# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shrv340
_database_code_depnum_ccdc_archive 'CCDC 1454188'
_audit_update_record             
;
2016-02-18 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H9 N7'
_chemical_formula_sum            'C6 H9 N7'
_chemical_formula_weight         179.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   5.3875(3)
_cell_length_b                   29.3488(15)
_cell_length_c                   5.9481(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.925(2)
_cell_angle_gamma                90
_cell_volume                     859.68(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2168
_cell_measurement_theta_min      3.81
_cell_measurement_theta_max      23.76

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.459
_exptl_crystal_size_mid          0.039
_exptl_crystal_size_min          0.021
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6483
_exptl_absorpt_correction_T_max  0.7454

_diffrn_ambient_temperature      296(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  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8071
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.811
_diffrn_reflns_theta_max         26.524
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1767
_reflns_number_gt                1262
_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       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2014/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_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)+(0.0528P)²+0.2027P] 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         1767
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1102
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2839(4) 0.03197(7) 0.6884(3) 0.0501(5) Uani 1 1 d . . . . .
H1A H 0.212(4) 0.0410(8) 0.540(5) 0.060 Uiso 1 1 d . U . . .
H1B H 0.420(5) 0.0127(8) 0.744(4) 0.060 Uiso 1 1 d . U . . .
C2 C 0.1782(4) 0.04615(6) 0.8446(3) 0.0340(4) Uani 1 1 d . . . . .
N3 N 0.2685(3) 0.03580(5) 1.0817(3) 0.0429(4) Uani 1 1 d . . . . .
N4 N 0.0988(4) 0.05821(6) 1.1642(3) 0.0477(5) Uani 1 1 d . . . . .
N5 N -0.0836(3) 0.08103(6) 0.9928(3) 0.0456(4) Uani 1 1 d . . . . .
N6 N -0.0390(3) 0.07352(5) 0.7849(3) 0.0350(4) Uani 1 1 d . . . . .
C7 C -0.1918(4) 0.09791(7) 0.5579(3) 0.0415(5) Uani 1 1 d . . . . .
H7A H -0.3653 0.1073 0.5559 0.050 Uiso 1 1 calc R U . . .
H7B H -0.2270 0.0777 0.4192 0.050 Uiso 1 1 calc R U . . .
C8 C -0.0394(4) 0.13927(7) 0.5320(4) 0.0498(5) Uani 1 1 d . . . . .
H8A H 0.1251 0.1296 0.5166 0.060 Uiso 1 1 calc R U . . .
H8B H -0.1506 0.1556 0.3833 0.060 Uiso 1 1 calc R U . . .
N9 N 0.0307(4) 0.16946(6) 0.7410(3) 0.0489(5) Uani 1 1 d . . . . .
N10 N -0.1676(4) 0.19067(6) 0.7839(4) 0.0605(5) Uani 1 1 d . . . . .
C11 C -0.0361(6) 0.21164(8) 0.9965(5) 0.0727(8) Uani 1 1 d . . . . .
H11 H -0.1201 0.2296 1.0742 0.087 Uiso 1 1 calc R U . . .
C12 C 0.2368(7) 0.20388(11) 1.0886(6) 0.0932(10) Uani 1 1 d . . . . .
H12 H 0.3688 0.2150 1.2347 0.112 Uiso 1 1 calc R U . . .
C13 C 0.2745(6) 0.17649(10) 0.9210(6) 0.0797(8) Uani 1 1 d . . . . .
H13 H 0.4389 0.1649 0.9302 0.096 Uiso 1 1 calc R U . . .

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
N1 0.0555(11) 0.0710(13) 0.0258(9) 0.0082(8) 0.0185(8) 0.0218(9)
C2 0.0393(10) 0.0381(10) 0.0237(9) 0.0004(7) 0.0120(7) -0.0016(8)
N3 0.0565(10) 0.0490(10) 0.0246(8) 0.0031(7) 0.0178(7) 0.0053(8)
N4 0.0681(12) 0.0507(10) 0.0289(9) 0.0022(7) 0.0243(8) 0.0035(8)
N5 0.0614(11) 0.0504(10) 0.0327(9) -0.0003(7) 0.0270(8) 0.0038(8)
N6 0.0429(9) 0.0394(8) 0.0245(8) 0.0008(6) 0.0155(6) 0.0024(7)
C7 0.0440(11) 0.0505(11) 0.0261(9) 0.0020(8) 0.0102(8) 0.0071(9)
C8 0.0669(14) 0.0499(12) 0.0406(12) 0.0107(9) 0.0299(10) 0.0120(10)
N9 0.0611(11) 0.0411(9) 0.0554(11) 0.0027(8) 0.0350(9) -0.0005(8)
N10 0.0767(14) 0.0489(11) 0.0674(13) 0.0044(10) 0.0412(11) 0.0143(10)
C11 0.114(2) 0.0428(13) 0.0856(19) -0.0111(13) 0.0655(18) -0.0080(13)
C12 0.094(2) 0.096(2) 0.096(2) -0.0430(18) 0.0451(19) -0.0357(18)
C13 0.0607(16) 0.088(2) 0.096(2) -0.0293(16) 0.0374(15) -0.0199(14)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.338(2) . ?
N1 H1A 0.85(2) . ?
N1 H1B 0.88(2) . ?
C2 N3 1.327(2) . ?
C2 N6 1.343(2) . ?
N3 N4 1.369(2) . ?
N4 N5 1.281(2) . ?
N5 N6 1.369(2) . ?
N6 C7 1.453(2) . ?
C7 C8 1.508(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N9 1.447(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N9 C13 1.332(3) . ?
N9 N10 1.347(2) . ?
N10 C11 1.324(3) . ?
C11 C12 1.364(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.358(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

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
C2 N1 H1A 118.8(16) . . ?
C2 N1 H1B 117.9(15) . . ?
H1A N1 H1B 123(2) . . ?
N3 C2 N1 126.21(18) . . ?
N3 C2 N6 108.82(15) . . ?
N1 C2 N6 124.97(17) . . ?
C2 N3 N4 105.11(15) . . ?
N5 N4 N3 111.94(15) . . ?
N4 N5 N6 106.03(15) . . ?
C2 N6 N5 108.09(14) . . ?
C2 N6 C7 130.14(15) . . ?
N5 N6 C7 121.27(15) . . ?
N6 C7 C8 111.40(15) . . ?
N6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
N9 C8 C7 111.63(16) . . ?
N9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
N9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C13 N9 N10 112.0(2) . . ?
C13 N9 C8 127.9(2) . . ?
N10 N9 C8 119.68(18) . . ?
C11 N10 N9 103.7(2) . . ?
N10 C11 C12 112.2(2) . . ?
N10 C11 H11 123.9 . . ?
C12 C11 H11 123.9 . . ?
C13 C12 C11 105.2(3) . . ?
C13 C12 H12 127.4 . . ?
C11 C12 H12 127.4 . . ?
N9 C13 C12 106.8(3) . . ?
N9 C13 H13 126.6 . . ?
C12 C13 H13 126.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 N3 N4 179.56(19) . . . . ?
N6 C2 N3 N4 -0.4(2) . . . . ?
C2 N3 N4 N5 -0.2(2) . . . . ?
N3 N4 N5 N6 0.8(2) . . . . ?
N3 C2 N6 N5 0.9(2) . . . . ?
N1 C2 N6 N5 -179.10(18) . . . . ?
N3 C2 N6 C7 172.66(17) . . . . ?
N1 C2 N6 C7 -7.3(3) . . . . ?
N4 N5 N6 C2 -1.0(2) . . . . ?
N4 N5 N6 C7 -173.65(16) . . . . ?
C2 N6 C7 C8 -75.4(2) . . . . ?
N5 N6 C7 C8 95.4(2) . . . . ?
N6 C7 C8 N9 -56.1(2) . . . . ?
C7 C8 N9 C13 107.2(3) . . . . ?
C7 C8 N9 N10 -65.4(2) . . . . ?
C13 N9 N10 C11 0.8(3) . . . . ?
C8 N9 N10 C11 174.47(17) . . . . ?
N9 N10 C11 C12 -0.6(3) . . . . ?
N10 C11 C12 C13 0.2(4) . . . . ?
N10 N9 C13 C12 -0.7(3) . . . . ?
C8 N9 C13 C12 -173.8(2) . . . . ?
C11 C12 C13 N9 0.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A N4 0.85(2) 2.12(3) 2.964(2) 169(2) 1_554
N1 H1B N3 0.88(2) 2.12(3) 2.994(2) 172(2) 3_657

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.039

# start Validation Reply Form
_vrf_PLAT015_shrv340             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
# end Validation Reply Form
####################################################################### 
# 
# 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_shrv341
_database_code_depnum_ccdc_archive 'CCDC 1454189'
_audit_update_record             
;
2016-02-18 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H7 N9 O4, H2 O'
_chemical_formula_sum            'C6 H9 N9 O5'
_chemical_formula_weight         287.22

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'

_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                   13.6239(4)
_cell_length_b                   8.6674(3)
_cell_length_c                   10.3971(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.8200(10)
_cell_angle_gamma                90
_cell_volume                     1155.00(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3244
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      25.41

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.024
_exptl_absorpt_coefficient_mu    0.143
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6937
_exptl_absorpt_correction_T_max  0.7454

