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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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#  fide research purposes only. It may contain copyright material 
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data_k1161
_database_code_depnum_ccdc_archive 'CCDC 859327'
#TrackingRef 'k1161.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H18 N8 O2, H2 O'
_chemical_formula_sum            'C13 H20 N8 O3'
_chemical_formula_weight         336.37

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3159(3)
_cell_length_b                   9.6944(3)
_cell_length_c                   10.0824(4)
_cell_angle_alpha                78.237(1)
_cell_angle_beta                 85.529(1)
_cell_angle_gamma                84.457(1)
_cell_volume                     790.61(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    4304
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      26.04

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6947
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            6348
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         26.04
_reflns_number_total             3095
_reflns_number_gt                2645
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0507P)²+0.1861P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3095
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0954
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.33209(12) 0.78442(9) 0.52651(10) 0.0327(2) Uani 1 1 d . . .
O2 O -0.05241(11) 0.09587(9) 0.22441(10) 0.0321(2) Uani 1 1 d . . .
N1 N 0.02946(14) 0.46247(11) 0.17269(11) 0.0294(3) Uani 1 1 d . . .
N2 N 0.09811(14) 0.52847(11) 0.24915(11) 0.0295(3) Uani 1 1 d . . .
N3 N 0.13583(12) 0.43168(10) 0.36428(10) 0.0229(2) Uani 1 1 d . . .
N4 N -0.09741(14) 0.27495(13) 0.04494(12) 0.0315(3) Uani 1 1 d . . .
H1N H -0.0763(19) 0.3620(18) 0.0057(17) 0.038(4) Uiso 1 1 d . . .
H2N H -0.1212(19) 0.2183(18) -0.0084(17) 0.040(4) Uiso 1 1 d . . .
N5 N 0.27525(12) 0.37459(10) 0.55974(10) 0.0241(2) Uani 1 1 d . . .
N6 N 0.23168(13) 0.61489(10) 0.44496(11) 0.0263(2) Uani 1 1 d . . .
N7 N 0.37963(12) 0.55875(10) 0.64587(11) 0.0250(2) Uani 1 1 d . . .
N8 N 0.41471(13) 0.32506(11) 0.75488(11) 0.0276(3) Uani 1 1 d . . .
C1 C 0.08790(14) 0.30127(12) 0.35888(13) 0.0233(3) Uani 1 1 d . . .
C2 C 0.02088(14) 0.32379(12) 0.23571(12) 0.0239(3) Uani 1 1 d . . .
C3 C -0.04640(14) 0.22111(13) 0.16776(13) 0.0250(3) Uani 1 1 d . . .
C4 C 0.10193(18) 0.17160(13) 0.46650(14) 0.0343(3) Uani 1 1 d . . .
H4A H 0.0610 0.1944 0.5540 0.051 Uiso 1 1 calc R . .
H4B H 0.2157 0.1348 0.4718 0.051 Uiso 1 1 calc R . .
H4C H 0.0383 0.1000 0.4448 0.051 Uiso 1 1 calc R . .
C5 C 0.22013(14) 0.47670(12) 0.46369(12) 0.0223(3) Uani 1 1 d . . .
C6 C 0.31589(15) 0.64613(12) 0.54242(13) 0.0249(3) Uani 1 1 d . . .
C7 C 0.35541(14) 0.42069(12) 0.65310(12) 0.0234(3) Uani 1 1 d . . .
C8 C 0.41900(18) 0.82768(14) 0.62763(15) 0.0352(3) Uani 1 1 d . . .
H8A H 0.4243 0.9304 0.6054 0.053 Uiso 1 1 calc R . .
