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#                                CCDC 
# 
#######################################################################
# 
#  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. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
#  on your local computer system.
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#  data retrieval see:
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#
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data_k1116
_database_code_depnum_ccdc_archive 'CCDC 859326'
#TrackingRef 'k1116.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H15 N5 O'
_chemical_formula_sum            'C9 H15 N5 O'
_chemical_formula_weight         209.26

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                   8.3170(3)
_cell_length_b                   10.4123(4)
_cell_length_c                   13.3186(5)
_cell_angle_alpha                107.141(2)
_cell_angle_beta                 99.074(2)
_cell_angle_gamma                91.9490(19)
_cell_volume                     1084.39(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    12902
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.090
# Absorption correction

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;


_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            12902
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         27.52
_reflns_number_total             4909
_reflns_number_gt                3340
_reflns_threshold_expression     I>2σ(I)


_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        Denzo-SMN
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL V6.1'

_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)+(0.0823P)²+0.1005P] 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         4909
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1545
_refine_ls_wR_factor_gt          0.1333
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.20872(15) 0.75305(11) 0.00414(10) 0.0352(3) Uani 1 1 d . . .
N1A N 0.31552(16) 0.57631(13) 0.04231(10) 0.0268(3) Uani 1 1 d . . .
N2A N 0.18729(15) 0.46944(13) 0.14968(10) 0.0250(3) Uani 1 1 d . . .
N3A N 0.06746(16) 0.65217(13) 0.09911(10) 0.0269(3) Uani 1 1 d . . .
N4A N 0.41686(18) 0.39285(14) 0.08421(12) 0.0295(3) Uani 1 1 d . . .
N5A N -0.05672(16) 0.54351(14) 0.19838(11) 0.0293(3) Uani 1 1 d . . .
C1A C 0.19418(19) 0.65659(15) 0.05124(12) 0.0253(4) Uani 1 1 d . . .
C2A C 0.30407(19) 0.48127(15) 0.09208(12) 0.0238(3) Uani 1 1 d . . .
C3A C 0.06906(19) 0.55371(15) 0.14732(12) 0.0251(4) Uani 1 1 d . . .
