 
data_vm068 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C20 H16 N6 O9' 
_chemical_formula_weight          484.39 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0181   0.0091 
 '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'   0.0311   0.0180 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0492   0.0322 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            monoclinic 
_symmetry_space_group_name_H-M    P21/n 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
 
_cell_length_a                    7.434(4) 
_cell_length_b                    21.865(6) 
_cell_length_c                    12.827(3) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.51(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      2084.9(14) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     278(2) 
_cell_measurement_reflns_used     25
_cell_measurement_theta_min       25.0 
_cell_measurement_theta_max       35.0
 
_exptl_crystal_description        plate 
_exptl_crystal_colour             yellow 
_exptl_crystal_size_max           0.15 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.10 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.543 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1000 
_exptl_absorpt_coefficient_mu     1.071 
_exptl_absorpt_correction_type    psi-scan
_exptl_absorpt_correction_T_min   0.8559 
_exptl_absorpt_correction_T_max   0.9005 
_exptl_absorpt_process_details    '(North et al., 1968)'  
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       278(2) 
_diffrn_radiation_wavelength      1.54180 
_diffrn_radiation_type            CuK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius cad-4 diffractometer' 
_diffrn_measurement_method        'Ω-2\Scan' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          2 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   90
_diffrn_standards_decay_%         0 
_diffrn_reflns_number             3750 
_diffrn_reflns_av_R_equivalents   0.0000 
_diffrn_reflns_av_sigmaI/netI     0.0513 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        7 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        26 
_diffrn_reflns_limit_l_min        0 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          4.00 
_diffrn_reflns_theta_max          69.95 
_reflns_number_total              3750 
_reflns_number_gt                 2318 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS (Sheldrick, G.M. (2008) Acta Cryst. A64, 112-122)' 
_computing_structure_refinement   'SHELXL (Sheldrick, G.M. (2008) Acta Cryst. A64, 112-122)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_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)+(0.0606P)²+1.1766P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0033(3) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          3750 
_refine_ls_number_parameters      317 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1004 
_refine_ls_R_factor_gt            0.0516 
_refine_ls_wR_factor_ref          0.1428 
_refine_ls_wR_factor_gt           0.1121 
_refine_ls_goodness_of_fit_ref    1.026 
_refine_ls_restrained_S_all       1.026 
_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 
C1 C 0.7743(4) 0.30026(12) 0.97070(19) 0.0329(6) Uani 1 1 d . . . 
H1 H 0.7542 0.2882 1.0392 0.039 Uiso 1 1 calc R . . 
C2 C 0.8568(4) 0.35531(12) 0.95169(19) 0.0322(6) Uani 1 1 d . . . 
C3 C 0.8883(4) 0.37547(12) 0.8471(2) 0.0322(6) Uani 1 1 d . . . 
C4 C 0.8321(4) 0.33613(12) 0.76701(19) 0.0327(6) Uani 1 1 d . . . 
H4 H 0.8500 0.3483 0.6984 0.039 Uiso 1 1 calc R . . 
C5 C 0.7508(4) 0.27957(12) 0.78470(18) 0.0317(6) Uani 1 1 d . . . 
C6 C 0.7214(4) 0.26286(12) 0.89083(19) 0.0320(6) Uani 1 1 d . . . 
N7 N 0.6377(3) 0.20576(10) 0.92070(18) 0.0390(6) Uani 1 1 d . . . 
O8 O 0.5955(3) 0.19821(9) 1.01177(15) 0.0512(6) Uani 1 1 d . . . 
O9 O 0.6083(4) 0.16616(10) 0.85412(17) 0.0652(8) Uani 1 1 d . . . 
N10 N 0.9170(3) 0.38982(11) 1.04169(17) 0.0395(6) Uani 1 1 d . . . 
O11 O 0.9610(3) 0.44379(10) 1.03118(15) 0.0562(7) Uani 1 1 d . . . 
O12 O 0.9251(4) 0.36390(10) 1.12637(15) 0.0603(7) Uani 1 1 d . . . 
N13 N 0.7047(3) 0.24102(10) 0.70582(17) 0.0416(6) Uani 1 1 d . . . 
H13 H 0.6730 0.2048 0.7242 0.050 Uiso 1 1 calc R . . 
