 
data_vm068b 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C12 H8.50 N3.50 O5' 
_chemical_formula_weight          281.72 
 
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            orthorhombic 
_symmetry_space_group_name_H-M    Pnma 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 'x+1/2, -y+1/2, -z+1/2' 
 '-x, y+1/2, -z' 
 '-x, -y, -z' 
 'x-1/2, y, -z-1/2' 
 '-x-1/2, y-1/2, z-1/2' 
 'x, -y-1/2, z' 
 
_cell_length_a                    15.9840(10) 
_cell_length_b                    16.622(7) 
_cell_length_c                    9.1600(10) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      2433.7(11) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     25
_cell_measurement_theta_min       25.0 
_cell_measurement_theta_max       35.0
 
_exptl_crystal_description        prism 
_exptl_crystal_colour             red 
_exptl_crystal_size_max           0.25 
_exptl_crystal_size_mid           0.20 
_exptl_crystal_size_min           0.20 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.538 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1160 
_exptl_absorpt_coefficient_mu     1.055 
_exptl_absorpt_correction_type    psi-scan 
_exptl_absorpt_correction_T_min   0.7784 
_exptl_absorpt_correction_T_max   0.8167 
_exptl_absorpt_process_details    '(North et al., 1968)'
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(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             2232 
_diffrn_reflns_av_R_equivalents   0.0000 
_diffrn_reflns_av_sigmaI/netI     0.0137 
_diffrn_reflns_limit_h_min        -19 
_diffrn_reflns_limit_h_max        0 
_diffrn_reflns_limit_k_min        -18 
_diffrn_reflns_limit_k_max        0 
_diffrn_reflns_limit_l_min        -11 
_diffrn_reflns_limit_l_max        0 
_diffrn_reflns_theta_min          5.32 
_diffrn_reflns_theta_max          69.84 
_reflns_number_total              2232 
_reflns_number_gt                 1806 
_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)+(0.0870P)²+0.7371P] 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        0.0167(13) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          2232 
_refine_ls_number_parameters      194 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0618 
_refine_ls_R_factor_gt            0.0507 
_refine_ls_wR_factor_ref          0.1518 
_refine_ls_wR_factor_gt           0.1404 
_refine_ls_goodness_of_fit_ref    1.032 
_refine_ls_restrained_S_all       1.032 
_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 0.75311(16) 0.7500 0.2456(3) 0.0658(9) Uani 1 2 d S . . 
H1 H 0.7105 0.7500 0.3147 0.079 Uiso 1 2 calc SR . . 
C2 C 0.78357(11) 0.67771(15) 0.1962(2) 0.0615(6) Uani 1 1 d . . . 
C3 C 0.84823(10) 0.67609(13) 0.0883(2) 0.0553(5) Uani 1 1 d . . . 
C4 C 0.87632(15) 0.7500 0.0379(3) 0.0551(7) Uani 1 2 d S . . 
H4 H 0.9169 0.7500 -0.0349 0.066 Uiso 1 2 calc SR . . 
N5 N 0.74781(11) 0.60584(16) 0.2584(2) 0.0744(6) Uani 1 1 d . . . 
O6 O 0.69968(11) 0.61284(14) 0.3621(2) 0.1005(7) Uani 1 1 d . . . 
O7 O 0.76693(11) 0.53959(13) 0.2067(2) 0.0895(6) Uani 1 1 d . . . 
N8 N 0.87919(10) 0.60566(12) 0.0348(2) 0.0649(5) Uani 1 1 d . . . 
H8 H 0.8549 0.5623 0.0635 0.078 Uiso 1 1 calc R . . 
C9 C 0.94657(11) 0.59641(12) -0.0624(2) 0.0523(5) Uani 1 1 d . . . 
C10 C 0.93962(12) 0.53995(12) -0.1722(2) 0.0603(5) Uani 1 1 d . . . 
H10 H 0.8919 0.5081 -0.1783 0.072 Uiso 1 1 calc R . . 
C11 C 1.00264(13) 0.53056(13) -0.2722(2) 0.0632(6) Uani 1 1 d . . . 
