# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_1
_audit_block_doi                 10.5517/ccdc.csd.cc1n7tvk
_database_code_depnum_ccdc_archive 'CCDC 1526869'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CE00693D 2017
_audit_update_record             
;
2017-01-11 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 N5 O5'
_chemical_formula_weight         281.24

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 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8062(18)
_cell_length_b                   17.518(4)
_cell_length_c                   8.1176(16)
_cell_angle_alpha                90
_cell_angle_beta                 103.15(3)
_cell_angle_gamma                90
_cell_volume                     1219.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1614
_cell_measurement_theta_min      3.294
_cell_measurement_theta_max      27.481

_exptl_crystal_description       prism
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.125
_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_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8037
_diffrn_reflns_av_unetI/netI     0.0718
_diffrn_reflns_av_R_equivalents  0.0610
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.294
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2776
_reflns_number_gt                1614
_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 (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)+(0.0780P)²+0.2811P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2776
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1555
_refine_ls_R_factor_gt           0.0875
_refine_ls_wR_factor_ref         0.2043
_refine_ls_wR_factor_gt          0.1798
_refine_ls_goodness_of_fit_ref   1.169
_refine_ls_restrained_S_all      1.169
_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
N2 N 0.2996(3) 0.11529(14) 1.0365(3) 0.0371(7) Uani 1 1 d . . . . .
O4 O 0.0747(3) 0.53130(11) 0.8009(3) 0.0480(7) Uani 1 1 d . . . . .
N3 N 0.2343(3) 0.18475(14) 0.9691(3) 0.0419(7) Uani 1 1 d . . . . .
N5 N 0.3208(3) -0.00426(16) 1.0627(4) 0.0418(7) Uani 1 1 d . . . . .
C7 C 0.0603(4) 0.39862(17) 0.7879(4) 0.0378(8) Uani 1 1 d . . . . .
O5 O -0.0604(3) 0.41020(12) 0.6527(3) 0.0598(8) Uani 1 1 d . . . . .
H5A H -0.0972 0.3689 0.6160 0.090 Uiso 1 1 calc R U . . .
C6 C 0.1102(4) 0.32772(18) 0.8447(4) 0.0401(8) Uani 1 1 d . . . . .
H6 H 0.0599 0.2847 0.7914 0.048 Uiso 1 1 calc R U . . .
C2 C 0.1335(4) 0.46425(17) 0.8702(4) 0.0359(8) Uani 1 1 d . . . . .
C4 C 0.3095(4) 0.38421(18) 1.0649(4) 0.0460(9) Uani 1 1 d . . . . .
H4 H 0.3927 0.3792 1.1580 0.055 Uiso 1 1 calc R U . . .
C8 C 0.2954(4) 0.24432(18) 1.0437(4) 0.0430(8) Uani 1 1 d . . . . .
H8 H 0.3780 0.2401 1.1378 0.052 Uiso 1 1 calc R U . . .
C5 C 0.2372(4) 0.31944(17) 0.9834(4) 0.0389(8) Uani 1 1 d . . . . .
C9 C 0.4284(4) 0.09772(18) 1.1616(4) 0.0437(9) Uani 1 1 d . . . . .
H9 H 0.4951 0.1335 1.2250 0.052 Uiso 1 1 calc R U . . .
N4 N 0.4437(3) 0.02464(15) 1.1790(4) 0.0468(8) Uani 1 1 d . . . . .
C10 C 0.2353(4) 0.04965(18) 0.9777(4) 0.0407(8) Uani 1 1 d . . . . .
H10 H 0.1461 0.0432 0.8921 0.049 Uiso 1 1 calc R U . . .
C1 C 0.1475(5) 0.60058(18) 0.8740(5) 0.0558(10) Uani 1 1 d . . . . .
H1A H 0.0953 0.6436 0.8127 0.084 Uiso 1 1 calc R U . . .
H1B H 0.2551 0.6007 0.8679 0.084 Uiso 1 1 calc R U . . .
H1C H 0.1407 0.6038 0.9901 0.084 Uiso 1 1 calc R U . . .
C3 C 0.2574(4) 0.45633(18) 1.0072(4) 0.0433(8) Uani 1 1 d . . . . .
H3 H 0.3065 0.4995 1.0613 0.052 Uiso 1 1 calc R U . . .
O3 O 0.6204(3) 0.15616(14) 0.9216(4) 0.0633(8) Uani 1 1 d . . . . .
N1 N 0.6885(4) 0.21805(16) 0.9368(4) 0.0542(9) Uani 1 1 d . . . . .
O1 O 0.6198(4) 0.27642(16) 0.8843(5) 0.1024(13) Uani 1 1 d . . . . .
O2 O 0.8303(4) 0.22062(15) 1.0042(4) 0.0877(11) Uani 1 1 d . . . . .
H5 H 0.318(4) -0.060(2) 1.057(4) 0.052(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C10 1.322(4) . ?
N2 C9 1.374(4) . ?
N2 N3 1.403(3) . ?
O4 C2 1.353(4) . ?
O4 C1 1.436(4) . ?
N3 C8 1.264(4) . ?
N5 C10 1.303(4) . ?
N5 N4 1.362(3) . ?
C7 O5 1.358(4) . ?
C7 C6 1.362(4) . ?
C7 C2 1.410(4) . ?
C6 C5 1.403(4) . ?
C2 C3 1.376(5) . ?
C4 C3 1.388(4) . ?
C4 C5 1.392(4) . ?
C8 C5 1.456(4) . ?
C9 N4 1.292(4) . ?
O3 N1 1.232(4) . ?
N1 O1 1.215(4) . ?
N1 O2 1.245(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N2 C9 106.6(3) . . ?
C10 N2 N3 120.7(3) . . ?
C9 N2 N3 132.7(3) . . ?
C2 O4 C1 118.0(3) . . ?
C8 N3 N2 115.9(3) . . ?
C10 N5 N4 111.7(3) . . ?
O5 C7 C6 122.9(3) . . ?
O5 C7 C2 116.8(3) . . ?
C6 C7 C2 120.4(3) . . ?
C7 C6 C5 120.2(3) . . ?
O4 C2 C3 125.5(3) . . ?
O4 C2 C7 114.9(3) . . ?
C3 C2 C7 119.6(3) . . ?
C3 C4 C5 120.1(3) . . ?
N3 C8 C5 120.4(3) . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 C8 119.3(3) . . ?
C6 C5 C8 121.2(3) . . ?
N4 C9 N2 110.6(3) . . ?
C9 N4 N5 104.2(3) . . ?
N5 C10 N2 106.9(3) . . ?
C2 C3 C4 120.3(3) . . ?
O1 N1 O3 120.9(3) . . ?
O1 N1 O2 119.5(3) . . ?
O3 N1 O2 119.5(3) . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.085

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1526872'
_audit_update_record             
;
2017-09-25 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 N5 O5'
_chemical_formula_weight         281.24

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   Pn

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

_cell_length_a                   4.2000(8)
_cell_length_b                   8.5070(17)
_cell_length_c                   17.069(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.05(3)
_cell_angle_gamma                90.00
_cell_volume                     608.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      14