C14 C 0.7021(4) 0.25271(13) 0.59767(19) 0.0363(7) Uani 1 1 d . . . 
C15 C 0.6251(4) 0.30517(13) 0.5571(2) 0.0395(7) Uani 1 1 d . . . 
H15 H 0.5775 0.3344 0.6016 0.047 Uiso 1 1 calc R . . 
C16 C 0.6185(4) 0.31428(15) 0.4501(2) 0.0462(8) Uani 1 1 d . . . 
H16 H 0.5688 0.3497 0.4219 0.055 Uiso 1 1 calc R . . 
C17 C 0.6880(4) 0.26921(15) 0.3870(2) 0.0462(8) Uani 1 1 d . . . 
C18 C 0.7619(4) 0.21628(16) 0.4249(2) 0.0482(8) Uani 1 1 d . . . 
H18 H 0.8053 0.1865 0.3800 0.058 Uiso 1 1 calc R . . 
C19 C 0.7702(4) 0.20821(14) 0.5321(2) 0.0455(8) Uani 1 1 d . . . 
H19 H 0.8215 0.1729 0.5600 0.055 Uiso 1 1 calc R . . 
N20 N 0.6807(5) 0.27817(17) 0.2735(2) 0.0634(9) Uani 1 1 d . . . 
O21 O 0.5933(4) 0.32124(17) 0.2394(2) 0.0924(11) Uani 1 1 d . . . 
O22 O 0.7620(5) 0.24209(13) 0.21860(19) 0.0910(11) Uani 1 1 d . . . 
N23 N 0.9695(3) 0.43008(10) 0.82699(17) 0.0407(6) Uani 1 1 d . . . 
H23 H 0.9690 0.4564 0.8768 0.049 Uiso 1 1 calc R . . 
C24 C 1.0543(4) 0.44843(12) 0.7340(2) 0.0345(6) Uani 1 1 d . . . 
C25 C 1.0465(4) 0.50982(13) 0.7061(2) 0.0400(7) Uani 1 1 d . . . 
H25 H 0.9858 0.5375 0.7482 0.048 Uiso 1 1 calc R . . 
C26 C 1.1284(4) 0.52998(13) 0.6162(2) 0.0416(7) Uani 1 1 d . . . 
H26 H 1.1233 0.5710 0.5972 0.050 Uiso 1 1 calc R . . 
C27 C 1.2178(4) 0.48815(13) 0.5551(2) 0.0368(7) Uani 1 1 d . . . 
C28 C 1.2318(4) 0.42768(13) 0.5836(2) 0.0400(7) Uani 1 1 d . . . 
H28 H 1.2955 0.4004 0.5423 0.048 Uiso 1 1 calc R . . 
C29 C 1.1515(4) 0.40808(13) 0.6728(2) 0.0402(7) Uani 1 1 d . . . 
H29 H 1.1620 0.3673 0.6928 0.048 Uiso 1 1 calc R . . 
N30 N 1.2982(4) 0.50780(13) 0.4562(2) 0.0464(7) Uani 1 1 d . . . 
O31 O 1.2805(4) 0.56132(11) 0.43038(18) 0.0650(7) Uani 1 1 d . . . 
O32 O 1.3769(4) 0.46943(12) 0.40360(18) 0.0630(7) Uani 1 1 d . . . 
C51 C 0.5390(9) 0.5290(4) 0.0908(7) 0.154(3) Uani 1 1 d . . . 
H51A H 0.4997 0.5493 0.1539 0.185 Uiso 1 1 calc R . . 
H51B H 0.6692 0.5266 0.0931 0.185 Uiso 1 1 calc R . . 
C52 C 0.4637(10) 0.4666(3) 0.0876(7) 0.156(3) Uani 1 1 d . . . 
H52A H 0.5054 0.4439 0.1480 0.187 Uiso 1 1 calc R . . 
H52B H 0.3334 0.4688 0.0902 0.187 Uiso 1 1 calc R . . 
O53 O 0.5153(6) 0.43619(18) -0.0032(5) 0.146(2) 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 
C1 C6 1.366(4) . ? 
C1 C2 1.374(4) . ? 
C2 C3 1.433(4) . ? 
C2 N10 1.447(3) . ? 
C3 N23 1.364(3) . ? 
C3 C4 1.401(4) . ? 
