# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_exp_3692
_database_code_depnum_ccdc_archive 'CCDC 1443629'
_audit_update_record             
;
2015-12-21 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;
_audit_creation_date             2015-11-27
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C5 H2 N9 O6, C2 H7 N6'
_chemical_formula_sum            'C7 H9 N15 O6'
_chemical_formula_weight         399.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.0128(8)
_cell_length_b                   9.8962(10)
_cell_length_c                   10.5912(10)
_cell_angle_alpha                92.344(8)
_cell_angle_beta                 108.659(9)
_cell_angle_gamma                104.967(9)
_cell_volume                     761.67(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1642
_cell_measurement_temperature    104.1
_cell_measurement_theta_max      29.5785
_cell_measurement_theta_min      3.8664
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5065
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.87
_diffrn_ambient_temperature      104.1
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -7.00   83.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   77.0000    0.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega  -46.00   45.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -77.0000   90.0000 91

#__ type_ start__ end____ width___ exp.time_
  3 omega   18.00   45.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -77.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega  -41.00  -15.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   -8.00   86.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   77.0000 -150.0000 94
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0599934000
_diffrn_orient_matrix_UB_12      -0.0432176000
_diffrn_orient_matrix_UB_13      0.0093329000
_diffrn_orient_matrix_UB_21      -0.0545030000
_diffrn_orient_matrix_UB_22      -0.0466229000
_diffrn_orient_matrix_UB_23      0.0301929000
_diffrn_orient_matrix_UB_31      -0.0542339000
_diffrn_orient_matrix_UB_32      -0.0395537000
_diffrn_orient_matrix_UB_33      -0.0639948000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2459
_reflns_number_total             2990
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         2990
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0347P)²+0.1673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0945
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.10101(17) 0.37346(14) 0.17642(13) 0.0247(3) Uani 1 1 d . . .
O6 O -0.12641(18) 0.46598(14) 0.10511(14) 0.0286(3) Uani 1 1 d . . .
N8 N -0.0491(2) 0.37442(16) 0.09905(15) 0.0186(3) Uani 1 1 d . . .
N2 N -0.75249(19) -0.02057(15) -0.46846(14) 0.0164(3) Uani 1 1 d . . .
O2 O -0.24247(18) 0.33545(14) -0.36891(13) 0.0261(3) Uani 1 1 d . . .
O4 O -0.60696(17) -0.09711(14) -0.13869(13) 0.0252(3) Uani 1 1 d . . .
O1 O -0.43452(19) 0.30363(14) -0.57368(13) 0.0281(3) Uani 1 1 d . . .
N6 N -0.28823(19) 0.26664(15) -0.10870(14) 0.0158(3) Uani 1 1 d . . .
N3 N -0.3875(2) 0.27291(15) -0.45839(15) 0.0177(3) Uani 1 1 d . . .
N7 N -0.08975(19) 0.14102(15) -0.01140(14) 0.0161(3) Uani 1 1 d . . .
O3 O -0.84977(19) -0.20579(15) -0.30891(14) 0.0327(4) Uani 1 1 d . . .
C2 C -0.4837(2) 0.09807(18) -0.30631(17) 0.0143(4) Uani 1 1 d . . .
N9 N -0.2241(2) -0.06674(15) -0.17290(15) 0.0172(3) Uani 1 1 d . . .
H9A H -0.2716 -0.0906 -0.2576 0.021 Uiso 1 1 d R . .
H9B H -0.1265 -0.0931 -0.1345 0.021 Uiso 1 1 d R . .
N5 N -0.33342(19) 0.13746(14) -0.18560(14) 0.0139(3) Uani 1 1 d . . .
N1 N -0.66842(19) 0.08557(15) -0.52264(14) 0.0160(3) Uani 1 1 d . . .
C5 C -0.1455(2) 0.25786(18) -0.00993(17) 0.0152(4) Uani 1 1 d . . .
N4 N -0.7051(2) -0.11210(16) -0.25773(15) 0.0197(3) Uani 1 1 d . . .
C3 C -0.5095(2) 0.15522(17) -0.42677(17) 0.0145(4) Uani 1 1 d . . .
C4 C -0.2122(2) 0.06446(18) -0.12565(17) 0.0141(4) Uani 1 1 d . . .
C1 C -0.6450(2) -0.01235(18) -0.34052(17) 0.0150(4) Uani 1 1 d . . .
N12 N -0.66939(19) 0.35886(15) -0.23723(15) 0.0159(3) Uani 1 1 d . . .
N11 N -0.8710(2) 0.16369(16) -0.22486(15) 0.0199(3) Uani 1 1 d . . .
N10 N -0.9204(2) 0.20534(15) -0.35273(15) 0.0189(3) Uani 1 1 d . . .
H10 H -1.0199 0.1596 -0.4202 0.023 Uiso 1 1 calc R . .
N13 N -0.5148(2) 0.47656(15) -0.20964(15) 0.0214(4) Uani 1 1 d . . .
H13A H -0.4165 0.4460 -0.1874 0.026 Uiso 1 1 d R . .
H13B H -0.5110 0.5338 -0.1430 0.026 Uiso 1 1 d R . .
N15 N -0.6184(2) 0.27363(16) -0.02285(15) 0.0206(3) Uani 1 1 d . . .
H15A H -0.6685 0.2112 0.0172 0.025 Uiso 1 1 d R . .
H15B H -0.5042 0.2771 -0.0067 0.025 Uiso 1 1 d R . .
N14 N -0.7967(2) 0.39079(16) -0.46414(15) 0.0247(4) Uani 1 1 d . . .
H14A H -0.8861 0.3662 -0.5384 0.030 Uiso 1 1 d R . .
H14B H -0.7259 0.4754 -0.4517 0.030 Uiso 1 1 d R . .
C7 C -0.8003(2) 0.32136(18) -0.36043(18) 0.0175(4) Uani 1 1 d . . .
C6 C -0.7193(2) 0.26008(18) -0.15701(18) 0.0163(4) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 N8 1.2226(19) . ?
O6 N8 1.2324(19) . ?
N8 C5 1.456(2) . ?
N2 N1 1.348(2) . ?
N2 C1 1.339(2) . ?
O2 N3 1.2276(19) . ?
O4 N4 1.2328(19) . ?
O1 N3 1.2331(19) . ?
N6 N5 1.3842(19) . ?
N6 C5 1.305(2) . ?
N3 C3 1.442(2) . ?
N7 C5 1.344(2) . ?
N7 C4 1.335(2) . ?
O3 N4 1.2244(19) . ?
C2 N5 1.403(2) . ?
C2 C3 1.393(2) . ?
C2 C1 1.391(2) . ?
N9 H9A 0.8506 . ?
N9 H9B 0.8699 . ?
N9 C4 1.341(2) . ?
N5 C4 1.369(2) . ?
N1 C3 1.338(2) . ?
N4 C1 1.439(2) . ?
N12 N13 1.404(2) . ?
N12 C7 1.351(2) . ?
N12 C6 1.386(2) . ?
N11 N10 1.396(2) . ?
N11 C6 1.300(2) . ?
N10 H10 0.8800 . ?
N10 C7 1.318(2) . ?
N13 H13A 0.8819 . ?
N13 H13B 0.8743 . ?
N15 H15A 0.8518 . ?
N15 H15B 0.8667 . ?
N15 C6 1.373(2) . ?
N14 H14A 0.8517 . ?
N14 H14B 0.8588 . ?
N14 C7 1.323(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 N8 O6 125.58(15) . . ?
O5 N8 C5 117.50(15) . . ?
O6 N8 C5 116.91(15) . . ?
C1 N2 N1 107.74(14) . . ?