_exptl_crystal_description       Rod
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             292
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9633
_exptl_absorpt_correction_T_max  0.9875
_exptl_absorpt_process_details   'CrystalClear (Rigaku, 2005)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Rigaku SCXmini diffractometer'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1278
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         25.37
_reflns_number_total             1278
_reflns_number_gt                1162
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY ( Cambridge Structural Database,2003)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.1000P)²+0.0200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.060(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   3(2)
_refine_ls_number_reflns         1278
_refine_ls_number_parameters     182
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.000
_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
O1 O 0.0320(7) 0.6261(3) 0.16133(14) 0.0473(7) Uani 1 1 d . . .
H1A H 0.0149 0.7053 0.1881 0.071 Uiso 1 1 calc R . .
N1 N 1.1671(8) 0.6518(4) -0.31891(17) 0.0435(8) Uani 1 1 d . . .
H1B H 1.2921 0.6097 -0.3508 0.052 Uiso 1 1 calc R . .
C1 C 1.0586(9) 0.5785(4) -0.2585(2) 0.0391(8) Uani 1 1 d . . .
H1C H 1.0984 0.4747 -0.2437 0.047 Uiso 1 1 calc R . .
O2 O 0.0602(7) 0.4053(3) 0.05870(14) 0.0454(7) Uani 1 1 d . . .
N2 N 1.0577(9) 0.8026(4) -0.32504(18) 0.0502(9) Uani 1 1 d . . .
C2 C 0.8837(10) 0.8181(4) -0.2659(2) 0.0477(9) Uani 1 1 d . . .
H2B H 0.7748 0.9093 -0.2541 0.057 Uiso 1 1 calc R . .
C3 C 0.6808(9) 0.7461(4) -0.1072(2) 0.0379(7) Uani 1 1 d . . .
H3A H 0.7753 0.8437 -0.1138 0.046 Uiso 1 1 calc R . .
N3 N 0.8816(7) 0.6812(3) -0.22282(17) 0.0382(7) Uani 1 1 d . . .
N4 N 0.7060(7) 0.6390(3) -0.15890(17) 0.0406(7) Uani 1 1 d . . .
C4 C 0.5058(8) 0.7169(4) -0.0382(2) 0.0354(7) Uani 1 1 d . . .
C5 C 0.4845(10) 0.8341(4) 0.0170(2) 0.0433(8) Uani 1 1 d . . .
H5A H 0.5773 0.9315 0.0090 0.052 Uiso 1 1 calc R . .
C6 C 0.3246(10) 0.8077(4) 0.0849(2) 0.0448(9) Uani 1 1 d . . .
H6A H 0.3111 0.8871 0.1220 0.054 Uiso 1 1 calc R . .
C7 C 0.1863(9) 0.6623(4) 0.0966(2) 0.0384(8) Uani 1 1 d . . .
C8 C 0.2074(8) 0.5435(4) 0.04035(18) 0.0345(7) Uani 1 1 d . . .
C9 C 0.3643(8) 0.5696(4) -0.0267(2) 0.0365(7) Uani 1 1 d . . .
H9A H 0.3764 0.4906 -0.0640 0.044 Uiso 1 1 calc R . .
C10 C 0.0641(14) 0.2790(5) 0.0034(3) 0.0605(12) Uani 1 1 d . . .
H10A H -0.0445 0.1897 0.0233 0.091 Uiso 1 1 calc R . .
H10B H 0.2810 0.2511 -0.0045 0.091 Uiso 1 1 calc R . .
H10C H -0.0415 0.3114 -0.0456 0.091 Uiso 1 1 calc R . .
O3 O 0.3005(11) 1.0363(4) -0.1450(2) 0.0916(13) Uani 1 1 d . . .
O4 O 0.4692(13) 1.1232(4) -0.2520(2) 0.0918(14) Uani 1 1 d . . .
O5 O 0.2404(18) 1.2758(5) -0.1785(3) 0.137(3) Uani 1 1 d . . .
N5 N 0.3343(10) 1.1456(4) -0.1912(2) 0.0594(10) 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
O1 C7 1.356(4) . ?
O1 H1A 0.8200 . ?
N1 C1 1.313(5) . ?
N1 N2 1.365(4) . ?
N1 H1B 0.8600 . ?
C1 N3 1.324(5) . ?
C1 H1C 0.9300 . ?
O2 C8 1.375(4) . ?
O2 C10 1.431(4) . ?
N2 C2 1.294(5) . ?
C2 N3 1.378(5) . ?
C2 H2B 0.9300 . ?
C3 N4 1.279(5) . ?
C3 C4 1.454(4) . ?
C3 H3A 0.9300 . ?
N3 N4 1.406(4) . ?
C4 C5 1.379(5) . ?
C4 C9 1.406(5) . ?
C5 C6 1.398(5) . ?
C5 H5A 0.9300 . ?
C6 C7 1.387(5) . ?
C6 H6A 0.9300 . ?
C7 C8 1.401(5) . ?
C8 C9 1.378(5) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O3 N5 1.234(5) . ?
O4 N5 1.231(5) . ?
O5 N5 1.201(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
C7 O1 H1A 109.5 . . ?
C1 N1 N2 111.9(3) . . ?
C1 N1 H1B 124.0 . . ?
N2 N1 H1B 124.0 . . ?
N1 C1 N3 106.6(3) . . ?
N1 C1 H1C 126.7 . . ?
N3 C1 H1C 126.7 . . ?
C8 O2 C10 117.7(3) . . ?
C2 N2 N1 104.0(3) . . ?
N2 C2 N3 110.8(3) . . ?
N2 C2 H2B 124.6 . . ?
N3 C2 H2B 124.6 . . ?
N4 C3 C4 120.6(3) . . ?
N4 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C1 N3 C2 106.7(3) . . ?
C1 N3 N4 122.1(3) . . ?
C2 N3 N4 130.8(3) . . ?
C3 N4 N3 115.3(3) . . ?
C5 C4 C9 120.0(3) . . ?
C5 C4 C3 119.4(3) . . ?
C9 C4 C3 120.6(3) . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 H6A 120.2 . . ?
C5 C6 H6A 120.2 . . ?
O1 C7 C6 123.3(3) . . ?
O1 C7 C8 116.9(3) . . ?
C6 C7 C8 119.9(3) . . ?
O2 C8 C9 125.2(3) . . ?
O2 C8 C7 114.2(3) . . ?
C9 C8 C7 120.6(3) . . ?
C8 C9 C4 119.4(3) . . ?
C8 C9 H9A 120.3 . . ?
C4 C9 H9A 120.3 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O5 N5 O4 118.1(4) . . ?
O5 N5 O3 121.7(4) . . ?
O4 N5 O3 120.2(4) . . ?

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
N2 N1 C1 N3 -1.4(4) . . . . ?
C1 N1 N2 C2 0.8(4) . . . . ?
N1 N2 C2 N3 0.1(4) . . . . ?
N1 C1 N3 C2 1.4(4) . . . . ?
N1 C1 N3 N4 174.8(3) . . . . ?
N2 C2 N3 C1 -0.9(4) . . . . ?
N2 C2 N3 N4 -173.6(4) . . . . ?
C4 C3 N4 N3 -179.8(3) . . . . ?
C1 N3 N4 C3 146.4(3) . . . . ?
C2 N3 N4 C3 -41.9(5) . . . . ?
N4 C3 C4 C5 179.5(4) . . . . ?
N4 C3 C4 C9 0.7(5) . . . . ?
C9 C4 C5 C6 0.4(6) . . . . ?
C3 C4 C5 C6 -178.4(3) . . . . ?
C4 C5 C6 C7 0.0(6) . . . . ?
C5 C6 C7 O1 178.8(3) . . . . ?
C5 C6 C7 C8 -0.1(6) . . . . ?
C10 O2 C8 C9 -1.2(5) . . . . ?
C10 O2 C8 C7 178.6(4) . . . . ?
O1 C7 C8 O2 1.2(4) . . . . ?
C6 C7 C8 O2 -179.8(3) . . . . ?
O1 C7 C8 C9 -179.1(3) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
O2 C8 C9 C4 -179.8(3) . . . . ?
C7 C8 C9 C4 0.4(5) . . . . ?
C5 C4 C9 C8 -0.6(5) . . . . ?
C3 C4 C9 C8 178.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.048

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1526873'
_audit_update_record             
;
2017-09-25 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 Cl N4 O6'
_chemical_formula_weight         318.68

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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+1/2'

_cell_length_a                   4.4190(9)
_cell_length_b                   8.5810(17)
_cell_length_c                   17.499(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.35(3)
_cell_angle_gamma                90
_cell_volume                     663.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1201
_cell_measurement_theta_min      2.328
_cell_measurement_theta_max      25.337

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.324
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.562
_exptl_absorpt_correction_T_max  0.7689
_exptl_absorpt_process_details   'CrystalClear (Rigaku, 2005)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Rigaku SCXmini diffractometer'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1510
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         2.328
_diffrn_reflns_theta_max         25.337
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.571
_diffrn_reflns_point_group_measured_fraction_full 0.571
_reflns_number_total             1390
_reflns_number_gt                1201
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.137
_reflns_Friedel_fraction_max     0.138
_reflns_Friedel_fraction_full    0.139