H8B H 0.5289 0.7810 0.6291 0.053 Uiso 1 1 calc R . .
H8C H 0.3627 0.8010 0.7170 0.053 Uiso 1 1 calc R . .
C9 C 0.49556(17) 0.36323(14) 0.86467(14) 0.0307(3) Uani 1 1 d . . .
H9A H 0.5090 0.4659 0.8441 0.037 Uiso 1 1 calc R . .
H9B H 0.6043 0.3118 0.8728 0.037 Uiso 1 1 calc R . .
C10 C 0.39512(18) 0.32546(14) 0.99733(14) 0.0348(3) Uani 1 1 d . . .
H10A H 0.2911 0.3847 0.9922 0.042 Uiso 1 1 calc R . .
H10B H 0.4534 0.3454 1.0724 0.042 Uiso 1 1 calc R . .
C11 C 0.36234(18) 0.16987(15) 1.02650(14) 0.0352(3) Uani 1 1 d . . .
H11A H 0.4652 0.1107 1.0442 0.042 Uiso 1 1 calc R . .
H11B H 0.2886 0.1497 1.1088 0.042 Uiso 1 1 calc R . .
C12 C 0.28639(17) 0.13219(14) 0.90741(15) 0.0332(3) Uani 1 1 d . . .
H12A H 0.2756 0.0291 0.9251 0.040 Uiso 1 1 calc R . .
H12B H 0.1767 0.1814 0.8978 0.040 Uiso 1 1 calc R . .
C13 C 0.38885(17) 0.17423(12) 0.77659(13) 0.0290(3) Uani 1 1 d . . .
H13A H 0.4944 0.1173 0.7819 0.035 Uiso 1 1 calc R . .
H13B H 0.3335 0.1556 0.6994 0.035 Uiso 1 1 calc R . .
O1W O 0.16310(13) -0.14153(11) 0.18185(11) 0.0365(2) Uani 1 1 d . . .
H1W H 0.094(2) -0.073(2) 0.201(2) 0.064(6) Uiso 1 1 d . . .
H2W H 0.162(3) -0.209(2) 0.251(3) 0.074(7) 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
O1 C6 1.3360(14) . ?
O1 C8 1.4441(17) . ?
O2 C3 1.2358(15) . ?
N1 N2 1.2923(15) . ?
N1 C2 1.3709(16) . ?
N2 N3 1.3719(14) . ?
N3 C1 1.3744(15) . ?
N3 C5 1.4260(16) . ?
N4 C3 1.3271(17) . ?
N5 C5 1.3110(16) . ?
N5 C7 1.3627(16) . ?
N6 C5 1.3261(15) . ?
N6 C6 1.3480(17) . ?
N7 C6 1.3136(17) . ?
N7 C7 1.3591(15) . ?
N8 C7 1.3260(16) . ?
N8 C9 1.4648(16) . ?
N8 C13 1.4680(15) . ?
C1 C2 1.3691(18) . ?
C1 C4 1.4854(17) . ?
C2 C3 1.4895(17) . ?
C9 C10 1.519(2) . ?
C10 C11 1.5238(19) . ?
C11 C12 1.5217(19) . ?
C12 C13 1.518(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
C6 O1 C8 116.53(10) . . ?
N2 N1 C2 109.59(10) . . ?
N1 N2 N3 106.91(10) . . ?
N2 N3 C1 110.81(10) . . ?
N2 N3 C5 118.15(9) . . ?
C1 N3 C5 130.99(10) . . ?
C5 N5 C7 113.52(10) . . ?
C5 N6 C6 110.79(10) . . ?
C6 N7 C7 114.51(11) . . ?
C7 N8 C9 122.59(10) . . ?
C7 N8 C13 123.26(10) . . ?
C9 N8 C13 113.77(10) . . ?
C2 C1 N3 103.27(10) . . ?
C2 C1 C4 130.05(11) . . ?
N3 C1 C4 126.63(11) . . ?
C1 C2 N1 109.42(11) . . ?
C1 C2 C3 129.34(11) . . ?
N1 C2 C3 121.18(11) . . ?
O2 C3 N4 124.10(12) . . ?
O2 C3 C2 120.96(12) . . ?
N4 C3 C2 114.94(11) . . ?
N5 C5 N6 129.76(12) . . ?
N5 C5 N3 114.82(10) . . ?
N6 C5 N3 115.42(10) . . ?
N7 C6 O1 119.23(11) . . ?
N7 C6 N6 127.99(11) . . ?
O1 C6 N6 112.78(11) . . ?
N8 C7 N7 118.63(11) . . ?
N8 C7 N5 117.95(11) . . ?
N7 C7 N5 123.41(11) . . ?
N8 C9 C10 109.60(11) . . ?
C9 C10 C11 110.86(11) . . ?
C12 C11 C10 110.98(11) . . ?
C13 C12 C11 110.94(11) . . ?
N8 C13 C12 109.63(11) . . ?

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
N4 H1N N1 0.884(17) 2.248(18) 3.0693(16) 154.5(14) 2_565
N4 H2N O1W 0.888(18) 2.100(18) 2.9559(16) 161.7(15) 2
O1W H1W O2 0.88(2) 1.98(2) 2.8598(14) 173.5(19) .
O1W H2W N6 0.85(2) 2.39(3) 3.2187(15) 165(2) 1_545

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.036