C5 N6 N5 100.03(13) . . ?
O2 N3 O1 124.19(15) . . ?
O2 N3 C3 117.79(15) . . ?
O1 N3 C3 118.01(14) . . ?
C4 N7 C5 101.63(14) . . ?
C3 C2 N5 129.66(16) . . ?
C1 C2 N5 129.63(16) . . ?
C1 C2 C3 100.67(15) . . ?
H9A N9 H9B 114.8 . . ?
C4 N9 H9A 117.0 . . ?
C4 N9 H9B 113.8 . . ?
N6 N5 C2 120.98(13) . . ?
C4 N5 N6 109.86(14) . . ?
C4 N5 C2 129.16(14) . . ?
C3 N1 N2 106.80(14) . . ?
N6 C5 N8 119.67(15) . . ?
N6 C5 N7 119.07(15) . . ?
N7 C5 N8 121.26(16) . . ?
O4 N4 C1 117.48(15) . . ?
O3 N4 O4 124.03(16) . . ?
O3 N4 C1 118.49(15) . . ?
C2 C3 N3 128.45(16) . . ?
N1 C3 N3 118.85(15) . . ?
N1 C3 C2 112.67(15) . . ?
N7 C4 N9 126.39(16) . . ?
N7 C4 N5 109.42(14) . . ?
N9 C4 N5 124.10(15) . . ?
N2 C1 C2 112.11(16) . . ?
N2 C1 N4 119.26(15) . . ?
C2 C1 N4 128.63(16) . . ?
C7 N12 N13 121.71(15) . . ?
C7 N12 C6 107.11(14) . . ?
C6 N12 N13 131.16(15) . . ?
C6 N11 N10 103.86(15) . . ?
N11 N10 H10 124.0 . . ?
C7 N10 N11 112.00(15) . . ?
C7 N10 H10 124.0 . . ?
N12 N13 H13A 107.7 . . ?
N12 N13 H13B 108.5 . . ?
H13A N13 H13B 110.6 . . ?
H15A N15 H15B 111.0 . . ?
C6 N15 H15A 112.4 . . ?
C6 N15 H15B 114.1 . . ?
H14A N14 H14B 116.1 . . ?
C7 N14 H14A 120.5 . . ?
C7 N14 H14B 120.2 . . ?
N10 C7 N12 106.02(16) . . ?
N10 C7 N14 129.93(17) . . ?
N14 C7 N12 124.03(16) . . ?
N11 C6 N12 111.00(16) . . ?
N11 C6 N15 127.75(17) . . ?
N15 C6 N12 121.19(16) . . ?

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
O5 N8 C5 N6 -167.38(15) . . . . ?
O5 N8 C5 N7 12.3(2) . . . . ?
O6 N8 C5 N6 12.5(2) . . . . ?
O6 N8 C5 N7 -167.82(15) . . . . ?
N2 N1 C3 N3 178.23(13) . . . . ?
N2 N1 C3 C2 -0.29(18) . . . . ?
O2 N3 C3 C2 -1.8(2) . . . . ?
O2 N3 C3 N1 179.91(14) . . . . ?
O4 N4 C1 N2 -176.51(14) . . . . ?
O4 N4 C1 C2 3.2(3) . . . . ?
O1 N3 C3 C2 177.59(16) . . . . ?
O1 N3 C3 N1 -0.7(2) . . . . ?
N6 N5 C4 N7 0.49(19) . . . . ?
N6 N5 C4 N9 177.09(15) . . . . ?
O3 N4 C1 N2 3.2(2) . . . . ?
O3 N4 C1 C2 -177.13(16) . . . . ?
C2 N5 C4 N7 -179.97(15) . . . . ?
C2 N5 C4 N9 -3.4(3) . . . . ?
N5 N6 C5 N8 179.99(14) . . . . ?
N5 N6 C5 N7 0.31(19) . . . . ?
N5 C2 C3 N3 -1.1(3) . . . . ?
N5 C2 C3 N1 177.29(15) . . . . ?
N5 C2 C1 N2 -176.70(15) . . . . ?
N5 C2 C1 N4 3.6(3) . . . . ?
N1 N2 C1 C2 -1.26(18) . . . . ?
N1 N2 C1 N4 178.46(13) . . . . ?
C5 N6 N5 C2 179.95(14) . . . . ?
C5 N6 N5 C4 -0.46(17) . . . . ?
C5 N7 C4 N9 -176.77(16) . . . . ?
C5 N7 C4 N5 -0.27(17) . . . . ?
C3 C2 N5 N6 66.5(2) . . . . ?
C3 C2 N5 C4 -113.0(2) . . . . ?
C3 C2 C1 N2 1.02(18) . . . . ?
C3 C2 C1 N4 -178.67(16) . . . . ?
C4 N7 C5 N8 -179.71(15) . . . . ?
C4 N7 C5 N6 0.0(2) . . . . ?
C1 N2 N1 C3 0.92(17) . . . . ?
C1 C2 N5 N6 -116.40(19) . . . . ?
C1 C2 N5 C4 64.1(2) . . . . ?
C1 C2 C3 N3 -178.77(15) . . . . ?
C1 C2 C3 N1 -0.43(17) . . . . ?
N11 N10 C7 N12 -0.26(18) . . . . ?
N11 N10 C7 N14 178.16(16) . . . . ?
N10 N11 C6 N12 -1.14(17) . . . . ?
N10 N11 C6 N15 175.98(16) . . . . ?
N13 N12 C7 N10 177.88(13) . . . . ?
N13 N12 C7 N14 -0.7(2) . . . . ?
N13 N12 C6 N11 -177.05(15) . . . . ?
N13 N12 C6 N15 5.6(3) . . . . ?
C7 N12 C6 N11 1.05(18) . . . . ?
C7 N12 C6 N15 -176.30(15) . . . . ?
C6 N12 C7 N10 -0.44(17) . . . . ?
C6 N12 C7 N14 -178.97(16) . . . . ?
C6 N11 N10 C7 0.88(18) . . . . ?

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

data_exp_3601
_database_code_depnum_ccdc_archive 'CCDC 1443630'
_audit_update_record             
;
2015-12-21 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;
_audit_creation_date             2015-11-11
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C5 H2 N9 O6, C H9 N6'
_chemical_formula_sum            'C6 H11 N15 O6'
_chemical_formula_weight         389.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.3978(6)
_cell_length_b                   10.4201(8)
_cell_length_c                   10.9154(7)
_cell_angle_alpha                112.439(7)
_cell_angle_beta                 95.970(6)
_cell_angle_gamma                99.090(6)
_cell_volume                     755.40(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1901
_cell_measurement_temperature    104.4
_cell_measurement_theta_max      29.4506
_cell_measurement_theta_min      3.1804
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96241
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5249
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.19
_diffrn_ambient_temperature      104.4
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -16.00   11.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -77.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -43.00    3.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -77.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   35.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -37.0000   30.0000 85

#__ type_ start__ end____ width___ exp.time_
  4 omega   -8.00   84.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772   77.0000  -60.0000 92

#__ type_ start__ end____ width___ exp.time_
  5 omega  -48.00   45.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       18.5772  -77.0000 -180.0000 93
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0769756000
_diffrn_orient_matrix_UB_12      0.0329027000
_diffrn_orient_matrix_UB_13      0.0128616000
_diffrn_orient_matrix_UB_21      -0.0581676000
_diffrn_orient_matrix_UB_22      -0.0591110000
_diffrn_orient_matrix_UB_23      -0.0546990000
_diffrn_orient_matrix_UB_31      -0.0208650000
_diffrn_orient_matrix_UB_32      -0.0333171000
_diffrn_orient_matrix_UB_33      0.0441686000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2397
_reflns_number_total             2962
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2962
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0447P)²+0.1380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.1001
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.45078(17) 0.24912(14) 0.02524(13) 0.0260(3) Uani 1 1 d . . .