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY ( Cambridge Structural Database,2003)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0985P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.41(16)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1390
_refine_ls_number_parameters     190
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1530
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.079
_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
Cl Cl 0.1510(3) 0.88553(19) 0.71973(10) 0.0358(4) Uani 1 1 d . . . . .
O3 O -0.0974(12) 0.8337(9) 0.6620(3) 0.0653(19) Uani 1 1 d . . . . .
O4 O 0.2621(16) 1.0308(8) 0.6926(4) 0.0649(19) Uani 1 1 d . . . . .
O5 O 0.3838(13) 0.7639(7) 0.7186(4) 0.0573(16) Uani 1 1 d . . . . .
O6 O 0.0118(14) 0.8979(6) 0.7935(3) 0.0465(14) Uani 1 1 d . . . . .
O1 O 1.4328(13) 0.3551(6) 0.3761(3) 0.0449(14) Uani 1 1 d . . . . .
H1A H 1.5165 0.4430 0.3692 0.054 Uiso 1 1 d R U . . .
N1 N 0.3263(15) 0.3756(7) 0.8536(3) 0.0365(15) Uani 1 1 d . . . . .
H1 H 0.1971 0.4164 0.8836 0.044 Uiso 1 1 calc R U . . .
C1 C 0.4309(17) 0.4448(9) 0.7927(4) 0.0351(16) Uani 1 1 d . . . . .
H1C H 0.3829 0.5448 0.7759 0.042 Uiso 1 1 calc R U . . .
C2 C 0.6262(18) 0.2143(9) 0.8055(4) 0.0395(18) Uani 1 1 d . . . . .
H2A H 0.7430 0.1265 0.7961 0.047 Uiso 1 1 calc R U . . .
N2 N 0.4481(15) 0.2317(7) 0.8629(3) 0.0401(15) Uani 1 1 d . . . . .
O2 O 1.4222(13) 0.5849(6) 0.4712(3) 0.0388(13) Uani 1 1 d . . . . .
N3 N 0.6147(14) 0.3474(6) 0.7602(3) 0.0319(13) Uani 1 1 d . . . . .
C3 C 0.7991(17) 0.2790(9) 0.6461(4) 0.0356(16) Uani 1 1 d . . . . .
H3B H 0.6964 0.1862 0.6545 0.043 Uiso 1 1 calc R U . . .
N4 N 0.7907(15) 0.3847(7) 0.6958(3) 0.0356(15) Uani 1 1 d . . . . .
C4 C 0.9647(15) 0.2979(8) 0.5763(4) 0.0305(15) Uani 1 1 d . . . . .
C5 C 0.9752(19) 0.1764(9) 0.5242(4) 0.0412(18) Uani 1 1 d . . . . .
H5B H 0.8763 0.0832 0.5341 0.049 Uiso 1 1 calc R U . . .
C6 C 1.1338(19) 0.1940(9) 0.4570(4) 0.0416(19) Uani 1 1 d . . . . .
H6B H 1.1407 0.1118 0.4224 0.050 Uiso 1 1 calc R U . . .
C7 C 1.2797(18) 0.3305(9) 0.4410(4) 0.0338(16) Uani 1 1 d . . . . .
C8 C 1.2687(16) 0.4547(8) 0.4930(4) 0.0301(15) Uani 1 1 d . . . . .
C9 C 1.1115(17) 0.4381(8) 0.5599(4) 0.0311(15) Uani 1 1 d . . . . .
H9A H 1.1031 0.5207 0.5942 0.037 Uiso 1 1 calc R U . . .
C10 C 1.426(2) 0.7168(10) 0.5216(5) 0.058(2) Uani 1 1 d . . . . .
H10A H 1.5409 0.7995 0.4994 0.087 Uiso 1 1 calc R U . . .
H10B H 1.2224 0.7515 0.5292 0.087 Uiso 1 1 calc R U . . .
H10C H 1.5170 0.6876 0.5698 0.087 Uiso 1 1 calc R 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
Cl O4 1.425(6) . ?
Cl O6 1.447(6) . ?
Cl O5 1.466(6) . ?
Cl O3 1.540(6) . ?
O1 C7 1.352(8) . ?
O1 H1A 0.8500 . ?
N1 C1 1.312(9) . ?
N1 N2 1.356(8) . ?
N1 H1 0.8600 . ?
C1 N3 1.305(9) . ?
C1 H1C 0.9300 . ?
C2 N2 1.300(9) . ?
C2 N3 1.390(9) . ?
C2 H2A 0.9300 . ?
O2 C8 1.366(8) . ?
O2 C10 1.434(9) . ?
N3 N4 1.422(7) . ?
C3 N4 1.257(9) . ?
C3 C4 1.448(9) . ?
C3 H3B 0.9300 . ?
C4 C5 1.387(10) . ?
C4 C9 1.400(10) . ?
C5 C6 1.391(10) . ?
C5 H5B 0.9300 . ?
C6 C7 1.369(10) . ?
C6 H6B 0.9300 . ?
C7 C8 1.404(9) . ?
C8 C9 1.381(9) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
O4 Cl O6 113.0(4) . . ?
O4 Cl O5 111.8(4) . . ?
O6 Cl O5 112.1(3) . . ?
O4 Cl O3 106.2(4) . . ?
O6 Cl O3 107.2(3) . . ?
O5 Cl O3 106.0(4) . . ?
C7 O1 H1A 119.1 . . ?
C1 N1 N2 111.4(6) . . ?
C1 N1 H1 124.3 . . ?
N2 N1 H1 124.3 . . ?
N3 C1 N1 107.3(7) . . ?
N3 C1 H1C 126.3 . . ?
N1 C1 H1C 126.3 . . ?
N2 C2 N3 109.4(6) . . ?
N2 C2 H2A 125.3 . . ?
N3 C2 H2A 125.3 . . ?
C2 N2 N1 104.9(6) . . ?
C8 O2 C10 118.2(6) . . ?
C1 N3 C2 107.0(6) . . ?
C1 N3 N4 124.0(6) . . ?
C2 N3 N4 128.6(6) . . ?
N4 C3 C4 121.7(7) . . ?
N4 C3 H3B 119.1 . . ?
C4 C3 H3B 119.1 . . ?
C3 N4 N3 114.3(6) . . ?
C5 C4 C9 119.2(7) . . ?
C5 C4 C3 119.8(7) . . ?
C9 C4 C3 121.0(6) . . ?
C4 C5 C6 120.0(7) . . ?
C4 C5 H5B 120.0 . . ?
C6 C5 H5B 120.0 . . ?
C7 C6 C5 121.0(7) . . ?
C7 C6 H6B 119.5 . . ?
C5 C6 H6B 119.5 . . ?
O1 C7 C6 123.6(6) . . ?
O1 C7 C8 116.9(7) . . ?
C6 C7 C8 119.6(6) . . ?
O2 C8 C9 125.7(6) . . ?
O2 C8 C7 114.5(6) . . ?
C9 C8 C7 119.8(6) . . ?
C8 C9 C4 120.5(6) . . ?
C8 C9 H9A 119.8 . . ?
C4 C9 H9A 119.8 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
N2 N1 C1 N3 1.7(9) . . . . ?
N3 C2 N2 N1 -0.1(8) . . . . ?
C1 N1 N2 C2 -0.9(9) . . . . ?
N1 C1 N3 C2 -1.7(8) . . . . ?
N1 C1 N3 N4 -175.0(6) . . . . ?
N2 C2 N3 C1 1.1(8) . . . . ?
N2 C2 N3 N4 174.1(7) . . . . ?
C4 C3 N4 N3 179.2(6) . . . . ?
C1 N3 N4 C3 -138.1(8) . . . . ?
C2 N3 N4 C3 50.1(10) . . . . ?
N4 C3 C4 C5 178.1(8) . . . . ?
N4 C3 C4 C9 -2.8(11) . . . . ?
C9 C4 C5 C6 0.9(11) . . . . ?
C3 C4 C5 C6 180.0(7) . . . . ?
C4 C5 C6 C7 -0.3(12) . . . . ?
C5 C6 C7 O1 -178.9(7) . . . . ?
C5 C6 C7 C8 -0.2(12) . . . . ?
C10 O2 C8 C9 0.6(11) . . . . ?
C10 O2 C8 C7 -179.2(7) . . . . ?
O1 C7 C8 O2 -1.3(9) . . . . ?
C6 C7 C8 O2 180.0(7) . . . . ?
O1 C7 C8 C9 178.9(6) . . . . ?
C6 C7 C8 C9 0.1(11) . . . . ?
O2 C8 C9 C4 -179.4(7) . . . . ?
C7 C8 C9 C4 0.4(10) . . . . ?
C5 C4 C9 C8 -0.9(10) . . . . ?
C3 C4 C9 C8 -180.0(7) . . . . ?

