . ?
H4A O4 H4C 115.2 . . ?
H4B O4 H4C 85.1 . . ?
N4 C1 N1 109.2(2) . . ?
N4 C1 N5 129.9(3) . . ?
N1 C1 N5 120.9(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
C1 N1 N2 N3 0.3(4) . . . . ?
O1 N1 N2 N3 179.0(3) . . . . ?
N1 N2 N3 N4 -0.3(4) . . . . ?
N2 N3 N4 C1 0.2(4) . . . . ?
C1 N5 N6 N7 178(3) . . . . ?
C1 N1 O1 Li1 -106.3(4) . . . . ?
N2 N1 O1 Li1 75.4(4) . . . . ?
O2 Li1 O1 N1 -3.7(4) . . . . ?
O4 Li1 O1 N1 126.8(3) . . . . ?
O3 Li1 O1 N1 -125.9(3) . . . . ?
N3 N4 C1 N1 0.0(4) . . . . ?
N3 N4 C1 N5 180.0(3) . . . . ?
O1 N1 C1 N4 -178.7(3) . . . . ?
N2 N1 C1 N4 -0.2(4) . . . . ?
O1 N1 C1 N5 1.3(5) . . . . ?
N2 N1 C1 N5 179.8(3) . . . . ?
N6 N5 C1 N4 2.0(5) . . . . ?
N6 N5 C1 N1 -178.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.062
####################################################################### 
# 
# 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_200918f
_database_code_depnum_ccdc_archive 'CCDC 2044154'
loop_
_audit_author_name
_audit_author_address
'Max Hu'
;Beijing insitute of technology
China
;
_audit_update_record             
;
2020-11-13 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H4 N8 O'
_chemical_formula_weight         144.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.1819(8)
_cell_length_b                   31.960(3)
_cell_length_c                   7.6696(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.412(5)
_cell_angle_gamma                90.00
_cell_volume                     1780.4(3)
_cell_formula_units_Z            12
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2231
_cell_measurement_theta_min      2.756
_cell_measurement_theta_max      22.404

_exptl_crystal_description       stick
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9359
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8850
_diffrn_reflns_av_R_equivalents  0.0766
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3108
_reflns_number_gt                2214
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0888P)²+1.3918P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3108
_refine_ls_number_parameters     290
_refine_ls_number_restraints     177
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0796
_refine_ls_wR_factor_ref         0.2066
_refine_ls_wR_factor_gt          0.1903
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.155
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3724(5) 0.11335(10) 0.5491(5) 0.0367(8) Uani 1 1 d . . .
N2 N 0.5100(5) 0.08602(12) 0.6147(5) 0.0500(9) Uani 1 1 d . . .
N3 N 0.5556(5) 0.08110(12) 0.4757(5) 0.0486(9) Uani 1 1 d U . .
N4 N 0.4507(5) 0.10496(11) 0.3208(5) 0.0429(9) Uani 1 1 d . . .
N5 N 0.2046(5) 0.15448(11) 0.2724(5) 0.0440(9) Uani 1 1 d . . .
N6 N 0.1963(5) 0.16460(13) 0.1135(6) 0.0570(11) Uani 1 1 d . A 2
N7 N 0.1731(7) 0.17636(18) -0.0335(8) 0.0900(17) Uani 1 1 d . . .
N8 N 0.6205(4) 0.26311(10) 0.0158(5) 0.0380(8) Uani 1 1 d . . .
N9 N 0.6238(6) 0.30468(12) 0.0084(6) 0.0576(10) Uani 1 1 d . . .
N10 N 0.7752(6) 0.31425(13) 0.0032(7) 0.0651(12) Uani 1 1 d . . .
N11 N 0.8706(5) 0.27961(14) 0.0072(6) 0.0595(11) Uani 1 1 d . . .
N12 N 0.8221(6) 0.20787(15) 0.0176(7) 0.0699(13) Uani 1 1 d . . .
N13 N 0.7246(6) 0.17967(14) 0.0331(6) 0.0583(11) Uani 1 1 d . . .
N14 N 0.6559(8) 0.15099(16) 0.0457(8) 0.0881(17) Uani 1 1 d . . .
N15 N 0.8281(7) 0.04323(15) 1.0232(7) 0.0484(14) Uani 0.756(6) 1 d PDU B 1
N16 N 0.9427(10) 0.0770(2) 1.0980(8) 0.0543(17) Uani 0.756(6) 1 d PDU B 1
N17 N 1.0200(8) 0.08569(16) 0.9772(7) 0.0593(14) Uani 0.756(6) 1 d PDU B 1
N18 N 0.9559(7) 0.05671(16) 0.8246(7) 0.0447(13) Uani 0.756(6) 1 d PDU B 1
N15' N 0.921(2) 0.0494(6) 0.878(2) 0.0484(14) Uani 0.244(6) 1 d PD B 2
N16' N 0.968(3) 0.0761(8) 1.042(3) 0.0543(17) Uani 0.244(6) 1 d PD B 2
N17' N 0.853(2) 0.0659(5) 1.129(2) 0.0593(14) Uani 0.244(6) 1 d PD B 2
N18' N 0.732(2) 0.0328(5) 1.018(2) 0.0447(13) Uani 0.244(6) 1 d PD B 2
N19 N 0.7324(6) -0.00260(12) 0.7477(6) 0.0550(10) Uani 1 1 d DU . .
N20 N 0.7659(6) -0.00911(12) 0.6104(6) 0.0556(10) Uani 1 1 d U B .
N21 N 0.7814(8) -0.01896(17) 0.4808(8) 0.0888(16) Uani 1 1 d U . .
N22 N 0.2721(5) 0.21124(11) 0.6510(5) 0.0405(8) Uani 1 1 d . . .
H22C H 0.2784 0.1831 0.6538 0.049 Uiso 1 1 d R . .
H22D H 0.3427 0.2209 0.7733 0.049 Uiso 1 1 d R . .
H22A H 0.1548 0.2196 0.6082 0.049 Uiso 1 1 d R . .
H22B H 0.3122 0.2215 0.5682 0.049 Uiso 1 1 d R . .
N23 N 0.9169(5) 0.10135(13) 0.4752(5) 0.0522(10) Uani 1 1 d . . .
H23C H 0.9301 0.0869 0.5815 0.063 Uiso 1 1 d R . .
H23D H 0.8739 0.1270 0.4805 0.063 Uiso 1 1 d R . .
H23A H 0.8372 0.0881 0.3651 0.063 Uiso 1 1 d R . .
H23B H 1.0262 0.1035 0.4743 0.063 Uiso 1 1 d R . .
N24 N 0.3917(5) 0.06101(12) 0.9584(5) 0.0456(9) Uani 1 1 d . . .
H24C H 0.3595 0.0803 0.8629 0.055 Uiso 1 1 d R . .
H24D H 0.4104 0.0741 1.0701 0.055 Uiso 1 1 d R . .
H24A H 0.4954 0.0479 0.9755 0.055 Uiso 1 1 d R . .
H24B H 0.3016 0.0419 0.9253 0.055 Uiso 1 1 d R . .
O1 O 0.2861(4) 0.12462(9) 0.6511(4) 0.0462(8) Uani 1 1 d . . .
O2 O 0.4849(4) 0.24241(9) 0.0214(5) 0.0494(8) Uani 1 1 d . . .
O3 O 0.7448(7) 0.02792(18) 1.1086(8) 0.0740(16) Uani 0.756(6) 1 d PU B 1
O3' O 1.021(2) 0.0499(6) 0.788(3) 0.0740(16) Uani 0.244(6) 1 d P B 2
C1 C 0.3381(5) 0.12506(11) 0.3704(5) 0.0335(9) Uani 1 1 d . A .
C2 C 0.7713(6) 0.24811(14) 0.0161(6) 0.0412(10) Uani 1 1 d . . .
C3 C 0.8365(9) 0.03016(18) 0.8576(8) 0.0396(15) Uani 0.756(6) 1 d PDU B 1
C3' C 0.778(3) 0.0233(6) 0.868(3) 0.0396(15) Uani 0.244(6) 1 d PD B 2