_diffrn_ambient_temperature      296(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  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10873
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.837
_diffrn_reflns_theta_max         26.541
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2372
_reflns_number_gt                1859
_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       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2014/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_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)+(0.0690P)²+0.2983P] 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         2372
_refine_ls_number_parameters     190
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0363
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.1040
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_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
O1 O 0.41048(11) 0.78271(13) 0.34451(15) 0.0582(4) Uani 1 1 d . . . . .
O2 O 0.40942(13) 0.64425(16) 0.17077(15) 0.0631(4) Uani 1 1 d . . . . .
N3 N 0.40115(11) 0.65886(15) 0.28432(16) 0.0423(4) Uani 1 1 d . . . . .
C4 C 0.38179(12) 0.52490(17) 0.35091(16) 0.0335(4) Uani 1 1 d . . . . .
C5 C 0.36379(12) 0.51630(18) 0.47477(18) 0.0381(4) Uani 1 1 d . . . . .
H5 H 0.3592 0.6010 0.5273 0.046 Uiso 1 1 calc R U . . .
N6 N 0.35408(11) 0.37097(15) 0.50741(14) 0.0394(3) Uani 1 1 d . . . . .
N7 N 0.36771(10) 0.28747(14) 0.40272(13) 0.0339(3) Uani 1 1 d . . . . .
C8 C 0.38387(12) 0.37580(17) 0.30771(16) 0.0352(4) Uani 1 1 d . . . . .
H8 H 0.3944 0.3433 0.2281 0.042 Uiso 1 1 calc R U . . .
C9 C 0.35965(14) 0.11969(18) 0.40270(17) 0.0413(4) Uani 1 1 d . . . . .
H9A H 0.3970 0.0815 0.4939 0.050 Uiso 1 1 calc R U . . .
H9B H 0.3930 0.0774 0.3415 0.050 Uiso 1 1 calc R U . . .
C10 C 0.24794(15) 0.06306(19) 0.35871(17) 0.0437(4) Uani 1 1 d . . . . .
H10A H 0.2477 -0.0460 0.3797 0.052 Uiso 1 1 calc R U . . .
H10B H 0.2114 0.1174 0.4104 0.052 Uiso 1 1 calc R U . . .
N11 N 0.19270(11) 0.08627(15) 0.21302(15) 0.0383(3) Uani 1 1 d . . . . .
N12 N 0.16445(12) 0.22874(16) 0.15881(18) 0.0486(4) Uani 1 1 d . . . . .
N13 N 0.11645(12) 0.21213(16) 0.03078(18) 0.0513(4) Uani 1 1 d . . . . .
N14 N 0.11240(11) 0.05885(16) 0.00110(16) 0.0402(3) Uani 1 1 d . . . . .
H14 H 0.0823(15) 0.024(2) -0.094(2) 0.048 Uiso 1 1 d . U . . .
C15 C 0.15928(12) -0.02214(18) 0.11500(17) 0.0343(4) Uani 1 1 d . . . . .
N16 N 0.17454(12) -0.17106(16) 0.14910(15) 0.0431(4) Uani 1 1 d . . . . .
N17 N 0.13905(11) -0.27129(15) 0.04532(15) 0.0407(3) Uani 1 1 d . . . . .
O18 O 0.10473(12) -0.22844(15) -0.07526(13) 0.0588(4) Uani 1 1 d . . . . .
O19 O 0.14357(13) -0.40897(14) 0.07619(15) 0.0614(4) Uani 1 1 d . . . . .
O1S O 0.98778(12) 0.51374(18) 0.76275(14) 0.0588(4) Uani 1 1 d D . . . .
H1S H 1.0163(18) 0.582(2) 0.817(2) 0.088 Uiso 1 1 d D U . . .
H2S H 0.9563(19) 0.484(3) 0.812(2) 0.088 Uiso 1 1 d D U . . .

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 0.0736(9) 0.0238(6) 0.0741(9) -0.0047(6) 0.0209(7) -0.0041(6)
O2 0.0979(12) 0.0440(8) 0.0568(9) 0.0077(6) 0.0383(8) -0.0071(7)
N3 0.0460(8) 0.0268(7) 0.0521(9) 0.0024(6) 0.0139(7) -0.0010(6)
C4 0.0361(8) 0.0249(8) 0.0379(8) -0.0009(6) 0.0102(7) -0.0011(6)
C5 0.0423(9) 0.0286(8) 0.0447(9) -0.0110(7) 0.0163(7) -0.0033(6)
N6 0.0520(8) 0.0333(7) 0.0357(7) -0.0079(6) 0.0187(6) -0.0061(6)
N7 0.0456(8) 0.0245(7) 0.0309(7) -0.0039(5) 0.0123(6) -0.0029(5)
C8 0.0454(9) 0.0293(8) 0.0315(8) -0.0013(6) 0.0137(7) -0.0015(6)
C9 0.0630(11) 0.0234(8) 0.0360(9) -0.0009(6) 0.0150(8) -0.0016(7)
C10 0.0699(12) 0.0293(8) 0.0398(9) -0.0070(7) 0.0290(9) -0.0135(8)
N11 0.0473(8) 0.0249(6) 0.0466(8) -0.0056(6) 0.0210(6) -0.0064(5)
N12 0.0527(9) 0.0269(7) 0.0665(11) -0.0014(7) 0.0208(8) -0.0016(6)
N13 0.0479(9) 0.0309(8) 0.0700(11) 0.0052(7) 0.0133(8) 0.0009(6)
N14 0.0375(7) 0.0328(7) 0.0481(9) 0.0021(6) 0.0119(6) -0.0031(6)
C15 0.0354(8) 0.0291(8) 0.0420(9) -0.0037(6) 0.0178(7) -0.0045(6)
N16 0.0630(9) 0.0276(7) 0.0376(8) -0.0060(6) 0.0156(7) -0.0029(6)
N17 0.0524(9) 0.0299(7) 0.0412(8) -0.0051(6) 0.0179(7) -0.0029(6)
O18 0.0897(11) 0.0414(7) 0.0379(7) -0.0042(6) 0.0118(7) -0.0064(7)
O19 0.1002(12) 0.0267(7) 0.0585(8) -0.0044(6) 0.0283(8) -0.0033(6)
O1S 0.0657(9) 0.0618(9) 0.0440(8) -0.0125(7) 0.0123(7) -0.0047(7)

_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 N3 1.2272(18) . ?
O2 N3 1.230(2) . ?
N3 C4 1.422(2) . ?
C4 C8 1.372(2) . ?
C4 C5 1.392(2) . ?
C5 N6 1.323(2) . ?
C5 H5 0.9300 . ?
N6 N7 1.3712(18) . ?
N7 C8 1.326(2) . ?
N7 C9 1.4584(19) . ?
C8 H8 0.9300 . ?
C9 C10 1.515(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N11 1.459(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N11 C15 1.347(2) . ?
N11 N12 1.358(2) . ?
N12 N13 1.277(2) . ?
N13 N14 1.361(2) . ?
N14 C15 1.338(2) . ?
N14 H14 0.98(2) . ?
C15 N16 1.336(2) . ?
N16 N17 1.3413(19) . ?
N17 O19 1.2318(18) . ?
N17 O18 1.2372(19) . ?
O1S H1S 0.823(10) . ?
O1S H2S 0.817(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N3 O2 123.51(15) . . ?
O1 N3 C4 118.06(15) . . ?
O2 N3 C4 118.42(14) . . ?
C8 C4 C5 106.39(13) . . ?
C8 C4 N3 125.61(15) . . ?
C5 C4 N3 127.89(14) . . ?
N6 C5 C4 110.64(13) . . ?
N6 C5 H5 124.7 . . ?
C4 C5 H5 124.7 . . ?
C5 N6 N7 104.29(13) . . ?
C8 N7 N6 112.83(13) . . ?
C8 N7 C9 127.39(14) . . ?
N6 N7 C9 119.74(13) . . ?
N7 C8 C4 105.84(14) . . ?
N7 C8 H8 127.1 . . ?
C4 C8 H8 127.1 . . ?
N7 C9 C10 113.02(14) . . ?
N7 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
N7 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
N11 C10 C9 112.37(13) . . ?
N11 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
N11 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C15 N11 N12 110.17(14) . . ?
C15 N11 C10 127.76(14) . . ?
N12 N11 C10 122.03(13) . . ?
N13 N12 N11 107.65(13) . . ?
N12 N13 N14 108.27(14) . . ?
C15 N14 N13 109.94(15) . . ?
C15 N14 H14 129.8(11) . . ?
N13 N14 H14 120.2(11) . . ?
N16 C15 N14 136.59(15) . . ?
N16 C15 N11 119.40(15) . . ?
N14 C15 N11 103.95(14) . . ?
C15 N16 N17 115.53(14) . . ?
O19 N17 O18 121.55(14) . . ?
O19 N17 N16 116.44(15) . . ?
O18 N17 N16 122.00(14) . . ?
H1S O1S H2S 91.0(13) . . ?

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 N3 C4 C8 -170.29(16) . . . . ?
O2 N3 C4 C8 8.5(2) . . . . ?
O1 N3 C4 C5 5.3(2) . . . . ?
O2 N3 C4 C5 -175.89(16) . . . . ?
C8 C4 C5 N6 -0.56(19) . . . . ?
N3 C4 C5 N6 -176.85(15) . . . . ?
C4 C5 N6 N7 0.80(18) . . . . ?
C5 N6 N7 C8 -0.80(18) . . . . ?
C5 N6 N7 C9 -178.55(14) . . . . ?
N6 N7 C8 C4 0.46(18) . . . . ?
C9 N7 C8 C4 178.01(15) . . . . ?
C5 C4 C8 N7 0.05(18) . . . . ?
N3 C4 C8 N7 176.45(14) . . . . ?
C8 N7 C9 C10 -100.11(19) . . . . ?
N6 N7 C9 C10 77.29(18) . . . . ?
N7 C9 C10 N11 71.23(18) . . . . ?
C9 C10 N11 C15 111.57(18) . . . . ?
C9 C10 N11 N12 -70.9(2) . . . . ?
C15 N11 N12 N13 -1.05(19) . . . . ?
C10 N11 N12 N13 -179.00(15) . . . . ?
N11 N12 N13 N14 0.5(2) . . . . ?
N12 N13 N14 C15 0.2(2) . . . . ?
N13 N14 C15 N16 176.14(18) . . . . ?
N13 N14 C15 N11 -0.83(18) . . . . ?
N12 N11 C15 N16 -176.47(14) . . . . ?
C10 N11 C15 N16 1.3(3) . . . . ?
N12 N11 C15 N14 1.14(17) . . . . ?
C10 N11 C15 N14 178.93(15) . . . . ?
N14 C15 N16 N17 3.5(3) . . . . ?
N11 C15 N16 N17 -179.88(14) . . . . ?
C15 N16 N17 O19 -173.43(15) . . . . ?
C15 N16 N17 O18 7.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9B O1 0.97 2.56 3.108(2) 115.5 1_545
C10 H10B N13 0.97 2.55 3.519(2) 173.4 4_566
N14 H14 O1S 0.98(2) 1.69(2) 2.646(2) 163.0(17) 2_645
O1S H1S O18 0.823(10) 2.115(10) 2.9239(19) 167(2) 1_666
O1S H2S O19 0.817(10) 2.165(10) 2.977(2) 173(3) 3_656

