# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_exp_8578
_database_code_depnum_ccdc_archive 'CCDC 2279208'
loop_
_audit_author_name
_audit_author_address
'Baolong Kuang'
;Beijing Institute of technology
China
;
_audit_update_record             
;
2023-07-04 deposited with the CCDC.	2024-03-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_exp_8578            
;
PROBLEM: Short Inter D...A Contact  O2       ..N4       .       2.86 Ang.
RESPONSE: there is hydrogen bond
;
# Added during the CSD deposition process: Tuesday 04 July 2023 01:05 PM
# end Validation Reply Form

_audit_creation_date             2023-06-05
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H3 Cl3 N4 O5'
_chemical_formula_sum            'C9 H3 Cl3 N4 O5'
_chemical_formula_weight         353.50
_chemical_absolute_configuration ad
_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'
Cl Cl 0.1484 0.1585 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   5.4240(8)
_cell_length_b                   10.6544(14)
_cell_length_c                   11.243(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.40(3)
_cell_angle_gamma                90.00
_cell_volume                     636.9(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1505
_cell_measurement_temperature    120.1(2)
_cell_measurement_theta_max      26.1440
_cell_measurement_theta_min      4.1510
_exptl_absorpt_coefficient_mu    0.747
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_meas      1.843
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0768
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4110
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.70
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.1(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.8181
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    1.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289   19.0000   30.0000 86

#__ type_ start__ end____ width___ exp.time_
  2 omega  -51.00   49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289    0.0000    0.0000 100

#__ type_ start__ end____ width___ exp.time_
  3 omega  -23.00   28.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.7727   37.0000  -60.0000 51

#__ type_ start__ end____ width___ exp.time_
  4 omega    1.00   37.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289  -99.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
  5 omega   32.00   74.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       15.9289 -178.0000   60.0000 42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0826593000
_diffrn_orient_matrix_UB_12      -0.0084591000
_diffrn_orient_matrix_UB_13      0.0567322000
_diffrn_orient_matrix_UB_21      -0.0818254000
_diffrn_orient_matrix_UB_22      0.0361222000
_diffrn_orient_matrix_UB_23      0.0286077000
_diffrn_orient_matrix_UB_31      -0.0659232000
_diffrn_orient_matrix_UB_32      -0.0554426000
_diffrn_orient_matrix_UB_33      0.0099941000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2202
_reflns_number_total             2421
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.15(7)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2421
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0189P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0732
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.16572(17) 0.46090(8) 0.03308(8) 0.0180(2) Uani 1 1 d . . .
Cl2 Cl -0.32323(17) 0.50643(8) -0.11957(8) 0.0188(2) Uani 1 1 d . . .
Cl3 Cl -0.16269(18) 0.65244(8) 0.09900(8) 0.0202(2) Uani 1 1 d . . .
O3 O -0.1711(6) 0.9167(3) -0.7430(2) 0.0299(7) Uani 1 1 d . . .
N3 N -0.1838(6) 0.8614(3) -0.6497(3) 0.0210(8) Uani 1 1 d . . .
O2 O -0.3469(6) 0.7853(3) -0.6395(3) 0.0397(8) Uani 1 1 d . . .
O4 O 0.5871(6) 1.1297(3) -0.5582(2) 0.0356(8) Uani 1 1 d . . .
O5 O 0.7547(5) 1.0980(2) -0.3689(2) 0.0243(6) Uani 1 1 d . . .
N4 N 0.5893(6) 1.0820(3) -0.4584(3) 0.0219(8) Uani 1 1 d . . .
C1 C -0.0649(7) 0.5768(3) -0.0246(3) 0.0154(8) Uani 1 1 d . . .
O1 O 0.2672(5) 0.7266(2) -0.0335(2) 0.0181(6) Uani 1 1 d . . .
C7 C 0.2003(7) 0.9737(3) -0.5534(3) 0.0167(8) Uani 1 1 d . . .
H7 H 0.2064 1.0135 -0.6284 0.020 Uiso 1 1 calc R . .
C8 C 0.3793(7) 0.9960(3) -0.4495(3) 0.0160(8) Uani 1 1 d . . .
C6 C 0.0124(7) 0.8901(3) -0.5414(3) 0.0161(8) Uani 1 1 d . . .
N1 N -0.0129(6) 0.7045(3) -0.2061(3) 0.0153(7) Uani 1 1 d . . .
C5 C -0.0038(7) 0.8306(3) -0.4328(3) 0.0157(9) Uani 1 1 d . . .
H5 H -0.1379 0.7746 -0.4282 0.019 Uiso 1 1 calc R . .
C9 C 0.3750(7) 0.9401(3) -0.3392(3) 0.0157(9) Uani 1 1 d . . .
H9 H 0.5008 0.9586 -0.2699 0.019 Uiso 1 1 calc R . .
C2 C 0.0562(7) 0.6706(3) -0.0942(3) 0.0127(8) Uani 1 1 d . . .
N2 N 0.3456(6) 0.8078(3) -0.1190(3) 0.0171(7) Uani 1 1 d . . .
C4 C 0.1816(7) 0.8555(3) -0.3317(3) 0.0144(8) Uani 1 1 d . . .
C3 C 0.1748(7) 0.7905(3) -0.2171(3) 0.0138(8) Uani 1 1 d . . .