_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 C1 1.320(5) . ?
N1 O1 1.322(4) . ?
N1 N2 1.327(5) . ?
N2 N3 1.291(5) . ?
N3 N4 1.339(5) . ?
N4 C1 1.315(5) . ?
N5 N6 1.232(5) . ?
N5 C1 1.374(5) . ?
N6 N7 1.119(6) . ?
N8 O2 1.310(4) . ?
N8 C2 1.322(5) . ?
N8 N9 1.330(5) . ?
N9 N10 1.294(5) . ?
N10 N11 1.347(6) . ?
N11 C2 1.315(6) . ?
N12 N13 1.245(6) . ?
N12 C2 1.350(6) . ?
N13 N14 1.102(6) . ?
N15 O3 1.243(7) . ?
N15 C3 1.368(6) . ?
N15 N16 1.371(6) . ?
N16 N17 1.369(6) . ?
N17 N18 1.392(6) . ?
N18 C3 1.402(6) . ?
N15' O3' 1.296(19) . ?
N15' C3' 1.407(9) . ?
N15' N16' 1.417(9) . ?
N16' N17' 1.422(9) . ?
N17' N18' 1.429(9) . ?
N18' C3' 1.398(9) . ?
N19 C3' 1.166(11) . ?
N19 N20 1.221(6) . ?
N19 C3 1.368(6) . ?
N20 N21 1.105(6) . ?
N22 H22C 0.8999 . ?
N22 H22D 0.9000 . ?
N22 H22A 0.8999 . ?
N22 H22B 0.9001 . ?
N23 H23C 0.9000 . ?
N23 H23D 0.9001 . ?
N23 H23A 0.8999 . ?
N23 H23B 0.9000 . ?
N24 H24C 0.9001 . ?
N24 H24D 0.9001 . ?
N24 H24A 0.9001 . ?
N24 H24B 0.8999 . ?

