 
data_compound 16
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H17 N O6'
_chemical_formula_weight          283.28
 
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    P 21 21 21
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    7.1410(10)
_cell_length_b                    8.9370(10)
_cell_length_c                    20.605(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1315.0(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     27
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        prismatic
_exptl_crystal_colour             transparent
_exptl_crystal_size_max           ?
_exptl_crystal_size_mid           0.4
_exptl_crystal_size_min           ?
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.431
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              600
_exptl_absorpt_coefficient_mu     0.966
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   Siemens P4
_diffrn_measurement_method        'profile data from theta\2theta scan'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          3
_diffrn_standards_interval_count  300
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         0.50
_diffrn_reflns_number             1695
_diffrn_reflns_av_R_equivalents   0.0555
_diffrn_reflns_av_sigmaI/netI     0.0205
_diffrn_reflns_limit_h_min        -1
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -1
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -1
_diffrn_reflns_limit_l_max        24
_diffrn_reflns_theta_min          4.29
_diffrn_reflns_theta_max          64.20
_reflns_number_total              1528
_reflns_number_gt                 1507
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'Siemens P4'
_computing_cell_refinement        'Siemens P4'
_computing_data_reduction         'Siemens P4'
_computing_structure_solution     'SIR97 (Altomare, 1997)
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP3 (Johnson, 1996)'
_computing_publication_material   'CIFTAB'
 
_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)+(0.1043P)²+0.1565P] 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        0.039(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    -0.1(3)
_refine_ls_number_reflns          1528
_refine_ls_number_parameters      211
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0512
_refine_ls_R_factor_gt            0.0508
_refine_ls_wR_factor_ref          0.1259
_refine_ls_wR_factor_gt           0.1249
_refine_ls_goodness_of_fit_ref    1.052
_refine_ls_restrained_S_all       1.052
_refine_ls_shift/su_max           0.005
_refine_ls_shift/su_mean          0.001
 
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
N1 N -1.0828(3) -0.3512(2) -0.26860(10) 0.0432(5) Uani 1 1 d . . .
O1 O -1.4874(3) -0.2962(3) -0.10846(9) 0.0633(7) Uani 1 1 d . . .
O2 O -1.0109(3) -0.2389(2) -0.08948(9) 0.0535(5) Uani 1 1 d . . .
O3 O -0.9779(4) -0.4717(3) -0.04901(9) 0.0708(7) Uani 1 1 d . . .
O4 O -0.9416(2) -0.3772(2) -0.21970(8) 0.0495(5) Uani 1 1 d . . .
O5 O -1.4499(3) -0.22994(18) -0.31967(8) 0.0484(5) Uani 1 1 d . . .
O6 O -1.3583(4) -0.4232(2) -0.38215(9) 0.0612(6) Uani 1 1 d . . .
C1 C -0.9376(4) -0.3815(4) -0.10379(13) 0.0533(8) Uani 1 1 d . . .
H1 H -0.797(6) -0.373(5) -0.1139(17) 0.076(11) Uiso 1 1 d . . .
C2 C -1.0307(4) -0.4452(3) -0.16390(12) 0.0440(6) Uani 1 1 d . . .
H2 H -1.010(5) -0.557(3) -0.1661(14) 0.050(8) Uiso 1 1 d . . .
C3 C -1.2386(3) -0.4060(3) -0.16879(11) 0.0348(5) Uani 1 1 d . . .
H3 H -1.306(5) -0.491(4) -0.1729(14) 0.048(8) Uiso 1 1 d . . .
C4 C -1.3198(4) -0.3216(3) -0.11186(10) 0.0418(6) Uani 1 1 d . . .
C5 C -1.1860(4) -0.2748(3) -0.05990(11) 0.0454(6) Uani 1 1 d . . .
H5 H -1.220(4) -0.182(3) -0.0365(13) 0.040(6) Uiso 1 1 d . . .
C6 C -1.1364(4) -0.4081(4) -0.01690(12) 0.0546(7) Uani 1 1 d . . .
H6A H -1.1046 -0.3760 0.0267 0.091(4) Uiso 1 1 calc R . .
H6B H -1.2391 -0.4790 -0.0147 0.091(4) Uiso 1 1 calc R . .
C7 C -1.2488(4) -0.3089(3) -0.23170(10) 0.0355(5) Uani 1 1 d . . .
H7 H -1.256(4) -0.208(3) -0.2217(11) 0.029(5) Uiso 1 1 d . . .
C8 C -1.4127(4) -0.3472(3) -0.27457(11) 0.0391(6) Uani 1 1 d . . .
H8 H -1.515(6) -0.365(4) -0.2497(17) 0.058(9) Uiso 1 1 d . . .
C9 C -1.3388(5) -0.4772(3) -0.31775(12) 0.0471(7) Uani 1 1 d . . .
H9 H -1.400(5) -0.560(4) -0.3145(16) 0.052(9) Uiso 1 1 d . . .
C10 C -1.1335(4) -0.4942(3) -0.30043(14) 0.0545(7) Uani 1 1 d . . .
H10A H -1.1151 -0.5778 -0.2711 0.091(4) Uiso 1 1 calc R . .
H10B H -1.0585 -0.5102 -0.3391 0.091(4) Uiso 1 1 calc R . .
C11 C -1.4820(4) -0.2987(3) -0.38134(11) 0.0464(6) Uani 1 1 d . . .
C12 C -1.6837(5) -0.3473(5) -0.38754(15) 0.0732(10) Uani 1 1 d . . .
H12A H -1.7634 -0.2608 -0.3869 0.091(4) Uiso 1 1 calc R . .
H12B H -1.7154 -0.4119 -0.3520 0.091(4) Uiso 1 1 calc R . .
H12C H -1.7005 -0.4001 -0.4277 0.091(4) Uiso 1 1 calc R . .
C13 C -1.4232(6) -0.1936(4) -0.43426(14) 0.0662(9) Uani 1 1 d . . .
H13A H -1.5050 -0.1083 -0.4347 0.091(4) Uiso 1 1 calc R . .
H13B H -1.4300 -0.2439 -0.4754 0.091(4) Uiso 1 1 calc R . .
H13C H -1.2969 -0.1611 -0.4266 0.091(4) 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
N1 O4 1.444(3) . ?
N1 C7 1.458(3) . ?
N1 C10 1.482(3) . ?
O1 C4 1.220(3) . ?
O2 C1 1.409(4) . ?
O2 C5 1.428(3) . ?
O3 C1 1.417(3) . ?
O3 C6 1.429(4) . ?
O4 C2 1.448(3) . ?
O5 C8 1.426(3) . ?
O5 C11 1.430(3) . ?
O6 C9 1.419(3) . ?
O6 C11 1.420(4) . ?
C1 C2 1.517(4) . ?
C1 H1 1.03(4) . ?
C2 C3 1.529(3) . ?
C2 H2 1.01(3) . ?
C3 C4 1.510(3) . ?
C3 C7 1.562(3) . ?
C3 H3 0.90(3) . ?
C4 C5 1.495(3) . ?
C5 C6 1.526(4) . ?
C5 H5 0.99(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.506(3) . ?
C7 H7 0.93(3) . ?
C8 C9 1.555(3) . ?
C8 H8 0.91(4) . ?
C9 C10 1.517(5) . ?
C9 H9 0.86(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C13 1.500(4) . ?
C11 C12 1.510(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
 