N3 N 0.9185(2) 0.17059(16) -0.51727(14) 0.0188(3) Uani 1 1 d . . .
O2 O 0.65423(19) -0.08248(14) -0.43247(13) 0.0306(4) Uani 1 1 d . . .
O6 O 0.58163(18) 0.13841(14) 0.13160(12) 0.0257(3) Uani 1 1 d . . .
N4 N 1.0223(2) 0.29932(15) -0.43095(15) 0.0184(3) Uani 1 1 d . . .
O3 O 1.16509(18) 0.54415(13) -0.20727(13) 0.0282(3) Uani 1 1 d . . .
O4 O 1.1438(2) 0.42323(15) -0.08352(13) 0.0327(4) Uani 1 1 d . . .
N7 N 0.8381(2) 0.09092(15) -0.03033(14) 0.0177(3) Uani 1 1 d . . .
N6 N 0.6993(2) 0.20793(15) -0.13944(14) 0.0182(3) Uani 1 1 d . . .
N5 N 0.84991(19) 0.16414(15) -0.19444(14) 0.0162(3) Uani 1 1 d . . .
O1 O 0.69823(18) -0.09374(14) -0.62952(13) 0.0272(3) Uani 1 1 d . . .
N9 N 0.5686(2) 0.18458(16) 0.04351(14) 0.0202(3) Uani 1 1 d . . .
N2 N 1.1125(2) 0.43439(16) -0.19089(15) 0.0212(4) Uani 1 1 d . . .
N8 N 1.0778(2) 0.03813(16) -0.15960(15) 0.0213(4) Uani 1 1 d . . .
H8A H 1.1220 -0.0059 -0.1150 0.026 Uiso 1 1 calc R . .
H8B H 1.1286 0.0458 -0.2246 0.026 Uiso 1 1 calc R . .
N1 N 0.7248(2) -0.03197(16) -0.50643(15) 0.0205(3) Uani 1 1 d . . .
C5 C 0.9310(2) 0.09438(18) -0.12818(17) 0.0163(4) Uani 1 1 d . . .
C3 C 1.0112(2) 0.30959(18) -0.30621(17) 0.0162(4) Uani 1 1 d . . .
C2 C 0.8993(2) 0.19038(18) -0.30485(17) 0.0156(4) Uani 1 1 d . . .
C4 C 0.7046(2) 0.16006(18) -0.04510(17) 0.0162(4) Uani 1 1 d . . .
C1 C 0.8445(2) 0.10744(18) -0.44146(17) 0.0159(4) Uani 1 1 d . . .
N10 N 0.6809(2) 0.51971(16) -0.23160(15) 0.0200(3) Uani 1 1 d . . .
H10 H 0.7586 0.5888 -0.1675 0.024 Uiso 1 1 calc R . .
N13 N 0.6226(2) 0.33115(16) -0.58905(14) 0.0226(4) Uani 1 1 d . . .
H13A H 0.5139 0.3056 -0.6415 0.027 Uiso 1 1 d R . .
H13B H 0.6753 0.2573 -0.6153 0.027 Uiso 1 1 d R . .
N11 N 0.5361(2) 0.43381(16) -0.20430(15) 0.0213(4) Uani 1 1 d . . .
H11A H 0.4748 0.4903 -0.1525 0.026 Uiso 1 1 d R . .
H11B H 0.5863 0.3910 -0.1605 0.026 Uiso 1 1 d R . .
N12 N 0.5970(2) 0.36574(16) -0.45481(14) 0.0210(4) Uani 1 1 d . . .
H12 H 0.5216 0.3083 -0.4345 0.025 Uiso 1 1 calc R . .
N14 N 0.8022(2) 0.58015(16) -0.39260(15) 0.0220(4) Uani 1 1 d . . .
H14 H 0.8151 0.5616 -0.4746 0.026 Uiso 1 1 calc R . .
N15 N 0.8977(2) 0.70928(16) -0.28554(15) 0.0277(4) Uani 1 1 d . . .
H15A H 0.8942 0.7768 -0.3108 0.033 Uiso 1 1 d R . .
H15B H 1.0171 0.7028 -0.2751 0.033 Uiso 1 1 d R . .
C6 C 0.6921(2) 0.48934(18) -0.36046(17) 0.0172(4) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 N9 1.226(2) . ?
N3 N4 1.355(2) . ?
N3 C1 1.347(2) . ?
O2 N1 1.2356(18) . ?
O6 N9 1.2304(19) . ?
N4 C3 1.337(2) . ?
O3 N2 1.2334(19) . ?
O4 N2 1.2234(19) . ?
N7 C5 1.337(2) . ?
N7 C4 1.342(2) . ?
N6 N5 1.378(2) . ?
N6 C4 1.304(2) . ?
N5 C5 1.364(2) . ?
N5 C2 1.404(2) . ?
O1 N1 1.2260(19) . ?
N9 C4 1.452(2) . ?
N2 C3 1.444(2) . ?
N8 H8A 0.8600 . ?
N8 H8B 0.8600 . ?
N8 C5 1.329(2) . ?
N1 C1 1.440(2) . ?
C3 C2 1.385(2) . ?
C2 C1 1.384(2) . ?
N10 H10 0.8600 . ?
N10 N11 1.4157(19) . ?
N10 C6 1.334(2) . ?
N13 H13A 0.8754 . ?
N13 H13B 0.8810 . ?
N13 N12 1.410(2) . ?
N11 H11A 0.8694 . ?
N11 H11B 0.8628 . ?
N12 H12 0.8600 . ?
N12 C6 1.329(2) . ?
N14 H14 0.8600 . ?
N14 N15 1.415(2) . ?
N14 C6 1.323(2) . ?
N15 H15A 0.8510 . ?
N15 H15B 0.8958 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N3 N4 106.78(14) . . ?
C3 N4 N3 107.06(13) . . ?
C5 N7 C4 101.42(14) . . ?
C4 N6 N5 99.88(14) . . ?
N6 N5 C2 121.07(14) . . ?
C5 N5 N6 110.23(13) . . ?
C5 N5 C2 128.68(15) . . ?
O5 N9 O6 125.24(15) . . ?
O5 N9 C4 118.00(15) . . ?
O6 N9 C4 116.76(16) . . ?
O3 N2 C3 118.18(15) . . ?
O4 N2 O3 124.28(15) . . ?
O4 N2 C3 117.52(15) . . ?
H8A N8 H8B 120.0 . . ?
C5 N8 H8A 120.0 . . ?
C5 N8 H8B 120.0 . . ?
O2 N1 C1 116.79(14) . . ?
O1 N1 O2 123.71(15) . . ?
O1 N1 C1 119.50(14) . . ?
N7 C5 N5 109.28(15) . . ?
N8 C5 N7 126.60(16) . . ?
N8 C5 N5 124.11(15) . . ?
N4 C3 N2 120.27(15) . . ?
N4 C3 C2 112.73(15) . . ?
C2 C3 N2 126.99(16) . . ?
C3 C2 N5 129.20(16) . . ?
C1 C2 N5 129.80(15) . . ?
C1 C2 C3 100.96(14) . . ?
N7 C4 N9 121.17(15) . . ?
N6 C4 N7 119.18(15) . . ?
N6 C4 N9 119.63(16) . . ?
N3 C1 N1 119.42(15) . . ?
N3 C1 C2 112.46(15) . . ?
C2 C1 N1 128.12(15) . . ?