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.048

# start Validation Reply Form
_vrf_PLAT015_shrv341             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
# end Validation Reply Form
####################################################################### 
# 
# 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_shrv342
_database_code_depnum_ccdc_archive 'CCDC 1454190'
_audit_update_record             
;
2016-02-18 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H8 N8 O'
_chemical_formula_sum            'C6 H8 N8 O'
_chemical_formula_weight         208.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.7935(3)
_cell_length_b                   16.5200(7)
_cell_length_c                   8.3969(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.104(2)
_cell_angle_gamma                90
_cell_volume                     932.96(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1949
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      23.68

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.025
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6758
_exptl_absorpt_correction_T_max  0.7456

_diffrn_ambient_temperature      296(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  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9660
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.029
_diffrn_reflns_theta_max         27.595
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2152
_reflns_number_gt                1386
_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       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2014.11-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2014/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 2008)'
_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)+(0.0423P)²+0.1025P] 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         2152
_refine_ls_number_parameters     139
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.85279(18) 0.57802(8) 0.91303(17) 0.0477(4) Uani 1 1 d . . . . .
C2 C 0.8986(2) 0.60338(10) 1.0636(2) 0.0530(4) Uani 1 1 d . . . . .
H2 H 0.8153 0.5984 1.1420 0.064 Uiso 1 1 calc R U . . .
C3 C 1.0848(2) 0.63797(10) 1.0895(2) 0.0541(4) Uani 1 1 d . . . . .
H3 H 1.1491 0.6602 1.1845 0.065 Uiso 1 1 calc R U . . .
C4 C 1.1537(2) 0.63256(10) 0.9461(2) 0.0509(4) Uani 1 1 d . . . . .
H4 H 1.2765 0.6509 0.9240 0.061 Uiso 1 1 calc R U . . .
N5 N 1.01364(17) 0.59615(8) 0.84150(16) 0.0430(3) Uani 1 1 d . . . . .
C6 C 1.0130(2) 0.58153(10) 0.6722(2) 0.0470(4) Uani 1 1 d . . . . .
H6A H 0.9281 0.5355 0.6398 0.056 Uiso 1 1 calc R U . . .
H6B H 1.1467 0.5679 0.6534 0.056 Uiso 1 1 calc R U . . .
C7 C 0.9410(2) 0.65358(10) 0.5700(2) 0.0485(4) Uani 1 1 d . . . . .
H7A H 1.0196 0.7006 0.6074 0.058 Uiso 1 1 calc R U . . .
H7B H 0.9606 0.6433 0.4596 0.058 Uiso 1 1 calc R U . . .
N8 N 0.73094(18) 0.67090(8) 0.57506(16) 0.0462(3) Uani 1 1 d . . . . .
N9 N 0.6688(2) 0.72367(9) 0.67960(19) 0.0645(4) Uani 1 1 d . . . . .
N10 N 0.4753(2) 0.72115(11) 0.6540(2) 0.0737(5) Uani 1 1 d . . . . .
N11 N 0.4085(2) 0.66770(10) 0.5345(2) 0.0649(4) Uani 1 1 d . . . . .
C12 C 0.5707(2) 0.63729(10) 0.4892(2) 0.0461(4) Uani 1 1 d . . . . .
N13 N 0.60015(18) 0.58048(9) 0.37192(17) 0.0503(4) Uani 1 1 d . . . . .
N14 N 0.44406(18) 0.54386(9) 0.31733(17) 0.0508(4) Uani 1 1 d . . . . .
O15 O 0.48324(17) 0.49141(8) 0.20440(16) 0.0626(4) Uani 1 1 d D . . . .
H15 H 0.3687(19) 0.4717(12) 0.172(3) 0.094 Uiso 1 1 d D U . . .

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
N1 0.0402(7) 0.0475(8) 0.0571(9) -0.0004(7) 0.0123(6) -0.0056(6)
C2 0.0559(10) 0.0526(10) 0.0528(11) 0.0023(8) 0.0154(8) 0.0024(8)
C3 0.0554(10) 0.0483(10) 0.0562(11) -0.0066(8) -0.0009(8) 0.0019(8)
C4 0.0359(8) 0.0498(9) 0.0654(12) -0.0061(8) 0.0014(8) -0.0051(7)
N5 0.0323(6) 0.0450(7) 0.0523(8) -0.0037(6) 0.0080(6) -0.0023(5)
C6 0.0345(8) 0.0502(10) 0.0579(11) -0.0118(8) 0.0124(7) -0.0003(7)
C7 0.0348(8) 0.0601(10) 0.0526(10) -0.0042(8) 0.0138(7) -0.0071(7)
N8 0.0410(7) 0.0491(8) 0.0514(8) 0.0034(6) 0.0163(6) 0.0037(6)
N9 0.0683(10) 0.0606(9) 0.0692(11) -0.0015(8) 0.0256(8) 0.0119(8)
N10 0.0661(11) 0.0769(12) 0.0844(13) 0.0079(10) 0.0322(9) 0.0245(9)
N11 0.0442(8) 0.0776(11) 0.0769(11) 0.0145(9) 0.0223(7) 0.0174(7)
C12 0.0348(8) 0.0546(10) 0.0512(10) 0.0147(8) 0.0138(7) 0.0051(7)
N13 0.0328(7) 0.0630(9) 0.0557(9) 0.0038(7) 0.0088(6) -0.0046(6)
N14 0.0359(7) 0.0617(9) 0.0545(9) 0.0130(7) 0.0059(6) -0.0028(6)
O15 0.0413(7) 0.0757(9) 0.0702(9) -0.0066(7) 0.0060(6) -0.0097(6)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.327(2) . ?
N1 N5 1.3527(17) . ?
C2 C3 1.377(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.355(2) . ?
C3 H3 0.9300 . ?
C4 N5 1.343(2) . ?
C4 H4 0.9300 . ?
N5 C6 1.441(2) . ?
C6 C7 1.508(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 N8 1.4622(18) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N8 C12 1.339(2) . ?
N8 N9 1.3464(19) . ?
N9 N10 1.302(2) . ?
N10 N11 1.365(2) . ?
N11 C12 1.315(2) . ?
C12 N13 1.395(2) . ?
N13 N14 1.2504(17) . ?
N14 O15 1.3386(19) . ?
O15 H15 0.853(9) . ?

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
C2 N1 N5 104.94(13) . . ?
N1 C2 C3 111.58(15) . . ?
N1 C2 H2 124.2 . . ?
C3 C2 H2 124.2 . . ?
C4 C3 C2 104.94(15) . . ?
C4 C3 H3 127.5 . . ?
C2 C3 H3 127.5 . . ?
N5 C4 C3 107.98(14) . . ?
N5 C4 H4 126.0 . . ?
C3 C4 H4 126.0 . . ?
C4 N5 N1 110.56(13) . . ?
C4 N5 C6 128.55(13) . . ?
N1 N5 C6 120.71(12) . . ?
N5 C6 C7 112.63(13) . . ?
N5 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
N5 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
N8 C7 C6 112.17(12) . . ?
N8 C7 H7A 109.2 . . ?
C6 C7 H7A 109.2 . . ?
N8 C7 H7B 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C12 N8 N9 108.30(13) . . ?
C12 N8 C7 128.76(14) . . ?
N9 N8 C7 122.86(14) . . ?
N10 N9 N8 105.86(15) . . ?
N9 N10 N11 111.43(14) . . ?
C12 N11 N10 104.74(15) . . ?
N11 C12 N8 109.66(16) . . ?
N11 C12 N13 132.12(16) . . ?
N8 C12 N13 118.21(13) . . ?
N14 N13 C12 112.69(13) . . ?
N13 N14 O15 109.26(13) . . ?
N14 O15 H15 102.3(15) . . ?

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
N5 N1 C2 C3 0.51(18) . . . . ?
N1 C2 C3 C4 -0.2(2) . . . . ?
C2 C3 C4 N5 -0.17(19) . . . . ?
C3 C4 N5 N1 0.49(18) . . . . ?
C3 C4 N5 C6 175.68(15) . . . . ?
C2 N1 N5 C4 -0.61(17) . . . . ?
C2 N1 N5 C6 -176.24(14) . . . . ?
C4 N5 C6 C7 -83.79(18) . . . . ?
N1 N5 C6 C7 90.97(16) . . . . ?
N5 C6 C7 N8 -66.57(16) . . . . ?
C6 C7 N8 C12 -83.38(19) . . . . ?
C6 C7 N8 N9 93.05(17) . . . . ?
C12 N8 N9 N10 -0.45(18) . . . . ?
C7 N8 N9 N10 -177.52(14) . . . . ?
N8 N9 N10 N11 0.03(19) . . . . ?
N9 N10 N11 C12 0.4(2) . . . . ?
N10 N11 C12 N8 -0.68(18) . . . . ?
N10 N11 C12 N13 -179.45(16) . . . . ?
N9 N8 C12 N11 0.73(18) . . . . ?
C7 N8 C12 N11 177.57(14) . . . . ?
N9 N8 C12 N13 179.69(13) . . . . ?
C7 N8 C12 N13 -3.5(2) . . . . ?
N11 C12 N13 N14 -12.0(2) . . . . ?
N8 C12 N13 N14 169.36(13) . . . . ?
C12 N13 N14 O15 179.16(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 N13 0.93 2.60 3.526(2) 176.6 1_556
O15 H15 N1 0.853(9) 1.772(10) 2.6200(17) 172(2) 3_666

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.035


# start Validation Reply Form
_vrf_PLAT015_shrv342             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
# end Validation Reply Form
####################################################################### 
# 
# 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_shrv366
_database_code_depnum_ccdc_archive 'CCDC 1454191'
_audit_update_record             
;
2016-02-18 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 Cl N10 O6, H2 O'
_chemical_formula_sum            'C6 H6 Cl N10 O7'
_chemical_formula_weight         365.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   20.688(4)
_cell_length_b                   5.4867(11)
_cell_length_c                   12.0035(19)
_cell_angle_alpha                90
_cell_angle_beta                 104.552(12)
_cell_angle_gamma                90
_cell_volume                     1318.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2365
_cell_measurement_theta_min      4.42
_cell_measurement_theta_max      66.95

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_F_000             740
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.248
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    3.228
_shelx_estimated_absorpt_T_min   0.502
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.2735
_exptl_absorpt_correction_T_max  0.5201

