  
data_shelxl 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C16 H11 N5 O7' 
_chemical_formula_weight          385.30 
  
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            Monoclinic 
_symmetry_space_group_name_H-M    C2/c 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y, -z+1/2' 
 'x+1/2, y+1/2, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y, z-1/2' 
 '-x+1/2, -y+1/2, -z' 
 'x+1/2, -y+1/2, z-1/2' 
  
_cell_length_a                    13.818(3) 
_cell_length_b                    7.8964(16) 
_cell_length_c                    30.718(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  96.52(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      3330.0(12) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     113(2) 
_cell_measurement_reflns_used     4416 
_cell_measurement_theta_min       2.002 
_cell_measurement_theta_max       27.878 
  
_exptl_crystal_description        block 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.24 
_exptl_crystal_size_mid           0.22 
_exptl_crystal_size_min           0.20 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.537 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1584 
_exptl_absorpt_coefficient_mu     0.124 
_exptl_absorpt_correction_type    MULTI-SCAN 
_exptl_absorpt_correction_T_min   0.9708 
_exptl_absorpt_correction_T_max   0.9756 
_exptl_absorpt_process_details    crystalclear 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       113(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'rotating anode' 
_diffrn_radiation_monochromator   confocal 
_diffrn_measurement_device_type   'rigaku saturn CCD area detector' 
_diffrn_measurement_method        'ω and φ scans' 
_diffrn_detector_area_resol_mean  7.31 
_diffrn_standards_number          0 
_diffrn_standards_interval_count  0 
_diffrn_standards_interval_time   0 
_diffrn_standards_decay_%         0 
_diffrn_reflns_number             11605 
_diffrn_reflns_av_R_equivalents   0.0473 
_diffrn_reflns_av_sigmaI/netI     0.0653 
_diffrn_reflns_limit_h_min        -16 
_diffrn_reflns_limit_h_max        16 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -36 
_diffrn_reflns_limit_l_max        36 
_diffrn_reflns_theta_min          2.67 
_diffrn_reflns_theta_max          25.01 
_reflns_number_total              2917 
_reflns_number_gt                 2491 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'crystalclear(Rigaku/MSC Inc., 2005)' 
_computing_cell_refinement        'crystalclear' 
_computing_data_reduction         'crystalclear' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker 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)+(0.1318P)²+0.3766P] 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        0.037(4) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          2917 
_refine_ls_number_parameters      255 
_refine_ls_number_restraints      6 
_refine_ls_R_factor_all           0.0608 
_refine_ls_R_factor_gt            0.0489 
_refine_ls_wR_factor_ref          0.1821 
_refine_ls_wR_factor_gt           0.1650 
_refine_ls_goodness_of_fit_ref    1.058 
_refine_ls_restrained_S_all       1.059 
_refine_ls_shift/su_max           0.002 
_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 1.09921(14) 0.8270(2) 0.18421(5) 0.0471(5) Uani 1 1 d . . . 
O2 O 1.11237(18) 0.9638(2) 0.24459(6) 0.0685(7) Uani 1 1 d . . . 
O3 O 1.16203(10) 0.22659(18) 0.31741(4) 0.0296(4) Uani 1 1 d . . . 
O4 O 0.87401(9) 0.28668(17) 0.37272(5) 0.0295(4) Uani 1 1 d . . . 
O5 O 1.07248(10) -0.16647(18) 0.40969(5) 0.0342(4) Uani 1 1 d . . . 
O6 O 0.74567(12) -0.5071(3) 0.50475(7) 0.0602(6) Uani 1 1 d U . . 
O7 O 0.83850(13) -0.4103(2) 0.56039(5) 0.0537(5) Uani 1 1 d . . . 
N1 N 1.11148(13) 0.8323(2) 0.22396(6) 0.0329(5) Uani 1 1 d . . . 
N2 N 1.01412(11) 0.2622(2) 0.34345(5) 0.0247(4) Uani 1 1 d . . . 
N3 N 1.11891(11) 0.0290(2) 0.36359(5) 0.0277(5) Uani 1 1 d . . . 