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
Cl1 0.0182(5) 0.0159(4) 0.0197(5) 0.0037(4) 0.0032(4) 0.0025(4)
Cl2 0.0158(5) 0.0227(5) 0.0167(5) 0.0004(4) 0.0005(4) -0.0049(4)
Cl3 0.0223(5) 0.0233(5) 0.0162(5) -0.0019(4) 0.0065(4) 0.0015(4)
O3 0.0323(19) 0.0407(17) 0.0144(15) 0.0093(14) -0.0008(13) -0.0080(14)
N3 0.021(2) 0.0234(18) 0.0177(18) 0.0030(15) 0.0021(15) -0.0013(16)
O2 0.034(2) 0.052(2) 0.0272(18) 0.0098(16) -0.0077(15) -0.0248(17)
O4 0.0375(18) 0.047(2) 0.0213(17) 0.0127(15) 0.0022(15) -0.0199(16)
O5 0.0192(15) 0.0279(15) 0.0241(17) 0.0032(13) -0.0002(13) -0.0050(13)
N4 0.0188(19) 0.0214(19) 0.027(2) -0.0003(15) 0.0072(17) -0.0016(15)
C1 0.016(2) 0.0153(19) 0.015(2) 0.0020(15) 0.0026(17) 0.0031(16)
O1 0.0191(15) 0.0209(14) 0.0139(14) 0.0031(11) 0.0023(12) -0.0038(12)
C7 0.023(2) 0.015(2) 0.013(2) 0.0008(16) 0.0048(16) 0.0036(18)
C8 0.018(2) 0.0144(19) 0.018(2) 0.0028(16) 0.0083(17) 0.0013(16)
C6 0.018(2) 0.0148(19) 0.0138(19) -0.0009(16) -0.0011(16) 0.0055(18)
N1 0.0169(18) 0.0141(16) 0.0159(18) 0.0009(14) 0.0059(14) -0.0021(15)
C5 0.014(2) 0.013(2) 0.021(2) -0.0014(16) 0.0063(17) -0.0036(16)
C9 0.017(2) 0.0137(19) 0.017(2) -0.0026(15) 0.0035(17) 0.0029(16)
C2 0.0128(19) 0.0105(18) 0.0142(19) 0.0000(16) 0.0012(16) 0.0032(16)
N2 0.0192(19) 0.0162(16) 0.0163(17) 0.0063(14) 0.0043(15) -0.0029(15)
C4 0.017(2) 0.0135(18) 0.013(2) 0.0017(16) 0.0035(17) 0.0035(17)
C3 0.018(2) 0.0115(19) 0.012(2) -0.0051(16) 0.0040(17) 0.0035(17)

