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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. 
# 
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#  fide research purposes only. It may contain copyright material 
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#  except for the purpose of generating routine backup copies 
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#  data retrieval see:
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data_k09247
_database_code_depnum_ccdc_archive 'CCDC 859328'
#TrackingRef 'k09247.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 N8 O4, 2(H2 O)'
_chemical_formula_sum            'C19 H26 N8 O6'
_chemical_formula_weight         462.48

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                   9.2374(5)
_cell_length_b                   10.4329(8)
_cell_length_c                   11.8262(6)
_cell_angle_alpha                79.506(3)
_cell_angle_beta                 73.461(3)
_cell_angle_gamma                88.958(3)
_cell_volume                     1073.61(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(1)
_cell_measurement_reflns_used    11018
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.109
# Absorption correction

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_T_max  0.985
_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            11018
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_sigmaI/netI    0.0771
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         27.51
_reflns_number_total             4855
_reflns_number_gt                2786
_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)+(0.0993P)²] 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         4855
_refine_ls_number_parameters     305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1184
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1831
_refine_ls_wR_factor_gt          0.1457
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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
O1 O 0.00692(19) 0.91282(18) 0.86810(15) 0.0458(5) Uani 1 1 d . . .
O2 O 0.80105(17) 0.96956(17) 0.53983(14) 0.0348(4) Uani 1 1 d . . .
O3 O 0.35095(17) 0.39654(16) 0.27506(14) 0.0368(4) Uani 1 1 d . . .
O4 O 0.81997(18) 0.41165(18) -0.03950(14) 0.0409(5) Uani 1 1 d . . .
N1 N 0.6869(2) 0.82831(19) 0.46963(16) 0.0291(5) Uani 1 1 d . . .
N2 N 0.42500(19) 0.77232(18) 0.56056(15) 0.0275(4) Uani 1 1 d . . .
N3 N 0.5477(2) 0.92794(18) 0.63344(15) 0.0290(4) Uani 1 1 d . . .
N4 N 0.2957(2) 0.86457(19) 0.72176(16) 0.0297(5) Uani 1 1 d . . .
N5 N 0.56155(19) 0.68821(18) 0.39447(15) 0.0264(4) Uani 1 1 d . . .
N6 N 0.6932(2) 0.6907(2) 0.30219(16) 0.0316(5) Uani 1 1 d . . .
N7 N 0.6708(2) 0.60918(19) 0.23770(16) 0.0305(5) Uani 1 1 d . . .
N8 N 0.5765(2) 0.4332(2) 0.12908(17) 0.0303(5) Uani 1 1 d . . .
H1N H 0.654(4) 0.485(3) 0.104(3) 0.069(10) Uiso 1 1 d . . .
C1 C 0.6713(2) 0.9074(2) 0.5510(2) 0.0290(5) Uani 1 1 d . . .
C2 C 0.5572(2) 0.7685(2) 0.48156(18) 0.0249(5) Uani 1 1 d . . .
C3 C 0.4255(2) 0.8547(2) 0.63770(19) 0.0268(5) Uani 1 1 d . . .
C4 C 0.1676(2) 0.7719(2) 0.7484(2) 0.0333(6) Uani 1 1 d . . .
H4A H 0.1688 0.7039 0.8184 0.040 Uiso 1 1 calc R . .
H4B H 0.1774 0.7285 0.6789 0.040 Uiso 1 1 calc R . .
C5 C 0.0208(3) 0.8398(3) 0.7748(2) 0.0418(6) Uani 1 1 d . . .
H5A H 0.0140 0.8993 0.7011 0.050 Uiso 1 1 calc R . .
H5B H -0.0638 0.7744 0.7990 0.050 Uiso 1 1 calc R . .
C6 C 0.1254(3) 1.0111(3) 0.8319(2) 0.0406(6) Uani 1 1 d . . .
H6A H 0.1130 1.0636 0.8957 0.049 Uiso 1 1 calc R . .