N11 N10 H10 121.3 . . ?
C6 N10 H10 121.3 . . ?
C6 N10 N11 117.46(14) . . ?
H13A N13 H13B 106.9 . . ?
N12 N13 H13A 109.2 . . ?
N12 N13 H13B 109.3 . . ?
N10 N11 H11A 107.4 . . ?
N10 N11 H11B 108.0 . . ?
H11A N11 H11B 108.4 . . ?
N13 N12 H12 120.8 . . ?
C6 N12 N13 118.33(14) . . ?
C6 N12 H12 120.8 . . ?
N15 N14 H14 121.6 . . ?
C6 N14 H14 121.6 . . ?
C6 N14 N15 116.81(15) . . ?
N14 N15 H15A 108.7 . . ?
N14 N15 H15B 105.6 . . ?
H15A N15 H15B 106.1 . . ?
N12 C6 N10 119.39(15) . . ?
N14 C6 N10 119.83(15) . . ?
N14 C6 N12 120.74(16) . . ?

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
O5 N9 C4 N7 179.59(15) . . . . ?
O5 N9 C4 N6 0.7(2) . . . . ?
N3 N4 C3 N2 178.20(15) . . . . ?
N3 N4 C3 C2 -0.7(2) . . . . ?
O2 N1 C1 N3 -176.97(16) . . . . ?
O2 N1 C1 C2 3.7(3) . . . . ?
O6 N9 C4 N7 -0.3(2) . . . . ?
O6 N9 C4 N6 -179.19(14) . . . . ?
N4 N3 C1 N1 179.49(15) . . . . ?
N4 N3 C1 C2 -1.1(2) . . . . ?
N4 C3 C2 N5 -177.77(17) . . . . ?
N4 C3 C2 C1 0.0(2) . . . . ?
O3 N2 C3 N4 19.8(3) . . . . ?
O3 N2 C3 C2 -161.49(17) . . . . ?
O4 N2 C3 N4 -158.78(16) . . . . ?
O4 N2 C3 C2 19.9(3) . . . . ?
N6 N5 C5 N7 -0.08(18) . . . . ?
N6 N5 C5 N8 179.07(15) . . . . ?
N6 N5 C2 C3 86.3(2) . . . . ?
N6 N5 C2 C1 -90.9(2) . . . . ?
N5 N6 C4 N7 0.09(19) . . . . ?
N5 N6 C4 N9 178.96(14) . . . . ?
N5 C2 C1 N3 178.44(17) . . . . ?
N5 C2 C1 N1 -2.2(3) . . . . ?
O1 N1 C1 N3 3.1(2) . . . . ?
O1 N1 C1 C2 -176.22(17) . . . . ?
N2 C3 C2 N5 3.4(3) . . . . ?
N2 C3 C2 C1 -178.76(17) . . . . ?
C5 N7 C4 N6 -0.1(2) . . . . ?
C5 N7 C4 N9 -178.99(14) . . . . ?
C5 N5 C2 C3 -95.1(2) . . . . ?
C5 N5 C2 C1 87.7(2) . . . . ?
C3 C2 C1 N3 0.7(2) . . . . ?
C3 C2 C1 N1 -179.99(17) . . . . ?
C2 N5 C5 N7 -178.84(15) . . . . ?
C2 N5 C5 N8 0.3(3) . . . . ?
C4 N7 C5 N5 0.12(18) . . . . ?
C4 N7 C5 N8 -179.01(17) . . . . ?
C4 N6 N5 C5 0.00(17) . . . . ?
C4 N6 N5 C2 178.86(14) . . . . ?
C1 N3 N4 C3 1.04(19) . . . . ?
N13 N12 C6 N10 -175.00(16) . . . . ?
N13 N12 C6 N14 2.8(3) . . . . ?
N11 N10 C6 N12 -14.2(2) . . . . ?
N11 N10 C6 N14 168.00(16) . . . . ?
N15 N14 C6 N10 -2.4(2) . . . . ?
N15 N14 C6 N12 179.83(16) . . . . ?

####################################################################### 
# 
# 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_bwn16042
_database_code_depnum_ccdc_archive 'CCDC 1477983'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;
_audit_creation_date             2016-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C5 H3 N9 O6, C H4 O'
_chemical_formula_sum            'C6 H7 N9 O7'
_chemical_formula_weight         317.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.2011(16)
_cell_length_b                   11.917(2)
_cell_length_c                   14.159(3)
_cell_angle_alpha                89.83(3)
_cell_angle_beta                 76.32(3)
_cell_angle_gamma                87.38(3)
_cell_volume                     1343.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4178
_cell_measurement_temperature    293.1500
_cell_measurement_theta_max      27.4237
_cell_measurement_theta_min      1.4803
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7220
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0610
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9844
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.48
_diffrn_ambient_temperature      293.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 45.1736
	          2theta: -20.0043
scan:
	Number of images: 286
	           Slice: -76.0000 - 67.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 45.1736
	          2theta: -20.0043
scan:
	Number of images: 150
	           Slice: -110.0000 - -35.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.1736
	          2theta: -20.0043
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             5969
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0174
_diffrn_orient_matrix_UB_12      -0.0226
_diffrn_orient_matrix_UB_13      -0.1224
_diffrn_orient_matrix_UB_21      0.0004
_diffrn_orient_matrix_UB_22      0.0832
_diffrn_orient_matrix_UB_23      -0.0114
_diffrn_orient_matrix_UB_31      0.0723
_diffrn_orient_matrix_UB_32      0.0012
_diffrn_orient_matrix_UB_33      0.0071
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           90.0000
_diffrn_source_power             4.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3976
_reflns_number_total             4665
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.730
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         4665
_refine_ls_number_restraints     528
_refine_ls_R_factor_all          0.1639
_refine_ls_R_factor_gt           0.1492
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1730P)²+7.6340P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3894
_refine_ls_wR_factor_ref         0.4018
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H) groups, All N(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.02
3.a Riding coordinates:
 N5(H5A,H5B), N8(H8), N14(H14A,H14B), N16(H16), O13(H13), O14(H14)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.5402(8) 0.4615(6) 0.0955(4) 0.0669(17) Uani 1 d . . . U
O2 O 0.4462(7) 0.4746(6) 0.2523(5) 0.0687(18) Uani 1 d . . . U
O3 O 0.9784(12) 0.2462(7) 0.3039(7) 0.101(3) Uani 1 d . . . U
O4 O 1.0795(16) 0.2110(9) 0.4274(9) 0.144(4) Uani 1 d . . . U
O5 O 1.0067(13) 0.7145(7) 0.2759(7) 0.102(3) Uani 1 d . . . U
O6 O 1.1902(12) 0.7485(7) 0.3581(7) 0.105(3) Uani 1 d . . . U
N1 N 0.5596(8) 0.4701(6) 0.1779(5) 0.0489(15) Uani 1 d . . . U
N2 N 0.8600(7) 0.4860(5) 0.1095(4) 0.0423(14) Uani 1 d . . . U
N3 N 0.7649(8) 0.4711(5) 0.2734(4) 0.0424(14) Uani 1 d . . . U
N4 N 0.9400(8) 0.4770(5) 0.2472(4) 0.0420(13) Uani 1 d . . . U
N5 N 1.1520(8) 0.4978(6) 0.1017(4) 0.0542(17) Uani 1 d . . . U
H5A H 1.1786 0.5066 0.0397 0.065 Uiso 1 d . . R .
H5B H 1.2285 0.4967 0.1340 0.065 Uiso 1 d . . R .