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
C1 N1 O1 128.4(3) . . ?
C1 N1 N2 108.5(3) . . ?
O1 N1 N2 123.1(3) . . ?
N3 N2 N1 106.5(3) . . ?
N2 N3 N4 110.7(3) . . ?
C1 N4 N3 105.6(3) . . ?
N6 N5 C1 112.9(3) . . ?
N7 N6 N5 172.5(5) . . ?
O2 N8 C2 128.4(3) . . ?
O2 N8 N9 122.7(3) . . ?
C2 N8 N9 109.0(3) . . ?
N10 N9 N8 106.0(4) . . ?
N9 N10 N11 111.0(4) . . ?
C2 N11 N10 105.4(4) . . ?
N13 N12 C2 118.8(4) . . ?
N14 N13 N12 170.1(5) . . ?
O3 N15 C3 130.0(5) . . ?
O3 N15 N16 121.7(5) . . ?
C3 N15 N16 108.2(4) . . ?
N17 N16 N15 108.4(4) . . ?
N16 N17 N18 108.8(4) . . ?
N17 N18 C3 106.0(4) . . ?
O3' N15' C3' 133.6(17) . . ?
O3' N15' N16' 118.9(17) . . ?
C3' N15' N16' 106.9(6) . . ?
N15' N16' N17' 107.8(6) . . ?
N16' N17' N18' 108.4(6) . . ?
C3' N18' N17' 106.1(6) . . ?
C3' N19 N20 133.4(9) . . ?
C3' N19 C3 24.2(7) . . ?
N20 N19 C3 109.8(4) . . ?
N21 N20 N19 171.4(5) . . ?
H22C N22 H22D 108.4 . . ?
H22C N22 H22A 110.1 . . ?
H22D N22 H22A 110.1 . . ?
H22C N22 H22B 110.1 . . ?
H22D N22 H22B 110.1 . . ?
H22A N22 H22B 108.0 . . ?
H23C N23 H23D 108.3 . . ?
H23C N23 H23A 109.9 . . ?
H23D N23 H23A 109.9 . . ?
H23C N23 H23B 109.9 . . ?
H23D N23 H23B 109.9 . . ?
H23A N23 H23B 108.8 . . ?
H24C N24 H24D 108.3 . . ?
H24C N24 H24A 110.0 . . ?
H24D N24 H24A 110.0 . . ?
H24C N24 H24B 110.0 . . ?
H24D N24 H24B 110.0 . . ?
H24A N24 H24B 108.6 . . ?
N4 C1 N1 108.7(3) . . ?
N4 C1 N5 131.5(4) . . ?
N1 C1 N5 119.8(3) . . ?
N11 C2 N8 108.7(4) . . ?
N11 C2 N12 122.3(4) . . ?
N8 C2 N12 129.0(4) . . ?
N19 C3 N15 121.5(5) . . ?
N19 C3 N18 129.8(4) . . ?
N15 C3 N18 108.6(4) . . ?
N19 C3' N18' 134.3(13) . . ?
N19 C3' N15' 114.8(13) . . ?
N18' C3' N15' 110.7(6) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_200929d
_database_code_depnum_ccdc_archive 'CCDC 2044155'
loop_
_audit_author_name
_audit_author_address
'Max Hu'
;Beijing insitute of technology
China
;
_audit_update_record             
;
2020-11-13 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2 H6 N10 O'
_chemical_formula_weight         186.17

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   11.6030(11)
_cell_length_b                   7.7399(7)
_cell_length_c                   17.4853(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.915(3)
_cell_angle_gamma                90.00
_cell_volume                     1536.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1165
_cell_measurement_theta_min      2.381
_cell_measurement_theta_max      25.801

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9402
_exptl_absorpt_correction_T_max  0.9612
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3712
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         25.01
_reflns_number_total             1352
_reflns_number_gt                1033
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0644P)²+1.0923P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1352
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1330
_refine_ls_wR_factor_gt          0.1263
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.41159(17) 0.0930(3) 0.57531(11) 0.0339(5) Uani 1 1 d . . .
N2 N 0.3180(2) -0.0102(3) 0.56093(12) 0.0451(6) Uani 1 1 d . . .
N3 N 0.2724(2) 0.0039(3) 0.48770(13) 0.0513(7) Uani 1 1 d . . .
N4 N 0.33515(19) 0.1137(3) 0.45412(12) 0.0407(6) Uani 1 1 d . . .
N5 N 0.5091(2) 0.2821(3) 0.50613(12) 0.0430(6) Uani 1 1 d . . .
N6 N 0.5107(2) 0.3284(3) 0.43869(13) 0.0449(6) Uani 1 1 d . . .
N7 N 0.5235(3) 0.3793(4) 0.38181(15) 0.0704(9) Uani 1 1 d . . .
N8 N 0.1925(2) 0.7969(4) 0.66897(12) 0.0540(7) Uani 1 1 d . . .
H8A H 0.1230 0.7529 0.6614 0.065 Uiso 1 1 calc R . .
H8B H 0.2259 0.8136 0.6300 0.065 Uiso 1 1 calc R . .
N9 N 0.35218(18) 0.9040(3) 0.75065(12) 0.0464(6) Uani 1 1 d . . .
H9A H 0.3860 0.9202 0.7119 0.056 Uiso 1 1 calc R . .
H9B H 0.3880 0.9312 0.7972 0.056 Uiso 1 1 calc R . .
N10 N 0.1980(2) 0.8142(3) 0.79853(12) 0.0540(7) Uani 1 1 d . . .
H10A H 0.1286 0.7703 0.7919 0.065 Uiso 1 1 calc R . .
H10B H 0.2352 0.8422 0.8447 0.065 Uiso 1 1 calc R . .
O1 O 0.47788(15) 0.1068(2) 0.64525(9) 0.0429(5) Uani 1 1 d . . .
C1 C 0.4202(2) 0.1680(3) 0.50934(13) 0.0315(6) Uani 1 1 d . . .
C2 C 0.2468(2) 0.8382(3) 0.73893(13) 0.0357(6) 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
N1 O1 1.308(2) . ?
N1 C1 1.314(3) . ?
N1 N2 1.329(3) . ?
N2 N3 1.285(3) . ?
N3 N4 1.332(3) . ?
N4 C1 1.300(3) . ?
N5 N6 1.236(3) . ?
N5 C1 1.367(3) . ?
N6 N7 1.108(3) . ?
N8 C2 1.295(3) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N9 C2 1.301(3) . ?
N9 H9A 0.8600 . ?
N9 H9B 0.8600 . ?
N10 C2 1.298(3) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?