_refine_diff_density_max         0.413
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.091

_shelxl_version_number           2014-3

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1526871'
_audit_update_record             
;
2017-09-25 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H25 N8 O9 P'
_chemical_formula_weight         552.45

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   21.2012(14)
_cell_length_b                   7.069(3)
_cell_length_c                   17.137
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2568.2(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3532
_cell_measurement_theta_min      3.038
_cell_measurement_theta_max      27.482

_exptl_crystal_description       prism
_exptl_crystal_colour            lightyellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.172
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5807
_exptl_absorpt_correction_T_max  0.7502
_exptl_absorpt_process_details   'CrystalClear (Rigaku, 2005)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Rigaku SCXmini diffractometer'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16618
_diffrn_reflns_av_unetI/netI     0.0867
_diffrn_reflns_av_R_equivalents  0.0791
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.038
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_point_group_measured_fraction_full 0.907
_reflns_number_total             5235
_reflns_number_gt                3532
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_max     0.777
_reflns_Friedel_fraction_full    0.809

_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       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY ( Cambridge Structural Database,2003)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.1411P)²+0.2207P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1072 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.38(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5235
_refine_ls_number_parameters     352
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1354
_refine_ls_R_factor_gt           0.0923
_refine_ls_wR_factor_ref         0.2440
_refine_ls_wR_factor_gt          0.2198
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          1.778
_refine_ls_shift/su_mean         0.063

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
P1 P 0.42164(8) 0.7864(3) 0.11745(13) 0.0234(4) Uani 1 1 d . . . . .
O6 O 0.2732(3) 0.5756(10) 0.3598(4) 0.0445(16) Uani 1 1 d . . . . .
N1 N 0.3675(3) 0.5886(10) 0.7136(4) 0.0346(17) Uani 1 1 d . . . . .
O3 O 0.3521(3) 0.7856(9) 0.1073(4) 0.0422(16) Uani 1 1 d . . . . .
N2 N 0.4040(3) 0.5969(10) 0.7811(4) 0.0316(16) Uani 1 1 d . . . . .
C3 C 0.3946(4) 0.5412(13) 0.6506(5) 0.0315(19) Uani 1 1 d . . . . .
H3 H 0.4369 0.5058 0.6524 0.038 Uiso 1 1 calc R U . . .
C4 C 0.3623(4) 0.5399(11) 0.5752(5) 0.0278(18) Uani 1 1 d . . . . .
C8 C 0.2708(4) 0.6015(13) 0.4969(5) 0.0303(18) Uani 1 1 d . . . . .
C7 C 0.3062(4) 0.5575(13) 0.4282(5) 0.035(2) Uani 1 1 d . . . . .
C9 C 0.2982(4) 0.5881(12) 0.5678(5) 0.0292(18) Uani 1 1 d . . . . .
H9 H 0.2744 0.6112 0.6124 0.035 Uiso 1 1 calc R U . . .
N4 N 0.4254(4) 0.6602(12) 0.9022(5) 0.0418(19) Uani 1 1 d . . . . .
O4 O 0.4572(3) 0.7878(11) 0.0378(4) 0.0475(18) Uani 1 1 d . . . . .
H4 H 0.4376 0.7242 0.0060 0.071 Uiso 1 1 calc R U . . .
O5 O 0.2095(3) 0.6526(11) 0.4846(4) 0.0432(17) Uani 1 1 d . . . . .
H5 H 0.1916 0.6649 0.5267 0.065 Uiso 1 1 calc R U . . .
C2 C 0.3809(4) 0.6485(13) 0.8504(5) 0.0357(19) Uani 1 1 d . . . . .
H2 H 0.3385 0.6729 0.8602 0.043 Uiso 1 1 calc R U . . .
O2 O 0.4459(3) 0.9506(8) 0.1663(4) 0.0329(14) Uani 1 1 d . . . . .
C6 C 0.3683(4) 0.5067(12) 0.4343(5) 0.0295(18) Uani 1 1 d . . . . .
H6 H 0.3916 0.4773 0.3899 0.035 Uiso 1 1 calc R U . . .
C5 C 0.3959(4) 0.4997(13) 0.5070(5) 0.035(2) Uani 1 1 d . . . . .
H5A H 0.4383 0.4672 0.5108 0.042 Uiso 1 1 calc R U . . .
C10 C 0.3048(5) 0.5376(16) 0.2875(5) 0.051(3) Uani 1 1 d . . . . .
H10A H 0.2790 0.5790 0.2448 0.077 Uiso 1 1 calc R U . . .
H10B H 0.3124 0.4042 0.2829 0.077 Uiso 1 1 calc R U . . .
H10C H 0.3443 0.6041 0.2863 0.077 Uiso 1 1 calc R U . . .
N3 N 0.4819(4) 0.6175(16) 0.8643(5) 0.067(3) Uani 1 1 d . . . . .
O1 O 0.4431(4) 0.6049(10) 0.1618(5) 0.0542(19) Uani 1 1 d . . . . .
H1A H 0.4212 0.5151 0.1483 0.081 Uiso 1 1 calc R U . . .
C1 C 0.4683(5) 0.582(2) 0.7923(7) 0.069(4) Uani 1 1 d . . . . .
H1 H 0.4975 0.5501 0.7539 0.083 Uiso 1 1 calc R U . . .
N5 N 0.3679(3) 0.0040(11) 0.5002(4) 0.0340(17) Uani 1 1 d . . . . .
N6 N 0.4083(3) -0.0233(11) 0.4367(4) 0.0327(16) Uani 1 1 d . . . . .
C14 C 0.3583(4) 0.0499(12) 0.6381(5) 0.0310(19) Uani 1 1 d . . . . .
C17 C 0.2914(4) 0.0852(12) 0.7766(5) 0.0305(19) Uani 1 1 d . . . . .
C11 C 0.3939(4) 0.0314(13) 0.5664(6) 0.034(2) Uani 1 1 d . . . . .
H11 H 0.4376 0.0398 0.5686 0.041 Uiso 1 1 calc R U . . .
O8 O 0.1958(3) 0.0221(11) 0.7128(4) 0.0487(18) Uani 1 1 d . . . . .
H8 H 0.1856 -0.0780 0.6922 0.073 Uiso 1 1 calc R U . . .
O7 O 0.2541(3) 0.0968(10) 0.8419(3) 0.0444(17) Uani 1 1 d . . . . .
C18 C 0.2599(4) 0.0438(11) 0.7077(6) 0.0307(18) Uani 1 1 d . . . . .
C19 C 0.2925(4) 0.0312(13) 0.6385(5) 0.0295(19) Uani 1 1 d . . . . .
H19 H 0.2709 0.0104 0.5920 0.035 Uiso 1 1 calc R U . . .
C16 C 0.3570(4) 0.1030(12) 0.7770(5) 0.034(2) Uani 1 1 d . . . . .
H16 H 0.3784 0.1267 0.8234 0.041 Uiso 1 1 calc R U . . .
C15 C 0.3898(4) 0.0849(13) 0.7078(6) 0.037(2) Uani 1 1 d . . . . .
H15 H 0.4335 0.0963 0.7078 0.045 Uiso 1 1 calc R U . . .
C20 C 0.2840(5) 0.1348(17) 0.9157(5) 0.048(2) Uani 1 1 d . . . . .
H20A H 0.3091 0.2473 0.9116 0.072 Uiso 1 1 calc R U . . .
H20B H 0.3105 0.0300 0.9297 0.072 Uiso 1 1 calc R U . . .
H20C H 0.2523 0.1523 0.9551 0.072 Uiso 1 1 calc R U . . .
C12 C 0.4701(4) -0.0884(16) 0.4305(6) 0.049(3) Uani 1 1 d . . . . .
H12 H 0.4955 -0.1184 0.4730 0.058 Uiso 1 1 calc R U . . .
N8 N 0.4373(3) -0.0498(11) 0.3181(5) 0.0380(18) Uani 1 1 d . . . . .
H8A H 0.4359 -0.0479 0.2679 0.046 Uiso 1 1 calc R U . . .
N7 N 0.4879(4) -0.1021(13) 0.3581(4) 0.047(2) Uani 1 1 d . . . . .
C13 C 0.3900(4) -0.0016(14) 0.3622(6) 0.041(2) Uani 1 1 d . . . . .
H13 H 0.3507 0.0401 0.3453 0.049 Uiso 1 1 calc R U . . .
H3W H 0.412(2) 0.289(14) 0.064(5) 0.05(3) Uiso 1 1 d D . . . .
O2W O 0.4449(4) 0.2812(12) 0.0909(6) 0.066(2) Uiso 1 1 d D . . . .
H1W H 0.416(3) 0.283(9) 0.127(4) -0.001(14) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O3 1.484(6) . ?
P1 O2 1.520(6) . ?
P1 O4 1.559(7) . ?
P1 O1 1.559(7) . ?
O6 C7 1.371(10) . ?
O6 C10 1.436(11) . ?
N1 C3 1.269(11) . ?
N1 N2 1.394(10) . ?
N2 C2 1.336(12) . ?
N2 C1 1.381(12) . ?
C3 C4 1.463(11) . ?
C4 C5 1.399(12) . ?
C4 C9 1.406(11) . ?
C8 C9 1.350(11) . ?
C8 O5 1.365(10) . ?
C8 C7 1.430(12) . ?
C7 C6 1.370(12) . ?
N4 C2 1.299(11) . ?
N4 N3 1.395(11) . ?
C6 C5 1.377(12) . ?
N3 C1 1.292(13) . ?
N5 C11 1.276(12) . ?
N5 N6 1.400(9) . ?
N6 C13 1.342(12) . ?
N6 C12 1.392(11) . ?
C14 C15 1.391(12) . ?
C14 C19 1.401(11) . ?
C14 C11 1.448(12) . ?
C17 O7 1.373(10) . ?
C17 C18 1.387(12) . ?
C17 C16 1.397(11) . ?
O8 C18 1.369(9) . ?
O7 C20 1.440(11) . ?
C18 C19 1.377(12) . ?
C16 C15 1.380(13) . ?
C12 N7 1.301(12) . ?
N8 C13 1.302(12) . ?
N8 N7 1.325(11) . ?