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_measurement_device       'Bruker PLATINUM 135 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5815
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.206
_diffrn_reflns_theta_max         66.967
_diffrn_reflns_theta_full        66.967
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measured_fraction_theta_full 0.908
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_Laue_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_point_group_measured_fraction_full 0.908
_reflns_number_total             2141
_reflns_number_gt                1574
_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       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 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)+(0.0638P)²+2.7762P] 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         2141
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0743
_refine_ls_wR_factor_ref         0.1893
_refine_ls_wR_factor_gt          0.1752
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_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
O1 O 0.05515(19) 1.0201(7) 0.7506(3) 0.0463(10) Uani 1 1 d . . . . .
O2 O 0.02083(19) 0.9114(7) 0.9003(3) 0.0452(10) Uani 1 1 d . . . . .
N3 N 0.0542(2) 0.8740(8) 0.8291(3) 0.0377(10) Uani 1 1 d . . . . .
N4 N 0.0905(2) 0.6671(8) 0.8432(3) 0.0357(10) Uani 1 1 d . . . . .
C5 C 0.1236(3) 0.6221(9) 0.7623(4) 0.0352(12) Uani 1 1 d . . . . .
N6 N 0.1262(2) 0.7253(8) 0.6617(3) 0.0366(11) Uani 1 1 d . . . . .
N7 N 0.1695(2) 0.5941(9) 0.6161(3) 0.0421(11) Uani 1 1 d . . . . .
N8 N 0.1941(2) 0.4197(9) 0.6843(3) 0.0417(11) Uani 1 1 d . . . . .
N9 N 0.1656(2) 0.4312(8) 0.7757(3) 0.0351(10) Uani 1 1 d . . . . .
C10 C 0.1903(3) 0.2830(10) 0.8789(4) 0.0386(13) Uani 1 1 d . . . . .
H10A H 0.2143 0.1393 0.8596 0.046 Uiso 1 1 calc R U . . .
H10B H 0.1521 0.2238 0.9072 0.046 Uiso 1 1 calc R U . . .
C11 C 0.2372(3) 0.4306(10) 0.9729(4) 0.0369(12) Uani 1 1 d . . . . .
H11A H 0.2149 0.5832 0.9868 0.044 Uiso 1 1 calc R U . . .
H11B H 0.2484 0.3359 1.0454 0.044 Uiso 1 1 calc R U . . .
N12 N 0.2982(2) 0.4885(8) 0.9379(3) 0.0358(10) Uani 1 1 d . . . . .
N13 N 0.2948(2) 0.6805(8) 0.8683(3) 0.0370(10) Uani 1 1 d . . . . .
C14 C 0.3506(3) 0.6737(9) 0.8340(4) 0.0375(12) Uani 1 1 d . . . . .
N15 N 0.3609(3) 0.8625(9) 0.7546(4) 0.0474(12) Uani 1 1 d . . . . .
O16 O 0.4099(2) 0.8478(8) 0.7171(3) 0.0647(13) Uani 1 1 d . . . . .
O17 O 0.3192(2) 1.0257(8) 0.7327(3) 0.0600(12) Uani 1 1 d . . . . .
C18 C 0.3924(3) 0.4791(10) 0.8804(4) 0.0432(14) Uani 1 1 d . . . . .
Cl19 Cl 0.46587(8) 0.3970(3) 0.85513(13) 0.0599(5) Uani 1 1 d . . . . .
C20 C 0.3558(3) 0.3633(10) 0.9468(4) 0.0390(13) Uani 1 1 d . . . . .
N21 N 0.3722(3) 0.1440(9) 1.0143(4) 0.0472(12) Uani 1 1 d . . . . .
O22 O 0.3299(2) 0.0574(7) 1.0574(3) 0.0554(11) Uani 1 1 d . . . . .
O23 O 0.4266(2) 0.0557(9) 1.0203(4) 0.0725(14) Uani 1 1 d . . . . .
O1S O 0.0770(2) -1.6051(7) 0.0336(3) 0.0431(10) Uani 1 1 d . . . . .
H1S H 0.040(3) -1.687(11) 0.040(5) 0.052 Uiso 1 1 d . U . . .
H2S H 0.065(3) -1.543(11) -0.030(5) 0.052 Uiso 1 1 d . U . . .

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 0.069(3) 0.039(2) 0.037(2) 0.0096(17) 0.0263(19) 0.0054(18)
O2 0.062(3) 0.048(2) 0.034(2) -0.0039(16) 0.0287(19) -0.0003(18)
N3 0.050(3) 0.037(3) 0.029(2) -0.0056(19) 0.014(2) -0.004(2)
N4 0.052(3) 0.036(3) 0.024(2) -0.0010(17) 0.017(2) 0.005(2)
C5 0.047(3) 0.036(3) 0.026(3) -0.002(2) 0.015(2) -0.002(2)
N6 0.047(3) 0.042(3) 0.026(2) -0.0028(18) 0.017(2) -0.0003(19)
N7 0.054(3) 0.047(3) 0.029(2) 0.002(2) 0.017(2) 0.005(2)
N8 0.051(3) 0.053(3) 0.024(2) -0.004(2) 0.017(2) 0.000(2)
N9 0.047(3) 0.037(3) 0.025(2) 0.0007(18) 0.0174(19) -0.0001(19)
C10 0.054(3) 0.036(3) 0.029(3) 0.006(2) 0.016(3) 0.001(2)
C11 0.052(3) 0.038(3) 0.024(3) 0.001(2) 0.017(2) 0.002(2)
N12 0.047(3) 0.037(3) 0.025(2) -0.0007(18) 0.013(2) 0.0026(19)
N13 0.052(3) 0.035(3) 0.026(2) 0.0016(18) 0.014(2) -0.001(2)
C14 0.051(3) 0.037(3) 0.028(3) -0.003(2) 0.017(2) -0.005(2)
N15 0.063(3) 0.052(3) 0.031(3) -0.006(2) 0.018(2) -0.013(3)
O16 0.079(3) 0.072(3) 0.058(3) -0.008(2) 0.044(2) -0.019(2)
O17 0.076(3) 0.057(3) 0.050(3) 0.015(2) 0.020(2) -0.001(2)
C18 0.054(4) 0.044(4) 0.036(3) -0.010(2) 0.020(3) -0.003(3)
Cl19 0.0549(10) 0.0747(12) 0.0568(10) -0.0106(8) 0.0264(8) 0.0054(7)
C20 0.053(3) 0.042(3) 0.024(3) -0.003(2) 0.012(2) 0.003(2)
N21 0.059(3) 0.047(3) 0.037(3) -0.003(2) 0.014(2) 0.009(2)
O22 0.075(3) 0.049(3) 0.047(2) 0.0066(19) 0.024(2) 0.008(2)
O23 0.067(3) 0.070(3) 0.082(3) 0.020(3) 0.021(3) 0.026(2)
O1S 0.060(3) 0.044(2) 0.029(2) -0.0008(17) 0.0193(19) -0.0061(18)

_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 N3 1.241(5) . ?
O2 N3 1.243(5) . ?
N3 N4 1.348(6) . ?
N4 C5 1.344(6) . ?
C5 N9 1.344(6) . ?
C5 N6 1.346(6) . ?
N6 N7 1.367(5) . ?
N7 N8 1.279(6) . ?
N8 N9 1.372(5) . ?
N9 C10 1.463(6) . ?
C10 C11 1.523(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N12 1.462(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
N12 N13 1.335(5) . ?
N12 C20 1.357(6) . ?
N13 C14 1.319(6) . ?
C14 C18 1.399(8) . ?
C14 N15 1.459(7) . ?
N15 O16 1.211(6) . ?
N15 O17 1.225(6) . ?
C18 C20 1.384(7) . ?
C18 Cl19 1.684(5) . ?
C20 N21 1.443(7) . ?
N21 O23 1.210(6) . ?
N21 O22 1.219(6) . ?
O1S H1S 0.92(6) . ?
O1S H2S 0.82(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N3 O2 122.2(4) . . ?
O1 N3 N4 121.6(4) . . ?
O2 N3 N4 116.2(4) . . ?
C5 N4 N3 115.7(4) . . ?
N9 C5 N4 119.2(4) . . ?
N9 C5 N6 105.4(4) . . ?
N4 C5 N6 135.4(5) . . ?
C5 N6 N7 108.4(4) . . ?
N8 N7 N6 109.5(4) . . ?
N7 N8 N9 107.1(4) . . ?
C5 N9 N8 109.6(4) . . ?
C5 N9 C10 127.8(4) . . ?
N8 N9 C10 121.5(4) . . ?
N9 C10 C11 110.7(4) . . ?
N9 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
N9 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N12 C11 C10 109.7(4) . . ?
N12 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
N12 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
N13 N12 C20 110.8(4) . . ?
N13 N12 C11 116.0(4) . . ?
C20 N12 C11 132.3(4) . . ?
C14 N13 N12 105.1(4) . . ?
N13 C14 C18 113.5(4) . . ?
N13 C14 N15 117.8(5) . . ?
C18 C14 N15 128.7(5) . . ?
O16 N15 O17 125.4(5) . . ?
O16 N15 C14 117.9(5) . . ?
O17 N15 C14 116.7(5) . . ?
C20 C18 C14 101.9(5) . . ?
C20 C18 Cl19 129.0(5) . . ?
C14 C18 Cl19 128.9(4) . . ?
N12 C20 C18 108.6(5) . . ?
N12 C20 N21 123.0(4) . . ?
C18 C20 N21 128.4(5) . . ?
O23 N21 O22 125.1(5) . . ?
O23 N21 C20 116.8(5) . . ?
O22 N21 C20 118.1(5) . . ?
H1S O1S H2S 103(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
O1 N3 N4 C5 -4.6(7) . . . . ?
O2 N3 N4 C5 176.6(4) . . . . ?
N3 N4 C5 N9 174.1(4) . . . . ?
N3 N4 C5 N6 -6.3(9) . . . . ?
N9 C5 N6 N7 0.3(6) . . . . ?
N4 C5 N6 N7 -179.4(6) . . . . ?
C5 N6 N7 N8 -1.1(6) . . . . ?
N6 N7 N8 N9 1.4(6) . . . . ?
N4 C5 N9 N8 -179.7(5) . . . . ?
N6 C5 N9 N8 0.6(6) . . . . ?
N4 C5 N9 C10 -11.8(8) . . . . ?
N6 C5 N9 C10 168.4(5) . . . . ?
N7 N8 N9 C5 -1.3(6) . . . . ?
N7 N8 N9 C10 -170.0(4) . . . . ?
C5 N9 C10 C11 -68.5(6) . . . . ?
N8 N9 C10 C11 98.0(5) . . . . ?
N9 C10 C11 N12 -67.3(5) . . . . ?
C10 C11 N12 N13 82.2(5) . . . . ?
C10 C11 N12 C20 -85.5(6) . . . . ?
C20 N12 N13 C14 0.1(5) . . . . ?
C11 N12 N13 C14 -170.2(4) . . . . ?
N12 N13 C14 C18 -0.5(6) . . . . ?
N12 N13 C14 N15 179.3(4) . . . . ?
N13 C14 N15 O16 -175.2(5) . . . . ?
C18 C14 N15 O16 4.5(8) . . . . ?
N13 C14 N15 O17 5.7(7) . . . . ?
C18 C14 N15 O17 -174.6(5) . . . . ?
N13 C14 C18 C20 0.7(6) . . . . ?
N15 C14 C18 C20 -179.1(5) . . . . ?
N13 C14 C18 Cl19 177.1(4) . . . . ?
N15 C14 C18 Cl19 -2.6(9) . . . . ?
N13 N12 C20 C18 0.3(6) . . . . ?
C11 N12 C20 C18 168.6(5) . . . . ?
N13 N12 C20 N21 -178.5(4) . . . . ?
C11 N12 C20 N21 -10.3(8) . . . . ?
C14 C18 C20 N12 -0.6(6) . . . . ?
Cl19 C18 C20 N12 -177.0(4) . . . . ?
C14 C18 C20 N21 178.2(5) . . . . ?
Cl19 C18 C20 N21 1.8(9) . . . . ?
N12 C20 N21 O23 -176.3(5) . . . . ?
C18 C20 N21 O23 5.0(8) . . . . ?
N12 C20 N21 O22 6.1(7) . . . . ?
C18 C20 N21 O22 -172.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C10 H10B O1S 0.99 2.60 3.393(6) 136.6 1_576
C11 H11B O17 0.99 2.47 3.163(6) 126.4 4_576
C11 H11B O22 0.99 2.25 2.815(7) 114.8 .
O1S H1S O2 0.92(6) 2.01(6) 2.891(5) 161(5) 3_546
O1S H2S N4 0.82(6) 2.08(6) 2.803(5) 147(6) 1_534