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 C1 130.4(2) . . ?
O1 N1 N2 121.71(19) . . ?
C1 N1 N2 107.9(2) . . ?
N3 N2 N1 106.8(2) . . ?
N2 N3 N4 110.1(2) . . ?
C1 N4 N3 106.2(2) . . ?
N6 N5 C1 112.7(2) . . ?
N7 N6 N5 172.2(3) . . ?
C2 N8 H8A 120.0 . . ?
C2 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
C2 N9 H9A 120.0 . . ?
C2 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C2 N10 H10A 120.0 . . ?
C2 N10 H10B 120.0 . . ?
H10A N10 H10B 120.0 . . ?
N4 C1 N1 109.0(2) . . ?
N4 C1 N5 129.9(2) . . ?
N1 C1 N5 121.1(2) . . ?
N8 C2 N10 121.0(2) . . ?
N8 C2 N9 120.2(2) . . ?
N10 C2 N9 118.7(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
O1 N1 N2 N3 -179.6(2) . . . . ?
C1 N1 N2 N3 0.1(3) . . . . ?
N1 N2 N3 N4 0.3(3) . . . . ?
N2 N3 N4 C1 -0.6(3) . . . . ?
C1 N5 N6 N7 -175(2) . . . . ?
N3 N4 C1 N1 0.6(3) . . . . ?
N3 N4 C1 N5 -179.9(3) . . . . ?
O1 N1 C1 N4 179.2(2) . . . . ?
N2 N1 C1 N4 -0.4(3) . . . . ?
O1 N1 C1 N5 -0.3(4) . . . . ?
N2 N1 C1 N5 -179.9(2) . . . . ?
N6 N5 C1 N4 -5.7(4) . . . . ?
N6 N5 C1 N1 173.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_191214c
_database_code_depnum_ccdc_archive 'CCDC 2057903'
loop_
_audit_author_name
_audit_author_address
'Yong Hu'
;Beijing Institute of Technology
China
;
_audit_update_record             
;
2021-01-22 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H4 Br N5 O'
_chemical_formula_weight         182.00

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_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                   13.6300(12)
_cell_length_b                   7.5726(7)
_cell_length_c                   21.2621(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2194.6(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2119
_cell_measurement_theta_min      2.429
_cell_measurement_theta_max      27.417

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_absorpt_coefficient_mu    7.396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1559
_exptl_absorpt_correction_T_max  0.7087
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9136
_diffrn_reflns_av_R_equivalents  0.0844
_diffrn_reflns_av_sigmaI/netI    0.0594
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.02
_reflns_number_total             1915
_reflns_number_gt                1242
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1774P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1915
_refine_ls_number_parameters     145
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0793
_refine_ls_wR_factor_ref         0.2504
_refine_ls_wR_factor_gt          0.2274
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.88524(9) 0.5483(2) 0.64123(6) 0.0738(6) Uani 1 1 d U . .
Br2 Br 0.71050(10) 0.41655(19) 0.51614(7) 0.0785(6) Uani 1 1 d . . .
N1 N 0.8137(4) 0.7019(9) 0.7499(3) 0.0275(15) Uani 1 1 d . . .
N2 N 0.7301(5) 0.7374(11) 0.7810(3) 0.0424(19) Uani 1 1 d . . .
N3 N 0.6612(5) 0.6680(12) 0.7459(4) 0.048(2) Uani 1 1 d . . .
N4 N 0.6975(5) 0.5921(11) 0.6944(4) 0.043(2) Uani 1 1 d . . .
N5 N 0.6026(4) 0.6891(9) 0.4647(3) 0.0240(14) Uani 1 1 d . . .
N6 N 0.5305(5) 0.8025(10) 0.4783(3) 0.0359(17) Uani 1 1 d . . .
N7 N 0.5036(5) 0.7650(10) 0.5356(3) 0.0360(17) Uani 1 1 d . . .
N8 N 0.5542(5) 0.6328(10) 0.5585(3) 0.0337(17) Uani 1 1 d . . .
N9 N 0.4918(5) 0.4534(9) 0.6807(3) 0.0276(15) Uani 1 1 d . . .
H9A H 0.5376 0.5101 0.6579 0.033 Uiso 1 1 d R . .
H9B H 0.4579 0.5342 0.7029 0.033 Uiso 1 1 d R . .
H9C H 0.5206 0.3759 0.7069 0.033 Uiso 1 1 d R . .
H9D H 0.4509 0.3941 0.6550 0.033 Uiso 1 1 d R . .
N10 N 0.8474(5) 0.9336(8) 0.8859(3) 0.0287(15) Uani 1 1 d . . .
H10A H 0.8901 0.8764 0.9110 0.034 Uiso 1 1 d R . .
H10B H 0.8637 0.9117 0.8457 0.034 Uiso 1 1 d R . .
H10C H 0.8499 1.0504 0.8936 0.034 Uiso 1 1 d R . .
H10D H 0.7859 0.8958 0.8935 0.034 Uiso 1 1 d R . .
O1 O 0.9006(4) 0.7488(8) 0.7726(3) 0.0309(13) Uani 1 1 d . . .
O2 O 0.6469(4) 0.6892(8) 0.4108(3) 0.0347(14) Uani 1 1 d . . .
C1 C 0.7928(6) 0.6165(12) 0.6977(4) 0.033(2) Uani 1 1 d U . .
C2 C 0.6149(6) 0.5872(11) 0.5140(4) 0.0320(19) 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
Br1 C1 1.815(8) . ?
Br2 C2 1.835(9) . ?
N1 C1 1.316(10) . ?
N1 O1 1.328(8) . ?
N1 N2 1.344(9) . ?
N2 N3 1.310(11) . ?
N3 N4 1.333(11) . ?
N4 C1 1.314(10) . ?
N5 O2 1.296(8) . ?
N5 C2 1.312(11) . ?
N5 N6 1.336(9) . ?
N6 N7 1.304(10) . ?
N7 N8 1.309(10) . ?
N8 C2 1.304(11) . ?
N9 H9A 0.8999 . ?
N9 H9B 0.9001 . ?
N9 H9C 0.9001 . ?
N9 H9D 0.8999 . ?
N10 H10A 0.9001 . ?
N10 H10B 0.8999 . ?
N10 H10C 0.9000 . ?
N10 H10D 0.9000 . ?