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 P1 O2 113.8(3) . . ?
O3 P1 O4 112.2(4) . . ?
O2 P1 O4 108.3(3) . . ?
O3 P1 O1 110.1(4) . . ?
O2 P1 O1 105.1(4) . . ?
O4 P1 O1 106.9(4) . . ?
C7 O6 C10 118.8(7) . . ?
C3 N1 N2 117.7(7) . . ?
C2 N2 C1 105.1(8) . . ?
C2 N2 N1 123.0(7) . . ?
C1 N2 N1 131.4(8) . . ?
N1 C3 C4 122.7(7) . . ?
C5 C4 C9 117.8(8) . . ?
C5 C4 C3 120.0(7) . . ?
C9 C4 C3 122.1(8) . . ?
C9 C8 O5 124.6(8) . . ?
C9 C8 C7 120.0(7) . . ?
O5 C8 C7 115.4(7) . . ?
O6 C7 C6 125.5(8) . . ?
O6 C7 C8 114.6(7) . . ?
C6 C7 C8 119.9(8) . . ?
C8 C9 C4 120.9(8) . . ?
C2 N4 N3 107.0(7) . . ?
N4 C2 N2 111.0(8) . . ?
C7 C6 C5 119.2(8) . . ?
C6 C5 C4 122.1(7) . . ?
C1 N3 N4 107.2(8) . . ?
N3 C1 N2 109.7(9) . . ?
C11 N5 N6 116.6(7) . . ?
C13 N6 C12 103.8(8) . . ?
C13 N6 N5 123.1(7) . . ?
C12 N6 N5 132.9(8) . . ?
C15 C14 C19 119.3(8) . . ?
C15 C14 C11 119.7(7) . . ?
C19 C14 C11 120.9(8) . . ?
O7 C17 C18 115.4(7) . . ?
O7 C17 C16 124.3(7) . . ?
C18 C17 C16 120.2(8) . . ?
N5 C11 C14 122.9(7) . . ?
C17 O7 C20 118.3(7) . . ?
O8 C18 C19 123.1(8) . . ?
O8 C18 C17 116.6(8) . . ?
C19 C18 C17 120.3(7) . . ?
C18 C19 C14 119.9(7) . . ?
C15 C16 C17 119.2(8) . . ?
C16 C15 C14 120.9(7) . . ?
N7 C12 N6 111.7(9) . . ?
C13 N8 N7 113.3(8) . . ?
C12 N7 N8 103.8(8) . . ?
N8 C13 N6 107.4(8) . . ?

_refine_diff_density_max         2.124
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.102

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_2
_audit_block_doi                 10.5517/ccdc.csd.cc1n7twl
_database_code_depnum_ccdc_archive 'CCDC 1526870'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C7CE00693D 2017
_audit_update_record             
;
2017-01-11 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 Cl N8 O8'
_chemical_formula_weight         536.90

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'
Cl Cl 0.1484 0.1585 '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                   8.0110(16)
_cell_length_b                   11.071(2)
_cell_length_c                   13.968(3)
_cell_angle_alpha                100.75(3)
_cell_angle_beta                 91.99(3)
_cell_angle_gamma                108.46(3)
_cell_volume                     1148.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2983
_cell_measurement_theta_min      1.491
_cell_measurement_theta_max      25.378

