data_ys113 
  
_audit_creation_method            'Bruker SHELXTL'  
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C18 H21 N O6' 
_chemical_formula_weight          347.36 
_chemical_absolute_configuration  rm  
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    P2(1) 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
  
_cell_length_a                    9.5204(3) 
_cell_length_b                    6.5582(2) 
_cell_length_c                    13.2707(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  91.632(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      828.24(4) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     373(2) 
_cell_measurement_reflns_used     5536 
_cell_measurement_theta_min       2.67 
_cell_measurement_theta_max       48.24 
  
_exptl_crystal_description        cube 
_exptl_crystal_colour             clear 
_exptl_crystal_size_max           0.40 
_exptl_crystal_size_mid           0.31 
_exptl_crystal_size_min           0.16 
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_diffrn     1.393 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              368 
_exptl_absorpt_coefficient_mu     0.105 
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_correction_T_min   0.9597 
_exptl_absorpt_correction_T_max   0.9835 
_exptl_absorpt_process_details    'SADABS, Sheldrick, 1997'

  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       373(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_reflns_number             28445 
_diffrn_reflns_av_R_equivalents   0.0247 
_diffrn_reflns_av_sigmaI/netI     0.0383 
_diffrn_reflns_limit_h_min        -20 
_diffrn_reflns_limit_h_max        20 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -27 
_diffrn_reflns_limit_l_max        24 
_diffrn_reflns_theta_min          2.60 
_diffrn_reflns_theta_max          49.01 
_reflns_number_total              14322 
_reflns_number_gt                 12195 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'Bruker SMART' 
_computing_cell_refinement        'Bruker SMART' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'Bruker SHELXTL' 
_computing_structure_refinement   ''Bruker SHELXTL' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
  
_refine_special_details 
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment    constr