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.072

# start Validation Reply Form
_vrf_PLAT015_shrv366             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
_vrf_PLAT029_shrv366             
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.908 Note  
RESPONSE: ...
;
# end Validation Reply Form
####################################################################### 
# 
# 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_shrv365
_database_code_depnum_ccdc_archive 'CCDC 1454192'
_audit_update_record             
;
2016-02-18 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 N5 O6, C2 H7 Br N'
_chemical_formula_sum            'C5 H7 Br N6 O6'
_chemical_formula_weight         327.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.6681(16)
_cell_length_b                   9.2226(17)
_cell_length_c                   14.411(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.053(2)
_cell_angle_gamma                90
_cell_volume                     1122.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6738
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.50

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.936
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.107
_exptl_absorpt_coefficient_mu    3.698
_shelx_estimated_absorpt_T_min   0.430
_shelx_estimated_absorpt_T_max   0.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6271
_exptl_absorpt_correction_T_max  0.7456

_diffrn_ambient_temperature      150(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  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10798
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.271
_diffrn_reflns_theta_max         27.523
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2579
_reflns_number_gt                2374
_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       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 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)+(0.0245P)²+0.6305P] 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         2579
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0551
_refine_ls_wR_factor_gt          0.0538
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_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
N1 N 0.89640(13) 0.55385(12) -0.12516(8) 0.0152(2) Uani 1 1 d . . . . .
N2 N 0.92408(13) 0.68420(12) -0.16004(8) 0.0151(2) Uani 1 1 d . . . . .
C3 C 0.86603(16) 0.78468(14) -0.10958(10) 0.0151(3) Uani 1 1 d . . . . .
C4 C 0.79892(15) 0.72241(14) -0.04059(9) 0.0151(3) Uani 1 1 d . . . . .
C5 C 0.82155(16) 0.57618(14) -0.05422(9) 0.0148(3) Uani 1 1 d . . . . .
N6 N 0.87156(14) 0.93546(13) -0.13325(9) 0.0203(3) Uani 1 1 d . . . . .
O7 O 0.93249(14) 0.96979(11) -0.19894(9) 0.0278(2) Uani 1 1 d . . . . .
O8 O 0.81002(16) 1.02208(12) -0.08707(10) 0.0346(3) Uani 1 1 d . . . . .
N9 N 0.72838(15) 0.79179(13) 0.03041(9) 0.0201(2) Uani 1 1 d . . . . .
O10 O 0.58717(14) 0.81593(15) 0.00999(9) 0.0348(3) Uani 1 1 d . . . . .
O11 O 0.81632(17) 0.82016(19) 0.10671(10) 0.0474(4) Uani 1 1 d . . . . .
N12 N 0.77414(14) 0.45688(13) -0.00239(8) 0.0178(2) Uani 1 1 d . . . . .
O13 O 0.70517(16) 0.48862(13) 0.06036(9) 0.0331(3) Uani 1 1 d . . . . .
O14 O 0.80563(13) 0.33332(11) -0.02350(8) 0.0214(2) Uani 1 1 d . . . . .
N1S N 0.15908(15) 0.71498(13) 0.23344(9) 0.0184(2) Uani 1 1 d . . . . .
H1S H 0.122(2) 0.634(2) 0.2034(14) 0.022 Uiso 1 1 d . U . . .
H2S H 0.198(2) 0.768(2) 0.1952(14) 0.022 Uiso 1 1 d . U . . .
H3S H 0.077(2) 0.760(2) 0.2503(13) 0.022 Uiso 1 1 d . U . . .
C2S C 0.28264(18) 0.67839(17) 0.32045(11) 0.0225(3) Uani 1 1 d . . . . .
H5S H 0.2302 0.6442 0.3707 0.027 Uiso 1 1 calc R U . . .
H4S H 0.3431 0.7671 0.3441 0.027 Uiso 1 1 calc R U . . .
C3S C 0.39570(17) 0.56374(17) 0.30265(11) 0.0213(3) Uani 1 1 d . . . . .
H7S H 0.3356 0.4754 0.2777 0.026 Uiso 1 1 calc R U . . .
H6S H 0.4695 0.5383 0.3635 0.026 Uiso 1 1 calc R U . . .
Br4S Br 0.51635(2) 0.63002(3) 0.21179(2) 0.03982(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
N1 0.0189(5) 0.0129(5) 0.0138(5) 0.0004(4) 0.0042(4) -0.0017(4)
N2 0.0175(5) 0.0129(5) 0.0152(5) 0.0008(4) 0.0041(4) -0.0012(4)
C3 0.0164(6) 0.0124(6) 0.0165(6) 0.0001(5) 0.0034(5) -0.0004(5)
C4 0.0163(6) 0.0154(6) 0.0137(6) -0.0013(5) 0.0036(5) 0.0008(5)
C5 0.0175(6) 0.0138(6) 0.0131(6) 0.0004(5) 0.0036(5) -0.0007(5)
N6 0.0208(6) 0.0129(6) 0.0284(7) 0.0004(5) 0.0080(5) 0.0004(4)
O7 0.0331(6) 0.0170(5) 0.0383(7) 0.0072(5) 0.0185(5) 0.0003(4)
O8 0.0462(7) 0.0151(5) 0.0502(8) -0.0034(5) 0.0273(6) 0.0031(5)
N9 0.0245(6) 0.0191(6) 0.0183(6) -0.0019(5) 0.0080(5) 0.0027(5)
O10 0.0261(6) 0.0497(7) 0.0307(6) 0.0009(6) 0.0107(5) 0.0150(5)
O11 0.0365(7) 0.0761(10) 0.0273(7) -0.0290(7) 0.0023(6) 0.0055(7)
N12 0.0218(6) 0.0171(6) 0.0152(5) 0.0036(4) 0.0057(5) 0.0004(4)
O13 0.0500(7) 0.0266(6) 0.0327(6) 0.0071(5) 0.0301(6) 0.0063(5)
O14 0.0301(6) 0.0132(5) 0.0208(5) 0.0015(4) 0.0059(4) -0.0007(4)
N1S 0.0223(6) 0.0125(6) 0.0227(6) -0.0016(5) 0.0100(5) 0.0015(5)
C2S 0.0233(7) 0.0267(7) 0.0188(7) -0.0069(6) 0.0073(6) -0.0008(6)
C3S 0.0188(6) 0.0262(7) 0.0192(7) -0.0008(6) 0.0050(5) 0.0000(6)
Br4S 0.01900(9) 0.07814(16) 0.02489(10) 0.00108(8) 0.01037(7) -0.00132(8)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.3447(18) . ?
N1 N2 1.3453(16) . ?
N2 C3 1.3439(18) . ?
C3 C4 1.3849(19) . ?
C3 N6 1.4352(18) . ?
C4 C5 1.3832(19) . ?
C4 N9 1.4536(17) . ?
C5 N12 1.4409(17) . ?
N6 O7 1.2252(17) . ?
N6 O8 1.2353(17) . ?
N9 O10 1.2131(17) . ?
N9 O11 1.2165(18) . ?
N12 O14 1.2261(16) . ?
N12 O13 1.2268(16) . ?
N1S C2S 1.492(2) . ?
N1S H1S 0.884(19) . ?
N1S H2S 0.86(2) . ?
N1S H3S 0.899(19) . ?
C2S C3S 1.503(2) . ?
C2S H5S 0.9900 . ?
C2S H4S 0.9900 . ?
C3S Br4S 1.9495(15) . ?
C3S H7S 0.9900 . ?
C3S H6S 0.9900 . ?

