data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Prof. R. C. F. Jones
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C11 H10 N2 O5'
_chemical_formula_weight          250.21
 
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                    7.4038(5)
_cell_length_b                    7.5670(6)
_cell_length_c                    10.7531(11)
_cell_angle_alpha                 89.924(4)
_cell_angle_beta                  72.445(4)
_cell_angle_gamma                 73.549(6)
_cell_volume                      548.53(8)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2289
_cell_measurement_theta_min       0.998
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Needle
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.02
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.515
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              260
_exptl_absorpt_coefficient_mu     0.122
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9643
_exptl_absorpt_correction_T_max   0.9976
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
 
_exptl_special_details
;
 PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
 the entire data set is used to refine the cell, which is indexed from all
 observed reflections in a 10 degree phi range.
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             9153
_diffrn_reflns_av_R_equivalents   0.1680
_diffrn_reflns_av_sigmaI/netI     0.1235
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          3.99
_diffrn_reflns_theta_max          26.37
_reflns_number_total              2231
_reflns_number_gt                 1260
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection
' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement        
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction         
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'PLATON (Spek, 1990)'
_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)+(0.0421P)²+0.5117P] 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      SHELXL
_refine_ls_extinction_coef        0.029(6)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          2231
_refine_ls_number_parameters      204
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1517
_refine_ls_R_factor_gt            0.0759
_refine_ls_wR_factor_ref          0.1693
_refine_ls_wR_factor_gt           0.1387
_refine_ls_goodness_of_fit_ref    1.035
_refine_ls_restrained_S_all       1.035
_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 0.3498(4) 0.0834(4) 0.3696(3) 0.0349(8) Uani 1 1 d . . .
O2 O 0.1383(4) 0.0691(4) 0.7448(2) 0.0261(7) Uani 1 1 d . . .
O3 O -0.1814(4) 0.1866(4) 0.8678(3) 0.0321(7) Uani 1 1 d . . .
O4 O 0.1434(4) 0.5028(4) 1.3387(3) 0.0355(8) Uani 1 1 d . . .
O5 O 0.4459(4) 0.4075(4) 1.2087(3) 0.0344(8) Uani 1 1 d . . .
N1 N 0.2362(5) -0.0927(4) 0.5407(3) 0.0257(8) Uani 1 1 d . . .
N2 N 0.2686(5) 0.4226(4) 1.2363(3) 0.0264(8) Uani 1 1 d . . .
C1 C 0.3577(6) -0.0556(6) 0.4266(4) 0.0268(9) Uani 1 1 d . . .
C2 C 0.4924(6) -0.2553(6) 0.4012(4) 0.0290(9) Uani 1 1 d . . .
C3 C 0.3521(6) -0.2878(6) 0.5336(4) 0.0281(9) Uani 1 1 d . . .
C4 C 0.0690(6) 0.0229(6) 0.6393(4) 0.0275(9) Uani 1 1 d . . .
C5 C -0.0061(5) 0.1538(5) 0.8546(4) 0.0228(8) Uani 1 1 d . . .
C6 C 0.0721(5) 0.2082(5) 0.9566(4) 0.0210(8) Uani 1 1 d . . .
C7 C 0.2761(6) 0.1748(5) 0.9347(4) 0.0241(9) Uani 1 1 d . . .
C8 C 0.3417(6) 0.2434(5) 1.0270(4) 0.0247(9) Uani 1 1 d . . .
C9 C 0.2014(5) 0.3408(5) 1.1403(4) 0.0240(9) Uani 1 1 d . . .
C10 C -0.0014(6) 0.3699(6) 1.1666(4) 0.0258(9) Uani 1 1 d . . .
C11 C -0.0653(5) 0.3046(5) 1.0727(4) 0.0242(9) Uani 1 1 d . . .
H2A H 0.632(8) -0.261(7) 0.398(5) 0.052(14) Uiso 1 1 d . . .
H2B H 0.499(7) -0.345(7) 0.323(5) 0.053(14) Uiso 1 1 d . . .
H3A H 0.398(7) -0.309(6) 0.618(5) 0.043(12) Uiso 1 1 d . . .
H3B H 0.277(5) -0.378(5) 0.526(4) 0.022(10) Uiso 1 1 d . . .
H4A H 0.006(7) 0.139(7) 0.603(5) 0.043(12) Uiso 1 1 d . . .
H4B H -0.027(6) -0.049(5) 0.676(4) 0.021(10) Uiso 1 1 d . . .
H7 H 0.368(6) 0.120(5) 0.856(4) 0.022(10) Uiso 1 1 d . . .
H8 H 0.475(7) 0.222(7) 1.013(5) 0.046(13) Uiso 1 1 d . . .
H10 H -0.088(6) 0.442(6) 1.245(4) 0.027(10) Uiso 1 1 d . . .
H11 H -0.207(7) 0.327(6) 1.087(4) 0.044(13) Uiso 1 1 d . . .
 
loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
O1 0.0365(16) 0.0324(17) 0.0401(17) 0.0106(14) -0.0143(13) -0.0144(14)
O2 0.0197(13) 0.0338(16) 0.0229(15) -0.0040(12) -0.0060(11) -0.0056(12)
O3 0.0185(13) 0.0422(18) 0.0331(16) 0.0008(13) -0.0065(11) -0.0068(13)
O4 0.0367(16) 0.0361(18) 0.0290(17) -0.0070(14) -0.0071(14) -0.0067(14)
O5 0.0255(15) 0.0449(19) 0.0353(17) -0.0013(14) -0.0124(12) -0.0110(14)
N1 0.0271(17) 0.0247(18) 0.0223(18) 0.0002(14) -0.0067(14) -0.0045(15)
N2 0.0279(18) 0.0229(19) 0.0235(18) -0.0014(14) -0.0054(14) -0.0029(15)
C1 0.028(2) 0.029(2) 0.028(2) 0.0025(18) -0.0126(17) -0.0113(18)
C2 0.030(2) 0.026(2) 0.029(2) -0.0018(18) -0.0053(18) -0.0099(19)
C3 0.027(2) 0.027(2) 0.028(2) 0.0013(17) -0.0067(17) -0.0057(19)
C4 0.0215(19) 0.033(2) 0.028(2) -0.0037(18) -0.0119(17) -0.0042(19)
C5 0.0208(19) 0.022(2) 0.024(2) 0.0028(16) -0.0070(16) -0.0051(16)
C6 0.0194(18) 0.020(2) 0.026(2) 0.0067(16) -0.0103(15) -0.0063(16)
C7 0.0196(18) 0.025(2) 0.024(2) 0.0010(17) -0.0045(17) -0.0038(17)
C8 0.0198(19) 0.026(2) 0.025(2) 0.0019(16) -0.0062(16) -0.0032(17)
C9 0.026(2) 0.020(2) 0.028(2) 0.0025(16) -0.0115(16) -0.0047(17)
C10 0.024(2) 0.028(2) 0.020(2) -0.0002(18) -0.0014(17) -0.0048(18)
C11 0.0197(19) 0.022(2) 0.027(2) 0.0064(17) -0.0066(16) -0.0014(17)
 
_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 C1 1.213(5) . ?
O2 C5 1.342(5) . ?
O2 C4 1.458(4) . ?
O3 C5 1.214(4) . ?
O4 N2 1.227(4) . ?
O5 N2 1.226(4) . ?
N1 C1 1.367(5) . ?
N1 C4 1.421(5) . ?
N1 C3 1.472(5) . ?
N2 C9 1.478(5) . ?
C1 C2 1.528(6) . ?
C2 C3 1.555(6) . ?
C2 H2A 1.01(5) . ?
C2 H2B 1.06(5) . ?
C3 H3A 1.06(5) . ?
C3 H3B 1.02(4) . ?
C4 H4A 1.01(5) . ?
C4 H4B 1.00(4) . ?
C5 C6 1.492(5) . ?
C6 C11 1.394(5) . ?
C6 C7 1.404(5) . ?
C7 C8 1.388(6) . ?
C7 H7 0.92(4) . ?
C8 C9 1.383(6) . ?
C8 H8 0.92(5) . ?
C9 C10 1.393(5) . ?
C10 C11 1.382(6) . ?
C10 H10 0.95(5) . ?
C11 H11 0.98(5) . ?
 
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 O2 C4 114.8(3) . . ?
C1 N1 C4 132.0(4) . . ?
C1 N1 C3 95.5(3) . . ?
C4 N1 C3 132.1(3) . . ?
O5 N2 O4 123.9(3) . . ?
O5 N2 C9 118.1(3) . . ?
O4 N2 C9 118.0(3) . . ?
O1 C1 N1 132.1(4) . . ?
O1 C1 C2 136.2(4) . . ?
N1 C1 C2 91.7(3) . . ?
C1 C2 C3 86.0(3) . . ?
C1 C2 H2A 111(3) . . ?
C3 C2 H2A 117(3) . . ?
C1 C2 H2B 121(3) . . ?
C3 C2 H2B 112(3) . . ?
H2A C2 H2B 109(4) . . ?
N1 C3 C2 86.8(3) . . ?
N1 C3 H3A 109(3) . . ?
C2 C3 H3A 122(2) . . ?
N1 C3 H3B 114(2) . . ?
C2 C3 H3B 115(2) . . ?
H3A C3 H3B 110(3) . . ?
N1 C4 O2 107.4(3) . . ?
N1 C4 H4A 111(3) . . ?
O2 C4 H4A 110(3) . . ?
N1 C4 H4B 109(2) . . ?
O2 C4 H4B 108(2) . . ?
H4A C4 H4B 112(3) . . ?
O3 C5 O2 123.4(3) . . ?
O3 C5 C6 123.8(3) . . ?
O2 C5 C6 112.8(3) . . ?
C11 C6 C7 120.4(3) . . ?
C11 C6 C5 117.7(3) . . ?
C7 C6 C5 121.8(3) . . ?
C8 C7 C6 120.0(4) . . ?
C8 C7 H7 118(2) . . ?
C6 C7 H7 122(2) . . ?
C9 C8 C7 118.1(4) . . ?
C9 C8 H8 122(3) . . ?
C7 C8 H8 120(3) . . ?
C8 C9 C10 123.0(4) . . ?
C8 C9 N2 118.6(3) . . ?
C10 C9 N2 118.3(3) . . ?
C11 C10 C9 118.3(4) . . ?
C11 C10 H10 124(2) . . ?
C9 C10 H10 117(2) . . ?
C10 C11 C6 120.1(3) . . ?
C10 C11 H11 120(3) . . ?
C6 C11 H11 119(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.991
_diffrn_reflns_theta_full              26.37
_diffrn_measured_fraction_theta_full   0.991
_refine_diff_density_max    0.293
_refine_diff_density_min   -0.321
_refine_diff_density_rms    0.071