_refine_ls_number_reflns          14322 
_refine_ls_number_parameters      226 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0492 
_refine_ls_R_factor_gt            0.0382 
_refine_ls_wR_factor_ref          0.1184 
_refine_ls_wR_factor_gt           0.1066 
_refine_ls_goodness_of_fit_ref    0.825 
_refine_ls_restrained_S_all       0.825 
_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 
O1 O 1.19732(5) 0.35630(8) 0.46646(4) 0.01551(7) Uani 1 1 d . . . 
O2 O 1.40316(4) 0.47845(8) 0.53868(3) 0.01476(7) Uani 1 1 d . . . 
O3 O 1.03141(4) 0.30715(7) 0.65373(4) 0.01440(7) Uani 1 1 d . . . 
O4 O 1.24348(5) 0.70585(7) 0.66851(4) 0.01712(7) Uani 1 1 d . . . 
O5 O 1.18238(4) 0.28716(7) 0.79737(4) 0.01434(6) Uani 1 1 d . . . 
O6 O 0.88832(5) 0.20381(8) 0.95817(4) 0.01831(8) Uani 1 1 d . . . 
C1 C 1.11361(5) 0.41514(8) 0.72624(4) 0.01212(7) Uani 1 1 d . . . 
C2 C 1.10634(6) 0.14958(9) 0.60244(5) 0.01604(9) Uani 1 1 d . . . 
H2A H 1.0436 0.0861 0.5529 0.019 Uiso 1 1 calc R . . 
H2B H 1.1352 0.0459 0.6509 0.019 Uiso 1 1 calc R . . 
C3 C 1.23479(6) 0.22805(9) 0.55011(5) 0.01419(8) Uani 1 1 d . . . 
H3A H 1.2919 0.1134 0.5275 0.017 Uiso 1 1 calc R . . 
C4 C 1.32074(6) 0.47305(10) 0.44471(4) 0.01475(8) Uani 1 1 d . . . 
C5 C 1.27648(7) 0.68700(11) 0.41528(6) 0.02002(11) Uani 1 1 d . . . 
H5A H 1.2224 0.7455 0.4680 0.030 Uiso 1 1 calc R . . 
H5B H 1.2205 0.6824 0.3540 0.030 Uiso 1 1 calc R . . 
H5C H 1.3585 0.7689 0.4052 0.030 Uiso 1 1 calc R . . 
C6 C 1.40668(8) 0.36759(14) 0.36575(5) 0.02223(12) Uani 1 1 d . . . 
H6A H 1.4314 0.2331 0.3886 0.033 Uiso 1 1 calc R . . 
H6B H 1.4906 0.4446 0.3548 0.033 Uiso 1 1 calc R . . 
H6C H 1.3524 0.3583 0.3038 0.033 Uiso 1 1 calc R . . 
C7 C 1.32601(5) 0.37665(9) 0.61248(4) 0.01280(7) Uani 1 1 d . . . 
H7A H 1.3892 0.3022 0.6590 0.015 Uiso 1 1 calc R . . 
C8 C 1.23191(5) 0.52218(8) 0.67031(4) 0.01198(7) Uani 1 1 d . . . 
C9 C 1.01687(6) 0.56430(8) 0.77757(5) 0.01462(8) Uani 1 1 d . . . 
H9A H 1.0723 0.6582 0.8188 0.018 Uiso 1 1 calc R . . 
H9B H 0.9651 0.6429 0.7270 0.018 Uiso 1 1 calc R . . 
C10 C 0.95664(6) 0.28234(9) 0.89121(4) 0.01365(8) Uani 1 1 d . . . 
C11 C 1.08730(6) 0.17237(9) 0.85662(5) 0.01615(9) Uani 1 1 d . . . 
H11A H 1.1386 0.1231 0.9160 0.019 Uiso 1 1 calc R . . 
H11B H 1.0574 0.0539 0.8178 0.019 Uiso 1 1 calc R . . 
C12 C 0.78632(5) 0.55235(8) 0.86077(4) 0.01253(7) Uani 1 1 d . . . 
C13 C 0.78426(6) 0.75254(8) 0.89580(5) 0.01355(8) Uani 1 1 d . . . 
H13A H 0.8681 0.8206 0.9103 0.016 Uiso 1 1 calc R . . 
C14 C 0.65577(6) 0.85073(9) 0.90906(4) 0.01438(8) Uani 1 1 d . . . 
