# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_ptac
_database_code_depnum_ccdc_archive 'CCDC 918727'
_audit_update_record             
;
2016-08-25 deposited with the CCDC.
2016-09-05 downloaded from the CCDC.
;
_audit_creation_date             2016-08-15
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r3563)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H7 N4 O8, C H9 N6'
_chemical_formula_sum            'C11 H16 N10 O8'
_chemical_formula_weight         416.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7785(4)
_cell_length_b                   9.7547(4)
_cell_length_c                   10.2957(5)
_cell_angle_alpha                93.527(2)
_cell_angle_beta                 101.291(2)
_cell_angle_gamma                102.406(2)
_cell_volume                     839.43(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3845
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      56.195
_cell_measurement_theta_min      4.864
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  0.9590
_exptl_absorpt_correction_T_min  0.9459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
SADABS 1999, Bruker AXS, Madison, WI, USA
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5492
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.814
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  
'Bruker Kappa APEX-II diffractometer with CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2730
_reflns_number_total             3221
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3221
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0671P)²+0.1944P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1137
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H6 of N6, H1 of N1
 At 1.5 times of:
  All N(H,H) groups, H8A of N8, All O(H) groups
2. Restrained distances
 N5-H5A
 0.85 with sigma of 0.01
 N5-H5B
 0.85 with sigma of 0.01
 H5A-H5B
 1.388291 with sigma of 0.03
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
O2 O 1.21416(12) 1.47343(11) -0.20622(11) 0.0359(3) Uani 1 1 d . . . . .
O3 O 1.13761(14) 1.01323(13) 0.23002(12) 0.0444(3) Uani 1 1 d . . . . .
O4 O 0.89409(14) 1.05570(13) 0.20824(12) 0.0412(3) Uani 1 1 d . . . . .
O1 O 1.40989(13) 1.36760(13) -0.12970(12) 0.0415(3) Uani 1 1 d . . . . .
N8 N 0.5284(2) 1.09717(17) 0.69711(17) 0.0490(4) Uani 1 1 d . . . . .
H8A H 0.628(3) 1.142(3) 0.742(2) 0.073 Uiso 1 1 d R . . . .
N7 N 0.48237(17) 0.99713(14) 0.78436(16) 0.0407(3) Uani 1 1 d . . . . .
N9 N 0.39121(15) 0.76516(14) 0.81526(13) 0.0341(3) Uani 1 1 d . . . . .
O8 O 0.56315(12) 0.50353(12) 0.72391(11) 0.0368(3) Uani 1 1 d . . . . .
H8 H 0.494(2) 0.4412(19) 0.7889(19) 0.055 Uiso 1 1 d R . . . .
O5 O 1.08096(14) 0.82760(15) 0.39563(14) 0.0502(3) Uani 1 1 d . . . . .
O6 O 0.83797(14) 0.86963(13) 0.37528(13) 0.0472(3) Uani 1 1 d . . . . .
O7 O 0.76547(13) 0.41207(12) 0.81453(11) 0.0384(3) Uani 1 1 d . . . . .
C1 C 1.27137(16) 1.38956(15) -0.13697(14) 0.0275(3) Uani 1 1 d . . . . .
C2 C 1.17301(16) 1.30622(14) -0.05454(14) 0.0268(3) Uani 1 1 d . . . . .
N6 N 0.42889(16) 0.82477(14) 0.60934(14) 0.0386(3) Uani 1 1 d . . . . .
H6 H 0.451(2) 0.899(2) 0.554(2) 0.046 Uiso 1 1 d R . . . .
N5 N 0.37084(17) 0.68652(14) 0.54699(14) 0.0375(3) Uani 1 1 d D . . . .
C3 C 1.20497(17) 1.21167(16) 0.03467(15) 0.0299(3) Uani 1 1 d . . . . .
H3 H 1.305(2) 1.1761(18) 0.0618(17) 0.036 Uiso 1 1 d R . . . .
C4 C 1.06525(17) 1.17213(15) 0.08192(14) 0.0281(3) Uani 1 1 d . . . . .
C5 C 1.03268(17) 1.07341(15) 0.18029(14) 0.0296(3) Uani 1 1 d . . . . .
N2 N 0.95324(15) 1.23672(14) 0.02588(13) 0.0327(3) Uani 1 1 d . . . . .
N1 N 1.02178(15) 1.31740(13) -0.05601(13) 0.0308(3) Uani 1 1 d . . . . .
H1 H 0.958(2) 1.3635(19) -0.1044(18) 0.037 Uiso 1 1 d R . . . .
C11 C 0.43258(16) 0.86223(15) 0.73606(15) 0.0317(3) Uani 1 1 d . . . . .
N10 N 0.39540(17) 0.80739(15) 0.95018(14) 0.0352(3) Uani 1 1 d . . . . .
C10 C 0.70801(16) 0.48847(15) 0.73927(14) 0.0270(3) Uani 1 1 d . . . . .
C9 C 0.80347(16) 0.57350(14) 0.65662(14) 0.0262(3) Uani 1 1 d . . . . .
C8 C 0.76823(18) 0.66363(16) 0.56413(15) 0.0307(3) Uani 1 1 d . . . . .
H8C H 0.672(2) 0.6926(18) 0.5312(17) 0.037 Uiso 1 1 d R . . . .
C7 C 0.91038(17) 0.70909(15) 0.52140(14) 0.0281(3) Uani 1 1 d . . . . .
C6 C 0.94263(18) 0.80902(16) 0.42430(15) 0.0316(3) Uani 1 1 d . . . . .
N3 N 1.02606(14) 0.65190(13) 0.58361(12) 0.0301(3) Uani 1 1 d . . . . .
N4 N 0.95798(15) 0.57029(13) 0.66441(12) 0.0283(3) Uani 1 1 d . . . . .
H5A H 0.420(2) 0.6315(17) 0.5920(16) 0.042 Uiso 1 1 d DR . . . .