C4A C 0.0804(3) 0.84273(19) 0.00556(16) 0.0434(5) Uani 1 1 d . . .
H4AA H 0.1024 0.9051 -0.0342 0.065 Uiso 1 1 calc R . .
H4AB H 0.0759 0.8941 0.0795 0.065 Uiso 1 1 calc R . .
H4AC H -0.0245 0.7900 -0.0277 0.065 Uiso 1 1 calc R . .
C5A C -0.0800(2) 0.43407(17) 0.24408(14) 0.0325(4) Uani 1 1 d . . .
H5AA H 0.0156 0.3798 0.2397 0.039 Uiso 1 1 calc R . .
H5AB H -0.1782 0.3742 0.2027 0.039 Uiso 1 1 calc R . .
C6A C -0.1003(2) 0.49121(19) 0.36044(14) 0.0418(5) Uani 1 1 d . . .
H6AA H -0.1245 0.4163 0.3889 0.050 Uiso 1 1 calc R . .
H6AB H 0.0027 0.5423 0.4034 0.050 Uiso 1 1 calc R . .
C7A C -0.2383(3) 0.5836(2) 0.36965(16) 0.0473(5) Uani 1 1 d . . .
H7AA H -0.3435 0.5299 0.3345 0.057 Uiso 1 1 calc R . .
H7AB H -0.2439 0.6258 0.4459 0.057 Uiso 1 1 calc R . .
C8A C -0.2123(2) 0.69283(18) 0.31799(14) 0.0378(4) Uani 1 1 d . . .
H8AA H -0.1149 0.7538 0.3591 0.045 Uiso 1 1 calc R . .
H8AB H -0.3080 0.7469 0.3198 0.045 Uiso 1 1 calc R . .
C9A C -0.1889(2) 0.63265(18) 0.20302(14) 0.0336(4) Uani 1 1 d . . .
H9AA H -0.2914 0.5811 0.1595 0.040 Uiso 1 1 calc R . .
H9AB H -0.1625 0.7059 0.1733 0.040 Uiso 1 1 calc R . .
O1B O 0.45243(17) 0.93581(12) 0.85965(9) 0.0414(3) Uani 1 1 d . . .
N1B N 0.55018(17) 0.75911(13) 0.75445(11) 0.0293(3) Uani 1 1 d . . .
N2B N 0.46432(16) 0.69638(13) 0.56504(10) 0.0252(3) Uani 1 1 d . . .
N3B N 0.36695(16) 0.89087(13) 0.67922(10) 0.0271(3) Uani 1 1 d . . .
N4B N 0.64217(18) 0.57521(14) 0.64275(13) 0.0299(3) Uani 1 1 d . . .
N5B N 0.31027(16) 0.84128(13) 0.49577(10) 0.0257(3) Uani 1 1 d . . .
C1B C 0.4545(2) 0.85994(15) 0.75934(13) 0.0292(4) Uani 1 1 d . . .
C2B C 0.54919(19) 0.67949(15) 0.65396(13) 0.0254(4) Uani 1 1 d . . .
C3B C 0.38106(18) 0.80740(15) 0.58164(12) 0.0231(3) Uani 1 1 d . . .
C4B C 0.3614(3) 1.05280(18) 0.87483(15) 0.0466(5) Uani 1 1 d . . .
H4BA H 0.3684 1.0979 0.9514 0.070 Uiso 1 1 calc R . .
H4BB H 0.2467 1.0253 0.8417 0.070 Uiso 1 1 calc R . .
H4BC H 0.4068 1.1150 0.8418 0.070 Uiso 1 1 calc R . .
C5B C 0.3216(2) 0.76068(15) 0.38673(12) 0.0271(4) Uani 1 1 d . . .
H5BA H 0.2172 0.7051 0.3529 0.033 Uiso 1 1 calc R . .
H5BB H 0.4093 0.6991 0.3890 0.033 Uiso 1 1 calc R . .
C6B C 0.3580(2) 0.85129(16) 0.32047(13) 0.0279(4) Uani 1 1 d . . .
H6BA H 0.3556 0.7954 0.2458 0.033 Uiso 1 1 calc R . .
H6BB H 0.4690 0.8976 0.3487 0.033 Uiso 1 1 calc R . .
C7B C 0.2340(2) 0.95604(17) 0.32276(13) 0.0313(4) Uani 1 1 d . . .
H7BA H 0.1241 0.9104 0.2886 0.038 Uiso 1 1 calc R . .
H7BB H 0.2636 1.0166 0.2823 0.038 Uiso 1 1 calc R . .
C8B C 0.2315(2) 1.03830(16) 0.43796(13) 0.0298(4) Uani 1 1 d . . .