H11 H 0.9983 0.4920 -0.3454 0.076 Uiso 1 1 calc R . . 
C12 C 1.07270(12) 0.57893(12) -0.2633(2) 0.0545(5) Uani 1 1 d . . . 
C13 C 1.08315(11) 0.63152(12) -0.1490(2) 0.0566(5) Uani 1 1 d . . . 
H13 H 1.1321 0.6615 -0.1407 0.068 Uiso 1 1 calc R . . 
C14 C 1.02067(11) 0.63944(13) -0.0473(2) 0.0581(5) Uani 1 1 d . . . 
H14 H 1.0279 0.6737 0.0319 0.070 Uiso 1 1 calc R . . 
N15 N 1.13574(12) 0.57444(13) -0.3778(2) 0.0720(6) Uani 1 1 d . . . 
O16 O 1.12873(12) 0.52201(15) -0.4709(2) 0.1083(8) Uani 1 1 d . . . 
O17 O 1.19363(12) 0.62222(13) -0.3751(2) 0.0959(7) Uani 1 1 d . . . 
C20 C 0.9383(2) 0.7500 0.4710(3) 0.0695(9) Uani 1 2 d S . . 
C21 C 0.90492(16) 0.67815(16) 0.5167(3) 0.0777(7) Uani 1 1 d . . . 
H21 H 0.9268 0.6296 0.4835 0.093 Uiso 1 1 calc R . . 
C22 C 0.83891(16) 0.67914(16) 0.6118(3) 0.0778(7) Uani 1 1 d . . . 
H22 H 0.8162 0.6309 0.6445 0.093 Uiso 1 1 calc R . . 
C23 C 0.8064(2) 0.7500 0.6590(4) 0.0737(9) Uani 1 2 d S . . 
H23 H 0.7616 0.7500 0.7239 0.088 Uiso 1 2 calc SR . . 
N24 N 1.0093(2) 0.7500 0.3713(4) 0.1097(13) Uani 1 2 d S . . 
O25 O 1.0371(2) 0.6869(2) 0.3300(4) 0.1728(15) 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 C2 1.373(3) 8_575 ? 
C1 C2 1.373(3) . ? 
C2 C3 1.430(3) . ? 
C2 N5 1.442(3) . ? 
C3 N8 1.362(3) . ? 
C3 C4 1.387(2) . ? 
C4 C3 1.387(2) 8_575 ? 
N5 O6 1.228(2) . ? 
N5 O7 1.237(3) . ? 
N8 C9 1.406(2) . ? 
C9 C10 1.380(3) . ? 
C9 C14 1.391(3) . ? 
C10 C11 1.371(3) . ? 
C11 C12 1.381(3) . ? 
C12 C13 1.374(3) . ? 
C12 N15 1.456(3) . ? 
C13 C14 1.372(3) . ? 
N15 O17 1.220(2) . ? 
N15 O16 1.225(2) . ? 
C20 C21 1.374(3) 8_575 ? 
C20 C21 1.374(3) . ? 
C20 N24 1.457(5) . ? 
C21 C22 1.369(4) . ? 
C22 C23 1.358(3) . ? 
C23 C22 1.358(3) 8_575 ? 
N24 O25 1.200(3) 8_575 ? 
N24 O25 1.200(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 
C2 C1 C2 122.1(3) 8_575 . ? 
C1 C2 C3 120.0(2) . . ? 
C1 C2 N5 117.01(19) . . ? 
C3 C2 N5 123.0(2) . . ? 
N8 C3 C4 121.58(18) . . ? 
N8 C3 C2 121.84(19) . . ? 
C4 C3 C2 116.6(2) . . ? 
C3 C4 C3 124.7(2) . 8_575 ? 
O6 N5 O7 122.4(2) . . ? 
O6 N5 C2 118.4(2) . . ? 
O7 N5 C2 119.20(19) . . ? 
C3 N8 C9 126.89(17) . . ? 
C10 C9 C14 119.39(18) . . ? 