H6B H 0.1183 1.0701 0.7582 0.049 Uiso 1 1 calc R . .
C7 C 0.2795(3) 0.9517(2) 0.8083(2) 0.0325(6) Uani 1 1 d . . .
H7A H 0.3591 1.0218 0.7765 0.039 Uiso 1 1 calc R . .
H7B H 0.2923 0.9021 0.8844 0.039 Uiso 1 1 calc R . .
C8 C 0.7976(3) 1.0583(3) 0.6207(2) 0.0388(6) Uani 1 1 d . . .
H8A H 0.8979 1.0998 0.6022 0.058 Uiso 1 1 calc R . .
H8B H 0.7684 1.0101 0.7035 0.058 Uiso 1 1 calc R . .
H8C H 0.7240 1.1253 0.6113 0.058 Uiso 1 1 calc R . .
C9 C 0.4558(2) 0.6027(2) 0.38679(19) 0.0268(5) Uani 1 1 d . . .
C10 C 0.3008(2) 0.5738(2) 0.46909(19) 0.0298(5) Uani 1 1 d . . .
H10A H 0.3045 0.5601 0.5524 0.045 Uiso 1 1 calc R . .
H10B H 0.2588 0.4949 0.4544 0.045 Uiso 1 1 calc R . .
H10C H 0.2367 0.6473 0.4548 0.045 Uiso 1 1 calc R . .
C11 C 0.5284(2) 0.5531(2) 0.28582(19) 0.0277(5) Uani 1 1 d . . .
C12 C 0.4745(2) 0.4549(2) 0.23048(19) 0.0290(5) Uani 1 1 d . . .
C13 C 0.5674(2) 0.3449(2) 0.05403(19) 0.0289(5) Uani 1 1 d . . .
C14 C 0.4397(3) 0.2705(2) 0.0661(2) 0.0359(6) Uani 1 1 d . . .
H14A H 0.3497 0.2777 0.1279 0.043 Uiso 1 1 calc R . .
C15 C 0.4427(3) 0.1852(3) -0.0119(2) 0.0421(6) Uani 1 1 d . . .
H15A H 0.3548 0.1344 -0.0041 0.051 Uiso 1 1 calc R . .
C16 C 0.5749(3) 0.1746(3) -0.1015(2) 0.0424(7) Uani 1 1 d . . .
H16A H 0.5769 0.1155 -0.1543 0.051 Uiso 1 1 calc R . .
C17 C 0.7040(3) 0.2483(3) -0.1153(2) 0.0402(6) Uani 1 1 d . . .
H17A H 0.7937 0.2410 -0.1773 0.048 Uiso 1 1 calc R . .
C18 C 0.6995(3) 0.3334(2) -0.03641(19) 0.0320(6) Uani 1 1 d . . .
C19 C 0.9691(3) 0.3750(3) -0.0974(2) 0.0443(7) Uani 1 1 d . . .
H19A H 1.0437 0.4327 -0.0852 0.066 Uiso 1 1 calc R . .
H19B H 0.9818 0.3827 -0.1835 0.066 Uiso 1 1 calc R . .
H19C H 0.9839 0.2846 -0.0631 0.066 Uiso 1 1 calc R . .
O1W O 0.03404(18) 0.41588(19) 0.36150(15) 0.0466(5) Uani 1 1 d . . .
H1WA H 0.0170 0.4950 0.3679 0.070 Uiso 1 1 d R . .
H1WB H 0.1279 0.4145 0.3259 0.070 Uiso 1 1 d R . .
O2W O -0.01801(18) 0.67907(17) 0.39744(15) 0.0453(5) Uani 1 1 d . . .
H2WA H -0.0998 0.7121 0.3887 0.068 Uiso 1 1 d R . .
H2WB H -0.0195 0.6518 0.4700 0.068 Uiso 1 1 d 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
O1 C5 1.427(3) . ?
O1 C6 1.431(3) . ?
O2 C1 1.334(3) . ?
O2 C8 1.441(3) . ?