N4 N 0.96985(11) 0.05980(19) 0.39513(5) 0.0224(4) Uani 1 1 d . . . 
N5 N 0.81799(13) -0.4307(2) 0.52091(6) 0.0377(5) Uani 1 1 d . . . 
C1 C 1.14577(13) 0.3801(2) 0.29462(6) 0.0256(5) Uani 1 1 d . . . 
C2 C 1.14796(15) 0.5311(3) 0.31719(6) 0.0299(5) Uani 1 1 d . . . 
H2 H 1.1561 0.5320 0.3483 0.036 Uiso 1 1 calc R . . 
C3 C 1.13819(15) 0.6814(3) 0.29399(7) 0.0305(5) Uani 1 1 d . . . 
H3 H 1.1398 0.7873 0.3087 0.037 Uiso 1 1 calc R . . 
C4 C 1.12592(14) 0.6734(2) 0.24866(7) 0.0257(5) Uani 1 1 d . . . 
C5 C 1.12382(14) 0.5227(3) 0.22590(7) 0.0285(5) Uani 1 1 d . . . 
H5 H 1.1154 0.5216 0.1948 0.034 Uiso 1 1 calc R . . 
C6 C 1.13425(14) 0.3730(2) 0.24943(6) 0.0281(5) Uani 1 1 d . . . 
H6 H 1.1335 0.2671 0.2347 0.034 Uiso 1 1 calc R . . 
C7 C 1.09481(14) 0.1727(2) 0.34247(6) 0.0246(5) Uani 1 1 d . . . 
C8 C 1.05195(13) -0.0187(2) 0.38841(6) 0.0250(5) Uani 1 1 d . . . 
C9 C 0.95494(13) 0.1979(2) 0.37053(6) 0.0228(5) Uani 1 1 d . . . 
C10 C 0.80633(14) 0.2223(3) 0.40139(7) 0.0319(5) Uani 1 1 d . . . 
H10A H 0.7965 0.1007 0.3963 0.048 Uiso 1 1 calc R . . 
H10B H 0.7439 0.2813 0.3953 0.048 Uiso 1 1 calc R . . 
H10C H 0.8328 0.2413 0.4320 0.048 Uiso 1 1 calc R . . 
C11 C 1.00550(14) -0.2279(2) 0.43678(7) 0.0272(5) Uani 1 1 d . . . 
C12 C 1.02986(15) -0.2143(3) 0.48126(7) 0.0304(5) Uani 1 1 d . . . 
H12 H 1.0887 -0.1602 0.4927 0.036 Uiso 1 1 calc R . . 
C13 C 0.96739(15) -0.2808(3) 0.50918(7) 0.0307(5) Uani 1 1 d . . . 
H13 H 0.9824 -0.2727 0.5401 0.037 Uiso 1 1 calc R . . 
C14 C 0.88292(14) -0.3588(2) 0.49107(7) 0.0269(5) Uani 1 1 d . . . 
C15 C 0.85838(15) -0.3724(3) 0.44644(7) 0.0329(5) Uani 1 1 d . . . 
H15 H 0.7995 -0.4261 0.4350 0.039 Uiso 1 1 calc R . . 
C16 C 0.92090(16) -0.3065(3) 0.41864(7) 0.0337(5) Uani 1 1 d . . . 
H16 H 0.9061 -0.3151 0.3878 0.040 Uiso 1 1 calc 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 N1 1.214(2) . ? 
O2 N1 1.216(2) . ? 
O3 C7 1.341(2) . ? 
O3 C1 1.405(2) . ? 
O4 C9 1.328(2) . ? 
O4 C10 1.448(2) . ? 
O5 C8 1.352(2) . ? 
O5 C11 1.400(2) . ? 
O6 N5 1.223(2) . ? 
O7 N5 1.224(2) . ? 
N1 C4 1.468(2) . ? 
N2 C7 1.323(2) . ? 
N2 C9 1.331(2) . ? 
N3 C8 1.319(2) . ? 