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
O4 N1 C7 104.21(17) . . ?
O4 N1 C10 109.94(19) . . ?
C7 N1 C10 104.8(2) . . ?
C1 O2 C5 102.23(19) . . ?
C1 O3 C6 107.7(2) . . ?
N1 O4 C2 108.36(18) . . ?
C8 O5 C11 107.04(17) . . ?
C9 O6 C11 108.44(19) . . ?
O2 C1 O3 105.8(2) . . ?
O2 C1 C2 110.3(2) . . ?
O3 C1 C2 110.4(3) . . ?
O2 C1 H1 110(2) . . ?
O3 C1 H1 114(2) . . ?
C2 C1 H1 107(2) . . ?
O4 C2 C1 107.4(2) . . ?
O4 C2 C3 106.2(2) . . ?
C1 C2 C3 113.2(2) . . ?
O4 C2 H2 108.4(17) . . ?
C1 C2 H2 110.2(18) . . ?
C3 C2 H2 111(2) . . ?
C4 C3 C2 115.8(2) . . ?
C4 C3 C7 110.42(19) . . ?
C2 C3 C7 103.1(2) . . ?
C4 C3 H3 107(2) . . ?
C2 C3 H3 109(2) . . ?
C7 C3 H3 111.4(19) . . ?
O1 C4 C5 122.3(2) . . ?
O1 C4 C3 120.9(2) . . ?
C5 C4 C3 116.8(2) . . ?
O2 C5 C4 108.46(18) . . ?
O2 C5 C6 102.7(2) . . ?
C4 C5 C6 110.2(2) . . ?
O2 C5 H5 103.4(17) . . ?
C4 C5 H5 115.4(18) . . ?
C6 C5 H5 115.4(15) . . ?
O3 C6 C5 103.0(2) . . ?
O3 C6 H6A 111.2 . . ?
C5 C6 H6A 111.2 . . ?
O3 C6 H6B 111.2 . . ?
C5 C6 H6B 111.2 . . ?
H6A C6 H6B 109.1 . . ?
N1 C7 C8 105.48(17) . . ?
N1 C7 C3 104.51(19) . . ?
C8 C7 C3 113.4(2) . . ?
N1 C7 H7 114.4(17) . . ?
C8 C7 H7 108.0(17) . . ?
C3 C7 H7 111.1(14) . . ?
O5 C8 C7 111.1(2) . . ?
O5 C8 C9 103.85(18) . . ?
C7 C8 C9 104.0(2) . . ?
O5 C8 H8 110(2) . . ?
C7 C8 H8 110(2) . . ?
C9 C8 H8 118(2) . . ?
O6 C9 C10 110.4(3) . . ?
O6 C9 C8 104.35(19) . . ?
C10 C9 C8 105.6(2) . . ?
O6 C9 H9 108(2) . . ?
C10 C9 H9 113(2) . . ?
C8 C9 H9 115(2) . . ?
N1 C10 C9 104.7(2) . . ?
N1 C10 H10A 110.8 . . ?
C9 C10 H10A 110.8 . . ?
N1 C10 H10B 110.8 . . ?
C9 C10 H10B 110.8 . . ?
H10A C10 H10B 108.9 . . ?
O6 C11 O5 104.3(2) . . ?
O6 C11 C13 108.0(2) . . ?
O5 C11 C13 109.4(2) . . ?
O6 C11 C12 111.5(3) . . ?
O5 C11 C12 110.6(2) . . ?
C13 C11 C12 112.7(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
 
_diffrn_measured_fraction_theta_max    0.916
_diffrn_reflns_theta_full              64.20
_diffrn_measured_fraction_theta_full   0.916
_refine_diff_density_max    0.255
_refine_diff_density_min   -0.421
_refine_diff_density_rms    0.101