O3 C12 1.232(3) . ?
O4 C18 1.380(3) . ?
O4 C19 1.432(3) . ?
N1 C2 1.320(3) . ?
N1 C1 1.354(3) . ?
N2 C2 1.315(3) . ?
N2 C3 1.363(3) . ?
N3 C1 1.317(3) . ?
N3 C3 1.358(3) . ?
N4 C3 1.339(3) . ?
N4 C7 1.464(3) . ?
N4 C4 1.467(3) . ?
N5 C9 1.368(3) . ?
N5 N6 1.381(2) . ?
N5 C2 1.433(3) . ?
N6 N7 1.296(3) . ?
N7 C11 1.371(3) . ?
N8 C12 1.351(3) . ?
N8 C13 1.409(3) . ?
C4 C5 1.498(3) . ?
C6 C7 1.515(3) . ?
C9 C11 1.378(3) . ?
C9 C10 1.484(3) . ?
C11 C12 1.474(3) . ?
C13 C14 1.383(3) . ?
C13 C18 1.395(3) . ?
C14 C15 1.388(3) . ?
C15 C16 1.388(3) . ?
C16 C17 1.385(4) . ?
C17 C18 1.393(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C6 109.68(17) . . ?
C1 O2 C8 117.00(17) . . ?
C18 O4 C19 118.03(18) . . ?
C2 N1 C1 111.14(17) . . ?
C2 N2 C3 112.93(18) . . ?
C1 N3 C3 113.83(19) . . ?
C3 N4 C7 122.83(19) . . ?
C3 N4 C4 121.97(18) . . ?
C7 N4 C4 114.28(17) . . ?
C9 N5 N6 111.21(16) . . ?
C9 N5 C2 130.88(17) . . ?
N6 N5 C2 117.89(17) . . ?
N7 N6 N5 106.42(17) . . ?
N6 N7 C11 109.87(17) . . ?
C12 N8 C13 129.3(2) . . ?
N3 C1 O2 120.1(2) . . ?
N3 C1 N1 127.8(2) . . ?
O2 C1 N1 112.07(18) . . ?
N2 C2 N1 129.78(19) . . ?
N2 C2 N5 115.36(18) . . ?
N1 C2 N5 114.86(17) . . ?
N4 C3 N3 118.42(19) . . ?
N4 C3 N2 117.18(19) . . ?
N3 C3 N2 124.39(18) . . ?
N4 C4 C5 110.9(2) . . ?
O1 C5 C4 111.6(2) . . ?
O1 C6 C7 111.4(2) . . ?
N4 C7 C6 110.37(19) . . ?
N5 C9 C11 103.19(18) . . ?
N5 C9 C10 126.97(18) . . ?
C11 C9 C10 129.8(2) . . ?
N7 C11 C9 109.3(2) . . ?
N7 C11 C12 120.98(18) . . ?
C9 C11 C12 129.7(2) . . ?
O3 C12 N8 124.1(2) . . ?
O3 C12 C11 122.88(19) . . ?
N8 C12 C11 113.0(2) . . ?
C14 C13 C18 119.7(2) . . ?
C14 C13 N8 124.55(19) . . ?
C18 C13 N8 115.7(2) . . ?
C13 C14 C15 120.1(2) . . ?
C16 C15 C14 119.6(2) . . ?
C17 C16 C15 121.3(2) . . ?
C16 C17 C18 118.6(2) . . ?
O4 C18 C17 124.56(19) . . ?
O4 C18 C13 114.74(19) . . ?
C17 C18 C13 120.7(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N8 H1N N7 0.85(3) 2.26(3) 2.709(3) 113(2) .
O1W H1WA O2W 0.85 2.02 2.866(2) 174.7 .
O1W H1WB O3 0.85 1.99 2.829(2) 168.6 .
O2W H2WA N1 0.85 2.35 3.096(2) 146.5 1_455
O2W H2WA N6 0.85 2.44 3.170(3) 144.1 1_455

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.066