C4 C5 1.396(4) . ? 
C5 N13 1.358(3) . ? 
C5 C6 1.428(3) . ? 
C6 N7 1.448(3) . ? 
N7 O8 1.223(3) . ? 
N7 O9 1.234(3) . ? 
N10 O12 1.226(3) . ? 
N10 O11 1.232(3) . ? 
N13 C14 1.411(3) . ? 
C14 C15 1.382(4) . ? 
C14 C19 1.385(4) . ? 
C15 C16 1.387(4) . ? 
C16 C17 1.379(4) . ? 
C17 C18 1.368(5) . ? 
C17 N20 1.469(4) . ? 
C18 C19 1.388(4) . ? 
N20 O22 1.222(4) . ? 
N20 O21 1.223(4) . ? 
N23 C24 1.412(3) . ? 
C24 C29 1.388(4) . ? 
C24 C25 1.390(4) . ? 
C25 C26 1.381(4) . ? 
C26 C27 1.379(4) . ? 
C27 C28 1.376(4) . ? 
C27 N30 1.471(4) . ? 
C28 C29 1.365(4) . ? 
N30 O31 1.223(3) . ? 
N30 O32 1.228(3) . ? 
C51 O53 1.413(9) 3_665 ? 
C51 C52 1.474(9) . ? 
C52 O53 1.398(8) . ? 
O53 C51 1.413(9) 3_665 ? 
 
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 C1 C2 121.2(2) . . ? 
C1 C2 C3 120.8(2) . . ? 
C1 C2 N10 116.8(2) . . ? 
C3 C2 N10 122.3(2) . . ? 
N23 C3 C4 121.9(2) . . ? 
N23 C3 C2 121.5(2) . . ? 
C4 C3 C2 116.6(2) . . ? 
C5 C4 C3 123.5(2) . . ? 
N13 C5 C4 122.4(2) . . ? 
N13 C5 C6 120.8(2) . . ? 
C4 C5 C6 116.9(2) . . ? 
C1 C6 C5 121.1(2) . . ? 
C1 C6 N7 116.1(2) . . ? 
C5 C6 N7 122.9(2) . . ? 
O8 N7 O9 121.4(2) . . ? 
O8 N7 C6 118.9(2) . . ? 
O9 N7 C6 119.7(2) . . ? 
O12 N10 O11 121.9(2) . . ? 
O12 N10 C2 118.6(2) . . ? 
O11 N10 C2 119.5(2) . . ? 
C5 N13 C14 128.4(2) . . ? 
C15 C14 C19 120.5(3) . . ? 
C15 C14 N13 121.5(3) . . ? 
C19 C14 N13 117.9(3) . . ? 
C14 C15 C16 120.2(3) . . ? 
C17 C16 C15 117.9(3) . . ? 
C18 C17 C16 123.2(3) . . ? 
C18 C17 N20 118.4(3) . . ? 
C16 C17 N20 118.4(3) . . ? 
C17 C18 C19 118.3(3) . . ? 
C14 C19 C18 119.9(3) . . ? 
O22 N20 O21 123.7(3) . . ? 
O22 N20 C17 118.1(4) . . ? 
O21 N20 C17 118.2(3) . . ? 
C3 N23 C24 127.6(2) . . ? 
C29 C24 C25 119.3(3) . . ? 
C29 C24 N23 122.4(2) . . ? 
C25 C24 N23 118.3(3) . . ? 
C26 C25 C24 120.4(3) . . ? 
C27 C26 C25 118.8(3) . . ? 
C28 C27 C26 121.5(3) . . ? 
C28 C27 N30 118.7(3) . . ? 
C26 C27 N30 119.9(3) . . ? 
C29 C28 C27 119.5(3) . . ? 
C28 C29 C24 120.6(3) . . ? 
O31 N30 O32 123.7(3) . . ? 
O31 N30 C27 118.0(3) . . ? 
O32 N30 C27 118.2(3) . . ? 
O53 C51 C52 111.7(6) 3_665 . ? 
O53 C52 C51 110.9(7) . . ? 
C52 O53 C51 109.1(5) . 3_665 ? 
 
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 
C6 C1 C2 C3 0.6(4) . . . . ? 
C6 C1 C2 N10 -176.5(3) . . . . ? 
C1 C2 C3 N23 179.8(3) . . . . ? 