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
C5 N1 N2 107.73(11) . . ?
C3 N2 N1 107.09(11) . . ?
N2 C3 C4 111.83(12) . . ?
N2 C3 N6 120.19(12) . . ?
C4 C3 N6 127.91(12) . . ?
C5 C4 C3 101.91(12) . . ?
C5 C4 N9 128.67(12) . . ?
C3 C4 N9 129.38(12) . . ?
N1 C5 C4 111.45(12) . . ?
N1 C5 N12 121.35(12) . . ?
C4 C5 N12 127.21(12) . . ?
O7 N6 O8 124.27(12) . . ?
O7 N6 C3 118.52(12) . . ?
O8 N6 C3 117.19(12) . . ?
O10 N9 O11 124.88(13) . . ?
O10 N9 C4 118.15(12) . . ?
O11 N9 C4 116.97(12) . . ?
O14 N12 O13 125.28(12) . . ?
O14 N12 C5 118.40(12) . . ?
O13 N12 C5 116.32(12) . . ?
C2S N1S H1S 109.5(12) . . ?
C2S N1S H2S 110.7(12) . . ?
H1S N1S H2S 108.6(17) . . ?
C2S N1S H3S 109.7(12) . . ?
H1S N1S H3S 107.2(17) . . ?
H2S N1S H3S 111.2(17) . . ?
N1S C2S C3S 112.81(12) . . ?
N1S C2S H5S 109.0 . . ?
C3S C2S H5S 109.0 . . ?
N1S C2S H4S 109.0 . . ?
C3S C2S H4S 109.0 . . ?
H5S C2S H4S 107.8 . . ?
C2S C3S Br4S 111.31(11) . . ?
C2S C3S H7S 109.4 . . ?
Br4S C3S H7S 109.4 . . ?
C2S C3S H6S 109.4 . . ?
Br4S C3S H6S 109.4 . . ?
H7S C3S H6S 108.0 . . ?

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
C5 N1 N2 C3 0.19(14) . . . . ?
N1 N2 C3 C4 -0.05(15) . . . . ?
N1 N2 C3 N6 -177.16(11) . . . . ?
N2 C3 C4 C5 -0.10(15) . . . . ?
N6 C3 C4 C5 176.73(13) . . . . ?
N2 C3 C4 N9 177.76(13) . . . . ?
N6 C3 C4 N9 -5.4(2) . . . . ?
N2 N1 C5 C4 -0.27(15) . . . . ?
N2 N1 C5 N12 179.55(11) . . . . ?
C3 C4 C5 N1 0.22(15) . . . . ?
N9 C4 C5 N1 -177.66(13) . . . . ?
C3 C4 C5 N12 -179.58(13) . . . . ?
N9 C4 C5 N12 2.5(2) . . . . ?
N2 C3 N6 O7 -1.2(2) . . . . ?
C4 C3 N6 O7 -177.85(14) . . . . ?
N2 C3 N6 O8 176.85(13) . . . . ?
C4 C3 N6 O8 0.2(2) . . . . ?
C5 C4 N9 O10 -91.44(18) . . . . ?
C3 C4 N9 O10 91.24(19) . . . . ?
C5 C4 N9 O11 87.91(19) . . . . ?
C3 C4 N9 O11 -89.41(19) . . . . ?
N1 C5 N12 O14 1.02(19) . . . . ?
C4 C5 N12 O14 -179.19(13) . . . . ?
N1 C5 N12 O13 -179.28(13) . . . . ?
C4 C5 N12 O13 0.5(2) . . . . ?
N1S C2S C3S Br4S 63.42(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1S H1S N1 0.884(19) 2.06(2) 2.9110(17) 162.4(18) 3_665
N1S H2S O8 0.86(2) 2.47(2) 3.2644(18) 152.4(16) 3_675
N1S H3S N2 0.899(19) 2.117(19) 2.9637(17) 156.8(16) 4_476
C2S H4S O13 0.99 2.55 3.3265(19) 135.2 2_655
C3S H6S O10 0.99 2.52 3.267(2) 132.5 4_576

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.081


# start Validation Reply Form
_vrf_PLAT015_shrv365             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
# end Validation Reply Form
####################################################################### 
# 
# 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_shrv387
_database_code_depnum_ccdc_archive 'CCDC 1454193'
_audit_update_record             
;
2016-02-18 deposited with the CCDC.
2016-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H8 N10 O4'
_chemical_formula_sum            'C6 H8 N10 O4'
_chemical_formula_weight         284.22
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   7.1049(2)
_cell_length_b                   9.0630(3)
_cell_length_c                   17.4419(5)
_cell_angle_alpha                93.227(2)
_cell_angle_beta                 100.858(2)
_cell_angle_gamma                92.641(2)
_cell_volume                     1099.42(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1669
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      66.18

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.048
_exptl_crystal_size_mid          0.047
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.270
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.6398
_exptl_absorpt_correction_T_max  0.7528