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
C1 N1 O1 129.1(7) . . ?
C1 N1 N2 109.3(6) . . ?
O1 N1 N2 121.6(7) . . ?
N3 N2 N1 104.3(7) . . ?
N2 N3 N4 112.0(7) . . ?
C1 N4 N3 105.2(8) . . ?
O2 N5 C2 130.3(7) . . ?
O2 N5 N6 122.2(6) . . ?
C2 N5 N6 107.4(7) . . ?
N7 N6 N5 105.6(7) . . ?
N6 N7 N8 111.4(7) . . ?
C2 N8 N7 105.5(7) . . ?
H9A N9 H9B 108.3 . . ?
H9A N9 H9C 110.0 . . ?
H9B N9 H9C 110.0 . . ?
H9A N9 H9D 110.0 . . ?
H9B N9 H9D 110.0 . . ?
H9C N9 H9D 108.7 . . ?
H10A N10 H10B 108.4 . . ?
H10A N10 H10C 110.0 . . ?
H10B N10 H10C 110.0 . . ?
H10A N10 H10D 110.0 . . ?
H10B N10 H10D 110.0 . . ?
H10C N10 H10D 108.4 . . ?
N4 C1 N1 109.2(8) . . ?
N4 C1 Br1 127.6(7) . . ?
N1 C1 Br1 123.2(6) . . ?
N8 C2 N5 110.0(8) . . ?
N8 C2 Br2 128.3(7) . . ?
N5 C2 Br2 121.6(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 N3 1.0(10) . . . . ?
O1 N1 N2 N3 -178.1(7) . . . . ?
N1 N2 N3 N4 -0.4(10) . . . . ?
N2 N3 N4 C1 -0.3(11) . . . . ?
O2 N5 N6 N7 -179.9(7) . . . . ?
C2 N5 N6 N7 0.8(8) . . . . ?
N5 N6 N7 N8 -0.7(9) . . . . ?
N6 N7 N8 C2 0.4(9) . . . . ?
N3 N4 C1 N1 0.9(10) . . . . ?
N3 N4 C1 Br1 -178.9(7) . . . . ?
O1 N1 C1 N4 177.8(7) . . . . ?
N2 N1 C1 N4 -1.2(10) . . . . ?
O1 N1 C1 Br1 -2.4(13) . . . . ?
N2 N1 C1 Br1 178.6(6) . . . . ?
N7 N8 C2 N5 0.2(9) . . . . ?
N7 N8 C2 Br2 177.2(6) . . . . ?
O2 N5 C2 N8 -179.8(7) . . . . ?
N6 N5 C2 N8 -0.6(9) . . . . ?
O2 N5 C2 Br2 2.9(11) . . . . ?
N6 N5 C2 Br2 -177.9(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.724
_refine_diff_density_min         -1.496
_refine_diff_density_rms         0.200
####################################################################### 
# 
# 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_HY1_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2044152'
loop_
_audit_author_name
_audit_author_address
'Max Hu'
;Beijing insitute of technology
China
;
_audit_update_record             
;
2020-11-13 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H6 N7 Na O4'
_chemical_formula_weight         203.12

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5213(10)
_cell_length_b                   6.6446(10)
_cell_length_c                   10.3328(16)
_cell_angle_alpha                97.055(2)
_cell_angle_beta                 104.341(2)
_cell_angle_gamma                107.556(2)
_cell_volume                     404.01(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1983
_cell_measurement_theta_min      3.29
_cell_measurement_theta_max      27.40

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_F_000             208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.197
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2483
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.083
_diffrn_reflns_theta_max         27.395
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             1778
_reflns_number_gt                1645
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0688P)²+0.2387P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.26(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1778
_refine_ls_number_parameters     119
_refine_ls_number_restraints     133
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1125
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.990
_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 0.2937(2) -0.0418(2) 0.57216(14) 0.0261(3) Uani 1 1 d . U . . .
Na1 Na 0.40256(11) 0.71490(10) 0.94960(7) 0.0286(2) Uani 1 1 d . . . . .
N2 N 0.2357(2) -0.2495(2) 0.50573(15) 0.0310(3) Uani 1 1 d . U . . .
C3 C 0.2423(2) 0.0643(2) 0.47562(15) 0.0213(3) Uani 1 1 d . U . . .
O3 O 0.75447(19) 0.64979(19) 1.01795(12) 0.0315(3) Uani 1 1 d . . . . .
H3A H 0.859790 0.723280 1.102193 0.038 Uiso 1 1 d R U . . .
H3B H 0.827905 0.665724 0.963087 0.038 Uiso 1 1 d R U . . .
N3 N 0.1515(2) -0.2694(2) 0.37451(15) 0.0294(3) Uani 1 1 d . U . . .
N4 N 0.1529(2) -0.0730(2) 0.35439(13) 0.0226(3) Uani 1 1 d . U . . .
O4 O 0.4518(2) 0.9725(2) 1.14364(12) 0.0325(3) Uani 1 1 d . . . . .
H4A H 0.334975 1.021924 1.150563 0.039 Uiso 1 1 d R U . . .
H4B H 0.588238 1.024913 1.213222 0.039 Uiso 1 1 d R U . . .
N5 N 0.2686(2) 0.2816(2) 0.48716(14) 0.0285(3) Uani 1 1 d . U . . .
O5 O 0.0225(2) 0.6775(2) 0.83264(13) 0.0337(3) Uani 1 1 d . . . . .
H5A H -0.037797 0.547878 0.758895 0.040 Uiso 1 1 d R U . . .
H5B H 0.014873 0.790405 0.795682 0.040 Uiso 1 1 d R U . . .
N6 N 0.3478(2) 0.3842(2) 0.60847(14) 0.0278(3) Uani 1 1 d . U . . .
N7 N 0.4172(3) 0.4945(3) 0.71195(16) 0.0447(4) Uani 1 1 d . U . . .
O1 O 0.0811(2) -0.03408(19) 0.23126(11) 0.0307(3) Uani 1 1 d . U . . .