N6 N 1.0453(12) 0.2743(8) 0.3676(7) 0.078(2) Uani 1 d . . . U
N7 N 1.1703(9) 0.4223(6) 0.4334(5) 0.0544(16) Uani 1 d . . . U
N8 N 1.1864(8) 0.5312(6) 0.4197(4) 0.0494(15) Uani 1 d . . . U
H8 H 1.2409 0.5733 0.4494 0.059 Uiso 1 d . . R .
N9 N 1.1022(11) 0.6848(7) 0.3264(6) 0.071(2) Uani 1 d . . . U
C1 C 0.7333(9) 0.4761(6) 0.1872(5) 0.0383(14) Uani 1 d . . . U
C2 C 0.9920(9) 0.4865(6) 0.1480(5) 0.0400(15) Uani 1 d . . . U
C3 C 1.0822(10) 0.3904(7) 0.3721(5) 0.0511(17) Uani 1 d . . . U
C4 C 1.0331(9) 0.4800(7) 0.3185(5) 0.0440(16) Uani 1 d . . . U
C5 C 1.1046(9) 0.5692(7) 0.3522(5) 0.0451(16) Uani 1 d . . . U
O7 O 0.0333(7) 0.0268(6) 0.5971(4) 0.0637(17) Uani 1 d . . . U
O8 O -0.0558(7) 0.0190(6) 0.7536(4) 0.0650(17) Uani 1 d . . . U
O9 O 0.5311(14) -0.2116(7) 0.7762(7) 0.111(3) Uani 1 d . . . U
O10 O 0.6878(13) -0.2466(7) 0.8755(8) 0.111(3) Uani 1 d . . . U
O11 O 0.4423(11) 0.2584(6) 0.8033(6) 0.093(2) Uani 1 d . . . U
O12 O 0.5892(15) 0.3013(8) 0.9038(9) 0.135(4) Uani 1 d . . . U
N10 N 0.0570(7) 0.0226(5) 0.6784(5) 0.0449(14) Uani 1 d . . . U
N11 N 0.3577(7) 0.0129(5) 0.6104(4) 0.0386(13) Uani 1 d . . . U
N12 N 0.2642(7) 0.0269(5) 0.7737(4) 0.0373(13) Uani 1 d . . . U
N13 N 0.4343(7) 0.0231(5) 0.7479(4) 0.0356(12) Uani 1 d . . . U
N14 N 0.6503(7) 0.0067(6) 0.6007(4) 0.0519(17) Uani 1 d . . . U
H14A H 0.6764 0.0009 0.5383 0.062 Uiso 1 d . . R .
H14B H 0.7280 0.0082 0.6321 0.062 Uiso 1 d . . R .
N15 N 0.6096(11) -0.1822(7) 0.8346(6) 0.071(2) Uani 1 d . . . U
N16 N 0.6845(7) -0.0255(6) 0.9219(4) 0.0442(14) Uani 1 d . . . U
H16 H 0.7407 -0.0667 0.9542 0.053 Uiso 1 d . . R .
N17 N 0.6651(8) 0.0853(6) 0.9310(4) 0.0463(14) Uani 1 d . . . U
N18 N 0.5322(11) 0.2328(7) 0.8583(6) 0.0688(19) Uani 1 d . . . U
C6 C 0.2267(8) 0.0205(6) 0.6879(5) 0.0346(14) Uani 1 d . . . U
C7 C 0.4921(8) 0.0137(6) 0.6478(5) 0.0338(14) Uani 1 d . . . U
C8 C 0.6052(9) -0.0652(6) 0.8564(5) 0.0422(15) Uani 1 d . . . U
C9 C 0.5306(8) 0.0237(6) 0.8188(5) 0.0390(14) Uani 1 d . . . U
C10 C 0.5725(9) 0.1164(7) 0.8687(5) 0.0451(16) Uani 1 d . . . U
O13 O 0.6391(11) 0.3768(7) 0.4688(5) 0.093(2) Uani 1 d . . . U
H13 H 0.6749 0.4037 0.4133 0.111 Uiso 1 d . . R .
C11 C 0.5387(19) 0.2855(12) 0.4826(11) 0.114(4) Uani 1 d . . . U
H11A H 0.4840 0.2805 0.4299 0.171 Uiso 1 calc . . GR .
H11B H 0.4556 0.2944 0.5428 0.171 Uiso 1 calc . . GR .
H11C H 0.6066 0.2182 0.4846 0.171 Uiso 1 calc . . GR .
O14 O 0.8700(10) 0.8792(7) 0.0301(5) 0.090(2) Uani 1 d . . . U
H14 H 0.8317 0.9061 0.0862 0.108 Uiso 1 d . . R .
C12 C 0.9814(17) 0.7879(12) 0.0101(11) 0.106(4) Uani 1 d . . . U
H12A H 1.0099 0.7731 -0.0586 0.159 Uiso 1 calc . . GR .
H12B H 0.9309 0.7235 0.0439 0.159 Uiso 1 calc . . GR .
H12C H 1.0813 0.8033 0.0311 0.159 Uiso 1 calc . . GR .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.218(8) . ?
O2 N1 1.229(8) . ?
O3 N6 1.216(11) . ?
O4 N6 1.206(12) . ?
O5 N9 1.220(10) . ?
O6 N9 1.227(11) . ?
N1 C1 1.466(9) . ?
N2 C1 1.332(9) . ?
N2 C2 1.323(9) . ?
N3 N4 1.400(8) . ?
N3 C1 1.307(9) . ?
N4 C2 1.375(8) . ?
N4 C4 1.403(9) . ?
N5 H5A 0.8601 . ?
N5 H5B 0.8600 . ?
N5 C2 1.333(9) . ?
N6 C3 1.434(12) . ?
N7 N8 1.320(10) . ?
N7 C3 1.320(10) . ?
N8 H8 0.8601 . ?
N8 C5 1.357(9) . ?
N9 C5 1.424(11) . ?
C3 C4 1.406(11) . ?
C4 C5 1.377(11) . ?
O7 N10 1.213(8) . ?
O8 N10 1.236(8) . ?
O9 N15 1.223(10) . ?
O10 N15 1.210(11) . ?
O11 N18 1.222(10) . ?
O12 N18 1.217(11) . ?
N10 C6 1.429(8) . ?
N11 C6 1.342(8) . ?
N11 C7 1.332(8) . ?
N12 N13 1.354(7) . ?
N12 C6 1.324(8) . ?
N13 C7 1.386(8) . ?
N13 C9 1.418(8) . ?
N14 H14A 0.8602 . ?
N14 H14B 0.8597 . ?
N14 C7 1.310(8) . ?
N15 C8 1.426(11) . ?
N16 H16 0.8598 . ?
N16 N17 1.326(9) . ?
N16 C8 1.350(9) . ?
N17 C10 1.335(9) . ?
N18 C10 1.427(11) . ?
C8 C9 1.369(10) . ?
C9 C10 1.410(10) . ?
O13 H13 0.8400 . ?
O13 C11 1.380(15) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
O14 H14 0.8400 . ?
O14 C12 1.374(14) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 O2 125.3(7) . . ?
O1 N1 C1 116.4(6) . . ?
O2 N1 C1 118.3(6) . . ?
C2 N2 C1 102.6(6) . . ?
C1 N3 N4 99.6(5) . . ?
N3 N4 C4 120.8(5) . . ?
C2 N4 N3 109.3(5) . . ?
C2 N4 C4 129.8(6) . . ?
H5A N5 H5B 120.0 . . ?
C2 N5 H5A 120.2 . . ?
C2 N5 H5B 119.8 . . ?
O3 N6 C3 117.4(8) . . ?
O4 N6 O3 123.9(11) . . ?
O4 N6 C3 118.6(10) . . ?