N3 C7 1.330(3) . ? 
N4 C8 1.329(2) . ? 
N4 C9 1.330(2) . ? 
N5 C14 1.468(3) . ? 
C1 C2 1.378(3) . ? 
C1 C6 1.380(3) . ? 
C2 C3 1.383(3) . ? 
C2 H2 0.9500 . ? 
C3 C4 1.385(3) . ? 
C3 H3 0.9500 . ? 
C4 C5 1.379(3) . ? 
C5 C6 1.385(3) . ? 
C5 H5 0.9500 . ? 
C6 H6 0.9500 . ? 
C10 H10A 0.9800 . ? 
C10 H10B 0.9800 . ? 
C10 H10C 0.9800 . ? 
C11 C12 1.374(3) . ? 
C11 C16 1.384(3) . ? 
C12 C13 1.387(3) . ? 
C12 H12 0.9500 . ? 
C13 C14 1.380(3) . ? 
C13 H13 0.9500 . ? 
C14 C15 1.379(3) . ? 
C15 C16 1.383(3) . ? 
C15 H15 0.9500 . ? 
C16 H16 0.9500 . ? 
  
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 
C7 O3 C1 118.53(14) . . ? 
C9 O4 C10 116.84(15) . . ? 
C8 O5 C11 118.04(14) . . ? 
O1 N1 O2 123.06(18) . . ? 
O1 N1 C4 119.02(17) . . ? 
O2 N1 C4 117.92(18) . . ? 
C7 N2 C9 112.94(16) . . ? 
C8 N3 C7 111.87(16) . . ? 
C8 N4 C9 111.97(16) . . ? 
O6 N5 O7 123.6(2) . . ? 
O6 N5 C14 117.81(19) . . ? 
O7 N5 C14 118.58(18) . . ? 
C2 C1 C6 122.32(17) . . ? 
C2 C1 O3 120.20(17) . . ? 
C6 C1 O3 117.34(16) . . ? 
C1 C2 C3 119.22(18) . . ? 
C1 C2 H2 120.4 . . ? 
C3 C2 H2 120.4 . . ? 
C2 C3 C4 118.19(18) . . ? 
C2 C3 H3 120.9 . . ? 
C4 C3 H3 120.9 . . ? 
C5 C4 C3 122.85(18) . . ? 
C5 C4 N1 118.81(17) . . ? 
C3 C4 N1 118.31(17) . . ? 
C4 C5 C6 118.51(18) . . ? 
C4 C5 H5 120.7 . . ? 
C6 C5 H5 120.7 . . ? 
C1 C6 C5 118.90(17) . . ? 
C1 C6 H6 120.6 . . ? 
C5 C6 H6 120.6 . . ? 
N2 C7 N3 127.52(18) . . ? 
N2 C7 O3 118.95(17) . . ? 
N3 C7 O3 113.52(16) . . ? 
N3 C8 N4 128.58(18) . . ? 
N3 C8 O5 113.81(16) . . ? 
N4 C8 O5 117.61(16) . . ? 
O4 C9 N4 118.75(17) . . ? 
O4 C9 N2 114.27(16) . . ? 
N4 C9 N2 126.96(17) . . ? 
O4 C10 H10A 109.5 . . ? 
O4 C10 H10B 109.5 . . ? 
H10A C10 H10B 109.5 . . ? 
O4 C10 H10C 109.5 . . ? 
H10A C10 H10C 109.5 . . ? 
H10B C10 H10C 109.5 . . ? 
C12 C11 C16 122.41(19) . . ? 
C12 C11 O5 117.40(18) . . ? 
C16 C11 O5 120.11(18) . . ? 
C11 C12 C13 119.07(18) . . ? 
C11 C12 H12 120.5 . . ? 
C13 C12 H12 120.5 . . ? 
C14 C13 C12 118.49(19) . . ? 
C14 C13 H13 120.8 . . ? 
C12 C13 H13 120.8 . . ? 
C15 C14 C13 122.47(19) . . ? 
C15 C14 N5 119.48(18) . . ? 