_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 C3 1.324(2) . ?
N1 N2 1.357(2) . ?
Na1 O4 2.3579(14) . ?
Na1 O5 2.3950(14) . ?
Na1 O3 2.4133(14) . ?
Na1 O4 2.4288(14) 2_677 ?
Na1 O3 2.4302(14) 2_667 ?
Na1 N7 2.7388(18) . ?
Na1 Na1 3.5390(14) 2_677 ?
Na1 Na1 3.6222(13) 2_667 ?
N2 N3 1.304(2) . ?
C3 N4 1.3334(19) . ?
C3 N5 1.388(2) . ?
N3 N4 1.3440(19) . ?
N4 O1 1.3280(17) . ?
N5 N6 1.2490(19) . ?
N6 N7 1.119(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
C3 N1 N2 105.49(13) . . ?
O4 Na1 O5 97.10(5) . . ?
O4 Na1 O3 99.81(5) . . ?
O5 Na1 O3 162.34(5) . . ?
O4 Na1 O4 84.66(5) . 2_677 ?
O5 Na1 O4 91.09(5) . 2_677 ?
O3 Na1 O4 95.51(5) . 2_677 ?
O4 Na1 O3 110.78(5) . 2_667 ?
O5 Na1 O3 86.09(5) . 2_667 ?
O3 Na1 O3 83.19(5) . 2_667 ?
O4 Na1 O3 164.52(5) 2_677 2_667 ?
O4 Na1 N7 166.61(6) . . ?
O5 Na1 N7 87.94(5) . . ?
O3 Na1 N7 76.70(5) . . ?
O4 Na1 N7 82.84(5) 2_677 . ?
O3 Na1 N7 81.85(5) 2_667 . ?
O4 Na1 Na1 43.10(3) . 2_677 ?
O5 Na1 Na1 95.48(4) . 2_677 ?
O3 Na1 Na1 100.33(4) . 2_677 ?
O4 Na1 Na1 41.56(3) 2_677 2_677 ?
O3 Na1 Na1 153.87(5) 2_667 2_677 ?
N7 Na1 Na1 124.24(5) . 2_677 ?
O4 Na1 Na1 110.58(4) . 2_667 ?
O5 Na1 Na1 126.09(4) . 2_667 ?
O3 Na1 Na1 41.77(3) . 2_667 ?
O4 Na1 Na1 135.27(5) 2_677 2_667 ?
O3 Na1 Na1 41.42(3) 2_667 2_667 ?
N7 Na1 Na1 75.62(4) . 2_667 ?
Na1 Na1 Na1 136.20(4) 2_677 2_667 ?
N3 N2 N1 110.38(13) . . ?
N1 C3 N4 109.26(13) . . ?
N1 C3 N5 129.51(14) . . ?
N4 C3 N5 121.23(14) . . ?
Na1 O3 Na1 96.81(5) . 2_667 ?
N2 N3 N4 106.88(13) . . ?
O1 N4 C3 129.04(13) . . ?
O1 N4 N3 122.95(12) . . ?
C3 N4 N3 107.98(13) . . ?
Na1 O4 Na1 95.34(5) . 2_677 ?
N6 N5 C3 112.44(13) . . ?
N7 N6 N5 172.76(17) . . ?
N6 N7 Na1 156.59(16) . . ?

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
C3 N1 N2 N3 -0.32(17) . . . . ?
N2 N1 C3 N4 0.87(16) . . . . ?
N2 N1 C3 N5 -179.43(15) . . . . ?
N1 N2 N3 N4 -0.34(18) . . . . ?
N1 C3 N4 O1 -179.06(14) . . . . ?
N5 C3 N4 O1 1.2(2) . . . . ?
N1 C3 N4 N3 -1.10(17) . . . . ?
N5 C3 N4 N3 179.17(13) . . . . ?
N2 N3 N4 O1 178.99(13) . . . . ?
N2 N3 N4 C3 0.87(17) . . . . ?
N1 C3 N5 N6 -2.0(2) . . . . ?
N4 C3 N5 N6 177.72(14) . . . . ?

_refine_diff_density_max         0.306
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.057



####################################################################### 
# 
# 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_201024f
_database_code_depnum_ccdc_archive 'CCDC 2044153'
loop_
_audit_author_name
_audit_author_address
'Max Hu'
;Beijing insitute of technology
China
;
_audit_update_record             
;
2020-11-13 deposited with the CCDC.	2021-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H2 K N7 O2'
_chemical_formula_weight         183.20

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'
K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   4.1780(5)
_cell_length_b                   5.2749(6)
_cell_length_c                   8.0471(8)
_cell_angle_alpha                97.332(3)
_cell_angle_beta                 91.810(2)
_cell_angle_gamma                91.691(2)
_cell_volume                     175.71(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    826
_cell_measurement_theta_min      2.554
_cell_measurement_theta_max      27.94