N8 N7 C3 105.4(6) . . ?
N7 N8 H8 125.1 . . ?
N7 N8 C5 111.1(6) . . ?
C5 N8 H8 123.8 . . ?
O5 N9 O6 124.1(9) . . ?
O5 N9 C5 116.8(8) . . ?
O6 N9 C5 119.1(8) . . ?
N2 C1 N1 121.3(6) . . ?
N3 C1 N1 119.5(6) . . ?
N3 C1 N2 119.2(6) . . ?
N2 C2 N4 109.3(6) . . ?
N2 C2 N5 127.4(6) . . ?
N5 C2 N4 123.2(6) . . ?
N7 C3 N6 119.3(7) . . ?
N7 C3 C4 113.0(8) . . ?
C4 C3 N6 127.6(7) . . ?
N4 C4 C3 128.5(7) . . ?
C5 C4 N4 129.7(7) . . ?
C5 C4 C3 101.7(6) . . ?
N8 C5 N9 121.2(7) . . ?
N8 C5 C4 108.7(7) . . ?
C4 C5 N9 130.1(7) . . ?
O7 N10 O8 124.3(6) . . ?
O7 N10 C6 117.8(6) . . ?
O8 N10 C6 117.8(6) . . ?
C7 N11 C6 104.4(6) . . ?
C6 N12 N13 101.6(5) . . ?
N12 N13 C7 110.9(5) . . ?
N12 N13 C9 121.3(5) . . ?
C7 N13 C9 127.8(5) . . ?
H14A N14 H14B 120.0 . . ?
C7 N14 H14A 120.0 . . ?
C7 N14 H14B 120.0 . . ?
O9 N15 C8 117.5(8) . . ?
O10 N15 O9 123.8(9) . . ?
O10 N15 C8 118.6(8) . . ?
N17 N16 H16 123.7 . . ?
N17 N16 C8 111.8(6) . . ?
C8 N16 H16 124.5 . . ?
N16 N17 C10 104.9(6) . . ?
O11 N18 C10 117.8(8) . . ?
O12 N18 O11 123.4(10) . . ?
O12 N18 C10 118.8(9) . . ?
N11 C6 N10 122.0(6) . . ?
N12 C6 N10 122.0(6) . . ?
N12 C6 N11 116.0(6) . . ?
N11 C7 N13 107.1(5) . . ?
N14 C7 N11 127.4(6) . . ?
N14 C7 N13 125.4(6) . . ?
N16 C8 N15 121.6(7) . . ?
N16 C8 C9 108.5(7) . . ?
C9 C8 N15 129.9(7) . . ?
C8 C9 N13 128.7(7) . . ?
C8 C9 C10 102.7(6) . . ?
C10 C9 N13 128.6(7) . . ?
N17 C10 N18 119.3(7) . . ?
N17 C10 C9 112.1(7) . . ?
C9 C10 N18 128.6(7) . . ?
C11 O13 H13 121.2 . . ?
O13 C11 H11A 109.5 . . ?
O13 C11 H11B 109.5 . . ?
O13 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 O14 H14 123.8 . . ?
O14 C12 H12A 109.5 . . ?
O14 C12 H12B 109.5 . . ?
O14 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 N2 8.3(10) . . . . ?
O1 N1 C1 N3 -171.5(7) . . . . ?
O2 N1 C1 N2 -171.4(7) . . . . ?
O2 N1 C1 N3 8.9(10) . . . . ?
O3 N6 C3 N7 -173.0(9) . . . . ?
O3 N6 C3 C4 8.1(15) . . . . ?
O4 N6 C3 N7 8.2(15) . . . . ?
O4 N6 C3 C4 -170.8(11) . . . . ?
O5 N9 C5 N8 -169.9(9) . . . . ?
O5 N9 C5 C4 10.2(14) . . . . ?
O6 N9 C5 N8 7.8(13) . . . . ?
O6 N9 C5 C4 -172.1(9) . . . . ?
N3 N4 C2 N2 -0.5(8) . . . . ?
N3 N4 C2 N5 177.6(7) . . . . ?
N3 N4 C4 C3 79.1(10) . . . . ?
N3 N4 C4 C5 -103.1(9) . . . . ?
N4 N3 C1 N1 178.7(6) . . . . ?
N4 N3 C1 N2 -1.1(8) . . . . ?
N4 C4 C5 N8 -178.4(7) . . . . ?
N4 C4 C5 N9 1.5(14) . . . . ?
N6 C3 C4 N4 -1.3(14) . . . . ?
N6 C3 C4 C5 -179.6(8) . . . . ?
N7 N8 C5 N9 179.0(7) . . . . ?
N7 N8 C5 C4 -1.1(8) . . . . ?
N7 C3 C4 N4 179.7(7) . . . . ?
N7 C3 C4 C5 1.4(9) . . . . ?
N8 N7 C3 N6 178.8(7) . . . . ?
N8 N7 C3 C4 -2.1(9) . . . . ?
C1 N2 C2 N4 -0.1(8) . . . . ?
C1 N2 C2 N5 -178.1(8) . . . . ?
C1 N3 N4 C2 0.9(7) . . . . ?
C1 N3 N4 C4 176.9(7) . . . . ?
C2 N2 C1 N1 -179.0(6) . . . . ?
C2 N2 C1 N3 0.8(9) . . . . ?
C2 N4 C4 C3 -105.8(10) . . . . ?
C2 N4 C4 C5 72.0(11) . . . . ?
C3 N7 N8 C5 1.9(8) . . . . ?
C3 C4 C5 N8 -0.2(8) . . . . ?
C3 C4 C5 N9 179.7(8) . . . . ?
C4 N4 C2 N2 -176.1(7) . . . . ?
C4 N4 C2 N5 2.0(12) . . . . ?
O7 N10 C6 N11 -6.1(10) . . . . ?
O7 N10 C6 N12 173.3(7) . . . . ?
O8 N10 C6 N11 173.3(7) . . . . ?
O8 N10 C6 N12 -7.3(10) . . . . ?
O9 N15 C8 N16 178.3(9) . . . . ?
O9 N15 C8 C9 -3.0(15) . . . . ?
O10 N15 C8 N16 -0.6(13) . . . . ?
O10 N15 C8 C9 178.1(9) . . . . ?
O11 N18 C10 N17 -177.5(8) . . . . ?
O11 N18 C10 C9 4.2(14) . . . . ?
O12 N18 C10 N17 3.0(14) . . . . ?
O12 N18 C10 C9 -175.3(10) . . . . ?
N12 N13 C7 N11 0.8(8) . . . . ?
N12 N13 C7 N14 -179.1(7) . . . . ?
N12 N13 C9 C8 97.4(9) . . . . ?
N12 N13 C9 C10 -82.1(9) . . . . ?
N13 N12 C6 N10 -179.4(6) . . . . ?
N13 N12 C6 N11 0.0(8) . . . . ?
N13 C9 C10 N17 179.8(6) . . . . ?
N13 C9 C10 N18 -1.8(13) . . . . ?
N15 C8 C9 N13 1.0(13) . . . . ?
N15 C8 C9 C10 -179.4(8) . . . . ?
N16 N17 C10 N18 -178.2(7) . . . . ?
N16 N17 C10 C9 0.3(8) . . . . ?
N16 C8 C9 N13 179.8(6) . . . . ?
N16 C8 C9 C10 -0.6(8) . . . . ?
N17 N16 C8 N15 179.8(7) . . . . ?
N17 N16 C8 C9 0.8(8) . . . . ?
C6 N11 C7 N13 -0.7(7) . . . . ?
C6 N11 C7 N14 179.2(7) . . . . ?