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.233
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4560
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.491
_diffrn_reflns_theta_max         25.378
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4234
_reflns_number_gt                2983
_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 (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)+(0.0941P)²+0.3820P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4234
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1712
_refine_ls_wR_factor_gt          0.1522
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_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
Cl Cl 0.36226(11) 0.97527(7) 0.78284(6) 0.0415(3) Uani 1 1 d . . . . .
O5 O 0.1779(3) 0.9083(3) 0.7668(2) 0.0772(9) Uani 1 1 d . . . . .
O6 O 0.4499(3) 0.8989(3) 0.72303(18) 0.0606(7) Uani 1 1 d . . . . .
O7 O 0.4216(4) 0.9920(3) 0.88362(18) 0.0732(8) Uani 1 1 d . . . . .
O8 O 0.4043(4) 1.0997(3) 0.7576(2) 0.0778(9) Uani 1 1 d . . . . .
O1 O -0.1486(3) 0.6599(2) 0.54836(16) 0.0480(6) Uani 1 1 d . . . . .
H1A H -0.2050 0.5829 0.5266 0.072 Uiso 1 1 calc R U . . .
O2 O -0.1424(3) 0.5004(2) 0.38253(17) 0.0507(6) Uani 1 1 d . . . . .
N1 N 0.6113(3) 1.4100(2) 0.54439(19) 0.0434(7) Uani 1 1 d . . . . .
N2 N 0.5322(4) 1.4203(2) 0.63009(19) 0.0420(7) Uani 1 1 d . . . . .
N3 N 0.4160(3) 1.2225(2) 0.55140(17) 0.0351(6) Uani 1 1 d . . . . .
N4 N 0.2999(3) 1.0941(2) 0.53523(19) 0.0399(6) Uani 1 1 d . . . . .
C1 C 0.5385(4) 1.2902(3) 0.4983(2) 0.0421(8) Uani 1 1 d . . . . .
H1C H 0.5659 1.2552 0.4374 0.051 Uiso 1 1 calc R U . . .
C2 C 0.4167(4) 1.3076(3) 0.6330(2) 0.0403(8) Uani 1 1 d . . . . .
H2B H 0.3465 1.2896 0.6836 0.048 Uiso 1 1 calc R U . . .
C3 C 0.3032(4) 1.0185(3) 0.4560(2) 0.0399(8) Uani 1 1 d . . . . .
H3A H 0.3799 1.0489 0.4108 0.048 Uiso 1 1 calc R U . . .
C4 C 0.1868(4) 0.8835(3) 0.4355(2) 0.0368(7) Uani 1 1 d . . . . .
C5 C 0.0742(4) 0.8338(3) 0.5034(2) 0.0361(7) Uani 1 1 d . . . . .
H5B H 0.0731 0.8875 0.5629 0.043 Uiso 1 1 calc R U . . .
C6 C -0.0348(4) 0.7064(3) 0.4828(2) 0.0350(7) Uani 1 1 d . . . . .
C7 C -0.0305(4) 0.6246(3) 0.3937(2) 0.0368(7) Uani 1 1 d . . . . .
C8 C 0.0797(5) 0.6742(3) 0.3263(2) 0.0454(8) Uani 1 1 d . . . . .
H8B H 0.0808 0.6209 0.2665 0.055 Uiso 1 1 calc R U . . .
C9 C 0.1882(4) 0.8029(3) 0.3472(2) 0.0460(8) Uani 1 1 d . . . . .
H9A H 0.2626 0.8354 0.3017 0.055 Uiso 1 1 calc R U . . .
C10 C -0.1315(5) 0.4071(3) 0.2996(3) 0.0542(9) Uani 1 1 d . . . . .
H10A H -0.2170 0.3239 0.3004 0.081 Uiso 1 1 calc R U . . .
H10B H -0.1554 0.4343 0.2407 0.081 Uiso 1 1 calc R U . . .
H10C H -0.0150 0.4003 0.3019 0.081 Uiso 1 1 calc R U . . .
O3 O -0.3077(3) 0.5932(2) 0.16112(15) 0.0462(6) Uani 1 1 d . . . . .
H3B H -0.3734 0.5139 0.1478 0.055 Uiso 1 1 d R U . . .
O4 O -0.3156(3) 0.4358(2) -0.00814(16) 0.0472(6) Uani 1 1 d . . . . .
N5 N 0.4575(4) 1.3402(2) 0.1592(2) 0.0441(7) Uani 1 1 d . . . . .
N6 N 0.3748(4) 1.3504(2) 0.24351(19) 0.0450(7) Uani 1 1 d . . . . .
H6 H 0.3974 1.4198 0.2883 0.054 Uiso 1 1 calc R U . . .
N7 N 0.2586(3) 1.1532(2) 0.16346(18) 0.0346(6) Uani 1 1 d . . . . .
N8 N 0.1458(3) 1.0245(2) 0.14877(19) 0.0382(6) Uani 1 1 d . . . . .
C11 C 0.3850(4) 1.2208(3) 0.1130(2) 0.0419(8) Uani 1 1 d . . . . .
H11A H 0.4153 1.1858 0.0529 0.050 Uiso 1 1 calc R U . . .
C12 C 0.2566(4) 1.2384(3) 0.2448(2) 0.0399(7) Uani 1 1 d . . . . .
H12A H 0.1831 1.2206 0.2941 0.048 Uiso 1 1 calc R U . . .
C13 C 0.1380(4) 0.9525(3) 0.0653(2) 0.0358(7) Uani 1 1 d . . . . .
H13A H 0.2077 0.9849 0.0180 0.043 Uiso 1 1 calc R U . . .
C14 C 0.0180(4) 0.8181(3) 0.0447(2) 0.0344(7) Uani 1 1 d . . . . .
C15 C -0.0942(4) 0.7685(3) 0.1133(2) 0.0346(7) Uani 1 1 d . . . . .
H15A H -0.0956 0.8224 0.1726 0.042 Uiso 1 1 calc R U . . .
C16 C -0.2012(4) 0.6414(3) 0.0932(2) 0.0329(7) Uani 1 1 d . . . . .
C17 C -0.2014(4) 0.5597(3) 0.0029(2) 0.0353(7) Uani 1 1 d . . . . .
C18 C -0.0914(4) 0.6087(3) -0.0644(2) 0.0428(8) Uani 1 1 d . . . . .
H18A H -0.0912 0.5551 -0.1242 0.051 Uiso 1 1 calc R U . . .
C19 C 0.0191(4) 0.7372(3) -0.0436(2) 0.0410(8) Uani 1 1 d . . . . .
H19A H 0.0940 0.7692 -0.0891 0.049 Uiso 1 1 calc R U . . .
C20 C -0.3250(5) 0.3467(3) -0.0982(2) 0.0514(9) Uani 1 1 d . . . . .
H20A H -0.4096 0.2635 -0.0966 0.077 Uiso 1 1 calc R U . . .
H20B H -0.3607 0.3792 -0.1517 0.077 Uiso 1 1 calc R U . . .
H20C H -0.2109 0.3375 -0.1066 0.077 Uiso 1 1 calc R 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
Cl O5 1.415(3) . ?
Cl O8 1.425(3) . ?
Cl O7 1.429(3) . ?
Cl O6 1.435(2) . ?
O1 C6 1.367(3) . ?
O1 H1A 0.8200 . ?
O2 C7 1.359(3) . ?
O2 C10 1.425(4) . ?
N1 C1 1.296(4) . ?
N1 N2 1.377(4) . ?
N2 C2 1.306(4) . ?
N3 C2 1.335(4) . ?
N3 C1 1.367(4) . ?
N3 N4 1.402(3) . ?
N4 C3 1.264(4) . ?
C1 H1C 0.9300 . ?
C2 H2B 0.9300 . ?
C3 C4 1.457(4) . ?
C3 H3A 0.9300 . ?
C4 C9 1.384(4) . ?
C4 C5 1.399(4) . ?
C5 C6 1.373(4) . ?
C5 H5B 0.9300 . ?
C6 C7 1.405(4) . ?
C7 C8 1.383(4) . ?
C8 C9 1.383(4) . ?
C8 H8B 0.9300 . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
O3 C16 1.367(3) . ?
O3 H3B 0.8499 . ?
O4 C17 1.363(3) . ?
O4 C20 1.430(4) . ?
N5 C11 1.292(4) . ?
N5 N6 1.375(4) . ?
N6 C12 1.304(4) . ?
N6 H6 0.8600 . ?
N7 C12 1.339(4) . ?
N7 C11 1.360(4) . ?
N7 N8 1.397(3) . ?
N8 C13 1.271(4) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.461(4) . ?
C13 H13A 0.9300 . ?
C14 C19 1.385(4) . ?
C14 C15 1.403(4) . ?
C15 C16 1.366(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.407(4) . ?
C17 C18 1.379(4) . ?
C18 C19 1.386(4) . ?
C18 H18A 0.9300 . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
O5 Cl O8 111.0(2) . . ?
O5 Cl O7 109.60(19) . . ?
O8 Cl O7 109.13(18) . . ?
O5 Cl O6 108.41(17) . . ?
O8 Cl O6 109.20(18) . . ?
O7 Cl O6 109.44(17) . . ?
C6 O1 H1A 109.5 . . ?
C7 O2 C10 117.8(2) . . ?
C1 N1 N2 105.5(2) . . ?
C2 N2 N1 109.2(3) . . ?
C2 N3 C1 105.7(2) . . ?
C2 N3 N4 120.3(2) . . ?
C1 N3 N4 133.9(2) . . ?
C3 N4 N3 117.5(2) . . ?
N1 C1 N3 110.6(3) . . ?
N1 C1 H1C 124.7 . . ?
N3 C1 H1C 124.7 . . ?
N2 C2 N3 108.8(3) . . ?
N2 C2 H2B 125.6 . . ?
N3 C2 H2B 125.6 . . ?
N4 C3 C4 120.0(3) . . ?
N4 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C9 C4 C5 119.4(3) . . ?
C9 C4 C3 119.3(3) . . ?
C5 C4 C3 121.3(3) . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5B 119.7 . . ?
C4 C5 H5B 119.7 . . ?
O1 C6 C5 120.1(3) . . ?
O1 C6 C7 120.2(3) . . ?
C5 C6 C7 119.7(3) . . ?
O2 C7 C8 126.2(3) . . ?
O2 C7 C6 114.2(3) . . ?
C8 C7 C6 119.6(3) . . ?
C7 C8 C9 120.3(3) . . ?
C7 C8 H8B 119.8 . . ?
C9 C8 H8B 119.8 . . ?
C8 C9 C4 120.4(3) . . ?
C8 C9 H9A 119.8 . . ?
C4 C9 H9A 119.8 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 O3 H3B 119.1 . . ?
C17 O4 C20 117.8(2) . . ?
C11 N5 N6 105.3(2) . . ?
C12 N6 N5 109.3(2) . . ?
C12 N6 H6 125.3 . . ?
N5 N6 H6 125.3 . . ?
C12 N7 C11 105.4(2) . . ?
C12 N7 N8 119.7(2) . . ?
C11 N7 N8 134.9(3) . . ?
C13 N8 N7 116.7(2) . . ?
N5 C11 N7 111.2(3) . . ?
N5 C11 H11A 124.4 . . ?
N7 C11 H11A 124.4 . . ?
N6 C12 N7 108.7(3) . . ?
N6 C12 H12A 125.6 . . ?
N7 C12 H12A 125.6 . . ?
N8 C13 C14 119.1(3) . . ?
N8 C13 H13A 120.5 . . ?
C14 C13 H13A 120.5 . . ?
C19 C14 C15 119.4(3) . . ?
C19 C14 C13 118.9(3) . . ?
C15 C14 C13 121.6(3) . . ?
C16 C15 C14 120.3(3) . . ?
C16 C15 H15A 119.8 . . ?
C14 C15 H15A 119.8 . . ?
C15 C16 O3 119.9(3) . . ?
C15 C16 C17 120.2(3) . . ?
O3 C16 C17 119.9(2) . . ?
O4 C17 C18 126.4(3) . . ?
O4 C17 C16 114.2(3) . . ?
C18 C17 C16 119.4(3) . . ?
C17 C18 C19 120.5(3) . . ?
C17 C18 H18A 119.8 . . ?
C19 C18 H18A 119.8 . . ?
C14 C19 C18 120.2(3) . . ?
C14 C19 H19A 119.9 . . ?
C18 C19 H19A 119.9 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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 C2 0.4(4) . . . . ?
C2 N3 N4 C3 178.9(3) . . . . ?
C1 N3 N4 C3 0.8(5) . . . . ?
N2 N1 C1 N3 -0.4(4) . . . . ?
C2 N3 C1 N1 0.3(4) . . . . ?
N4 N3 C1 N1 178.6(3) . . . . ?
N1 N2 C2 N3 -0.3(4) . . . . ?
C1 N3 C2 N2 0.0(4) . . . . ?
N4 N3 C2 N2 -178.6(3) . . . . ?
N3 N4 C3 C4 179.4(3) . . . . ?
N4 C3 C4 C9 178.1(3) . . . . ?
N4 C3 C4 C5 -2.1(5) . . . . ?
C9 C4 C5 C6 -0.3(5) . . . . ?
C3 C4 C5 C6 179.9(3) . . . . ?
C4 C5 C6 O1 -177.8(3) . . . . ?
C4 C5 C6 C7 1.3(5) . . . . ?
C10 O2 C7 C8 8.3(5) . . . . ?
C10 O2 C7 C6 -172.8(3) . . . . ?
O1 C6 C7 O2 -1.8(4) . . . . ?
C5 C6 C7 O2 179.1(3) . . . . ?
O1 C6 C7 C8 177.2(3) . . . . ?
C5 C6 C7 C8 -2.0(5) . . . . ?
O2 C7 C8 C9 -179.6(3) . . . . ?
C6 C7 C8 C9 1.5(5) . . . . ?
C7 C8 C9 C4 -0.5(5) . . . . ?
C5 C4 C9 C8 -0.1(5) . . . . ?
C3 C4 C9 C8 179.6(3) . . . . ?
C11 N5 N6 C12 -0.2(4) . . . . ?
C12 N7 N8 C13 171.7(3) . . . . ?
C11 N7 N8 C13 -10.2(5) . . . . ?
N6 N5 C11 N7 0.1(4) . . . . ?
C12 N7 C11 N5 0.0(4) . . . . ?
N8 N7 C11 N5 -178.3(3) . . . . ?
N5 N6 C12 N7 0.2(4) . . . . ?
C11 N7 C12 N6 -0.1(4) . . . . ?
N8 N7 C12 N6 178.5(3) . . . . ?
N7 N8 C13 C14 -178.1(2) . . . . ?
N8 C13 C14 C19 -175.4(3) . . . . ?
N8 C13 C14 C15 2.8(5) . . . . ?
C19 C14 C15 C16 0.1(5) . . . . ?
C13 C14 C15 C16 -178.1(3) . . . . ?
C14 C15 C16 O3 178.8(3) . . . . ?
C14 C15 C16 C17 -0.8(5) . . . . ?
C20 O4 C17 C18 -0.5(5) . . . . ?
C20 O4 C17 C16 179.5(3) . . . . ?
C15 C16 C17 O4 -179.3(3) . . . . ?
O3 C16 C17 O4 1.1(4) . . . . ?
C15 C16 C17 C18 0.7(5) . . . . ?
O3 C16 C17 C18 -178.9(3) . . . . ?
O4 C17 C18 C19 -179.9(3) . . . . ?
C16 C17 C18 C19 0.2(5) . . . . ?
C15 C14 C19 C18 0.7(5) . . . . ?
C13 C14 C19 C18 179.0(3) . . . . ?
C17 C18 C19 C14 -0.9(5) . . . . ?