H8BA H 0.3383 1.0909 0.4696 0.036 Uiso 1 1 calc R . .
H8BB H 0.1462 1.1026 0.4394 0.036 Uiso 1 1 calc R . .
C9B C 0.19690(19) 0.94660(15) 0.50366(13) 0.0269(4) Uani 1 1 d . . .
H9BA H 0.2061 1.0012 0.5793 0.032 Uiso 1 1 calc R . .
H9BB H 0.0836 0.9042 0.4784 0.032 Uiso 1 1 calc R . .
H1N H 0.497(2) 0.3989(17) 0.0501(14) 0.032(5) Uiso 1 1 d . . .
H2N H 0.414(2) 0.3329(18) 0.1219(15) 0.035(5) Uiso 1 1 d . . .
H3N H 0.631(2) 0.511(2) 0.5799(17) 0.045(6) Uiso 1 1 d . . .
H4N H 0.694(2) 0.5610(18) 0.7028(17) 0.042(5) 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
O1A C1A 1.3431(18) . ?
O1A C4A 1.441(2) . ?
N1A C1A 1.330(2) . ?
N1A C2A 1.352(2) . ?
N2A C3A 1.3428(19) . ?
N2A C2A 1.3526(19) . ?
N3A C1A 1.3211(19) . ?
N3A C3A 1.360(2) . ?
N4A C2A 1.331(2) . ?
N4A H1N 0.876(19) . ?
N4A H2N 0.911(19) . ?
N5A C3A 1.352(2) . ?
N5A C9A 1.460(2) . ?
N5A C5A 1.462(2) . ?
C4A H4AA 0.9800 . ?
C4A H4AB 0.9800 . ?
C4A H4AC 0.9800 . ?
C5A C6A 1.527(2) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C6A C7A 1.519(3) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C7A C8A 1.519(3) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C8A C9A 1.521(2) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
O1B C1B 1.3399(19) . ?
O1B C4B 1.437(2) . ?
N1B C1B 1.331(2) . ?
N1B C2B 1.349(2) . ?
N2B C2B 1.341(2) . ?
N2B C3B 1.3478(19) . ?
N3B C1B 1.321(2) . ?
N3B C3B 1.3591(19) . ?
N4B C2B 1.341(2) . ?
N4B H3N 0.89(2) . ?
N4B H4N 0.90(2) . ?
N5B C3B 1.349(2) . ?
N5B C9B 1.4616(18) . ?
N5B C5B 1.4671(19) . ?
C4B H4BA 0.9800 . ?
C4B H4BB 0.9800 . ?
C4B H4BC 0.9800 . ?
C5B C6B 1.522(2) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C6B C7B 1.523(2) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C7B C8B 1.525(2) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C8B C9B 1.521(2) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A O1A C4A 117.40(12) . . ?
C1A N1A C2A 113.09(12) . . ?
C3A N2A C2A 114.82(13) . . ?
C1A N3A C3A 113.36(13) . . ?
C2A N4A H1N 120.5(11) . . ?
C2A N4A H2N 117.3(11) . . ?
H1N N4A H2N 121.8(16) . . ?
C3A N5A C9A 122.72(13) . . ?
C3A N5A C5A 122.60(13) . . ?
C9A N5A C5A 114.40(12) . . ?
N3A C1A N1A 128.57(14) . . ?
N3A C1A O1A 118.66(14) . . ?
N1A C1A O1A 112.77(13) . . ?
N4A C2A N1A 117.49(13) . . ?
N4A C2A N2A 117.45(13) . . ?
N1A C2A N2A 125.07(14) . . ?
N2A C3A N5A 118.47(13) . . ?
N2A C3A N3A 124.84(13) . . ?
N5A C3A N3A 116.67(14) . . ?
O1A C4A H4AA 109.5 . . ?
O1A C4A H4AB 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
O1A C4A H4AC 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
N5A C5A C6A 110.26(14) . . ?
