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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1962863'
loop_
_audit_author_name
_audit_author_address
'Chao Li'
;UESTC
China
;
_audit_update_record             
;
2019-11-01 deposited with the CCDC.	2020-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        'C7 H3 K N O4'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H3 K N O4'
_chemical_formula_weight         204.20

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

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

_cell_length_a                   7.0581(5)
_cell_length_b                   11.6424(7)
_cell_length_c                   9.2407(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.046(7)
_cell_angle_gamma                90
_cell_volume                     739.74(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    837
_cell_measurement_theta_min      3.3570
_cell_measurement_theta_max      28.5170

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.834
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.693
_shelx_estimated_absorpt_T_min   0.793
_shelx_estimated_absorpt_T_max   0.846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85236
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1679
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0120
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.441
_diffrn_reflns_theta_max         29.234
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             853
_reflns_number_gt                743
_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0472P)²+0.3243P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         853
_refine_ls_number_parameters     61
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0984
_refine_ls_wR_factor_gt          0.0916
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_restrained_S_all      1.212
_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
C1 C 0.3246(2) -0.04599(15) 0.12327(17) 0.0215(4) Uani 1 1 d . . . . .
C2 C 0.3963(3) 0.02060(15) 0.26586(19) 0.0246(4) Uani 1 1 d . . . . .
C3 C 0.3322(3) -0.16524(17) 0.12642(18) 0.0280(4) Uani 1 1 d . . . . .
H3 H 0.3922 -0.2036 0.2130 0.034 Uiso 1 1 calc R U . . .
C4 C 0.2500 -0.2261(2) 0.0000 0.0306(6) Uani 1 2 d S T P . .
H4 H 0.2500 -0.3060 0.0000 0.037 Uiso 1 2 calc R U P . .
N1 N 0.2500 0.01406(17) 0.0000 0.0212(4) Uani 1 2 d S T P . .
O1 O 0.3768(2) 0.12506(11) 0.26901(15) 0.0348(4) Uani 1 1 d . . . . .
O2 O 0.4718(2) -0.04336(12) 0.37755(14) 0.0380(4) Uani 1 1 d . . . . .
K1 K 0.2500 0.26193(5) 0.0000 0.0351(2) Uani 1 2 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0261(8) 0.0235(9) 0.0138(8) -0.0005(7) 0.0021(6) 0.0005(7)
C2 0.0322(9) 0.0254(9) 0.0149(8) -0.0013(7) 0.0028(6) -0.0008(7)
C3 0.0421(10) 0.0227(8) 0.0163(9) 0.0042(7) 0.0006(7) 0.0039(7)
C4 0.0498(16) 0.0163(11) 0.0234(13) 0.000 0.0038(11) 0.000
N1 0.0279(10) 0.0206(10) 0.0143(9) 0.000 0.0032(7) 0.000
O1 0.0539(9) 0.0245(7) 0.0216(7) -0.0048(6) -0.0005(6) -0.0022(6)
O2 0.0617(9) 0.0311(7) 0.0147(7) -0.0001(6) -0.0051(6) 0.0080(6)
K1 0.0515(4) 0.0262(3) 0.0270(3) 0.000 0.0072(3) 0.000