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.069

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1526874'
_audit_update_record             
;
2017-09-25 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 N4 O6 P'
_chemical_formula_weight         316.21

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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+1/2'

_cell_length_a                   4.4091(9)
_cell_length_b                   8.6022(17)
_cell_length_c                   17.525(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.34(3)
_cell_angle_gamma                90
_cell_volume                     664.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2092
_cell_measurement_theta_min      3.319
_cell_measurement_theta_max      27.460

_exptl_crystal_description       acicular
_exptl_crystal_colour            lightyellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.243
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6754
_exptl_absorpt_correction_T_max  0.8595
_exptl_absorpt_process_details   'CrystalClear (Rigaku, 2005)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Rigaku SCXmini diffractometer'
_diffrn_measurement_method       CCD_Profile_fitting
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4481
_diffrn_reflns_av_unetI/netI     0.0713
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.319
_diffrn_reflns_theta_max         27.460
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.867
_diffrn_reflns_point_group_measured_fraction_full 0.899
_reflns_number_total             2636
_reflns_number_gt                2092
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_max     0.744
_reflns_Friedel_fraction_full    0.801

_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       'CrystalClear (Rigaku, 2005)'
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY ( Cambridge Structural Database,2003)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0778P)²] 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_abs_structure_details 
;
 Flack x determined using 725 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2636
_refine_ls_number_parameters     196
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1404
_refine_ls_wR_factor_gt          0.1205
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.079
_refine_ls_shift/su_mean         0.009

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
P1 P 0.7831(3) 0.88555(16) 0.01319(9) 0.0295(4) Uani 1 1 d . . . . .
O4 O 0.9259(11) 0.8975(5) -0.0608(3) 0.0476(13) Uani 1 1 d . . . . .
O2 O 0.5522(11) 0.7660(6) 0.0145(3) 0.0594(14) Uani 1 1 d . . . . .
O5 O 1.0321(11) 0.8339(8) 0.0719(3) 0.0717(17) Uani 1 1 d . . . . .
H5 H 1.1944 0.8251 0.0503 0.108 Uiso 1 1 calc R U . . .
O3 O 0.6761(13) 1.0316(6) 0.0404(3) 0.0647(16) Uani 1 1 d . . . . .
H3 H 0.5162 1.0187 0.0625 0.097 Uiso 1 1 calc R U . . .
O6 O 0.5004(11) 0.3583(5) 0.3565(3) 0.0431(12) Uani 1 1 d . . . . .
H6 H 0.4829 0.2767 0.3801 0.065 Uiso 1 1 calc R U . . .
N1 N 1.1482(12) 0.3847(6) 0.0372(3) 0.0385(13) Uani 1 1 d . . . . .
C10 C 1.3087(15) 0.2141(7) -0.0720(3) 0.0354(15) Uani 1 1 d . . . . .
H10 H 1.1921 0.1264 -0.0626 0.043 Uiso 1 1 calc R U . . .
O1 O 0.5131(10) 0.5851(4) 0.2621(2) 0.0377(11) Uani 1 1 d . . . . .
N3 N 1.6111(13) 0.3758(6) -0.1199(3) 0.0395(13) Uani 1 1 d . . . . .
H3A H 1.7413 0.4160 -0.1498 0.047 Uiso 1 1 calc R U . . .
N2 N 1.3175(12) 0.3459(5) -0.0277(3) 0.0318(11) Uani 1 1 d . . . . .
C2 C 0.6679(13) 0.4554(6) 0.2395(3) 0.0287(12) Uani 1 1 d . . . . .
N4 N 1.4900(13) 0.2310(6) -0.1296(3) 0.0425(14) Uani 1 1 d . . . . .
C9 C 1.5073(14) 0.4462(7) -0.0600(4) 0.0369(14) Uani 1 1 d . . . . .
H9 H 1.5555 0.5460 -0.0432 0.044 Uiso 1 1 calc R U . . .
C8 C 1.1393(14) 0.2766(7) 0.0876(3) 0.0356(14) Uani 1 1 d . . . . .
H8 H 1.2409 0.1835 0.0795 0.043 Uiso 1 1 calc R U . . .
C3 C 0.6574(15) 0.3319(7) 0.2920(4) 0.0346(14) Uani 1 1 d . . . . .
C5 C 0.9644(15) 0.1777(8) 0.2089(4) 0.0422(16) Uani 1 1 d . . . . .
H5A H 1.0650 0.0852 0.1987 0.051 Uiso 1 1 calc R U . . .
C7 C 0.8237(14) 0.4394(7) 0.1730(4) 0.0329(13) Uani 1 1 d . . . . .
H7 H 0.8308 0.5216 0.1386 0.040 Uiso 1 1 calc R U . . .
C6 C 0.9732(13) 0.2983(7) 0.1568(3) 0.0298(13) Uani 1 1 d . . . . .
C4 C 0.8061(16) 0.1933(7) 0.2765(4) 0.0418(16) Uani 1 1 d . . . . .
H4 H 0.8001 0.1114 0.3110 0.050 Uiso 1 1 calc R U . . .
C1 C 0.511(2) 0.7168(8) 0.2123(4) 0.057(2) Uani 1 1 d . . . . .
H1A H 0.7154 0.7483 0.2030 0.086 Uiso 1 1 calc R U . . .
H1B H 0.4035 0.8008 0.2356 0.086 Uiso 1 1 calc R U . . .
H1C H 0.4115 0.6896 0.1648 0.086 Uiso 1 1 calc R 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
P1 O3 1.428(5) . ?
P1 O2 1.448(5) . ?
P1 O4 1.459(5) . ?
P1 O5 1.551(5) . ?
O6 C3 1.358(7) . ?
N1 C8 1.284(8) . ?
N1 N2 1.415(7) . ?
C10 N4 1.310(7) . ?
C10 N2 1.374(7) . ?
O1 C2 1.371(7) . ?
O1 C1 1.430(7) . ?
N3 C9 1.303(8) . ?
N3 N4 1.364(7) . ?
N2 C9 1.337(8) . ?
C2 C7 1.373(8) . ?
C2 C3 1.407(8) . ?
C8 C6 1.443(8) . ?
C3 C4 1.391(8) . ?
C5 C6 1.383(9) . ?
C5 C4 1.395(9) . ?
C7 C6 1.413(8) . ?