_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
Cl1 C1 1.786(4) . ?
Cl2 C1 1.753(4) . ?
Cl3 C1 1.776(4) . ?
O3 N3 1.217(4) . ?
N3 O2 1.222(4) . ?
N3 C6 1.481(5) . ?
O4 N4 1.229(4) . ?
O5 N4 1.221(4) . ?
N4 C8 1.480(4) . ?
C1 C2 1.499(5) . ?
O1 C2 1.350(4) . ?
O1 N2 1.419(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(5) . ?
C7 C6 1.380(5) . ?
C8 C9 1.380(5) . ?
C6 C5 1.394(5) . ?
N1 C2 1.291(4) . ?
N1 C3 1.394(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.387(5) . ?
C9 H9 0.9500 . ?
C9 C4 1.398(5) . ?
N2 C3 1.306(5) . ?
C4 C3 1.469(5) . ?

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 N3 O2 124.6(3) . . ?
O3 N3 C6 117.0(3) . . ?
O2 N3 C6 118.4(3) . . ?
O4 N4 C8 116.7(3) . . ?
O5 N4 O4 124.6(3) . . ?
O5 N4 C8 118.7(3) . . ?
Cl2 C1 Cl1 110.12(19) . . ?
Cl2 C1 Cl3 110.12(19) . . ?
Cl3 C1 Cl1 109.00(19) . . ?
C2 C1 Cl1 107.6(2) . . ?
C2 C1 Cl2 110.3(3) . . ?
C2 C1 Cl3 109.6(2) . . ?
C2 O1 N2 105.3(3) . . ?
C8 C7 H7 122.0 . . ?
C6 C7 H7 122.0 . . ?
C6 C7 C8 115.9(3) . . ?
C7 C8 N4 118.0(3) . . ?
C9 C8 N4 118.6(4) . . ?
C9 C8 C7 123.4(3) . . ?
C7 C6 N3 118.5(3) . . ?
C7 C6 C5 123.7(4) . . ?
C5 C6 N3 117.8(3) . . ?
C2 N1 C3 101.2(3) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 C6 118.1(3) . . ?
C4 C5 H5 121.0 . . ?
C8 C9 H9 120.7 . . ?
C8 C9 C4 118.6(4) . . ?
C4 C9 H9 120.7 . . ?
O1 C2 C1 116.5(3) . . ?
N1 C2 C1 128.5(3) . . ?
N1 C2 O1 115.0(3) . . ?
C3 N2 O1 103.2(3) . . ?
C5 C4 C9 120.3(3) . . ?
C5 C4 C3 119.3(3) . . ?
C9 C4 C3 120.4(4) . . ?
N1 C3 C4 122.3(3) . . ?
N2 C3 N1 115.2(3) . . ?
N2 C3 C4 122.5(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 O1 -56.1(3) . . . . ?
Cl1 C1 C2 N1 123.0(3) . . . . ?
Cl2 C1 C2 O1 -176.3(2) . . . . ?
Cl2 C1 C2 N1 2.9(4) . . . . ?
Cl3 C1 C2 O1 62.3(3) . . . . ?
Cl3 C1 C2 N1 -118.6(3) . . . . ?
O3 N3 C6 C7 -2.0(5) . . . . ?
O3 N3 C6 C5 178.0(3) . . . . ?
N3 C6 C5 C4 179.0(3) . . . . ?
O2 N3 C6 C7 178.5(3) . . . . ?
O2 N3 C6 C5 -1.5(5) . . . . ?
O4 N4 C8 C7 1.3(5) . . . . ?
O4 N4 C8 C9 179.8(3) . . . . ?
O5 N4 C8 C7 -176.7(3) . . . . ?
O5 N4 C8 C9 1.8(5) . . . . ?
N4 C8 C9 C4 -177.8(3) . . . . ?
O1 N2 C3 N1 -0.1(4) . . . . ?
O1 N2 C3 C4 -179.2(3) . . . . ?
C7 C8 C9 C4 0.6(5) . . . . ?
C7 C6 C5 C4 -1.0(5) . . . . ?
C8 C7 C6 N3 -179.5(3) . . . . ?
C8 C7 C6 C5 0.5(5) . . . . ?
C8 C9 C4 C5 -1.1(5) . . . . ?
C8 C9 C4 C3 177.8(3) . . . . ?
C6 C7 C8 N4 178.1(3) . . . . ?
C6 C7 C8 C9 -0.3(5) . . . . ?
C6 C5 C4 C9 1.3(5) . . . . ?
C6 C5 C4 C3 -177.7(3) . . . . ?
C5 C4 C3 N1 -0.3(5) . . . . ?
C5 C4 C3 N2 178.7(3) . . . . ?
C9 C4 C3 N1 -179.2(3) . . . . ?
C9 C4 C3 N2 -0.2(5) . . . . ?
C2 O1 N2 C3 0.3(3) . . . . ?
C2 N1 C3 N2 -0.1(4) . . . . ?
C2 N1 C3 C4 179.0(3) . . . . ?
N2 O1 C2 C1 178.9(3) . . . . ?
N2 O1 C2 N1 -0.4(4) . . . . ?
C3 N1 C2 C1 -178.8(3) . . . . ?
C3 N1 C2 O1 0.3(4) . . . . ?