H5B H 0.2711(12) 0.6575(18) 0.5461(18) 0.042 Uiso 1 1 d DR . . . .
H9 H 0.345(2) 0.676(2) 0.7793(19) 0.046(5) Uiso 1 1 d . . . . .
H7 H 0.492(3) 1.021(2) 0.882(2) 0.060(6) Uiso 1 1 d . . . . .
H10A H 0.289(2) 0.7943(19) 0.9616(18) 0.039(5) Uiso 1 1 d . . . . .
H10B H 0.435(2) 0.749(2) 1.001(2) 0.043(5) Uiso 1 1 d . . . . .
H8B H 0.462(3) 1.155(3) 0.694(2) 0.070(7) Uiso 1 1 d . . . . .
H4 H 1.017(2) 0.5270(19) 0.7117(18) 0.036(5) Uiso 1 1 d . . . . .
H4A H 0.871(3) 0.984(3) 0.267(3) 0.095(9) Uiso 1 1 d . . . . .
H5 H 1.108(4) 0.906(3) 0.330(3) 0.112(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.2402(17) . ?
O3 C5 1.2409(18) . ?
O4 C5 1.2829(17) . ?
O4 H4A 0.97(3) . ?
O1 C1 1.2681(17) . ?
N8 H8A 0.91(3) . ?
N8 N7 1.415(2) . ?
N8 H8B 0.89(3) . ?
N7 C11 1.326(2) . ?
N7 H7 1.01(2) . ?
N9 C11 1.325(2) . ?
N9 N10 1.4155(19) . ?
N9 H9 0.90(2) . ?
O8 H8 1.11(2) . ?
O8 C10 1.2916(17) . ?
O5 C6 1.2834(18) . ?
O5 H5 1.07(4) . ?
O6 C6 1.2398(19) . ?
O7 C10 1.2206(17) . ?
C1 C2 1.4822(18) . ?
C2 C3 1.3739(19) . ?
C2 N1 1.3524(18) . ?
N6 H6 0.96(2) . ?
N6 N5 1.4002(19) . ?
N6 C11 1.325(2) . ?
N5 H5A 0.859(9) . ?
N5 H5B 0.858(9) . ?
C3 H3 1.011(18) . ?
C3 C4 1.394(2) . ?
C4 C5 1.4662(19) . ?
C4 N2 1.3363(19) . ?
N2 N1 1.3301(16) . ?
N1 H1 0.889(19) . ?
N10 H10A 0.95(2) . ?
N10 H10B 0.88(2) . ?
C10 C9 1.4770(18) . ?
C9 C8 1.371(2) . ?
C9 N4 1.3501(18) . ?
C8 H8C 0.956(19) . ?
C8 C7 1.396(2) . ?
C7 C6 1.4635(19) . ?
C7 N3 1.3362(19) . ?
N3 N4 1.3247(16) . ?
N4 H4 0.842(19) . ?

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 O4 H4A 115.1(17) . . ?
H8A N8 H8B 111(2) . . ?
N7 N8 H8A 101.6(16) . . ?
N7 N8 H8B 105.8(16) . . ?
N8 N7 H7 124.2(13) . . ?
C11 N7 N8 118.27(14) . . ?
C11 N7 H7 117.4(13) . . ?
C11 N9 N10 119.44(13) . . ?
C11 N9 H9 119.1(13) . . ?
N10 N9 H9 120.6(13) . . ?
C10 O8 H8 113.0(9) . . ?
C6 O5 H5 116.5(17) . . ?
O2 C1 O1 125.45(13) . . ?
O2 C1 C2 118.88(12) . . ?
O1 C1 C2 115.67(12) . . ?
C3 C2 C1 132.19(13) . . ?
N1 C2 C1 121.41(12) . . ?
N1 C2 C3 106.38(12) . . ?
N5 N6 H6 117.7(11) . . ?
C11 N6 H6 117.4(11) . . ?
C11 N6 N5 124.10(13) . . ?
N6 N5 H5A 109.0(12) . . ?
N6 N5 H5B 110.8(12) . . ?
H5A N5 H5B 106.9(17) . . ?
C2 C3 H3 129.4(10) . . ?
C2 C3 C4 104.57(12) . . ?
C4 C3 H3 126.1(10) . . ?
C3 C4 C5 128.08(13) . . ?
N2 C4 C3 111.72(12) . . ?
N2 C4 C5 120.20(13) . . ?
O3 C5 O4 124.66(13) . . ?
O3 C5 C4 119.21(13) . . ?
O4 C5 C4 116.13(13) . . ?
N1 N2 C4 104.39(11) . . ?
C2 N1 H1 132.6(12) . . ?
N2 N1 C2 112.93(12) . . ?
N2 N1 H1 114.3(12) . . ?
N9 C11 N7 120.02(15) . . ?
N9 C11 N6 120.31(14) . . ?
N6 C11 N7 119.63(14) . . ?
N9 N10 H10A 108.3(11) . . ?
N9 N10 H10B 109.4(12) . . ?
H10A N10 H10B 103.9(17) . . ?
O8 C10 C9 114.11(12) . . ?
O7 C10 O8 124.75(13) . . ?
O7 C10 C9 121.14(13) . . ?
C8 C9 C10 132.82(13) . . ?
N4 C9 C10 120.54(12) . . ?
N4 C9 C8 106.64(12) . . ?
C9 C8 H8C 131.5(11) . . ?
C9 C8 C7 104.29(12) . . ?
C7 C8 H8C 124.2(11) . . ?
C8 C7 C6 128.06(13) . . ?
N3 C7 C8 111.69(12) . . ?
N3 C7 C6 120.23(13) . . ?
O5 C6 C7 116.33(13) . . ?
O6 C6 O5 124.22(13) . . ?
O6 C6 C7 119.45(13) . . ?
N4 N3 C7 104.44(11) . . ?
C9 N4 H4 131.4(13) . . ?