C6 N12 N13 C7 -0.5(7) . . . . ?
C6 N12 N13 C9 -177.8(6) . . . . ?
C7 N11 C6 N10 179.8(6) . . . . ?
C7 N11 C6 N12 0.4(8) . . . . ?
C7 N13 C9 C8 -79.4(10) . . . . ?
C7 N13 C9 C10 101.1(9) . . . . ?
C8 N16 N17 C10 -0.7(8) . . . . ?
C8 C9 C10 N17 0.1(8) . . . . ?
C8 C9 C10 N18 178.5(8) . . . . ?
C9 N13 C7 N11 177.8(6) . . . . ?
C9 N13 C7 N14 -2.0(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_bwn16149
_database_code_depnum_ccdc_archive 'CCDC 1485362'
_audit_update_record             
;
2016-06-14 deposited with the CCDC.
2016-10-12 downloaded from the CCDC.
;
_audit_creation_date             2016-05-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 H8 Cu N18 O14, 2(C H4 O)'
_chemical_formula_sum            'C12 H16 Cu N18 O16'
_chemical_formula_weight         731.97
_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'
Cu Cu 0.3201 1.2651 '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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.6352(15)
_cell_length_b                   9.2541(19)
_cell_length_c                   9.994(2)
_cell_angle_alpha                103.05(3)
_cell_angle_beta                 100.98(3)
_cell_angle_gamma                101.31(3)
_cell_volume                     653.9(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2255
_cell_measurement_temperature    153.1500
_cell_measurement_theta_max      27.4507
_cell_measurement_theta_min      2.3333
_exptl_absorpt_coefficient_mu    0.948
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7866
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             371
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8886
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.81
_diffrn_ambient_temperature      153.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 44.8658
	          2theta: -20.1843
scan:
	Number of images: 356
	           Slice: -110.0000 - 68.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 44.8658
	          2theta: -20.1843
scan:
	Number of images: 338
	           Slice: -110.0000 - 59.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.8658
	          2theta: -20.1843
scan:
	Number of images: 150
	           Slice: -72.0000 - 3.0000
	     Image width: 0.5000
	        Exp time: 1.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.8658
	          2theta: -20.1843
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             2963
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0398
_diffrn_orient_matrix_UB_12      -0.0770
_diffrn_orient_matrix_UB_13      -0.1071
_diffrn_orient_matrix_UB_21      0.1018
_diffrn_orient_matrix_UB_22      0.0432
_diffrn_orient_matrix_UB_23      -0.0300
_diffrn_orient_matrix_UB_31      0.0724
_diffrn_orient_matrix_UB_32      -0.0658
_diffrn_orient_matrix_UB_33      0.0407
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           90.0000
_diffrn_source_power             4.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2868
_reflns_number_total             2961
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.116
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2961
_refine_ls_number_restraints     62
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.198
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0550P)²+0.6940P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1178
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C6A-O8A = C6-O8
 1.43 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O8A \\sim O8 \\sim C6 \\sim C6A: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.01
Uanis(O8A) \\sim Ueq, Uanis(O8) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C6A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.01
4. Others
 Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(H6AC)=Sof(O8A)=Sof(H8A)=1-FVAR(1)
 Sof(C6)=Sof(H6A)=Sof(H6B)=Sof(H6C)=Sof(O8)=Sof(H8)=FVAR(1)
5.a Riding coordinates:
 O1(H1A,H1B), N7(H7A,H7B), O8(H8), O8A(H8A)
5.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C6A(H6AA,H6AB,H6AC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cu1 Cu 0.5000 0.5000 1.0000 0.01555(14) Uani 1 d . . 2 S T P
O1 O 0.7188(3) 0.5634(2) 0.9251(2) 0.0237(4) Uani 1 d . . 1 . . .
H1A H 0.7665 0.4967 0.8851 0.028 Uiso 1 d . . 1 R . .
H1B H 0.7293 0.6431 0.8973 0.028 Uiso 1 d . . 1 R . .
O2 O 0.3032(3) 0.4040(2) 0.7568(2) 0.0230(4) Uani 1 d . . 1 . . .
O3 O 0.1207(3) 0.4909(2) 0.61674(19) 0.0251(4) Uani 1 d . . 1 . . .
O4 O 0.3774(3) 1.0836(2) 1.1631(2) 0.0285(4) Uani 1 d . . 1 . . .
O5 O 0.1734(3) 1.0748(2) 0.9756(2) 0.0298(4) Uani 1 d . . 1 . . .
O6 O -0.4884(3) 0.6252(2) 0.6156(2) 0.0294(4) Uani 1 d . . 1 . . .
O7 O -0.4716(3) 0.7739(3) 0.4758(2) 0.0367(5) Uani 1 d . . 1 . . .
N1 N 0.3953(3) 0.6674(2) 0.9589(2) 0.0152(4) Uani 1 d . . 1 . . .
N2 N 0.4141(3) 0.8065(2) 1.0461(2) 0.0163(4) Uani 1 d . . 1 . . .
N3 N 0.2799(3) 1.0189(2) 1.0436(2) 0.0213(5) Uani 1 d . . 1 . . .
N4 N 0.2259(3) 0.5040(2) 0.7296(2) 0.0170(4) Uani 1 d . . 1 . . .
N5 N 0.0551(3) 0.7929(2) 0.7416(2) 0.0175(4) Uani 1 d . . 1 . . .
N6 N -0.1249(3) 0.7136(2) 0.7198(2) 0.0177(4) Uani 1 d . . 1 . . .
N7 N 0.2247(3) 0.9802(3) 0.6526(3) 0.0269(5) Uani 1 d . . 1 . . .
H7A H 0.3236 0.9991 0.7219 0.032 Uiso 1 d . . 1 R . .
H7B H 0.2172 1.0359 0.5921 0.032 Uiso 1 d . . 1 R . .
N8 N -0.1006(3) 0.8717(2) 0.5751(2) 0.0179(4) Uani 1 d . . 1 . . .
N9 N -0.4032(3) 0.7168(3) 0.5654(2) 0.0214(4) Uani 1 d . . 1 . . .
C1 C 0.2669(3) 0.6455(3) 0.8381(2) 0.0149(4) Uani 1 d . . 1 . . .
C2 C 0.1946(3) 0.7721(3) 0.8435(3) 0.0155(5) Uani 1 d . . 1 . . .
C3 C 0.2930(3) 0.8671(3) 0.9761(3) 0.0169(5) Uani 1 d . . 1 . . .
C4 C 0.0671(3) 0.8885(3) 0.6545(3) 0.0178(5) Uani 1 d . . 1 . . .
C5 C -0.2048(3) 0.7668(3) 0.6192(3) 0.0158(4) Uani 1 d . . 1 . . .
C6 C 0.133(4) 0.761(2) 0.264(2) 0.038(3) Uani 0.533(6) d A 1 1 D U .
H6A H 0.2027 0.8484 0.2407 0.056 Uiso 0.533(6) calc A 1 1 GR . .
H6B H 0.2136 0.7337 0.3385 0.056 Uiso 0.533(6) calc A 1 1 GR . .
H6C H 0.0288 0.7883 0.2989 0.056 Uiso 0.533(6) calc A 1 1 GR . .
O8 O 0.0653(5) 0.6316(5) 0.1396(4) 0.0326(11) Uani 0.533(6) d A 1 1 D U .
H8 H 0.0133 0.6579 0.0728 0.049 Uiso 0.533(6) d A 1 1 R . .
C6A C 0.122(4) 0.7723(19) 0.258(2) 0.026(2) Uani 0.467(6) d A 2 1 D U .
H6AA H 0.0401 0.7656 0.1668 0.040 Uiso 0.467(6) calc A 2 1 GR . .