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

data_exp_8564
_database_code_depnum_ccdc_archive 'CCDC 2279209'
loop_
_audit_author_name
_audit_author_address
'Baolong Kuang'
;Beijing Institute of technology
China
;
_audit_update_record             
;
2023-07-04 deposited with the CCDC.	2024-03-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_exp_8564            
;
PROBLEM: Short Inter D...A Contact  O5       ..O5       .       2.72 Ang.
RESPONSE: there is hydrogen bond
;
# Added during the CSD deposition process: Tuesday 04 July 2023 01:11 PM
# end Validation Reply Form

_audit_creation_date             2023-06-01
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C8 H5 N5 O5'
_chemical_formula_sum            'C8 H5 N5 O5'
_chemical_formula_weight         251.17
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.8806(4)
_cell_length_b                   14.1354(8)
_cell_length_c                   10.3877(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.677(5)
_cell_angle_gamma                90.00
_cell_volume                     981.66(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1102
_cell_measurement_temperature    116.7(9)
_cell_measurement_theta_max      25.0530
_cell_measurement_theta_min      3.3690
_exptl_absorpt_coefficient_mu    0.145
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_density_meas      1.699
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       neddle
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4068
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.23
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      116.7(9)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.8460
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -24.00   23.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -10.8508  -99.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
  2 omega  -38.00   23.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -57.0000   90.0000 61

#__ type_ start__ end____ width___ exp.time_
  3 omega  -16.00   85.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852    0.0000  -90.0000 101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0947521000
_diffrn_orient_matrix_UB_12      0.0145724000
_diffrn_orient_matrix_UB_13      0.0383226000
_diffrn_orient_matrix_UB_21      -0.0476300000
_diffrn_orient_matrix_UB_22      0.0266198000
_diffrn_orient_matrix_UB_23      0.0416332000
_diffrn_orient_matrix_UB_31      0.0028624000
_diffrn_orient_matrix_UB_32      -0.0399403000
_diffrn_orient_matrix_UB_33      0.0417374000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1363
_reflns_number_total             1895
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1895
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0436P)²+0.0655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1161
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2004(2) 0.63633(11) 0.79836(14) 0.0323(4) Uani 1 1 d . . .
N2 N 0.2250(3) 0.57545(12) 0.99929(16) 0.0240(4) Uani 1 1 d . . .
N3 N -0.0796(3) 0.56429(13) 0.83383(17) 0.0304(5) Uani 1 1 d . . .
H3A H -0.1436 0.5339 0.8852 0.036 Uiso 1 1 calc R . .
H3B H -0.1413 0.5779 0.7516 0.036 Uiso 1 1 calc R . .
C8 C 0.7462(3) 0.67468(15) 1.0801(2) 0.0268(5) Uani 1 1 d . . .
H8 H 0.7438 0.7054 0.9984 0.032 Uiso 1 1 calc R . .
C4 C 0.5862(4) 0.58004(16) 1.2182(2) 0.0275(6) Uani 1 1 d . . .
H4 H 0.4748 0.5451 1.2318 0.033 Uiso 1 1 calc R . .
N1 N 0.3991(3) 0.65462(14) 0.87312(18) 0.0325(5) Uani 1 1 d . . .
C2 C 0.3997(3) 0.61782(15) 0.9886(2) 0.0235(5) Uani 1 1 d . . .
O4 O 0.8845(3) 0.57297(15) 1.54378(16) 0.0592(6) Uani 1 1 d . . .
C3 C 0.5789(3) 0.62429(15) 1.0975(2) 0.0239(5) Uani 1 1 d . . .
N4 N 1.0869(3) 0.73346(15) 1.1635(2) 0.0424(6) Uani 1 1 d . . .
C7 C 0.9131(3) 0.67898(16) 1.1823(2) 0.0308(6) Uani 1 1 d . . .
C1 C 0.1095(4) 0.58957(15) 0.8802(2) 0.0257(5) Uani 1 1 d . . .
C6 C 0.9252(4) 0.63640(17) 1.3039(2) 0.0350(6) Uani 1 1 d . . .
H6 H 1.0422 0.6404 1.3738 0.042 Uiso 1 1 calc R . .
O5 O 0.6542(3) 0.47348(18) 1.44667(18) 0.0611(6) Uani 1 1 d . . .
O3 O 1.2427(3) 0.72836(14) 1.2507(2) 0.0543(6) Uani 1 1 d . . .
N5 N 0.7650(4) 0.54111(19) 1.4458(2) 0.0459(6) Uani 1 1 d . . .
O2 O 1.0667(3) 0.77978(14) 1.0619(2) 0.0625(6) Uani 1 1 d . . .
C5 C 0.7580(4) 0.58787(17) 1.3177(2) 0.0315(6) Uani 1 1 d . . .