N10 C2 C3 N23 -3.2(4) . . . . ? 
C1 C2 C3 C4 -0.5(4) . . . . ? 
N10 C2 C3 C4 176.5(3) . . . . ? 
N23 C3 C4 C5 179.1(3) . . . . ? 
C2 C3 C4 C5 -0.6(4) . . . . ? 
C3 C4 C5 N13 -177.0(3) . . . . ? 
C3 C4 C5 C6 1.5(4) . . . . ? 
C2 C1 C6 C5 0.3(4) . . . . ? 
C2 C1 C6 N7 179.4(2) . . . . ? 
N13 C5 C6 C1 177.2(3) . . . . ? 
C4 C5 C6 C1 -1.3(4) . . . . ? 
N13 C5 C6 N7 -1.8(4) . . . . ? 
C4 C5 C6 N7 179.7(2) . . . . ? 
C1 C6 N7 O8 10.6(4) . . . . ? 
C5 C6 N7 O8 -170.4(3) . . . . ? 
C1 C6 N7 O9 -170.3(3) . . . . ? 
C5 C6 N7 O9 8.7(4) . . . . ? 
C1 C2 N10 O12 14.4(4) . . . . ? 
C3 C2 N10 O12 -162.7(3) . . . . ? 
C1 C2 N10 O11 -166.6(3) . . . . ? 
C3 C2 N10 O11 16.3(4) . . . . ? 
C4 C5 N13 C14 -10.5(5) . . . . ? 
C6 C5 N13 C14 171.1(3) . . . . ? 
C5 N13 C14 C15 -46.7(4) . . . . ? 
C5 N13 C14 C19 137.0(3) . . . . ? 
C19 C14 C15 C16 -1.3(5) . . . . ? 
N13 C14 C15 C16 -177.5(3) . . . . ? 
C14 C15 C16 C17 1.1(4) . . . . ? 
C15 C16 C17 C18 0.3(5) . . . . ? 
C15 C16 C17 N20 179.6(3) . . . . ? 
C16 C17 C18 C19 -1.3(5) . . . . ? 
N20 C17 C18 C19 179.4(3) . . . . ? 
C15 C14 C19 C18 0.2(5) . . . . ? 
N13 C14 C19 C18 176.6(3) . . . . ? 
C17 C18 C19 C14 1.0(5) . . . . ? 
C18 C17 N20 O22 -9.7(4) . . . . ? 
C16 C17 N20 O22 170.9(3) . . . . ? 
C18 C17 N20 O21 170.2(3) . . . . ? 
C16 C17 N20 O21 -9.1(4) . . . . ? 
C4 C3 N23 C24 -19.2(5) . . . . ? 
C2 C3 N23 C24 160.5(3) . . . . ? 
C3 N23 C24 C29 -35.8(4) . . . . ? 
C3 N23 C24 C25 147.3(3) . . . . ? 
C29 C24 C25 C26 2.6(5) . . . . ? 
N23 C24 C25 C26 179.6(3) . . . . ? 
C24 C25 C26 C27 -0.1(5) . . . . ? 
C25 C26 C27 C28 -2.1(5) . . . . ? 
C25 C26 C27 N30 176.8(3) . . . . ? 
C26 C27 C28 C29 1.8(5) . . . . ? 
N30 C27 C28 C29 -177.2(3) . . . . ? 
C27 C28 C29 C24 0.8(5) . . . . ? 
C25 C24 C29 C28 -3.0(5) . . . . ? 
N23 C24 C29 C28 -179.9(3) . . . . ? 
C28 C27 N30 O31 178.0(3) . . . . ? 
C26 C27 N30 O31 -1.0(4) . . . . ? 
C28 C27 N30 O32 -1.0(4) . . . . ? 
C26 C27 N30 O32 -180.0(3) . . . . ? 
O53 C51 C52 O53 58.0(8) 3_665 . . . ? 
C51 C52 O53 C51 -56.5(8) . . . 3_665 ? 
 
_diffrn_measured_fraction_theta_max    0.954 
_diffrn_reflns_theta_full              69.95 
_diffrn_measured_fraction_theta_full   0.954 
_refine_diff_density_max    0.212 
_refine_diff_density_min   -0.190 
_refine_diff_density_rms    0.048 