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             92
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7616
_exptl_absorpt_correction_T_max  0.8935
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            870
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         25.00
_reflns_number_total             733
_reflns_number_gt                719
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1355P)²+0.0122P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(10)
_refine_ls_number_reflns         733
_refine_ls_number_parameters     100
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1582
_refine_ls_wR_factor_gt          0.1571
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
K1 K 0.15070(16) 0.22764(14) 0.74460(13) 0.0444(5) Uani 1 1 d . . .
N1 N 0.6732(14) -0.2464(10) 0.5410(7) 0.0378(12) Uani 1 1 d . . .
N2 N 0.8637(14) -0.4550(11) 0.5166(7) 0.0424(13) Uani 1 1 d . . .
N3 N 0.8623(16) -0.5235(11) 0.3534(8) 0.0467(14) Uani 1 1 d . . .
N4 N 0.6768(15) -0.3722(10) 0.2715(7) 0.0415(13) Uani 1 1 d . . .
N5 N 0.3502(16) 0.0005(11) 0.3773(7) 0.0410(13) Uani 1 1 d . . .
N6 N 0.2816(16) 0.0252(12) 0.2252(8) 0.0466(15) Uani 1 1 d . . .
N7 N 0.202(2) 0.0686(18) 0.0987(9) 0.070(2) Uani 1 1 d . . .
O1 O 0.6284(14) -0.1192(9) 0.6909(6) 0.0480(13) Uani 1 1 d . . .
O2 O -0.3297(14) 0.5042(10) 0.9035(7) 0.0536(14) Uani 1 1 d . . .
H2A H -0.3250 0.6589 0.8841 0.064 Uiso 1 1 d R . .
H2B H -0.3234 0.4988 1.0087 0.064 Uiso 1 1 d R . .
C1 C 0.5577(15) -0.2021(12) 0.3899(8) 0.0343(14) 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 O1 2.754(5) . ?
K1 O2 2.764(6) 1_655 ?
K1 O2 2.766(6) . ?
K1 O1 2.793(6) 1_455 ?
K1 N2 2.893(6) 1_465 ?
K1 N7 3.075(8) 1_556 ?
K1 N5 3.190(6) . ?
K1 N1 3.372(6) 1_455 ?
K1 K1 4.1780(5) 1_455 ?
K1 K1 4.1780(5) 1_655 ?
N1 O1 1.325(7) . ?
N1 C1 1.345(9) . ?
N1 N2 1.375(8) . ?
N1 K1 3.372(5) 1_655 ?
N2 N3 1.316(8) . ?
N2 K1 2.893(6) 1_645 ?
N3 N4 1.346(10) . ?
N4 C1 1.341(9) . ?
N5 N6 1.273(9) . ?
N5 C1 1.408(9) . ?
N6 N7 1.114(11) . ?
N7 K1 3.075(8) 1_554 ?
O1 K1 2.793(6) 1_655 ?
O2 K1 2.764(6) 1_455 ?
O2 H2A 0.8500 . ?
O2 H2B 0.8500 . ?