N3 N4 C9 112.94(12) . . ?
N3 N4 H4 115.6(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
N8 H8A O7 0.91(3) 2.64(3) 3.322(2) 132.2(19) 1_565
O8 H8 O1 1.11(2) 1.36(2) 2.4725(14) 178.6(17) 1_446
N6 H6 N8 0.96(2) 2.63(2) 3.363(2) 133.8(14) 2_676
N1 H1 O7 0.889(19) 1.902(19) 2.7499(16) 158.9(17) 1_564
N5 H5A O8 0.859(9) 2.281(10) 3.1377(17) 174.7(17) .
N5 H5B N3 0.858(9) 2.249(11) 3.0725(18) 160.8(17) 1_455
N9 H9 O2 0.90(2) 2.09(2) 2.9070(17) 150.3(17) 1_446
N7 H7 N10 1.01(2) 2.24(2) 3.097(2) 142.1(18) 2_677
N10 H10A N2 0.95(2) 2.11(2) 3.0587(18) 176.5(16) 2_676
N10 H10B O1 0.88(2) 2.25(2) 3.1075(17) 166.8(17) 2_776
N8 H8B O6 0.89(3) 2.54(3) 3.247(2) 136.4(19) 2_676
N4 H4 O2 0.842(19) 1.960(19) 2.7603(16) 158.5(18) 1_546
O4 H4A O6 0.97(3) 1.65(3) 2.6128(14) 176(3) .
O5 H5 O3 1.07(4) 1.53(4) 2.5997(15) 177(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
O2 C1 C2 C3 -176.83(15) . . . . ?
O2 C1 C2 N1 1.6(2) . . . . ?
O1 C1 C2 C3 3.2(2) . . . . ?
O1 C1 C2 N1 -178.36(14) . . . . ?
N8 N7 C11 N9 178.77(15) . . . . ?
N8 N7 C11 N6 0.7(2) . . . . ?
O8 C10 C9 C8 -1.6(2) . . . . ?
O8 C10 C9 N4 178.70(13) . . . . ?
O7 C10 C9 C8 178.51(15) . . . . ?
O7 C10 C9 N4 -1.2(2) . . . . ?
C1 C2 C3 C4 178.49(15) . . . . ?
C1 C2 N1 N2 -178.85(13) . . . . ?
C2 C3 C4 C5 -179.69(14) . . . . ?
C2 C3 C4 N2 0.29(18) . . . . ?
N5 N6 C11 N7 -176.61(14) . . . . ?
N5 N6 C11 N9 5.4(2) . . . . ?
C3 C2 N1 N2 -0.04(17) . . . . ?
C3 C4 C5 O3 -0.9(2) . . . . ?
C3 C4 C5 O4 179.33(15) . . . . ?
C3 C4 N2 N1 -0.31(17) . . . . ?
C4 N2 N1 C2 0.22(17) . . . . ?
C5 C4 N2 N1 179.67(13) . . . . ?
N2 C4 C5 O3 179.15(14) . . . . ?
N2 C4 C5 O4 -0.7(2) . . . . ?
N1 C2 C3 C4 -0.15(16) . . . . ?
N10 N9 C11 N7 2.2(2) . . . . ?
N10 N9 C11 N6 -179.77(13) . . . . ?
C10 C9 C8 C7 -179.50(15) . . . . ?
C10 C9 N4 N3 179.76(13) . . . . ?
C9 C8 C7 C6 -178.80(15) . . . . ?
C9 C8 C7 N3 -0.37(18) . . . . ?
C8 C9 N4 N3 0.00(17) . . . . ?
C8 C7 C6 O5 -175.98(15) . . . . ?
C8 C7 C6 O6 4.0(3) . . . . ?
C8 C7 N3 N4 0.37(17) . . . . ?
C7 N3 N4 C9 -0.22(16) . . . . ?
C6 C7 N3 N4 178.94(13) . . . . ?
N3 C7 C6 O5 5.7(2) . . . . ?
N3 C7 C6 O6 -174.33(15) . . . . ?
N4 C9 C8 C7 0.22(16) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_c1
_database_code_depnum_ccdc_archive 'CCDC 955243'
_audit_update_record             
;
2016-08-25 deposited with the CCDC.
2016-09-05 downloaded from the CCDC.
;
_audit_creation_date             2016-08-15
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r3563)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'H2 O, C5 H3 N2 O4, C H6 N3'
_chemical_formula_sum            'C6 H11 N5 O5'
_chemical_formula_weight         233.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.7602(4)
_cell_length_b                   9.0277(4)
_cell_length_c                   17.1544(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.503(3)
_cell_angle_gamma                90
_cell_volume                     1967.00(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4663
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      56.212
_cell_measurement_theta_min      4.771
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.9732
_exptl_absorpt_correction_T_min  0.9601
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
SADABS (1999) Bruker AXS, Madison, EI, USA
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7327
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.314
_diffrn_reflns_theta_min         2.768
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker AXS Kappa Apex 2 CCD diffractomer'
_diffrn_measurement_method       'phi and omgea scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2118
_reflns_number_total             2410
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR97 (Burla et al., 2007)'
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2410
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0575P)²+0.9335P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0996
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups, All O(H) groups, All
  O(H,H) groups
2. Restrained distances
 O1S-H1SA = O1S-H1SB = O1-H1
 0.86 with sigma of 0.02
 N3-H3A = N3-H3B = N4-H4A = N4-H4B = N5-H5A = N5-H5B = N1-H1A
 0.86 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O1S O 0.14375(9) 0.45120(13) -0.07574(6) 0.0467(3) Uani 1 1 d D . . . .
H1SA H 0.1187(14) 0.3913(19) -0.1118(11) 0.056 Uiso 1 1 d DR . . . .
H1SB H 0.2077(12) 0.422(2) -0.0779(11) 0.056 Uiso 1 1 d DR . . . .
O1 O 0.13367(9) 0.85172(9) 0.17467(5) 0.0403(3) Uani 1 1 d D . . . .