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
O1 0.0275(9) 0.0395(10) 0.0271(8) 0.0077(7) 0.0012(7) -0.0086(8)
N2 0.0246(11) 0.0246(10) 0.0230(9) 0.0015(8) 0.0063(8) -0.0019(8)
N3 0.0271(12) 0.0399(12) 0.0232(9) 0.0038(8) 0.0039(9) -0.0062(9)
C8 0.0287(13) 0.0195(12) 0.0337(12) -0.0025(10) 0.0102(11) 0.0022(10)
C4 0.0258(13) 0.0302(13) 0.0275(11) -0.0019(10) 0.0078(10) 0.0041(10)
N1 0.0260(12) 0.0391(12) 0.0306(10) 0.0060(9) 0.0034(9) -0.0073(9)
C2 0.0259(13) 0.0204(12) 0.0243(11) 0.0012(9) 0.0065(10) 0.0017(10)
O4 0.0511(13) 0.0943(16) 0.0257(9) -0.0105(9) -0.0041(9) 0.0388(12)
C3 0.0244(13) 0.0216(12) 0.0259(11) -0.0031(9) 0.0065(10) 0.0035(10)
N4 0.0275(13) 0.0290(12) 0.0701(16) -0.0173(12) 0.0103(12) -0.0039(10)
C7 0.0208(13) 0.0227(13) 0.0484(14) -0.0130(11) 0.0071(11) -0.0007(10)
C1 0.0290(14) 0.0230(12) 0.0267(11) -0.0001(9) 0.0096(10) 0.0003(10)
C6 0.0270(14) 0.0369(14) 0.0374(13) -0.0135(12) 0.0005(11) 0.0103(11)
O5 0.0473(14) 0.0889(17) 0.0480(12) 0.0299(12) 0.0129(10) 0.0098(12)
O3 0.0251(11) 0.0598(13) 0.0753(13) -0.0339(10) 0.0065(10) -0.0062(9)
N5 0.0370(14) 0.0712(18) 0.0288(12) 0.0033(12) 0.0064(11) 0.0298(13)
O2 0.0404(13) 0.0408(12) 0.1072(17) 0.0214(12) 0.0192(12) -0.0057(10)
C5 0.0315(15) 0.0384(14) 0.0237(11) -0.0032(10) 0.0050(11) 0.0115(11)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.427(2) . ?
O1 C1 1.342(3) . ?
N2 C2 1.371(3) . ?
N2 C1 1.318(3) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N3 C1 1.326(3) . ?
C8 H8 0.9500 . ?
C8 C3 1.401(3) . ?
C8 C7 1.369(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.392(3) . ?
C4 C5 1.378(3) . ?
N1 C2 1.307(3) . ?
C2 C3 1.465(3) . ?
O4 N5 1.232(3) . ?
N4 C7 1.474(3) . ?
N4 O3 1.231(3) . ?
N4 O2 1.221(3) . ?
C7 C6 1.384(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.376(3) . ?
O5 N5 1.224(3) . ?
N5 C5 1.477(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
C1 O1 N1 105.92(15) . . ?