_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
C1 N1 1.3390(18) . ?
C1 C3 1.389(2) . ?
C1 C2 1.514(2) . ?
C2 O1 1.225(2) . ?
C2 O2 1.287(2) . ?
C3 C4 1.378(2) . ?
C3 H3 0.9300 . ?
C4 C3 1.378(2) 2 ?
C4 H4 0.9300 . ?
N1 C1 1.3390(18) 2 ?
N1 K1 2.886(2) . ?
O1 K1 2.8198(14) 7 ?
O1 K1 2.9181(14) . ?
O2 K1 3.0450(14) 3_545 ?
K1 O1 2.8198(14) 7 ?
K1 O1 2.8198(14) 8_554 ?
K1 O1 2.9181(14) 2 ?
K1 O2 3.0450(14) 4 ?
K1 O2 3.0450(14) 3_454 ?
K1 K1 4.6287(3) 7_554 ?
K1 K1 4.6287(3) 7 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C3 123.05(15) . . ?
N1 C1 C2 117.58(15) . . ?
C3 C1 C2 119.32(15) . . ?
O1 C2 O2 125.73(16) . . ?
O1 C2 C1 120.79(16) . . ?
O2 C2 C1 113.47(14) . . ?
C4 C3 C1 119.31(16) . . ?
C4 C3 H3 120.3 . . ?
C1 C3 H3 120.3 . . ?
C3 C4 C3 118.1(2) 2 . ?
C3 C4 H4 121.0 2 . ?
C3 C4 H4 121.0 . . ?
C1 N1 C1 117.1(2) . 2 ?
C1 N1 K1 121.47(10) . . ?
C1 N1 K1 121.47(10) 2 . ?
C2 O1 K1 122.52(12) . 7 ?
C2 O1 K1 122.44(12) . . ?
K1 O1 K1 107.54(4) 7 . ?
C2 O2 K1 147.62(11) . 3_545 ?
O1 K1 O1 124.38(6) 7 8_554 ?
O1 K1 N1 117.81(3) 7 . ?
O1 K1 N1 117.81(3) 8_554 . ?
O1 K1 O1 144.18(6) 7 2 ?
O1 K1 O1 72.46(4) 8_554 2 ?
N1 K1 O1 56.90(3) . 2 ?
O1 K1 O1 72.46(4) 7 . ?
O1 K1 O1 144.18(6) 8_554 . ?
N1 K1 O1 56.90(3) . . ?
O1 K1 O1 113.81(5) 2 . ?
O1 K1 O2 70.10(4) 7 4 ?
O1 K1 O2 69.25(4) 8_554 4 ?
N1 K1 O2 138.11(3) . 4 ?
O1 K1 O2 140.46(4) 2 4 ?
O1 K1 O2 92.40(4) . 4 ?
O1 K1 O2 69.25(4) 7 3_454 ?
O1 K1 O2 70.10(4) 8_554 3_454 ?
N1 K1 O2 138.11(3) . 3_454 ?
O1 K1 O2 92.40(4) 2 3_454 ?
O1 K1 O2 140.46(4) . 3_454 ?
O2 K1 O2 83.77(6) 4 3_454 ?
O1 K1 K1 148.78(3) 7 7_554 ?
O1 K1 K1 36.95(3) 8_554 7_554 ?
N1 K1 K1 86.559(15) . 7_554 ?
O1 K1 K1 35.51(3) 2 7_554 ?
O1 K1 K1 138.46(3) . 7_554 ?
O2 K1 K1 105.68(3) 4 7_554 ?
O2 K1 K1 79.58(3) 3_454 7_554 ?
O1 K1 K1 36.95(3) 7 7 ?
O1 K1 K1 148.78(3) 8_554 7 ?
N1 K1 K1 86.559(15) . 7 ?
O1 K1 K1 138.46(3) 2 7 ?
O1 K1 K1 35.51(3) . 7 ?
O2 K1 K1 79.58(3) 4 7 ?
O2 K1 K1 105.68(3) 3_454 7 ?
K1 K1 K1 173.12(3) 7_554 7 ?

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
N1 C1 C2 O1 3.7(2) . . . . ?
C3 C1 C2 O1 -173.97(18) . . . . ?
N1 C1 C2 O2 -177.71(14) . . . . ?
C3 C1 C2 O2 4.6(2) . . . . ?
N1 C1 C3 C4 -3.8(3) . . . . ?
C2 C1 C3 C4 173.76(13) . . . . ?
C1 C3 C4 C3 1.78(12) . . . 2 ?
C3 C1 N1 C1 1.92(13) . . . 2 ?
C2 C1 N1 C1 -175.69(16) . . . 2 ?
C3 C1 N1 K1 -178.08(13) . . . . ?
C2 C1 N1 K1 4.30(16) . . . . ?
O2 C2 O1 K1 -42.3(3) . . . 7 ?
C1 C2 O1 K1 136.08(13) . . . 7 ?
O2 C2 O1 K1 171.76(14) . . . . ?
C1 C2 O1 K1 -9.9(2) . . . . ?
O1 C2 O2 K1 -134.28(19) . . . 3_545 ?
C1 C2 O2 K1 47.3(3) . . . 3_545 ?