H14A H 0.6550 0.9842 0.9327 0.017 Uiso 1 1 calc R . . 
C15 C 0.52841(6) 0.75191(9) 0.88741(4) 0.01384(8) Uani 1 1 d . . . 
C16 C 0.53272(6) 0.54842(10) 0.85542(4) 0.01483(8) Uani 1 1 d . . . 
H16A H 0.4490 0.4783 0.8434 0.018 Uiso 1 1 calc R . . 
C17 C 0.66023(6) 0.44914(9) 0.84134(4) 0.01415(8) Uani 1 1 d . . . 
H17A H 0.6612 0.3147 0.8191 0.017 Uiso 1 1 calc R . . 
C18 C 0.39037(6) 0.86359(12) 0.89450(5) 0.01930(10) Uani 1 1 d . . . 
H18A H 0.4074 1.0002 0.9177 0.029 Uiso 1 1 calc R . . 
H18B H 0.3317 0.7940 0.9410 0.029 Uiso 1 1 calc R . . 
H18C H 0.3443 0.8675 0.8292 0.029 Uiso 1 1 calc R . . 
N1 N 0.91778(5) 0.45488(7) 0.84110(4) 0.01344(7) Uani 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 0.01221(14) 0.01965(16) 0.01456(17) -0.00069(13) -0.00141(12) -0.00057(12) 
O2 0.00940(13) 0.02224(17) 0.01267(15) -0.00134(13) 0.00082(11) -0.00029(12) 
O3 0.01031(13) 0.01507(14) 0.01781(17) -0.00242(12) 0.00012(12) -0.00042(11) 
O4 0.01697(17) 0.01297(14) 0.0217(2) -0.00220(13) 0.00511(14) -0.00130(12) 
O5 0.01115(13) 0.01617(15) 0.01577(17) 0.00155(12) 0.00171(11) 0.00299(11) 
O6 0.01611(17) 0.01948(18) 0.01965(19) 0.00504(15) 0.00580(14) 0.00154(14) 
C1 0.00994(15) 0.01179(15) 0.01471(19) -0.00082(13) 0.00165(14) 0.00116(12) 
C2 0.0161(2) 0.01335(17) 0.0187(2) -0.00318(15) 0.00110(17) -0.00142(15) 
C3 0.01350(18) 0.01404(17) 0.0150(2) -0.00344(14) 0.00016(15) 0.00183(14) 
C4 0.01091(16) 0.0206(2) 0.01273(19) -0.00059(16) 0.00071(14) 0.00229(15) 
C5 0.0145(2) 0.0228(2) 0.0228(3) 0.0051(2) 0.00157(19) 0.00214(18) 
C6 0.0187(2) 0.0334(3) 0.0148(2) -0.0035(2) 0.00302(18) 0.0060(2) 
C7 0.00983(15) 0.01583(18) 0.01276(18) -0.00194(14) 0.00055(13) 0.00176(13) 
C8 0.00974(15) 0.01316(16) 0.01307(18) -0.00205(13) 0.00092(13) 0.00049(12) 
C9 0.01299(17) 0.01242(16) 0.0188(2) 0.00050(15) 0.00610(16) 0.00181(14) 
C10 0.01213(17) 0.01402(17) 0.0149(2) 0.00082(14) 0.00173(14) 0.00167(14) 
C11 0.01513(19) 0.01587(19) 0.0176(2) 0.00342(16) 0.00379(17) 0.00486(15) 
C12 0.01022(16) 0.01368(17) 0.01380(19) 0.00010(14) 0.00238(13) 0.00184(13) 
C13 0.01124(16) 0.01376(17) 0.0157(2) -0.00120(14) 0.00161(14) 0.00131(13) 
C14 0.01331(18) 0.01531(18) 0.0146(2) -0.00115(15) 0.00209(15) 0.00296(14) 
C15 0.01101(16) 0.0197(2) 0.01089(18) -0.00007(15) 0.00186(13) 0.00340(14) 
C16 0.01076(16) 0.0200(2) 0.0137(2) -0.00082(16) 0.00059(14) 0.00046(15) 
C17 0.01190(17) 0.01573(18) 0.0149(2) -0.00155(15) 0.00164(14) 0.00053(14) 
C18 0.01332(19) 0.0279(3) 0.0167(2) -0.0017(2) 0.00152(16) 0.00740(19) 
N1 0.01069(14) 0.01343(15) 0.01641(18) 0.00167(13) 0.00413(13) 0.00266(12) 
  