H1 H 0.1326(13) 0.9445(17) 0.1956(10) 0.048 Uiso 1 1 d DR . . . .
O2 O 0.12982(8) 0.12231(9) 0.21471(5) 0.0336(2) Uani 1 1 d . . . . .
O3 O 0.11750(7) 0.75296(9) 0.29200(5) 0.0320(2) Uani 1 1 d . . . . .
O4 O 0.14267(8) 0.13903(9) 0.08569(5) 0.0347(2) Uani 1 1 d . . . . .
N5 N 0.37815(10) 0.71064(12) 0.12138(6) 0.0357(3) Uani 1 1 d D . . . .
H5A H 0.3696(12) 0.8057(16) 0.1096(10) 0.043 Uiso 1 1 d DR . . . .
H5B H 0.3775(12) 0.686(2) 0.1702(8) 0.043 Uiso 1 1 d DR . . . .
N3 N 0.37678(11) 0.64641(12) -0.00802(6) 0.0407(3) Uani 1 1 d D . . . .
H3A H 0.3744(14) 0.7360(16) -0.0243(11) 0.049 Uiso 1 1 d DR . . . .
H3B H 0.3762(14) 0.5769(18) -0.0433(10) 0.049 Uiso 1 1 d DR . . . .
C1 C 0.12383(9) 0.74155(11) 0.22202(6) 0.0243(2) Uani 1 1 d . . . . .
C2 C 0.12197(9) 0.59562(11) 0.18236(6) 0.0231(2) Uani 1 1 d . . . . .
C3 C 0.12590(9) 0.45566(11) 0.21718(6) 0.0258(2) Uani 1 1 d . . . . .
H3 H 0.1285 0.4335 0.2703 0.031 Uiso 1 1 calc R . . . .
C4 C 0.12517(8) 0.35768(11) 0.15572(6) 0.0229(2) Uani 1 1 d . . . . .
C5 C 0.13272(9) 0.19373(11) 0.15145(6) 0.0245(2) Uani 1 1 d . . . . .
N1 N 0.12010(8) 0.44046(10) 0.08999(5) 0.0263(2) Uani 1 1 d D . . . .
H1A H 0.1218(11) 0.4107(16) 0.0428(8) 0.032 Uiso 1 1 d DR . . . .
N2 N 0.11830(8) 0.58571(9) 0.10429(5) 0.0277(2) Uani 1 1 d . . . . .
C6 C 0.37975(9) 0.60879(12) 0.06625(6) 0.0268(2) Uani 1 1 d . . . . .
N4 N 0.38447(10) 0.46594(12) 0.08460(7) 0.0391(3) Uani 1 1 d D . . . .
H4A H 0.3847(13) 0.439(2) 0.1309(9) 0.047 Uiso 1 1 d DR . . . .
H4B H 0.3866(13) 0.4025(18) 0.0474(9) 0.047 Uiso 1 1 d DR . . . .


_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
O1S H1SA 0.859(15) . ?
O1S H1SB 0.861(14) . ?
O1 H1 0.912(14) . ?
O1 C1 1.2978(13) . ?
O2 C5 1.2659(13) . ?
O3 C1 1.2154(14) . ?
O4 C5 1.2490(13) . ?
N5 H5A 0.886(14) . ?
N5 H5B 0.868(14) . ?
N5 C6 1.3205(15) . ?
N3 H3A 0.856(14) . ?
N3 H3B 0.871(14) . ?
N3 C6 1.3156(15) . ?
C1 C2 1.4818(14) . ?
C2 C3 1.3964(14) . ?
C2 N2 1.3386(14) . ?
C3 H3 0.9300 . ?
C3 C4 1.3755(15) . ?
C4 C5 1.4854(14) . ?
C4 N1 1.3492(13) . ?
N1 H1A 0.855(13) . ?
N1 N2 1.3346(12) . ?
C6 N4 1.3275(15) . ?
N4 H4A 0.830(14) . ?
N4 H4B 0.860(14) . ?

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
H1SA O1S H1SB 93.9(17) . . ?
C1 O1 H1 116.8(11) . . ?
H5A N5 H5B 117.1(17) . . ?
C6 N5 H5A 121.4(11) . . ?
C6 N5 H5B 121.1(12) . . ?
H3A N3 H3B 117.2(17) . . ?
C6 N3 H3A 123.9(13) . . ?
C6 N3 H3B 119.0(12) . . ?
O1 C1 C2 113.10(9) . . ?
O3 C1 O1 124.95(10) . . ?
O3 C1 C2 121.95(10) . . ?
C3 C2 C1 127.58(10) . . ?
N2 C2 C1 121.08(9) . . ?
N2 C2 C3 111.33(9) . . ?
C2 C3 H3 127.6 . . ?
C4 C3 C2 104.88(9) . . ?
C4 C3 H3 127.6 . . ?
C3 C4 C5 133.07(10) . . ?
N1 C4 C3 106.29(9) . . ?
N1 C4 C5 120.59(9) . . ?
O2 C5 C4 117.25(9) . . ?
O4 C5 O2 125.92(10) . . ?
O4 C5 C4 116.82(9) . . ?
C4 N1 H1A 127.9(10) . . ?
N2 N1 C4 113.01(9) . . ?
N2 N1 H1A 119.0(10) . . ?
N1 N2 C2 104.48(8) . . ?
N5 C6 N4 120.67(11) . . ?
N3 C6 N5 120.85(11) . . ?
N3 C6 N4 118.48(11) . . ?
C6 N4 H4A 120.4(13) . . ?
C6 N4 H4B 118.4(12) . . ?
H4A N4 H4B 121.3(17) . . ?