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 K1 O2 78.86(15) . 1_655 ?
O1 K1 O2 159.82(17) . . ?
O2 K1 O2 98.14(15) 1_655 . ?
O1 K1 O1 97.74(15) . 1_455 ?
O2 K1 O1 159.97(17) 1_655 1_455 ?
O2 K1 O1 78.17(14) . 1_455 ?
O1 K1 N2 129.46(15) . 1_465 ?
O2 K1 N2 106.87(18) 1_655 1_465 ?
O2 K1 N2 70.63(16) . 1_465 ?
O1 K1 N2 90.63(16) 1_455 1_465 ?
O1 K1 N7 81.6(2) . 1_556 ?
O2 K1 N7 74.1(2) 1_655 1_556 ?
O2 K1 N7 78.4(2) . 1_556 ?
O1 K1 N7 85.9(2) 1_455 1_556 ?
N2 K1 N7 148.9(2) 1_465 1_556 ?
O1 K1 N5 57.74(17) . . ?
O2 K1 N5 108.25(15) 1_655 . ?
O2 K1 N5 140.24(17) . . ?
O1 K1 N5 85.70(14) 1_455 . ?
N2 K1 N5 73.50(15) 1_465 . ?
N7 K1 N5 136.8(2) 1_556 . ?
O1 K1 N1 84.46(15) . 1_455 ?
O2 K1 N1 163.21(17) 1_655 1_455 ?
O2 K1 N1 96.85(16) . 1_455 ?
O1 K1 N1 22.40(13) 1_455 1_455 ?
N2 K1 N1 85.24(15) 1_465 1_455 ?
N7 K1 N1 101.7(2) 1_556 1_455 ?
N5 K1 N1 63.32(14) . 1_455 ?
O1 K1 K1 138.52(11) . 1_455 ?
O2 K1 K1 139.05(11) 1_655 1_455 ?
O2 K1 K1 40.91(11) . 1_455 ?
O1 K1 K1 40.78(11) 1_455 1_455 ?
N2 K1 K1 65.70(11) 1_465 1_455 ?
N7 K1 K1 92.76(19) 1_556 1_455 ?
N5 K1 K1 107.56(12) . 1_455 ?
N1 K1 K1 56.33(10) 1_455 1_455 ?
O1 K1 K1 41.48(11) . 1_655 ?
O2 K1 K1 40.95(11) 1_655 1_655 ?
O2 K1 K1 139.09(11) . 1_655 ?
O1 K1 K1 139.22(11) 1_455 1_655 ?
N2 K1 K1 114.30(11) 1_465 1_655 ?
N7 K1 K1 87.24(19) 1_556 1_655 ?
N5 K1 K1 72.44(12) . 1_655 ?
N1 K1 K1 123.67(10) 1_455 1_655 ?
K1 K1 K1 180.00(4) 1_455 1_655 ?
O1 N1 C1 129.4(6) . . ?
O1 N1 N2 123.0(6) . . ?
C1 N1 N2 107.7(5) . . ?
O1 N1 K1 53.4(3) . 1_655 ?
C1 N1 K1 114.9(4) . 1_655 ?
N2 N1 K1 105.2(4) . 1_655 ?
N3 N2 N1 106.0(6) . . ?
N3 N2 K1 120.7(4) . 1_645 ?
N1 N2 K1 132.6(4) . 1_645 ?
N2 N3 N4 111.3(5) . . ?
C1 N4 N3 106.0(6) . . ?
N6 N5 C1 111.6(5) . . ?
N6 N5 K1 139.3(5) . . ?
C1 N5 K1 108.9(4) . . ?
N7 N6 N5 172.3(8) . . ?
N6 N7 K1 166.3(8) . 1_554 ?
N1 O1 K1 122.0(4) . . ?
N1 O1 K1 104.2(4) . 1_655 ?
K1 O1 K1 97.74(15) . 1_655 ?
K1 O2 K1 98.14(15) 1_455 . ?
K1 O2 H2A 112.1 1_455 . ?
K1 O2 H2A 112.1 . . ?
K1 O2 H2B 112.1 1_455 . ?
K1 O2 H2B 112.1 . . ?
H2A O2 H2B 109.8 . . ?
N4 C1 N1 109.0(6) . . ?
N4 C1 N5 131.0(6) . . ?
N1 C1 N5 120.0(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 N2 N3 -177.4(6) . . . . ?
C1 N1 N2 N3 1.6(7) . . . . ?
K1 N1 N2 N3 -121.4(5) 1_655 . . . ?
O1 N1 N2 K1 12.5(9) . . . 1_645 ?
C1 N1 N2 K1 -168.5(4) . . . 1_645 ?
K1 N1 N2 K1 68.5(5) 1_655 . . 1_645 ?
N1 N2 N3 N4 -0.9(7) . . . . ?
K1 N2 N3 N4 170.6(4) 1_645 . . . ?
N2 N3 N4 C1 0.0(7) . . . . ?
O1 K1 N5 N6 -176.5(7) . . . . ?
O2 K1 N5 N6 -113.2(7) 1_655 . . . ?
O2 K1 N5 N6 15.8(8) . . . . ?
O1 K1 N5 N6 81.5(7) 1_455 . . . ?
N2 K1 N5 N6 -10.4(6) 1_465 . . . ?
N7 K1 N5 N6 160.9(7) 1_556 . . . ?
N1 K1 N5 N6 82.6(7) 1_455 . . . ?
K1 K1 N5 N6 46.6(7) 1_455 . . . ?
K1 K1 N5 N6 -133.4(7) 1_655 . . . ?
O1 K1 N5 C1 10.2(4) . . . . ?
O2 K1 N5 C1 73.5(4) 1_655 . . . ?
O2 K1 N5 C1 -157.4(4) . . . . ?
O1 K1 N5 C1 -91.7(4) 1_455 . . . ?
N2 K1 N5 C1 176.3(4) 1_465 . . . ?
N7 K1 N5 C1 -12.4(5) 1_556 . . . ?
N1 K1 N5 C1 -90.7(4) 1_455 . . . ?
K1 K1 N5 C1 -126.6(4) 1_455 . . . ?
K1 K1 N5 C1 53.4(4) 1_655 . . . ?
C1 N5 N6 N7 -180(6) . . . . ?
K1 N5 N6 N7 7(7) . . . . ?
N5 N6 N7 K1 112(6) . . . 1_554 ?
C1 N1 O1 K1 14.8(8) . . . . ?
N2 N1 O1 K1 -166.5(4) . . . . ?
K1 N1 O1 K1 108.7(4) 1_655 . . . ?
C1 N1 O1 K1 -94.0(7) . . . 1_655 ?
N2 N1 O1 K1 84.7(6) . . . 1_655 ?
O2 K1 O1 N1 -132.1(5) 1_655 . . . ?
O2 K1 O1 N1 144.6(5) . . . . ?
O1 K1 O1 N1 67.9(5) 1_455 . . . ?
N2 K1 O1 N1 -29.4(5) 1_465 . . . ?
N7 K1 O1 N1 152.6(5) 1_556 . . . ?
N5 K1 O1 N1 -12.0(4) . . . . ?
N1 K1 O1 N1 49.8(4) 1_455 . . . ?
K1 K1 O1 N1 67.9(5) 1_455 . . . ?
K1 K1 O1 N1 -112.1(5) 1_655 . . . ?
O2 K1 O1 K1 -20.02(16) 1_655 . . 1_655 ?
O2 K1 O1 K1 -103.3(5) . . . 1_655 ?
O1 K1 O1 K1 180.0 1_455 . . 1_655 ?
N2 K1 O1 K1 82.7(2) 1_465 . . 1_655 ?
N7 K1 O1 K1 -95.3(2) 1_556 . . 1_655 ?
N5 K1 O1 K1 100.09(19) . . . 1_655 ?
N1 K1 O1 K1 161.92(16) 1_455 . . 1_655 ?
K1 K1 O1 K1 180.0 1_455 . . 1_655 ?
O1 K1 O2 K1 -100.1(5) . . . 1_455 ?
O2 K1 O2 K1 180.0 1_655 . . 1_455 ?
O1 K1 O2 K1 -20.00(17) 1_455 . . 1_455 ?
N2 K1 O2 K1 74.91(19) 1_465 . . 1_455 ?
N7 K1 O2 K1 -108.2(2) 1_556 . . 1_455 ?
N5 K1 O2 K1 48.2(3) . . . 1_455 ?
N1 K1 O2 K1 -7.57(19) 1_455 . . 1_455 ?
K1 K1 O2 K1 180.0 1_655 . . 1_455 ?
N3 N4 C1 N1 1.1(7) . . . . ?
N3 N4 C1 N5 -179.9(6) . . . . ?
O1 N1 C1 N4 177.2(6) . . . . ?
N2 N1 C1 N4 -1.6(7) . . . . ?
K1 N1 C1 N4 115.2(4) 1_655 . . . ?
O1 N1 C1 N5 -1.9(10) . . . . ?
N2 N1 C1 N5 179.2(5) . . . . ?
K1 N1 C1 N5 -63.9(7) 1_655 . . . ?
N6 N5 C1 N4 -3.3(10) . . . . ?
K1 N5 C1 N4 172.0(6) . . . . ?
N6 N5 C1 N1 175.6(6) . . . . ?
K1 N5 C1 N1 -9.1(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.106