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_measurement_device       'Bruker PLATINUM 135 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6472
_diffrn_reflns_av_unetI/netI     0.0658
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.585
_diffrn_reflns_theta_max         66.607
_diffrn_reflns_theta_full        66.607
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measured_fraction_theta_full 0.871
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_Laue_measured_fraction_full 0.871
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_point_group_measured_fraction_full 0.871
_reflns_number_total             3385
_reflns_number_gt                2246
_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       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_cell_refinement       'Bruker APEX3 v2015.5-2 (Bruker, 2015)'
_computing_data_reduction        
;
Bruker SAINT v8.34A (Bruker, 2013), Bruker XPREP v2014/2 (Bruker, 2014)
;
_computing_structure_solution    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_structure_refinement  
'SHELXL-2014/7 (Sheldrick, 2014) within WINGX (Farrugia, 2012)'
_computing_molecular_graphics    'Bruker SHELXTL v2014/7 (Bruker, 2014)'
_computing_publication_material  'Bruker SHELXTL v2014/7 (Bruker, 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)+(0.0919P)²+0.0874P] 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         3385
_refine_ls_number_parameters     393
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1620
_refine_ls_wR_factor_gt          0.1364
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.019
_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
N1A N 0.9871(6) 0.7040(4) 0.4609(2) 0.0418(10) Uani 1 1 d . . . . .
C2A C 0.9289(5) 0.8303(4) 0.4312(2) 0.0283(9) Uani 1 1 d . . . . .
N3A N 0.7727(5) 0.8985(3) 0.4422(2) 0.0366(9) Uani 1 1 d . . . . .
N4A N 0.7730(5) 1.0220(4) 0.4008(2) 0.0389(9) Uani 1 1 d . . . . .
N5A N 0.9180(5) 1.0323(3) 0.3664(2) 0.0352(9) Uani 1 1 d . . . . .
N6A N 1.0214(4) 0.9118(3) 0.38637(18) 0.0273(8) Uani 1 1 d . . . . .
C7A C 1.1980(5) 0.8866(4) 0.3572(2) 0.0271(9) Uani 1 1 d . . . . .
H7A1 H 1.2869 0.8368 0.3970 0.032 Uiso 1 1 calc R U . . .
H7A2 H 1.2605 0.9835 0.3502 0.032 Uiso 1 1 calc R U . . .
C8A C 1.1667(5) 0.7940(4) 0.2807(2) 0.0251(9) Uani 1 1 d . . . . .
H8A1 H 1.2925 0.7674 0.2692 0.030 Uiso 1 1 calc R U . . .
H8A2 H 1.0921 0.7012 0.2856 0.030 Uiso 1 1 calc R U . . .
N9A N 1.0639(4) 0.8728(3) 0.21580(18) 0.0245(7) Uani 1 1 d . . . . .
N10A N 1.1678(4) 0.9539(3) 0.17677(18) 0.0276(8) Uani 1 1 d . . . . .
C11A C 1.0403(5) 1.0237(4) 0.1272(2) 0.0247(8) Uani 1 1 d . . . . .
N12A N 1.1100(4) 1.1171(3) 0.07480(18) 0.0279(8) Uani 1 1 d . . . . .
O13A O 0.9877(4) 1.1806(3) 0.02962(16) 0.0398(8) Uani 1 1 d . . . . .
O14A O 1.2831(4) 1.1302(3) 0.07528(17) 0.0385(7) Uani 1 1 d . . . . .
C15A C 0.8485(5) 0.9939(4) 0.1343(2) 0.0255(9) Uani 1 1 d . . . . .
N16A N 0.6867(5) 1.0481(4) 0.0954(2) 0.0329(8) Uani 1 1 d D . . . .
C17A C 0.8704(5) 0.8932(4) 0.1927(2) 0.0275(9) Uani 1 1 d . . . . .
N18A N 0.7258(4) 0.8179(3) 0.22132(19) 0.0311(8) Uani 1 1 d . . . . .
O19A O 0.5590(4) 0.8530(3) 0.19692(18) 0.0435(8) Uani 1 1 d . . . . .
O20A O 0.7631(4) 0.7203(3) 0.26759(17) 0.0401(7) Uani 1 1 d . . . . .
N1B N 0.5191(5) 0.7966(4) 0.5480(2) 0.0313(8) Uani 1 1 d . . . . .
C2B C 0.5669(5) 0.6630(4) 0.5721(2) 0.0232(8) Uani 1 1 d . . . . .
N3B N 0.7058(4) 0.5852(3) 0.55187(18) 0.0267(7) Uani 1 1 d . . . . .
N4B N 0.7060(4) 0.4611(3) 0.59235(18) 0.0289(8) Uani 1 1 d . . . . .
N5B N 0.5751(4) 0.4586(3) 0.63414(18) 0.0279(8) Uani 1 1 d . . . . .
N6B N 0.4831(4) 0.5867(3) 0.62237(17) 0.0219(7) Uani 1 1 d . . . . .
C7B C 0.3377(5) 0.6288(4) 0.6667(2) 0.0260(9) Uani 1 1 d . . . . .
H7B1 H 0.2670 0.5384 0.6780 0.031 Uiso 1 1 calc R U . . .
H7B2 H 0.2447 0.6893 0.6345 0.031 Uiso 1 1 calc R U . . .
C8B C 0.4233(5) 0.7165(4) 0.7435(2) 0.0257(9) Uani 1 1 d . . . . .
H8B1 H 0.5061 0.8009 0.7330 0.031 Uiso 1 1 calc R U . . .
H8B2 H 0.3185 0.7568 0.7671 0.031 Uiso 1 1 calc R U . . .
N9B N 0.5374(4) 0.6235(3) 0.79933(18) 0.0269(7) Uani 1 1 d . . . . .
N10B N 0.4463(4) 0.5463(3) 0.84503(18) 0.0289(8) Uani 1 1 d . . . . .
C11B C 0.5789(5) 0.4668(4) 0.8856(2) 0.0294(9) Uani 1 1 d . . . . .
N12B N 0.5201(5) 0.3684(4) 0.9389(2) 0.0368(9) Uani 1 1 d . . . . .
O13B O 0.3512(4) 0.3586(3) 0.94557(18) 0.0465(8) Uani 1 1 d . . . . .
O14B O 0.6485(4) 0.2975(3) 0.97562(17) 0.0477(9) Uani 1 1 d . . . . .
C15B C 0.7618(5) 0.4879(4) 0.8678(2) 0.0286(9) Uani 1 1 d . . . . .
N16B N 0.9262(5) 0.4261(4) 0.8977(2) 0.0385(9) Uani 1 1 d D . . . .
C17B C 0.7285(5) 0.5901(4) 0.8105(2) 0.0277(9) Uani 1 1 d . . . . .
N18B N 0.8627(5) 0.6523(4) 0.7704(2) 0.0353(8) Uani 1 1 d . . . . .
O19B O 1.0253(4) 0.6045(4) 0.7849(2) 0.0564(10) Uani 1 1 d . . . . .
O20B O 0.8185(4) 0.7475(3) 0.72376(17) 0.0396(7) Uani 1 1 d . . . . .
H16A H 0.690(5) 1.119(4) 0.0602(19) 0.033(11) Uiso 1 1 d D . . . .
H1B H 0.581(6) 0.833(4) 0.512(2) 0.035(11) Uiso 1 1 d . . . . .
H1A H 0.906(6) 0.653(5) 0.487(3) 0.050(13) Uiso 1 1 d . . . . .
H17A H 0.583(5) 1.024(5) 0.118(3) 0.070(17) Uiso 1 1 d D . . . .
H2B H 0.428(6) 0.841(5) 0.566(2) 0.041(13) Uiso 1 1 d . . . . .
H16B H 1.036(4) 0.466(4) 0.884(2) 0.028(11) Uiso 1 1 d D . . . .
H2A H 1.078(7) 0.661(5) 0.447(3) 0.054(15) Uiso 1 1 d . . . . .
H17B H 0.927(9) 0.377(6) 0.943(2) 0.11(2) Uiso 1 1 d 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
N1A 0.044(2) 0.037(2) 0.058(3) 0.022(2) 0.034(2) 0.0252(18)
C2A 0.034(2) 0.026(2) 0.030(2) 0.0063(18) 0.0149(17) 0.0108(17)
N3A 0.047(2) 0.0300(19) 0.043(2) 0.0143(17) 0.0266(17) 0.0196(16)
N4A 0.049(2) 0.037(2) 0.042(2) 0.0143(18) 0.0283(18) 0.0244(17)
N5A 0.043(2) 0.0280(19) 0.041(2) 0.0097(17) 0.0199(17) 0.0172(15)
N6A 0.0322(18) 0.0251(18) 0.0291(19) 0.0050(15) 0.0135(14) 0.0135(14)
C7A 0.026(2) 0.028(2) 0.029(2) 0.0082(18) 0.0101(16) 0.0066(16)
C8A 0.024(2) 0.028(2) 0.026(2) 0.0053(18) 0.0069(16) 0.0107(16)
N9A 0.0221(17) 0.0263(17) 0.0273(19) 0.0053(15) 0.0073(13) 0.0083(13)
N10A 0.0274(18) 0.0308(18) 0.0276(18) 0.0077(15) 0.0094(14) 0.0082(14)
C11A 0.027(2) 0.027(2) 0.022(2) 0.0042(17) 0.0071(15) 0.0075(16)
N12A 0.0285(19) 0.0333(19) 0.0232(18) 0.0043(16) 0.0058(14) 0.0083(14)
O13A 0.0342(17) 0.0495(19) 0.0362(17) 0.0178(15) 0.0023(13) 0.0100(14)
O14A 0.0281(17) 0.0493(19) 0.0413(18) 0.0138(15) 0.0113(13) 0.0050(13)
C15A 0.022(2) 0.028(2) 0.026(2) -0.0023(18) 0.0026(15) 0.0101(16)
N16A 0.0245(19) 0.042(2) 0.035(2) 0.0115(18) 0.0064(15) 0.0113(16)
C17A 0.022(2) 0.032(2) 0.030(2) 0.0014(19) 0.0061(16) 0.0067(16)
N18A 0.0256(19) 0.0326(19) 0.037(2) 0.0073(17) 0.0085(15) 0.0035(14)
O19A 0.0211(16) 0.055(2) 0.057(2) 0.0148(17) 0.0104(13) 0.0090(13)
O20A 0.0385(17) 0.0407(17) 0.0431(19) 0.0128(15) 0.0106(13) -0.0003(13)
N1B 0.033(2) 0.0288(19) 0.039(2) 0.0096(17) 0.0194(16) 0.0145(15)
C2B 0.025(2) 0.024(2) 0.021(2) 0.0011(17) 0.0039(15) 0.0073(15)
N3B 0.0315(19) 0.0253(17) 0.0267(18) 0.0047(15) 0.0109(14) 0.0105(14)
N4B 0.0317(19) 0.0279(18) 0.0298(19) 0.0034(15) 0.0096(14) 0.0119(14)
N5B 0.0279(18) 0.0279(18) 0.0304(19) 0.0052(15) 0.0084(14) 0.0134(14)
N6B 0.0241(17) 0.0224(16) 0.0214(17) 0.0055(14) 0.0063(12) 0.0106(13)
C7B 0.023(2) 0.026(2) 0.032(2) 0.0105(18) 0.0096(16) 0.0106(16)
C8B 0.028(2) 0.026(2) 0.026(2) 0.0026(18) 0.0116(16) 0.0069(16)
N9B 0.0251(18) 0.0340(19) 0.0236(18) 0.0036(15) 0.0083(13) 0.0051(14)
N10B 0.0265(18) 0.0347(19) 0.0264(18) 0.0035(16) 0.0062(14) 0.0035(14)
C11B 0.026(2) 0.038(2) 0.025(2) 0.0067(19) 0.0038(16) 0.0090(17)
N12B 0.032(2) 0.044(2) 0.035(2) 0.0108(18) 0.0034(16) 0.0101(16)
O13B 0.0304(18) 0.066(2) 0.049(2) 0.0247(17) 0.0152(14) 0.0086(14)
O14B 0.0358(18) 0.061(2) 0.047(2) 0.0256(17) 0.0001(14) 0.0129(15)
C15B 0.022(2) 0.034(2) 0.029(2) -0.0036(19) 0.0029(16) 0.0080(17)
N16B 0.027(2) 0.048(2) 0.040(2) 0.0038(19) 0.0039(16) 0.0094(17)
C17B 0.020(2) 0.037(2) 0.027(2) -0.0039(19) 0.0065(16) 0.0063(16)
N18B 0.027(2) 0.048(2) 0.032(2) 0.0029(18) 0.0085(15) 0.0035(16)
O19B 0.0223(18) 0.083(2) 0.069(2) 0.027(2) 0.0138(15) 0.0110(16)
O20B 0.0381(17) 0.0414(18) 0.0408(18) 0.0083(15) 0.0107(14) -0.0017(13)