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.092

_shelx_res_file                  
;

    shelx.res created by SHELXL-2014/7

TITL SIR2014 run in space group I 2/a
CELL  0.71073   7.0581  11.6424   9.2407   90.000  103.046   90.000
ZERR     4.00   0.0005   0.0007   0.0006    0.000    0.007    0.000
LATT   2
SYMM  1/2 - X,   Y, - Z
SFAC  C    H    N    O    K
UNIT  28 12 4 16 4
MERG   2
FMAP   2
PLAN   25
SIZE     0.250   0.300   0.350
ACTA
BOND   $H
CONF
L.S.  10
TEMP    20.00
WGHT    0.047200    0.324300
FVAR       0.65792
C1    1    0.324647   -0.045988    0.123274    11.00000    0.02607    0.02350 =
         0.01382   -0.00048    0.00206    0.00055
C2    1    0.396303    0.020604    0.265862    11.00000    0.03220    0.02545 =
         0.01492   -0.00131    0.00284   -0.00085
C3    1    0.332238   -0.165243    0.126421    11.00000    0.04208    0.02273 =
         0.01627    0.00422    0.00064    0.00395
AFIX  43
H3    2    0.392209   -0.203558    0.212965    11.00000   -1.20000
AFIX   0
C4    1    0.250000   -0.226135    0.000000    10.50000    0.04979    0.01631 =
         0.02343    0.00000    0.00377    0.00000
AFIX  43
H4    2    0.250001   -0.306016   -0.000001    10.50000   -1.20000
AFIX   0
N1    3    0.250000    0.014057    0.000000    10.50000    0.02788    0.02063 =
         0.01428    0.00000    0.00323    0.00000
O1    4    0.376844    0.125064    0.269009    11.00000    0.05389    0.02451 =
         0.02163   -0.00482   -0.00047   -0.00220
O2    4    0.471785   -0.043357    0.377554    11.00000    0.06171    0.03106 =
         0.01469   -0.00008   -0.00513    0.00802
K1    5    0.250000    0.261929    0.000000    10.50000    0.05150    0.02615 =
         0.02702    0.00000    0.00722    0.00000
HKLF    4

REM  SIR2014 run in space group I 2/a
REM R1 =  0.0348 for     743 Fo > 4sig(Fo)  and  0.0413 for all     853 data
REM     61 parameters refined using      0 restraints

END

WGHT      0.0481      0.5157

REM Highest difference peak  0.258,  deepest hole -0.343,  1-sigma level  0.092
Q1    1   0.4971 -0.0032  0.4815  11.00000  0.05    0.26
Q2    1   0.5234 -0.0604  0.0568  11.00000  0.05    0.24
Q3    1   0.5824 -0.0456  0.1802  11.00000  0.05    0.24
Q4    1   0.6736  0.0930  0.2951  11.00000  0.05    0.24
Q5    1   0.5030  0.0506  0.0326  11.00000  0.05    0.23
Q6    1   0.0266 -0.0996  0.0781  11.00000  0.05    0.23
Q7    1   0.5515 -0.1027  0.0965  11.00000  0.05    0.21
Q8    1   0.4821  0.1458  0.0221  11.00000  0.05    0.21
Q9    1   0.6078  0.0275  0.2492  11.00000  0.05    0.20
Q10   1   0.4093  0.1753 -0.0700  11.00000  0.05    0.19
Q11   1   0.3659  0.0761 -0.1178  11.00000  0.05    0.19
Q12   1   0.4949 -0.0993  0.1670  11.00000  0.05    0.19
Q13   1   0.5378 -0.2289  0.3135  11.00000  0.05    0.18
Q14   1   0.1099 -0.0229  0.1292  11.00000  0.05    0.18
Q15   1   0.6699 -0.0884  0.4386  11.00000  0.05    0.18
Q16   1   0.2086  0.3803  0.0696  11.00000  0.05    0.18
Q17   1   0.5109 -0.2353  0.0454  11.00000  0.05    0.18
Q18   1   0.2183 -0.0422  0.3372  11.00000  0.05    0.18
Q19   1   0.6414  0.0008  0.3271  11.00000  0.05    0.17
Q20   1   0.1661  0.0942  0.3026  11.00000  0.05    0.17
Q21   1   0.1431 -0.4340 -0.0710  11.00000  0.05    0.17
Q22   1   0.4831 -0.3095  0.3310  11.00000  0.05    0.16
Q23   1   0.4911 -0.1924  0.2048  11.00000  0.05    0.16
Q24   1   0.2419 -0.0494  0.4000  11.00000  0.05    0.15
Q25   1   0.7458 -0.0510  0.4431  11.00000  0.05    0.15
;
_shelx_res_checksum              97225