C10 C9 N8 118.31(17) . . ? 
C14 C9 N8 122.24(18) . . ? 
C11 C10 C9 120.36(18) . . ? 
C10 C11 C12 119.36(19) . . ? 
C13 C12 C11 120.91(19) . . ? 
C13 C12 N15 119.80(17) . . ? 
C11 C12 N15 119.28(18) . . ? 
C14 C13 C12 119.33(18) . . ? 
C13 C14 C9 120.21(18) . . ? 
O17 N15 O16 123.1(2) . . ? 
O17 N15 C12 118.51(18) . . ? 
O16 N15 C12 118.34(19) . . ? 
C21 C20 C21 120.8(3) 8_575 . ? 
C21 C20 N24 119.61(17) 8_575 . ? 
C21 C20 N24 119.61(17) . . ? 
C22 C21 C20 118.9(3) . . ? 
C23 C22 C21 120.6(3) . . ? 
C22 C23 C22 120.3(4) 8_575 . ? 
O25 N24 O25 121.9(5) 8_575 . ? 
O25 N24 C20 119.0(2) 8_575 . ? 
O25 N24 C20 119.0(2) . . ? 
 
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 
C2 C1 C2 C3 -0.9(4) 8_575 . . . ? 
C2 C1 C2 N5 178.73(17) 8_575 . . . ? 
C1 C2 C3 N8 -178.9(2) . . . . ? 
N5 C2 C3 N8 1.4(3) . . . . ? 
C1 C2 C3 C4 -0.6(3) . . . . ? 
N5 C2 C3 C4 179.72(19) . . . . ? 
N8 C3 C4 C3 -179.36(16) . . . 8_575 ? 
C2 C3 C4 C3 2.3(4) . . . 8_575 ? 
C1 C2 N5 O6 -8.0(3) . . . . ? 
C3 C2 N5 O6 171.69(19) . . . . ? 
C1 C2 N5 O7 172.5(2) . . . . ? 
C3 C2 N5 O7 -7.8(3) . . . . ? 
C4 C3 N8 C9 7.0(3) . . . . ? 
C2 C3 N8 C9 -174.80(17) . . . . ? 
C3 N8 C9 C10 -139.2(2) . . . . ? 
C3 N8 C9 C14 43.8(3) . . . . ? 
C14 C9 C10 C11 -4.9(3) . . . . ? 
N8 C9 C10 C11 177.97(19) . . . . ? 
C9 C10 C11 C12 -0.9(3) . . . . ? 
C10 C11 C12 C13 5.4(3) . . . . ? 
C10 C11 C12 N15 -174.0(2) . . . . ? 
C11 C12 C13 C14 -4.0(3) . . . . ? 
N15 C12 C13 C14 175.4(2) . . . . ? 
C12 C13 C14 C9 -1.9(3) . . . . ? 
C10 C9 C14 C13 6.3(3) . . . . ? 
N8 C9 C14 C13 -176.66(19) . . . . ? 
C13 C12 N15 O17 -5.5(3) . . . . ? 
C11 C12 N15 O17 173.9(2) . . . . ? 
C13 C12 N15 O16 173.4(2) . . . . ? 
C11 C12 N15 O16 -7.2(3) . . . . ? 
C21 C20 C21 C22 -1.7(5) 8_575 . . . ? 
N24 C20 C21 C22 179.2(3) . . . . ? 
C20 C21 C22 C23 0.7(4) . . . . ? 
C21 C22 C23 C22 0.2(5) . . . 8_575 ? 
C21 C20 N24 O25 -0.5(5) 8_575 . . 8_575 ? 
C21 C20 N24 O25 178.7(4) . . . 8_575 ? 
C21 C20 N24 O25 -178.7(4) 8_575 . . . ? 
C21 C20 N24 O25 0.5(5) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.935 
_diffrn_reflns_theta_full              69.84 
_diffrn_measured_fraction_theta_full   0.935 
_refine_diff_density_max    0.196 
_refine_diff_density_min   -0.206 
_refine_diff_density_rms    0.047 