H6AB H 0.2326 0.8553 0.2774 0.040 Uiso 0.467(6) calc A 2 1 GR . .
H6AC H 0.0572 0.7933 0.3332 0.040 Uiso 0.467(6) calc A 2 1 GR . .
O8A O 0.1733(6) 0.6273(5) 0.2513(5) 0.0296(11) Uani 0.467(6) d A 2 1 D U .
H8A H 0.2191 0.6246 0.3316 0.044 Uiso 0.467(6) d A 2 1 R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9964(19) . ?
Cu1 O1 1.9965(19) 2_667 ?
Cu1 N1 1.964(2) . ?
Cu1 N1 1.964(2) 2_667 ?
O1 H1A 0.8399 . ?
O1 H1B 0.8399 . ?
O2 N4 1.243(3) . ?
O3 N4 1.219(3) . ?
O4 N3 1.226(3) . ?
O5 N3 1.226(3) . ?
O6 N9 1.222(3) . ?
O7 N9 1.224(3) . ?
N1 N2 1.345(3) . ?
N1 C1 1.349(3) . ?
N2 C3 1.339(3) . ?
N3 C3 1.446(3) . ?
N4 C1 1.434(3) . ?
N5 N6 1.376(3) . ?
N5 C2 1.401(3) . ?
N5 C4 1.377(3) . ?
N6 C5 1.316(3) . ?
N7 H7A 0.8800 . ?
N7 H7B 0.8799 . ?
N7 C4 1.335(3) . ?
N8 C4 1.331(3) . ?
N8 C5 1.339(3) . ?
N9 C5 1.449(3) . ?
C1 C2 1.385(3) . ?
C2 C3 1.389(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C6 O8 1.447(16) . ?
O8 H8 0.8203 . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A H6AC 0.9800 . ?
C6A O8A 1.463(16) . ?
O8A H8A 0.8202 . ?

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 Cu1 O1 180.00(11) . 2_667 ?
N1 Cu1 O1 87.04(8) . 2_667 ?
N1 Cu1 O1 87.04(8) 2_667 . ?
N1 Cu1 O1 92.96(8) . . ?
N1 Cu1 O1 92.96(8) 2_667 2_667 ?
N1 Cu1 N1 180.00(10) . 2_667 ?
Cu1 O1 H1A 119.8 . . ?
Cu1 O1 H1B 117.9 . . ?
H1A O1 H1B 115.6 . . ?
N2 N1 Cu1 128.31(16) . . ?
N2 N1 C1 109.79(19) . . ?
C1 N1 Cu1 121.25(16) . . ?
C3 N2 N1 104.9(2) . . ?
O4 N3 O5 124.6(2) . . ?
O4 N3 C3 118.1(2) . . ?
O5 N3 C3 117.2(2) . . ?
O2 N4 C1 117.3(2) . . ?
O3 N4 O2 124.6(2) . . ?
O3 N4 C1 118.1(2) . . ?
N6 N5 C2 120.32(19) . . ?
N6 N5 C4 110.33(19) . . ?
C4 N5 C2 129.3(2) . . ?
C5 N6 N5 99.89(19) . . ?
H7A N7 H7B 121.8 . . ?
C4 N7 H7A 120.1 . . ?
C4 N7 H7B 116.5 . . ?
C4 N8 C5 102.4(2) . . ?
O6 N9 O7 125.5(2) . . ?
O6 N9 C5 117.7(2) . . ?
O7 N9 C5 116.7(2) . . ?
N1 C1 N4 119.0(2) . . ?
N1 C1 C2 110.2(2) . . ?
C2 C1 N4 130.8(2) . . ?
C1 C2 N5 128.0(2) . . ?
C1 C2 C3 101.4(2) . . ?
C3 C2 N5 130.5(2) . . ?
N2 C3 N3 118.2(2) . . ?
N2 C3 C2 113.7(2) . . ?
C2 C3 N3 128.1(2) . . ?
N7 C4 N5 123.8(2) . . ?
N8 C4 N5 108.8(2) . . ?
N8 C4 N7 127.4(2) . . ?
N6 C5 N8 118.6(2) . . ?
N6 C5 N9 119.2(2) . . ?
N8 C5 N9 122.1(2) . . ?
C6 O8 H8 110.0 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
O8A C6A H6AA 109.5 . . ?
O8A C6A H6AB 109.5 . . ?
O8A C6A H6AC 109.5 . . ?
C6A O8A H8A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N1 N2 C3 -169.98(16) . . . . ?
Cu1 N1 C1 N4 -8.9(3) . . . . ?
Cu1 N1 C1 C2 170.78(15) . . . . ?
O1 Cu1 N1 N2 85.5(2) 2_667 . . . ?
O1 Cu1 N1 N2 -94.5(2) . . . . ?
O1 Cu1 N1 C1 95.77(19) . . . . ?
O1 Cu1 N1 C1 -84.23(19) 2_667 . . . ?
O2 N4 C1 N1 4.6(3) . . . . ?
O2 N4 C1 C2 -174.9(2) . . . . ?
O3 N4 C1 N1 -174.2(2) . . . . ?
O3 N4 C1 C2 6.2(4) . . . . ?
O4 N3 C3 N2 -1.7(3) . . . . ?
O4 N3 C3 C2 178.8(2) . . . . ?
O5 N3 C3 N2 177.3(2) . . . . ?
O5 N3 C3 C2 -2.2(4) . . . . ?
O6 N9 C5 N6 -0.6(3) . . . . ?
O6 N9 C5 N8 -177.1(2) . . . . ?
O7 N9 C5 N6 177.4(2) . . . . ?
O7 N9 C5 N8 0.8(4) . . . . ?
N1 Cu1 N1 N2 77(8) 2_667 . . . ?
N1 Cu1 N1 C1 -93(8) 2_667 . . . ?
N1 N2 C3 N3 179.9(2) . . . . ?
N1 N2 C3 C2 -0.5(3) . . . . ?
N1 C1 C2 N5 -178.0(2) . . . . ?
N1 C1 C2 C3 0.3(3) . . . . ?
N2 N1 C1 N4 179.65(19) . . . . ?
N2 N1 C1 C2 -0.7(3) . . . . ?
N4 C1 C2 N5 1.7(4) . . . . ?
N4 C1 C2 C3 180.0(2) . . . . ?
N5 N6 C5 N8 -1.0(3) . . . . ?
N5 N6 C5 N9 -177.7(2) . . . . ?
N5 C2 C3 N2 178.4(2) . . . . ?
N5 C2 C3 N3 -2.1(4) . . . . ?
N6 N5 C2 C1 71.4(3) . . . . ?
N6 N5 C2 C3 -106.4(3) . . . . ?
N6 N5 C4 N7 179.8(2) . . . . ?
N6 N5 C4 N8 -0.8(3) . . . . ?
C1 N1 N2 C3 0.7(2) . . . . ?
C1 C2 C3 N2 0.1(3) . . . . ?
C1 C2 C3 N3 179.6(2) . . . . ?
C2 N5 N6 C5 179.9(2) . . . . ?
C2 N5 C4 N7 1.0(4) . . . . ?
C2 N5 C4 N8 -179.5(2) . . . . ?
C4 N5 N6 C5 1.1(3) . . . . ?
C4 N5 C2 C1 -110.0(3) . . . . ?
C4 N5 C2 C3 72.2(4) . . . . ?
C4 N8 C5 N6 0.6(3) . . . . ?
C4 N8 C5 N9 177.2(2) . . . . ?
C5 N8 C4 N5 0.2(3) . . . . ?
C5 N8 C4 N7 179.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