_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 C3 1.4298(8) . ? 
O1 C4 1.4386(7) . ? 
O2 C7 1.4090(7) . ? 
O2 C4 1.4547(7) . ? 
O3 C1 1.4131(7) . ? 
O3 C2 1.4379(7) . ? 
O4 C8 1.2099(7) . ? 
O5 C1 1.4103(7) . ? 
O5 C11 1.4300(8) . ? 
O6 C10 1.2292(8) . ? 
C1 C9 1.5182(7) . ? 
C1 C8 1.5361(7) . ? 
C2 C3 1.5136(9) . ? 
C2 H2A 0.9700 . ? 
C2 H2B 0.9700 . ? 
C3 C7 1.5324(8) . ? 
C3 H3A 0.9800 . ? 
C4 C5 1.5131(9) . ? 
C4 C6 1.5148(9) . ? 
C5 H5A 0.9600 . ? 
C5 H5B 0.9600 . ? 
C5 H5C 0.9600 . ? 
C6 H6A 0.9600 . ? 
C6 H6B 0.9600 . ? 
C6 H6C 0.9600 . ? 
C7 C8 1.5302(7) . ? 
C7 H7A 0.9800 . ? 
C9 N1 1.4700(7) . ? 
C9 H9A 0.9700 . ? 
C9 H9B 0.9700 . ? 
C10 N1 1.3584(7) . ? 
C10 C11 1.5202(8) . ? 
C11 H11A 0.9700 . ? 
C11 H11B 0.9700 . ? 
C12 C13 1.3931(8) . ? 
C12 C17 1.3958(8) . ? 
C12 N1 1.4359(7) . ? 
C13 C14 1.3980(7) . ? 
C13 H13A 0.9300 . ? 
C14 C15 1.3975(8) . ? 
C14 H14A 0.9300 . ? 
C15 C16 1.4015(9) . ? 
C15 C18 1.5097(8) . ? 
C16 C17 1.3947(8) . ? 
C16 H16A 0.9300 . ? 
C17 H17A 0.9300 . ? 
C18 H18A 0.9600 . ? 
C18 H18B 0.9600 . ? 
C18 H18C 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 
C3 O1 C4 106.36(4) . . ? 
C7 O2 C4 107.77(4) . . ? 
C1 O3 C2 114.20(4) . . ? 
C1 O5 C11 113.10(4) . . ? 
O5 C1 O3 113.26(4) . . ? 
O5 C1 C9 111.05(5) . . ? 
O3 C1 C9 107.29(4) . . ? 
O5 C1 C8 105.22(4) . . ? 
O3 C1 C8 107.43(5) . . ? 
C9 C1 C8 112.63(4) . . ? 
O3 C2 C3 113.02(5) . . ? 
O3 C2 H2A 109.0 . . ? 
C3 C2 H2A 109.0 . . ? 
O3 C2 H2B 109.0 . . ? 
C3 C2 H2B 109.0 . . ? 
H2A C2 H2B 107.8 . . ? 
O1 C3 C2 111.67(5) . . ? 
O1 C3 C7 99.81(5) . . ? 
C2 C3 C7 114.91(5) . . ? 
O1 C3 H3A 110.0 . . ? 
C2 C3 H3A 110.0 . . ? 
C7 C3 H3A 110.0 . . ? 
O1 C4 O2 105.35(5) . . ? 
O1 C4 C5 108.80(5) . . ? 
O2 C4 C5 109.76(5) . . ? 
O1 C4 C6 110.86(6) . . ? 
O2 C4 C6 108.38(5) . . ? 
C5 C4 C6 113.38(6) . . ? 
C4 C5 H5A 109.5 . . ? 
C4 C5 H5B 109.5 . . ? 
H5A C5 H5B 109.5 . . ? 
C4 C5 H5C 109.5 . . ? 
H5A C5 H5C 109.5 . . ? 
H5B C5 H5C 109.5 . . ? 
C4 C6 H6A 109.5 . . ? 
C4 C6 H6B 109.5 . . ? 
H6A C6 H6B 109.5 . . ? 
C4 C6 H6C 109.5 . . ? 
H6A C6 H6C 109.5 . . ? 
H6B C6 H6C 109.5 . . ? 
O2 C7 C8 112.17(5) . . ? 
O2 C7 C3 102.97(5) . . ? 
C8 C7 C3 109.67(4) . . ? 
O2 C7 H7A 110.6 . . ? 
C8 C7 H7A 110.6 . . ? 
C3 C7 H7A 110.6 . . ? 
O4 C8 C7 123.79(5) . . ? 
O4 C8 C1 122.20(5) . . ? 
C7 C8 C1 113.90(4) . . ? 
N1 C9 C1 110.50(5) . . ? 
N1 C9 H9A 109.6 . . ? 
C1 C9 H9A 109.6 . . ? 
N1 C9 H9B 109.6 . . ? 
C1 C9 H9B 109.6 . . ? 
H9A C9 H9B 108.1 . . ? 
O6 C10 N1 124.10(5) . . ? 
O6 C10 C11 118.29(5) . . ? 
N1 C10 C11 117.46(5) . . ? 
O5 C11 C10 116.91(5) . . ? 
O5 C11 H11A 108.1 . . ? 
C10 C11 H11A 108.1 . . ? 
O5 C11 H11B 108.1 . . ? 
C10 C11 H11B 108.1 . . ? 
H11A C11 H11B 107.3 . . ? 
C13 C12 C17 119.90(5) . . ? 
C13 C12 N1 120.06(5) . . ? 
C17 C12 N1 120.00(5) . . ? 
C12 C13 C14 119.79(5) . . ? 
C12 C13 H13A 120.1 . . ? 
C14 C13 H13A 120.1 . . ? 
C15 C14 C13 121.18(5) . . ? 
C15 C14 H14A 119.4 . . ? 
C13 C14 H14A 119.4 . . ? 
C14 C15 C16 118.11(5) . . ? 
C14 C15 C18 120.93(6) . . ? 
C16 C15 C18 120.93(6) . . ? 
C17 C16 C15 121.22(5) . . ? 
C17 C16 H16A 119.4 . . ? 
C15 C16 H16A 119.4 . . ? 
C16 C17 C12 119.74(5) . . ? 
C16 C17 H17A 120.1 . . ? 
C12 C17 H17A 120.1 . . ? 
C15 C18 H18A 109.5 . . ? 
C15 C18 H18B 109.5 . . ? 
H18A C18 H18B 109.5 . . ? 
C15 C18 H18C 109.5 . . ? 
H18A C18 H18C 109.5 . . ? 
H18B C18 H18C 109.5 . . ? 
C10 N1 C12 120.56(5) . . ? 
C10 N1 C9 121.14(5) . . ? 
C12 N1 C9 117.63(4) . . ? 
  
_diffrn_measured_fraction_theta_max    0.965 
_diffrn_reflns_theta_full              49.01 
_diffrn_measured_fraction_theta_full   0.965 
_refine_diff_density_max    0.471 
_refine_diff_density_min   -0.262 
_refine_diff_density_rms    0.057