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 P1 O2 112.4(3) . . ?
O3 P1 O4 112.8(3) . . ?
O2 P1 O4 112.5(3) . . ?
O3 P1 O5 105.4(4) . . ?
O2 P1 O5 105.9(4) . . ?
O4 P1 O5 107.2(3) . . ?
C8 N1 N2 114.1(5) . . ?
N4 C10 N2 109.5(5) . . ?
C2 O1 C1 117.7(5) . . ?
C9 N3 N4 112.4(5) . . ?
C9 N2 C10 107.6(5) . . ?
C9 N2 N1 122.4(5) . . ?
C10 N2 N1 129.8(5) . . ?
O1 C2 C7 126.1(5) . . ?
O1 C2 C3 113.7(5) . . ?
C7 C2 C3 120.3(5) . . ?
C10 N4 N3 104.4(5) . . ?
N3 C9 N2 106.0(5) . . ?
N1 C8 C6 120.6(6) . . ?
O6 C3 C4 123.9(5) . . ?
O6 C3 C2 116.3(5) . . ?
C4 C3 C2 119.8(6) . . ?
C6 C5 C4 120.7(6) . . ?
C2 C7 C6 120.1(5) . . ?
C5 C6 C7 119.4(6) . . ?
C5 C6 C8 118.7(6) . . ?
C7 C6 C8 121.9(5) . . ?
C3 C4 C5 119.8(6) . . ?

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.100

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_HL1
_database_code_depnum_ccdc_archive 'CCDC 1526868'
_audit_update_record             
;
2017-01-11 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 N4 O2'
_chemical_formula_weight         218.22

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   P21/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                   5.4220(11)
_cell_length_b                   10.436(2)
_cell_length_c                   17.944(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.20(3)
_cell_angle_gamma                90.00
_cell_volume                     1015.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      13

_exptl_crystal_description       blocky
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.9794
_exptl_absorpt_correction_T_max  0.9896
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            2075
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_sigmaI/netI    0.0587
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         25.41
_reflns_number_total             1869
_reflns_number_gt                1186
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0780P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1869
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1581
_refine_ls_wR_factor_gt          0.1331
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
O1 O -0.0503(4) 0.87693(19) 0.43548(12) 0.0519(6) Uani 1 1 d . . .
N1 N 1.1040(5) 0.2090(2) 0.29495(15) 0.0532(7) Uani 1 1 d . . .
C1 C 1.0008(5) 0.3181(3) 0.30950(17) 0.0469(8) Uani 1 1 d . . .
H1B H 1.0716 0.3978 0.3012 0.056 Uiso 1 1 calc R . .
O2 O 0.2870(4) 0.92665(18) 0.33135(12) 0.0545(7) Uani 1 1 d . . .
H2A H 0.1877 0.9842 0.3457 0.065 Uiso 1 1 d R . .
N2 N 0.9389(5) 0.1133(2) 0.31481(14) 0.0489(7) Uani 1 1 d . . .
C2 C 0.7465(5) 0.1709(3) 0.34123(17) 0.0459(8) Uani 1 1 d . . .
H2C H 0.6086 0.1292 0.3594 0.055 Uiso 1 1 calc R . .
N3 N 0.7740(4) 0.2990(2) 0.33865(13) 0.0389(6) Uani 1 1 d . . .
C3 C 0.6151(5) 0.4999(3) 0.34517(15) 0.0380(7) Uani 1 1 d . . .
H3A H 0.7368 0.5235 0.3121 0.046 Uiso 1 1 calc R . .
C4 C 0.4432(5) 0.5954(2) 0.37259(15) 0.0354(7) Uani 1 1 d . . .
N4 N 0.5983(4) 0.3839(2) 0.36663(13) 0.0431(7) Uani 1 1 d . . .
C5 C 0.2798(5) 0.5693(3) 0.42858(17) 0.0480(8) Uani 1 1 d . . .
H5A H 0.2824 0.4893 0.4514 0.058 Uiso 1 1 calc R . .
C6 C 0.1123(6) 0.6608(3) 0.45110(17) 0.0477(8) Uani 1 1 d . . .
H6A H 0.0025 0.6416 0.4886 0.057 Uiso 1 1 calc R . .
C7 C 0.1073(5) 0.7800(3) 0.41829(15) 0.0378(7) Uani 1 1 d . . .
C8 C 0.2774(5) 0.8085(2) 0.36298(15) 0.0361(7) Uani 1 1 d . . .
C9 C 0.4429(5) 0.7173(2) 0.34081(15) 0.0360(7) Uani 1 1 d . . .
H9A H 0.5559 0.7371 0.3043 0.043 Uiso 1 1 calc R . .
C10 C -0.2200(6) 0.8559(3) 0.49385(17) 0.0564(9) Uani 1 1 d . . .
H10A H -0.3199 0.9310 0.5000 0.085 Uiso 1 1 calc R . .
H10B H -0.1306 0.8383 0.5394 0.085 Uiso 1 1 calc R . .
H10C H -0.3239 0.7842 0.4814 0.085 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.364(3) . ?
O1 C10 1.426(3) . ?
N1 C1 1.297(4) . ?
N1 N2 1.393(3) . ?
C1 N3 1.361(4) . ?
C1 H1B 0.9300 . ?
O2 C8 1.359(3) . ?
O2 H2A 0.8500 . ?
N2 C2 1.302(3) . ?
C2 N3 1.346(3) . ?
C2 H2C 0.9300 . ?
N3 N4 1.402(3) . ?
C3 N4 1.274(3) . ?
C3 C4 1.458(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.380(4) . ?
C4 C9 1.394(4) . ?
C5 C6 1.383(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.377(4) . ?
C6 H6A 0.9300 . ?
C7 C8 1.401(4) . ?
C8 C9 1.373(3) . ?
C9 H9A 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
C7 O1 C10 118.0(2) . . ?
C1 N1 N2 107.2(2) . . ?
N1 C1 N3 110.3(3) . . ?
N1 C1 H1B 124.9 . . ?
N3 C1 H1B 124.9 . . ?
C8 O2 H2A 119.0 . . ?
C2 N2 N1 106.6(2) . . ?
N2 C2 N3 110.9(3) . . ?
N2 C2 H2C 124.6 . . ?
N3 C2 H2C 124.6 . . ?
C2 N3 C1 105.1(2) . . ?
C2 N3 N4 122.6(2) . . ?
C1 N3 N4 132.2(2) . . ?
N4 C3 C4 119.8(3) . . ?
N4 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C5 C4 C9 118.8(2) . . ?
C5 C4 C3 122.4(3) . . ?
C9 C4 C3 118.8(3) . . ?
C3 N4 N3 116.0(2) . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 H6A 119.8 . . ?
C5 C6 H6A 119.8 . . ?
O1 C7 C6 125.5(3) . . ?
O1 C7 C8 115.3(2) . . ?
C6 C7 C8 119.2(2) . . ?
O2 C8 C9 118.5(2) . . ?
O2 C8 C7 121.4(2) . . ?
C9 C8 C7 120.2(2) . . ?
C8 C9 C4 120.6(3) . . ?
C8 C9 H9A 119.7 . . ?
C4 C9 H9A 119.7 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
N2 N1 C1 N3 0.3(4) . . . . ?
C1 N1 N2 C2 -0.8(3) . . . . ?
N1 N2 C2 N3 1.1(3) . . . . ?
N2 C2 N3 C1 -0.9(3) . . . . ?
N2 C2 N3 N4 -177.2(2) . . . . ?
N1 C1 N3 C2 0.3(3) . . . . ?
N1 C1 N3 N4 176.1(3) . . . . ?
N4 C3 C4 C5 8.3(4) . . . . ?
N4 C3 C4 C9 -171.3(3) . . . . ?
C4 C3 N4 N3 -178.8(2) . . . . ?
C2 N3 N4 C3 -163.6(3) . . . . ?
C1 N3 N4 C3 21.2(4) . . . . ?
C9 C4 C5 C6 2.3(5) . . . . ?
C3 C4 C5 C6 -177.3(3) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
C10 O1 C7 C6 2.1(4) . . . . ?
C10 O1 C7 C8 -177.1(2) . . . . ?
C5 C6 C7 O1 179.5(3) . . . . ?
C5 C6 C7 C8 -1.4(5) . . . . ?
O1 C7 C8 O2 2.3(4) . . . . ?
C6 C7 C8 O2 -177.0(3) . . . . ?
O1 C7 C8 C9 -179.3(2) . . . . ?
C6 C7 C8 C9 1.5(4) . . . . ?
O2 C8 C9 C4 178.8(3) . . . . ?
C7 C8 C9 C4 0.4(4) . . . . ?
C5 C4 C9 C8 -2.2(4) . . . . ?
C3 C4 C9 C8 177.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.41
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.047