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
O1S H1SA O3 0.859(15) 2.102(16) 2.9173(13) 158.3(18) 6_565
O1S H1SB O4 0.861(14) 2.004(15) 2.8651(15) 177.8(19) 7
O1 H1 O2 0.912(14) 1.639(15) 2.5393(11) 168.3(17) 1_565
N5 H5A O1S 0.886(14) 2.273(14) 3.1573(17) 176.7(15) 7_565
N5 H5B O2 0.868(14) 2.067(14) 2.9338(14) 177.5(16) 4
N3 H3A N2 0.856(14) 2.123(15) 2.9325(14) 157.8(17) 7_565
N3 H3B O4 0.871(14) 2.087(15) 2.9006(14) 155.2(17) 7
N1 H1A O1S 0.855(13) 2.111(14) 2.8893(14) 151.1(13) .
N4 H4A O3 0.830(14) 2.141(16) 2.8616(13) 145.1(17) 4_545
N4 H4B O4 0.860(14) 2.308(15) 3.0590(15) 146.0(15) 7

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 171.08(12) . . . . ?
O1 C1 C2 N2 -7.40(16) . . . . ?
O3 C1 C2 C3 -8.34(19) . . . . ?
O3 C1 C2 N2 173.18(11) . . . . ?
C1 C2 C3 C4 -178.21(11) . . . . ?
C1 C2 N2 N1 178.60(10) . . . . ?
C2 C3 C4 C5 176.79(12) . . . . ?
C2 C3 C4 N1 -0.51(12) . . . . ?
C3 C2 N2 N1 -0.11(13) . . . . ?
C3 C4 C5 O2 7.80(19) . . . . ?
C3 C4 C5 O4 -171.35(12) . . . . ?
C3 C4 N1 N2 0.48(13) . . . . ?
C4 N1 N2 C2 -0.23(13) . . . . ?
C5 C4 N1 N2 -177.22(10) . . . . ?
N1 C4 C5 O2 -175.22(10) . . . . ?
N1 C4 C5 O4 5.63(16) . . . . ?
N2 C2 C3 C4 0.39(14) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_rpg
_database_code_depnum_ccdc_archive 'CCDC 955244'
_audit_update_record             
;
2016-08-25 deposited with the CCDC.
2016-09-05 downloaded from the CCDC.
;
_audit_creation_date             2016-08-15
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2016.07.26 svn.r3321 for OlexSys, GUI svn.r3563)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C5 H2 N2 O4, 2(C H6 N3), H2 O, 1.58(O)'
_chemical_formula_sum            'C7 H19.16 N8 O6.59'
_chemical_formula_weight         320.83
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7868(14)
_cell_length_b                   10.0032(18)
_cell_length_c                   10.6058(19)
_cell_angle_alpha                72.744(6)
_cell_angle_beta                 70.282(6)
_cell_angle_gamma                75.842(6)
_cell_volume                     733.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1893
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      55.309
_cell_measurement_theta_min      5.270
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.9672
_exptl_absorpt_correction_T_min  0.9619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
SADABS, Bruker AXS, Madison, WI, USA
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3555
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.160
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker AXS Kappa Apex II with CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1949
_reflns_number_total             2522
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR92 (Altomare et al. 1993)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2522
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0655P)²+0.0833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1322
_refine_special_details          ', Lattice water disorder'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2. Restrained distances
 N6-H6A
 0.86 with sigma of 0.02
 N6-H6B
 0.86 with sigma of 0.02
 N7-H7A
 0.86 with sigma of 0.02
 N7-H7B
 0.86 with sigma of 0.02
 H1SB-O1S = O1S-H1SA
 0.85 with sigma of 0.02
 H6A-H6B
 1.36 with sigma of 0.04
 H7A-H7B
 1.36 with sigma of 0.04
 H1SB-H1SA
 1.349 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(O2AA) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
4. Others
 Fixed Sof: O1AA(0.75) O0AA(0.3333) O2AA(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3), N2(H2)
5.b X=CH2 refined with riding coordinates:
 N3(H3A,H3B), N4(H4A,H4B), N5(H5A,H5B), N7(H7A,H7B), N8(H8A,H8B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1742(2) 0.4631(2) 0.6286(2) 0.0383(5) Uani 1 1 d . . . . .
C2 C 0.2747(2) 0.32091(19) 0.67859(19) 0.0350(4) Uani 1 1 d . . . . .
C3 C 0.2200(2) 0.20584(19) 0.78135(19) 0.0367(4) Uani 1 1 d . . . . .
H3 H 0.1029 0.1986 0.8427 0.044 Uiso 1 1 calc R . . . .
C4 C 0.3764(3) 0.1020(2) 0.7746(2) 0.0373(4) Uani 1 1 d . . . . .
C5 C 0.3942(3) -0.0452(2) 0.8614(2) 0.0428(5) Uani 1 1 d . . . . .
C7 C -0.4649(3) 0.4214(2) 0.8562(2) 0.0400(5) Uani 1 1 d . . . . .
C8 C 0.8879(3) -0.1459(2) 0.4984(2) 0.0408(5) Uani 1 1 d . . . . .
N1 N 0.5220(2) 0.14953(17) 0.67357(18) 0.0446(4) Uani 1 1 d . . . . .
N2 N 0.4557(2) 0.28172(17) 0.61727(17) 0.0420(4) Uani 1 1 d . . . . .
H2 H 0.5215 0.3365 0.5489 0.050 Uiso 1 1 calc R . . . .
N3 N -0.3002(2) 0.34395(19) 0.84831(19) 0.0518(5) Uani 1 1 d . . . . .
H3A H -0.2861 0.2678 0.9108 0.062 Uiso 1 1 calc R . . . .
H3B H -0.2067 0.3694 0.7807 0.062 Uiso 1 1 calc R . . . .
N4 N -0.6069(2) 0.38260(19) 0.95900(18) 0.0502(5) Uani 1 1 d . . . . .
H4A H -0.5927 0.3065 1.0214 0.060 Uiso 1 1 calc R . . . .
H4B H -0.7145 0.4332 0.9642 0.060 Uiso 1 1 calc R . . . .