C1 N2 C2 101.73(17) . . ?
H3A N3 H3B 120.0 . . ?
C1 N3 H3A 120.0 . . ?
C1 N3 H3B 120.0 . . ?
C3 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C7 C8 C3 119.1(2) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C5 C4 C3 118.8(2) . . ?
C2 N1 O1 102.82(17) . . ?
N2 C2 C3 123.96(18) . . ?
N1 C2 N2 115.84(19) . . ?
N1 C2 C3 120.2(2) . . ?
C8 C3 C2 119.93(19) . . ?
C4 C3 C8 119.3(2) . . ?
C4 C3 C2 120.8(2) . . ?
O3 N4 C7 117.7(2) . . ?
O2 N4 C7 117.7(2) . . ?
O2 N4 O3 124.6(2) . . ?
C8 C7 N4 118.6(2) . . ?
C8 C7 C6 123.2(2) . . ?
C6 C7 N4 118.2(2) . . ?
N2 C1 O1 113.7(2) . . ?
N2 C1 N3 128.5(2) . . ?
N3 C1 O1 117.84(19) . . ?
C7 C6 H6 121.9 . . ?
C5 C6 C7 116.1(2) . . ?
C5 C6 H6 121.9 . . ?
O4 N5 C5 117.0(3) . . ?
O5 N5 O4 125.1(2) . . ?
O5 N5 C5 117.9(2) . . ?
C4 C5 N5 118.6(2) . . ?
C6 C5 C4 123.5(2) . . ?
C6 C5 N5 117.8(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 C2 N2 1.1(2) . . . . ?
O1 N1 C2 C3 -178.20(17) . . . . ?
N2 C2 C3 C8 -175.57(19) . . . . ?
N2 C2 C3 C4 5.1(3) . . . . ?
C8 C7 C6 C5 0.3(3) . . . . ?
N1 O1 C1 N2 0.2(2) . . . . ?
N1 O1 C1 N3 179.80(18) . . . . ?
N1 C2 C3 C8 3.6(3) . . . . ?
N1 C2 C3 C4 -175.7(2) . . . . ?
C2 N2 C1 O1 0.4(2) . . . . ?
C2 N2 C1 N3 -179.2(2) . . . . ?
O4 N5 C5 C4 -156.5(2) . . . . ?
O4 N5 C5 C6 24.1(3) . . . . ?
C3 C8 C7 N4 -179.05(18) . . . . ?
C3 C8 C7 C6 -0.6(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C5 N5 179.8(2) . . . . ?
N4 C7 C6 C5 178.79(19) . . . . ?
C7 C8 C3 C4 0.1(3) . . . . ?
C7 C8 C3 C2 -179.21(19) . . . . ?
C7 C6 C5 C4 0.4(3) . . . . ?
C7 C6 C5 N5 179.81(19) . . . . ?
C1 O1 N1 C2 -0.7(2) . . . . ?
C1 N2 C2 N1 -1.0(2) . . . . ?
C1 N2 C2 C3 178.3(2) . . . . ?
O5 N5 C5 C4 24.3(3) . . . . ?
O5 N5 C5 C6 -155.2(2) . . . . ?
O3 N4 C7 C8 -172.4(2) . . . . ?
O3 N4 C7 C6 9.0(3) . . . . ?
O2 N4 C7 C8 6.9(3) . . . . ?
O2 N4 C7 C6 -171.6(2) . . . . ?
C5 C4 C3 C8 0.5(3) . . . . ?
C5 C4 C3 C2 179.85(19) . . . . ?