N5A C5A H5AA 109.6 . . ?
C6A C5A H5AA 109.6 . . ?
N5A C5A H5AB 109.6 . . ?
C6A C5A H5AB 109.6 . . ?
H5AA C5A H5AB 108.1 . . ?
C7A C6A C5A 110.40(16) . . ?
C7A C6A H6AA 109.6 . . ?
C5A C6A H6AA 109.6 . . ?
C7A C6A H6AB 109.6 . . ?
C5A C6A H6AB 109.6 . . ?
H6AA C6A H6AB 108.1 . . ?
C8A C7A C6A 110.94(14) . . ?
C8A C7A H7AA 109.5 . . ?
C6A C7A H7AA 109.5 . . ?
C8A C7A H7AB 109.5 . . ?
C6A C7A H7AB 109.5 . . ?
H7AA C7A H7AB 108.0 . . ?
C7A C8A C9A 111.32(15) . . ?
C7A C8A H8AA 109.4 . . ?
C9A C8A H8AA 109.4 . . ?
C7A C8A H8AB 109.4 . . ?
C9A C8A H8AB 109.4 . . ?
H8AA C8A H8AB 108.0 . . ?
N5A C9A C8A 109.94(14) . . ?
N5A C9A H9AA 109.7 . . ?
C8A C9A H9AA 109.7 . . ?
N5A C9A H9AB 109.7 . . ?
C8A C9A H9AB 109.7 . . ?
H9AA C9A H9AB 108.2 . . ?
C1B O1B C4B 117.87(14) . . ?
C1B N1B C2B 113.31(14) . . ?
C2B N2B C3B 114.49(13) . . ?
C1B N3B C3B 113.60(13) . . ?
C2B N4B H3N 119.7(13) . . ?
C2B N4B H4N 117.4(12) . . ?
H3N N4B H4N 120.9(17) . . ?
C3B N5B C9B 122.31(13) . . ?
C3B N5B C5B 121.78(13) . . ?
C9B N5B C5B 115.22(12) . . ?
N3B C1B N1B 127.89(15) . . ?
N3B C1B O1B 119.31(14) . . ?
N1B C1B O1B 112.80(14) . . ?
N4B C2B N2B 117.64(14) . . ?
N4B C2B N1B 116.73(15) . . ?
N2B C2B N1B 125.64(14) . . ?
N2B C3B N5B 118.11(13) . . ?
N2B C3B N3B 124.78(14) . . ?
N5B C3B N3B 117.08(13) . . ?
O1B C4B H4BA 109.5 . . ?
O1B C4B H4BB 109.5 . . ?
H4BA C4B H4BB 109.5 . . ?
O1B C4B H4BC 109.5 . . ?
H4BA C4B H4BC 109.5 . . ?
H4BB C4B H4BC 109.5 . . ?
N5B C5B C6B 110.77(12) . . ?
N5B C5B H5BA 109.5 . . ?
C6B C5B H5BA 109.5 . . ?
N5B C5B H5BB 109.5 . . ?
C6B C5B H5BB 109.5 . . ?
H5BA C5B H5BB 108.1 . . ?
C5B C6B C7B 111.29(12) . . ?
C5B C6B H6BA 109.4 . . ?
C7B C6B H6BA 109.4 . . ?
C5B C6B H6BB 109.4 . . ?
C7B C6B H6BB 109.4 . . ?
H6BA C6B H6BB 108.0 . . ?
C6B C7B C8B 109.68(13) . . ?
C6B C7B H7BA 109.7 . . ?
C8B C7B H7BA 109.7 . . ?
C6B C7B H7BB 109.7 . . ?
C8B C7B H7BB 109.7 . . ?
H7BA C7B H7BB 108.2 . . ?
C9B C8B C7B 110.76(13) . . ?
C9B C8B H8BA 109.5 . . ?
C7B C8B H8BA 109.5 . . ?
C9B C8B H8BB 109.5 . . ?
C7B C8B H8BB 109.5 . . ?
H8BA C8B H8BB 108.1 . . ?
N5B C9B C8B 111.70(12) . . ?
N5B C9B H9BA 109.3 . . ?
C8B C9B H9BA 109.3 . . ?
N5B C9B H9BB 109.3 . . ?
C8B C9B H9BB 109.3 . . ?
H9BA C9B H9BB 107.9 . . ?

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
N4A H1N N1A 0.876(19) 2.185(19) 3.0578(19) 175.1(16) 2_665
N4A H2N N1B 0.911(19) 2.12(2) 3.0073(19) 162.8(16) 2_666
N4B H3N N2B 0.89(2) 2.44(2) 3.299(2) 161.3(17) 2_666
N4B H4N N2A 0.90(2) 2.17(2) 3.072(2) 178.0(17) 2_666

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.055