N5 N -0.4847(3) 0.5390(2) 0.76027(19) 0.0569(5) Uani 1 1 d . . . . .
H5A H -0.5917 0.5906 0.7652 0.068 Uiso 1 1 calc R . . . .
H5B H -0.3906 0.5638 0.6929 0.068 Uiso 1 1 calc R . . . .
N6 N 1.0402(3) -0.1969(2) 0.4138(2) 0.0472(4) Uani 1 1 d D . . . .
N7 N 0.8178(2) -0.2275(2) 0.6191(2) 0.0582(5) Uani 1 1 d D . . . .
H7A H 0.8715 -0.3133 0.6420 0.070 Uiso 1 1 calc DR . . . .
H7B H 0.7182 -0.1951 0.6751 0.070 Uiso 1 1 calc DR . . . .
N8 N 0.8038(3) -0.0147(2) 0.4608(2) 0.0573(5) Uani 1 1 d . . . . .
H8A H 0.8488 0.0374 0.3808 0.069 Uiso 1 1 calc R . . . .
H8B H 0.7042 0.0184 0.5163 0.069 Uiso 1 1 calc R . . . .
O1 O 0.00972(19) 0.49408(16) 0.69628(17) 0.0568(4) Uani 1 1 d . . . . .
O1S O 0.1173(3) 0.0490(2) 1.1741(2) 0.0781(6) Uani 1 1 d D . . . .
O2 O 0.2508(2) -0.08203(15) 0.95216(16) 0.0570(4) Uani 1 1 d . . . . .
O3 O 0.26023(18) 0.54170(16) 0.52167(16) 0.0554(4) Uani 1 1 d . . . . .
O4 O 0.5493(2) -0.12313(15) 0.84001(16) 0.0596(5) Uani 1 1 d . . . . .
H6A H 1.086(3) -0.138(2) 0.341(2) 0.062(8) Uiso 1 1 d D . . . .
H6B H 1.105(3) -0.2756(19) 0.439(2) 0.056(7) Uiso 1 1 d D . . . .
O1AA O -0.8306(8) 0.7414(5) 0.8091(8) 0.153(2) Uani 0.75 1 d . . . A 2
O0AA O -1.0000 0.5000 1.0000 0.156(3) Uani 0.6666 2 d S T P B 1
O2AA O -1.1081(13) 0.3508(11) 1.1406(11) 0.187(4) Uani 0.5 1 d . U . C 3
H1SA H 0.126(5) 0.034(5) 1.097(3) 0.147(17) Uiso 1 1 d D . . . .
H1SB H 0.217(4) 0.074(4) 1.170(4) 0.132(16) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.485(3) . ?
C1 O1 1.253(2) . ?
C1 O3 1.253(2) . ?
C2 C3 1.370(3) . ?
C2 N2 1.352(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(3) . ?
C4 C5 1.489(3) . ?
C4 N1 1.342(2) . ?
C5 O2 1.255(2) . ?
C5 O4 1.256(2) . ?
C7 N3 1.316(3) . ?
C7 N4 1.307(3) . ?
C7 N5 1.323(3) . ?
C8 N6 1.315(3) . ?
C8 N7 1.315(3) . ?
C8 N8 1.325(3) . ?
N1 N2 1.333(2) . ?
N2 H2 0.8600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N5 H5A 0.8600 . ?
N5 H5B 0.8600 . ?
N6 H6A 0.850(16) . ?
N6 H6B 0.849(16) . ?
N7 H7A 0.8600 . ?
N7 H7B 0.8600 . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
O1S H1SA 0.855(18) . ?
O1S H1SB 0.858(18) . ?

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 C1 C2 117.24(17) . . ?
O1 C1 O3 125.37(18) . . ?
O3 C1 C2 117.38(17) . . ?
C3 C2 C1 132.76(17) . . ?
N2 C2 C1 121.34(16) . . ?
N2 C2 C3 105.87(16) . . ?
C2 C3 H3 127.2 . . ?
C2 C3 C4 105.58(16) . . ?
C4 C3 H3 127.2 . . ?
C3 C4 C5 128.22(17) . . ?
N1 C4 C3 111.03(16) . . ?
N1 C4 C5 120.74(16) . . ?
O2 C5 C4 116.73(17) . . ?
O2 C5 O4 124.64(18) . . ?
O4 C5 C4 118.62(17) . . ?
N3 C7 N5 119.50(19) . . ?
N4 C7 N3 119.98(18) . . ?
N4 C7 N5 120.52(19) . . ?
N6 C8 N7 119.3(2) . . ?
N6 C8 N8 120.2(2) . . ?
N7 C8 N8 120.45(19) . . ?
N2 N1 C4 104.36(15) . . ?
C2 N2 H2 123.4 . . ?
N1 N2 C2 113.16(15) . . ?
N1 N2 H2 123.4 . . ?
C7 N3 H3A 120.0 . . ?
C7 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C7 N4 H4A 120.0 . . ?
C7 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
C7 N5 H5A 120.0 . . ?
C7 N5 H5B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C8 N6 H6A 115.6(17) . . ?
C8 N6 H6B 122.0(16) . . ?
H6A N6 H6B 120(2) . . ?
C8 N7 H7A 120.0 . . ?
C8 N7 H7B 120.0 . . ?
H7A N7 H7B 120.0 . . ?
C8 N8 H8A 120.0 . . ?
C8 N8 H8B 120.0 . . ?
H8A N8 H8B 120.0 . . ?
H1SA O1S H1SB 110(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
N2 H2 O3 0.86 2.13 2.890(2) 146.7 2_666
N3 H3A O2 0.86 2.01 2.874(2) 176.2 2_557
N3 H3B O1 0.86 2.13 2.897(2) 147.9 .
N4 H4A O4 0.86 2.02 2.877(2) 176.9 2_557
N4 H4B O0AA 0.86 2.09 2.9299(18) 163.8 .