_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
N1A C2A 1.334(5) . ?
N1A H1A 0.92(4) . ?
N1A H2A 0.83(5) . ?
C2A N3A 1.335(4) . ?
C2A N6A 1.342(5) . ?
N3A N4A 1.366(4) . ?
N4A N5A 1.288(4) . ?
N5A N6A 1.369(4) . ?
N6A C7A 1.463(4) . ?
C7A C8A 1.508(5) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A N9A 1.467(4) . ?
C8A H8A1 0.9900 . ?
C8A H8A2 0.9900 . ?
N9A N10A 1.320(4) . ?
N9A C17A 1.382(5) . ?
N10A C11A 1.337(4) . ?
C11A C15A 1.407(5) . ?
C11A N12A 1.419(5) . ?
N12A O14A 1.229(4) . ?
N12A O13A 1.244(4) . ?
C15A N16A 1.349(5) . ?
C15A C17A 1.397(5) . ?
N16A H16A 0.92(2) . ?
N16A H17A 0.92(2) . ?
C17A N18A 1.392(5) . ?
N18A O20A 1.235(4) . ?
N18A O19A 1.243(4) . ?
N1B C2B 1.341(4) . ?
N1B H1B 0.91(4) . ?
N1B H2B 0.88(4) . ?
C2B N3B 1.328(4) . ?
C2B N6B 1.352(4) . ?
N3B N4B 1.361(4) . ?
N4B N5B 1.285(4) . ?
N5B N6B 1.365(4) . ?
N6B C7B 1.454(4) . ?
C7B C8B 1.525(5) . ?
C7B H7B1 0.9900 . ?
C7B H7B2 0.9900 . ?
C8B N9B 1.473(4) . ?
C8B H8B1 0.9900 . ?
C8B H8B2 0.9900 . ?
N9B N10B 1.327(4) . ?
N9B C17B 1.385(4) . ?
N10B C11B 1.333(5) . ?
C11B C15B 1.399(5) . ?
C11B N12B 1.428(5) . ?
N12B O13B 1.226(4) . ?
N12B O14B 1.239(4) . ?
C15B N16B 1.347(5) . ?
C15B C17B 1.396(5) . ?
N16B H16B 0.92(2) . ?
N16B H17B 0.92(2) . ?
C17B N18B 1.401(5) . ?
N18B O20B 1.230(4) . ?
N18B O19B 1.239(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
C2A N1A H1A 118(3) . . ?
C2A N1A H2A 121(3) . . ?
H1A N1A H2A 119(4) . . ?
N1A C2A N3A 126.1(3) . . ?
N1A C2A N6A 125.3(3) . . ?
N3A C2A N6A 108.6(3) . . ?
C2A N3A N4A 104.9(3) . . ?
N5A N4A N3A 112.3(3) . . ?
N4A N5A N6A 105.5(3) . . ?
C2A N6A N5A 108.6(3) . . ?
C2A N6A C7A 130.6(3) . . ?
N5A N6A C7A 120.8(3) . . ?
N6A C7A C8A 113.8(3) . . ?
N6A C7A H7A1 108.8 . . ?
C8A C7A H7A1 108.8 . . ?
N6A C7A H7A2 108.8 . . ?
C8A C7A H7A2 108.8 . . ?
H7A1 C7A H7A2 107.7 . . ?
N9A C8A C7A 111.8(3) . . ?
N9A C8A H8A1 109.3 . . ?
C7A C8A H8A1 109.3 . . ?
N9A C8A H8A2 109.3 . . ?
C7A C8A H8A2 109.3 . . ?
H8A1 C8A H8A2 107.9 . . ?
N10A N9A C17A 111.2(3) . . ?
N10A N9A C8A 117.5(3) . . ?
C17A N9A C8A 130.7(3) . . ?
N9A N10A C11A 105.1(3) . . ?
N10A C11A C15A 114.0(3) . . ?
N10A C11A N12A 118.2(3) . . ?
C15A C11A N12A 127.8(3) . . ?
O14A N12A O13A 123.6(3) . . ?
O14A N12A C11A 119.9(3) . . ?
O13A N12A C11A 116.6(3) . . ?
N16A C15A C17A 129.3(4) . . ?
N16A C15A C11A 129.4(4) . . ?
C17A C15A C11A 101.3(3) . . ?
C15A N16A H16A 122(2) . . ?
C15A N16A H17A 111(3) . . ?
H16A N16A H17A 125(4) . . ?
N9A C17A N18A 124.2(3) . . ?
N9A C17A C15A 108.4(3) . . ?
N18A C17A C15A 127.3(3) . . ?
O20A N18A O19A 122.5(3) . . ?
O20A N18A C17A 121.1(3) . . ?
O19A N18A C17A 116.4(3) . . ?
C2B N1B H1B 117(2) . . ?
C2B N1B H2B 119(3) . . ?
H1B N1B H2B 124(4) . . ?
N3B C2B N1B 125.9(3) . . ?
N3B C2B N6B 108.8(3) . . ?
N1B C2B N6B 125.3(3) . . ?
C2B N3B N4B 105.1(3) . . ?
N5B N4B N3B 112.2(3) . . ?
N4B N5B N6B 106.1(3) . . ?
C2B N6B N5B 107.8(3) . . ?
C2B N6B C7B 130.4(3) . . ?
N5B N6B C7B 121.4(3) . . ?
N6B C7B C8B 112.5(3) . . ?
N6B C7B H7B1 109.1 . . ?
C8B C7B H7B1 109.1 . . ?
N6B C7B H7B2 109.1 . . ?
C8B C7B H7B2 109.1 . . ?
H7B1 C7B H7B2 107.8 . . ?
N9B C8B C7B 111.5(3) . . ?
N9B C8B H8B1 109.3 . . ?
C7B C8B H8B1 109.3 . . ?
N9B C8B H8B2 109.3 . . ?
C7B C8B H8B2 109.3 . . ?
H8B1 C8B H8B2 108.0 . . ?
N10B N9B C17B 110.2(3) . . ?
N10B N9B C8B 117.9(3) . . ?
C17B N9B C8B 131.7(3) . . ?
N9B N10B C11B 105.5(3) . . ?
N10B C11B C15B 114.1(3) . . ?
N10B C11B N12B 118.1(3) . . ?
C15B C11B N12B 127.7(3) . . ?
O13B N12B O14B 124.6(3) . . ?
O13B N12B C11B 119.7(3) . . ?
O14B N12B C11B 115.7(3) . . ?
N16B C15B C17B 129.2(4) . . ?
N16B C15B C11B 129.4(4) . . ?
C17B C15B C11B 101.3(3) . . ?
C15B N16B H16B 116(2) . . ?
C15B N16B H17B 116(4) . . ?
H16B N16B H17B 123(5) . . ?
N9B C17B C15B 108.8(3) . . ?
N9B C17B N18B 124.2(3) . . ?
C15B C17B N18B 127.0(3) . . ?
O20B N18B O19B 123.3(3) . . ?
O20B N18B C17B 121.1(3) . . ?
O19B N18B C17B 115.6(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
N1A C2A N3A N4A 180.0(4) . . . . ?
N6A C2A N3A N4A 1.4(5) . . . . ?
C2A N3A N4A N5A -0.3(5) . . . . ?
N3A N4A N5A N6A -0.9(5) . . . . ?
N1A C2A N6A N5A 179.4(4) . . . . ?
N3A C2A N6A N5A -1.9(5) . . . . ?
N1A C2A N6A C7A 1.6(7) . . . . ?
N3A C2A N6A C7A -179.7(4) . . . . ?
N4A N5A N6A C2A 1.7(5) . . . . ?
N4A N5A N6A C7A 179.8(4) . . . . ?
C2A N6A C7A C8A 87.1(5) . . . . ?
N5A N6A C7A C8A -90.4(4) . . . . ?
N6A C7A C8A N9A 68.5(4) . . . . ?
C7A C8A N9A N10A 90.0(4) . . . . ?
C7A C8A N9A C17A -80.8(5) . . . . ?
C17A N9A N10A C11A -1.5(4) . . . . ?
C8A N9A N10A C11A -174.0(3) . . . . ?
N9A N10A C11A C15A 2.1(5) . . . . ?
N9A N10A C11A N12A -178.0(3) . . . . ?
N10A C11A N12A O14A 0.9(5) . . . . ?
C15A C11A N12A O14A -179.2(4) . . . . ?
N10A C11A N12A O13A -179.8(3) . . . . ?
C15A C11A N12A O13A 0.0(6) . . . . ?
N10A C11A C15A N16A 178.1(4) . . . . ?
N12A C11A C15A N16A -1.8(7) . . . . ?
N10A C11A C15A C17A -1.8(5) . . . . ?
N12A C11A C15A C17A 178.3(4) . . . . ?
N10A N9A C17A N18A 177.3(4) . . . . ?
C8A N9A C17A N18A -11.5(6) . . . . ?
N10A N9A C17A C15A 0.4(4) . . . . ?
C8A N9A C17A C15A 171.6(3) . . . . ?
N16A C15A C17A N9A -179.1(4) . . . . ?
C11A C15A C17A N9A 0.8(4) . . . . ?
N16A C15A C17A N18A 4.1(7) . . . . ?
C11A C15A C17A N18A -176.0(4) . . . . ?
N9A C17A N18A O20A -3.7(6) . . . . ?
C15A C17A N18A O20A 172.6(4) . . . . ?
N9A C17A N18A O19A 177.3(3) . . . . ?
C15A C17A N18A O19A -6.4(6) . . . . ?
N1B C2B N3B N4B 177.8(4) . . . . ?
N6B C2B N3B N4B -1.1(4) . . . . ?
C2B N3B N4B N5B 1.1(4) . . . . ?
N3B N4B N5B N6B -0.6(4) . . . . ?
N3B C2B N6B N5B 0.8(4) . . . . ?
N1B C2B N6B N5B -178.2(4) . . . . ?
N3B C2B N6B C7B 173.7(3) . . . . ?
N1B C2B N6B C7B -5.2(6) . . . . ?
N4B N5B N6B C2B -0.1(4) . . . . ?
N4B N5B N6B C7B -173.8(3) . . . . ?
C2B N6B C7B C8B -84.3(4) . . . . ?
N5B N6B C7B C8B 87.8(4) . . . . ?
N6B C7B C8B N9B -68.5(4) . . . . ?
C7B C8B N9B N10B -86.7(4) . . . . ?
C7B C8B N9B C17B 87.6(5) . . . . ?
C17B N9B N10B C11B 1.0(4) . . . . ?
C8B N9B N10B C11B 176.5(3) . . . . ?
N9B N10B C11B C15B -0.5(5) . . . . ?
N9B N10B C11B N12B -178.3(3) . . . . ?
N10B C11B N12B O13B 0.6(6) . . . . ?
C15B C11B N12B O13B -177.0(4) . . . . ?
N10B C11B N12B O14B -179.6(4) . . . . ?
C15B C11B N12B O14B 2.8(6) . . . . ?
N10B C11B C15B N16B 179.7(4) . . . . ?
N12B C11B C15B N16B -2.7(8) . . . . ?
N10B C11B C15B C17B -0.2(5) . . . . ?
N12B C11B C15B C17B 177.4(4) . . . . ?
N10B N9B C17B C15B -1.2(4) . . . . ?
C8B N9B C17B C15B -175.8(4) . . . . ?
N10B N9B C17B N18B 179.4(4) . . . . ?
C8B N9B C17B N18B 4.8(6) . . . . ?
N16B C15B C17B N9B -179.2(4) . . . . ?
C11B C15B C17B N9B 0.8(4) . . . . ?
N16B C15B C17B N18B 0.2(7) . . . . ?
C11B C15B C17B N18B -179.8(4) . . . . ?
N9B C17B N18B O20B 3.0(6) . . . . ?
C15B C17B N18B O20B -176.3(4) . . . . ?
N9B C17B N18B O19B -176.6(4) . . . . ?
C15B C17B N18B O19B 4.1(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8A H8A1 O19A 0.99 2.58 3.417(4) 142.4 1_655
C8A H8A2 O20A 0.99 2.31 2.877(5) 115.1 .
C8B H8B1 O20B 0.99 2.33 2.895(4) 115.6 .
C8B H8B2 O19B 0.99 2.52 3.184(5) 123.9 1_455
N16A H16A O13A 0.92(2) 2.32(4) 2.859(4) 117(3) .
N16A H16A O14B 0.92(2) 2.24(2) 3.150(4) 170(3) 1_564
N1B H1B N3A 0.91(4) 2.07(4) 2.966(5) 168(3) .
N1A H1A N3B 0.92(4) 2.07(5) 2.976(5) 167(4) .
N16A H17A O14A 0.92(2) 2.38(4) 2.957(4) 120(4) 1_455
N16A H17A O19A 0.92(2) 2.16(4) 2.810(4) 127(4) .
N16B H16B O13B 0.92(2) 2.56(3) 3.077(4) 117(3) 1_655
N16B H16B O19B 0.92(2) 2.19(3) 2.785(5) 122(3) .
N16B H17B O13A 0.92(2) 2.41(3) 3.274(5) 157(5) 1_546
N16B H17B O14B 0.92(2) 2.26(6) 2.841(5) 121(5) .

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.070



# start Validation Reply Form
_vrf_PLAT015_shrv387             
;
PROBLEM: No _shelx_hkl_file record in SHELXL20xy CIF ....     Please Do ! 
RESPONSE: It is our policy to routinely not supply the HKL file unless 
specifically required.

;
# end Validation Reply Form