C13 C14 N5 118.05(19) . . ? 
C14 C15 C16 118.98(18) . . ? 
C14 C15 H15 120.5 . . ? 
C16 C15 H15 120.5 . . ? 
C15 C16 C11 118.57(19) . . ? 
C15 C16 H16 120.7 . . ? 
C11 C16 H16 120.7 . . ? 
  
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 
C7 O3 C1 C2 68.6(2) . . . . ? 
C7 O3 C1 C6 -115.56(19) . . . . ? 
C6 C1 C2 C3 0.1(3) . . . . ? 
O3 C1 C2 C3 175.75(17) . . . . ? 
C1 C2 C3 C4 0.4(3) . . . . ? 
C2 C3 C4 C5 -0.5(3) . . . . ? 
C2 C3 C4 N1 177.52(18) . . . . ? 
O1 N1 C4 C5 -0.8(3) . . . . ? 
O2 N1 C4 C5 179.1(2) . . . . ? 
O1 N1 C4 C3 -178.93(18) . . . . ? 
O2 N1 C4 C3 1.0(3) . . . . ? 
C3 C4 C5 C6 0.1(3) . . . . ? 
N1 C4 C5 C6 -177.89(18) . . . . ? 
C2 C1 C6 C5 -0.5(3) . . . . ? 
O3 C1 C6 C5 -176.25(17) . . . . ? 
C4 C5 C6 C1 0.4(3) . . . . ? 
C9 N2 C7 N3 2.7(3) . . . . ? 
C9 N2 C7 O3 -178.10(16) . . . . ? 
C8 N3 C7 N2 -1.8(3) . . . . ? 
C8 N3 C7 O3 179.00(16) . . . . ? 
C1 O3 C7 N2 2.7(3) . . . . ? 
C1 O3 C7 N3 -178.02(16) . . . . ? 
C7 N3 C8 N4 -2.3(3) . . . . ? 
C7 N3 C8 O5 178.52(16) . . . . ? 
C9 N4 C8 N3 4.5(3) . . . . ? 
C9 N4 C8 O5 -176.28(16) . . . . ? 
C11 O5 C8 N3 -179.80(17) . . . . ? 
C11 O5 C8 N4 0.9(3) . . . . ? 
C10 O4 C9 N4 -1.5(3) . . . . ? 
C10 O4 C9 N2 179.53(15) . . . . ? 
C8 N4 C9 O4 177.90(16) . . . . ? 
C8 N4 C9 N2 -3.3(3) . . . . ? 
C7 N2 C9 O4 178.98(16) . . . . ? 
C7 N2 C9 N4 0.1(3) . . . . ? 
C8 O5 C11 C12 -105.6(2) . . . . ? 
C8 O5 C11 C16 77.6(2) . . . . ? 
C16 C11 C12 C13 -0.4(3) . . . . ? 
O5 C11 C12 C13 -177.08(17) . . . . ? 
C11 C12 C13 C14 0.2(3) . . . . ? 
C12 C13 C14 C15 -0.2(3) . . . . ? 
C12 C13 C14 N5 179.16(17) . . . . ? 
O6 N5 C14 C15 3.0(3) . . . . ? 
O7 N5 C14 C15 -176.51(19) . . . . ? 
O6 N5 C14 C13 -176.4(2) . . . . ? 
O7 N5 C14 C13 4.1(3) . . . . ? 
C13 C14 C15 C16 0.4(3) . . . . ? 
N5 C14 C15 C16 -178.95(18) . . . . ? 
C14 C15 C16 C11 -0.6(3) . . . . ? 
C12 C11 C16 C15 0.6(3) . . . . ? 
O5 C11 C16 C15 177.19(17) . . . . ? 
  
_diffrn_measured_fraction_theta_max    0.989 
_diffrn_reflns_theta_full              25.01 
_diffrn_measured_fraction_theta_full   0.989 
_refine_diff_density_max    0.440 
_refine_diff_density_min   -0.386 
_refine_diff_density_rms    0.089 