N4 H4B O2AA 0.86 2.44 3.189(7) 145.6 2_367
N5 H5A O1AA 0.86 2.10 2.939(6) 164.6 .
N5 H5A O2AA 0.86 2.22 3.017(8) 155.1 2_367
N5 H5B O3 0.86 2.58 3.141(3) 123.6 2_566
O1S H1SA O2 0.855(18) 3.05(4) 3.461(3) 112(3) 2_557

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 177.91(19) . . . . ?
C1 C2 N2 N1 -178.48(17) . . . . ?
C2 C3 C4 C5 -178.91(19) . . . . ?
C2 C3 C4 N1 0.3(2) . . . . ?
C3 C2 N2 N1 -0.2(2) . . . . ?
C3 C4 C5 O2 0.3(3) . . . . ?
C3 C4 C5 O4 -179.3(2) . . . . ?
C3 C4 N1 N2 -0.4(2) . . . . ?
C4 N1 N2 C2 0.4(2) . . . . ?
C5 C4 N1 N2 178.85(18) . . . . ?
N1 C4 C5 O2 -178.84(18) . . . . ?
N1 C4 C5 O4 1.5(3) . . . . ?
N2 C2 C3 C4 -0.1(2) . . . . ?
O1 C1 C2 C3 6.5(3) . . . . ?
O1 C1 C2 N2 -175.79(18) . . . . ?
O3 C1 C2 C3 -172.9(2) . . . . ?
O3 C1 C2 N2 4.8(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_PAG
_database_code_depnum_ccdc_archive 'CCDC 1008628'
_audit_update_record             
;
2014-06-16 deposited with the CCDC.
2016-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H2 N2 O4, 2(C H7 N4), H2 O'
_chemical_formula_sum            'C7 H18 N10 O5'
_chemical_formula_weight         322.31

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      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                   3.9966(2)
_cell_length_b                   12.0312(6)
_cell_length_c                   15.5723(9)
_cell_angle_alpha                71.941(2)
_cell_angle_beta                 89.275(2)
_cell_angle_gamma                84.754(2)
_cell_volume                     708.81(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9924
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      30.46

_exptl_crystal_description       plate
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_F_000             340
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.303
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.470
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.695
_exptl_absorpt_correction_T_max  0.714
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
Bruker SAINT, Bruker AXS, wisconsin, USA 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II Photon CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29616
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0573
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.411
_diffrn_reflns_theta_max         30.552
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4324
_reflns_number_gt                3575
_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'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
Structure solved by direct methods to reveal ann non-H atoms which
were refined anisotropically. All H atoms located in subsequent 
difference maps and refined with DFIX constraints for E-H distances
and a riding model for their U(iso) parameters.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0693P)²+0.2559P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct methods'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4324
_refine_ls_number_parameters     258
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.988
_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
O1 O 0.8147(2) 0.42518(7) 0.13454(6) 0.02309(19) Uani 1 1 d . . . . .
N1 N 0.5446(3) 0.26987(8) 0.35524(6) 0.0184(2) Uani 1 1 d . . . . .
C1 C 0.6884(3) 0.41362(9) 0.21073(7) 0.0163(2) Uani 1 1 d . . . . .
O2 O 0.5858(3) 0.49700(7) 0.23974(6) 0.0246(2) Uani 1 1 d . . . . .
N2 N 0.5486(3) 0.15250(8) 0.38761(6) 0.0181(2) Uani 1 1 d D . . . .
H2 H 0.494(4) 0.1217(13) 0.4437(7) 0.022 Uiso 1 1 d D U . . .
C2 C 0.6568(3) 0.29095(9) 0.27039(7) 0.0153(2) Uani 1 1 d . . . . .
O3 O 0.7461(2) -0.07175(7) 0.28325(5) 0.02034(18) Uani 1 1 d . . . . .
C3 C 0.7311(3) 0.18631(9) 0.24926(7) 0.0167(2) Uani 1 1 d D . . . .
H3 H 0.819(4) 0.1763(14) 0.1914(11) 0.025(4) Uiso 1 1 d D . . . .
O4 O 0.5919(3) -0.09010(7) 0.42502(6) 0.02361(19) Uani 1 1 d . . . . .
C4 C 0.6565(3) 0.09866(9) 0.32642(7) 0.0154(2) Uani 1 1 d . . . . .
C5 C 0.6679(3) -0.03035(9) 0.34693(7) 0.0159(2) Uani 1 1 d . . . . .
N11 N -0.0855(3) 0.85018(9) 0.02815(7) 0.0255(2) Uani 1 1 d D . . . .
H11A H -0.172(4) 0.8720(15) -0.0253(8) 0.031 Uiso 1 1 d D U . . .
H11B H 0.005(4) 0.8964(13) 0.0517(11) 0.031 Uiso 1 1 d D U . . .
C11 C -0.0287(3) 0.73595(9) 0.07060(7) 0.0168(2) Uani 1 1 d . . . . .
N12 N 0.1277(3) 0.69976(9) 0.15128(7) 0.0229(2) Uani 1 1 d D . . . .
H12A H 0.214(4) 0.7545(12) 0.1669(11) 0.028 Uiso 1 1 d D U . . .
H12B H 0.220(4) 0.6278(10) 0.1694(11) 0.028 Uiso 1 1 d D U . . .
N13 N -0.1273(3) 0.65738(8) 0.03512(6) 0.0195(2) Uani 1 1 d D . . . .
H13 H -0.133(4) 0.5854(10) 0.0699(10) 0.023 Uiso 1 1 d D U . . .
N14 N -0.3034(3) 0.69958(9) -0.04871(7) 0.0221(2) Uani 1 1 d D . . . .
H14A H -0.180(4) 0.6684(14) -0.0862(10) 0.026 Uiso 1 1 d D U . . .
H14B H -0.498(4) 0.6656(14) -0.0414(11) 0.026 Uiso 1 1 d D U . . .
N21 N 0.3132(3) 0.53618(8) 0.39094(7) 0.0195(2) Uani 1 1 d D . . . .
H21A H 0.381(4) 0.5033(13) 0.3503(9) 0.023 Uiso 1 1 d D U . . .
H21B H 0.186(4) 0.5040(13) 0.4354(9) 0.023 Uiso 1 1 d D U . . .
C21 C 0.3932(3) 0.64430(9) 0.37792(7) 0.0149(2) Uani 1 1 d . . . . .
N22 N 0.5920(3) 0.69403(8) 0.30984(7) 0.0192(2) Uani 1 1 d D . . . .
H22A H 0.658(4) 0.7625(10) 0.3051(11) 0.023 Uiso 1 1 d D U . . .
H22B H 0.685(4) 0.6499(13) 0.2799(10) 0.023 Uiso 1 1 d D U . . .
N23 N 0.2773(2) 0.70745(8) 0.43034(7) 0.01801(19) Uani 1 1 d D . . . .
H23 H 0.349(4) 0.7756(10) 0.4250(11) 0.022 Uiso 1 1 d D U . . .
N24 N 0.0622(3) 0.65950(9) 0.50190(7) 0.01874(19) Uani 1 1 d . . . . .
H24A H -0.115(4) 0.7120(14) 0.4944(11) 0.022 Uiso 1 1 d . U . . .
H24B H 0.165(4) 0.6582(14) 0.5552(11) 0.022 Uiso 1 1 d . U . . .
O1W O 0.2185(2) 0.96217(8) 0.15073(6) 0.0255(2) Uani 1 1 d D . . . .
H1W H 0.069(4) 0.9582(15) 0.1921(11) 0.031 Uiso 1 1 d D U . . .
H2W H 0.398(4) 0.9651(16) 0.1798(11) 0.031 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2558(13) . ?
N1 N2 1.3427(12) . ?
N1 C2 1.3452(13) . ?
C1 O2 1.2569(13) . ?
C1 C2 1.4961(14) . ?
N2 C4 1.3546(13) . ?
N2 H2 0.869(10) . ?
C2 C3 1.4026(14) . ?
O3 C5 1.2646(13) . ?
C3 C4 1.3811(14) . ?
C3 H3 1.000(16) . ?
O4 C5 1.2555(13) . ?
C4 C5 1.4809(14) . ?
N11 C11 1.3270(14) . ?
N11 H11A 0.858(10) . ?
N11 H11B 0.861(10) . ?
C11 N13 1.3235(14) . ?
C11 N12 1.3377(15) . ?
N12 H12A 0.869(10) . ?
N12 H12B 0.871(10) . ?
N13 N14 1.4158(14) . ?
N13 H13 0.870(10) . ?
N14 H14A 0.905(13) . ?
N14 H14B 0.900(14) . ?
N21 C21 1.3215(14) . ?
N21 H21A 0.872(10) . ?
N21 H21B 0.864(10) . ?
C21 N23 1.3299(14) . ?
C21 N22 1.3362(14) . ?
N22 H22A 0.870(10) . ?
N22 H22B 0.865(10) . ?
N23 N24 1.4074(13) . ?
N23 H23 0.873(10) . ?
N24 H24A 0.887(18) . ?
N24 H24B 0.926(17) . ?
O1W H1W 0.867(14) . ?
O1W H2W 0.863(15) . ?

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
N2 N1 C2 104.56(8) . . ?
O1 C1 O2 124.89(10) . . ?
O1 C1 C2 116.91(9) . . ?
O2 C1 C2 118.19(9) . . ?
N1 N2 C4 112.74(9) . . ?
N1 N2 H2 117.9(10) . . ?
C4 N2 H2 129.3(10) . . ?
N1 C2 C3 111.35(9) . . ?
N1 C2 C1 121.02(9) . . ?
C3 C2 C1 127.63(9) . . ?
C4 C3 C2 104.77(9) . . ?
C4 C3 H3 127.0(9) . . ?
C2 C3 H3 128.2(9) . . ?
N2 C4 C3 106.58(9) . . ?
N2 C4 C5 121.64(9) . . ?
C3 C4 C5 131.75(10) . . ?
O4 C5 O3 124.86(10) . . ?
O4 C5 C4 118.03(9) . . ?
O3 C5 C4 117.08(9) . . ?
C11 N11 H11A 118.2(12) . . ?
C11 N11 H11B 116.6(12) . . ?
H11A N11 H11B 124.0(16) . . ?
N13 C11 N11 121.24(11) . . ?
N13 C11 N12 119.49(10) . . ?
N11 C11 N12 119.27(11) . . ?
C11 N12 H12A 114.9(11) . . ?
C11 N12 H12B 117.1(11) . . ?
H12A N12 H12B 120.6(16) . . ?
C11 N13 N14 117.61(9) . . ?
C11 N13 H13 118.5(11) . . ?
N14 N13 H13 121.6(11) . . ?
N13 N14 H14A 104.8(11) . . ?
N13 N14 H14B 107.2(11) . . ?
H14A N14 H14B 105.7(15) . . ?
C21 N21 H21A 116.5(11) . . ?
C21 N21 H21B 120.0(11) . . ?
H21A N21 H21B 123.3(15) . . ?
N21 C21 N23 121.86(10) . . ?
N21 C21 N22 120.18(10) . . ?
N23 C21 N22 117.95(10) . . ?
C21 N22 H22A 119.2(10) . . ?
C21 N22 H22B 117.3(11) . . ?
H22A N22 H22B 122.0(15) . . ?
C21 N23 N24 119.98(9) . . ?
C21 N23 H23 121.1(11) . . ?
N24 N23 H23 118.6(11) . . ?
N23 N24 H24A 105.4(10) . . ?
N23 N24 H24B 108.0(10) . . ?
H24A N24 H24B 105.3(14) . . ?
H1W O1W H2W 101.0(16) . . ?

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-3

