 
data_02src141
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
Paddy Murphy
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C14 H24 N3 O5' 
_chemical_formula_weight          314.36 
 
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    P21/c
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    19.380(2) 
_cell_length_b                    13.2761(11) 
_cell_length_c                    13.0097(11) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  91.600(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      3346.0(5) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     31578 
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       26.37
 
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.20 
_exptl_crystal_size_min           0.15 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.248 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1352 
_exptl_absorpt_coefficient_mu     0.095 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.9813 
_exptl_absorpt_correction_T_max   0.9859 
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD'
_diffrn_measurement_method        'Φ & ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             15984 
_diffrn_reflns_av_R_equivalents   0.1193 
_diffrn_reflns_av_sigmaI/netI     0.1388 
_diffrn_reflns_limit_h_min        -23 
_diffrn_reflns_limit_h_max        20 
_diffrn_reflns_limit_k_min        -15 
_diffrn_reflns_limit_k_max        15 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          3.15 
_diffrn_reflns_theta_max          25.03 
_reflns_number_total              5259 
_reflns_number_gt                 2675 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_cell_refinement        'DENZO & COLLECT'
_computing_data_reduction         'DENZO & COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_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)+(0.1413P)²+0.0000P] 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      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          5259 
_refine_ls_number_parameters      411 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1774 
_refine_ls_R_factor_gt            0.0849 
_refine_ls_wR_factor_ref          0.2612 
_refine_ls_wR_factor_gt           0.2158 
_refine_ls_goodness_of_fit_ref    1.013 
_refine_ls_restrained_S_all       1.013 
_refine_ls_shift/su_max           2.461 
_refine_ls_shift/su_mean          0.037 
 
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 0.0354(2) 0.4269(3) 0.3389(3) 0.0359(11) Uani 1 1 d . . . 
N2 N 0.0343(2) 0.5733(3) 0.2578(3) 0.0369(11) Uani 1 1 d . . . 
N3 N 0.0969(2) 0.5628(3) 0.4183(3) 0.0329(11) Uani 1 1 d . . . 
O1 O -0.1010(2) 0.5016(3) 0.3683(3) 0.0445(10) Uani 1 1 d . . . 
H1 H -0.0967 0.4881 0.4297 0.067 Uiso 1 1 calc R . . 
O2 O 0.02602(19) 0.2621(3) 0.3795(3) 0.0405(10) Uani 1 1 d . . . 
O3 O 0.11219(18) 0.3564(3) 0.4511(3) 0.0355(9) Uani 1 1 d . . . 
O4 O 0.10418(19) 0.7196(3) 0.3376(3) 0.0393(10) Uani 1 1 d . . . 
O5 O 0.15611(18) 0.6868(2) 0.4917(3) 0.0366(9) Uani 1 1 d . . . 
C1 C -0.0905(3) 0.4139(4) 0.3100(4) 0.0361(13) Uani 1 1 d . . . 
H1A H -0.1267 0.4082 0.2573 0.043 Uiso 1 1 calc R . . 
H1B H -0.0929 0.3553 0.3542 0.043 Uiso 1 1 calc R . . 
C2 C -0.0215(3) 0.4170(4) 0.2605(4) 0.0342(13) Uani 1 1 d . . . 
H2 H -0.0150 0.3561 0.2193 0.041 Uiso 1 1 calc R . . 
C3 C -0.0115(3) 0.5105(4) 0.1944(4) 0.0423(14) Uani 1 1 d . . . 
H3A H 0.0096 0.4933 0.1299 0.051 Uiso 1 1 calc R . . 
H3B H -0.0551 0.5442 0.1799 0.051 Uiso 1 1 calc R . . 
C4 C 0.0585(2) 0.5265(4) 0.3416(4) 0.0302(12) Uani 1 1 d . . . 
C5 C 0.0564(3) 0.3411(4) 0.3926(4) 0.0360(13) Uani 1 1 d . . . 
C6 C 0.1405(3) 0.2736(4) 0.5163(4) 0.0351(13) Uani 1 1 d . . . 
C7 C 0.0892(3) 0.2453(5) 0.5955(5) 0.0488(16) Uani 1 1 d . . . 
H7A H 0.0784 0.3034 0.6359 0.073 Uiso 1 1 calc R . . 
H7B H 0.1085 0.1938 0.6395 0.073 Uiso 1 1 calc R . . 
H7C H 0.0479 0.2205 0.5619 0.073 Uiso 1 1 calc R . . 
C8 C 0.1612(3) 0.1856(4) 0.4507(5) 0.0465(15) Uani 1 1 d . . . 
H8A H 0.1205 0.1513 0.4254 0.070 Uiso 1 1 calc R . . 
H8B H 0.1891 0.1400 0.4912 0.070 Uiso 1 1 calc R . . 
H8C H 0.1870 0.2096 0.3937 0.070 Uiso 1 1 calc R . . 
C9 C 0.2042(3) 0.3206(4) 0.5652(4) 0.0453(15) Uani 1 1 d . . . 
H9A H 0.2339 0.3442 0.5125 0.068 Uiso 1 1 calc R . . 
H9B H 0.2282 0.2713 0.6066 0.068 Uiso 1 1 calc R . . 
H9C H 0.1911 0.3762 0.6076 0.068 Uiso 1 1 calc R . . 
C10 C 0.1172(3) 0.6616(4) 0.4081(4) 0.0328(13) Uani 1 1 d . . . 
C11 C 0.1832(3) 0.7908(4) 0.5039(4) 0.0378(14) Uani 1 1 d . . . 
C12 C 0.1232(3) 0.8649(4) 0.5050(5) 0.0475(15) Uani 1 1 d . . . 
H1C H 0.1025 0.8696 0.4373 0.071 Uiso 1 1 calc R . . 
H1D H 0.1399 0.9300 0.5261 0.071 Uiso 1 1 calc R . . 
H1E H 0.0895 0.8418 0.5522 0.071 Uiso 1 1 calc R . . 
C13 C 0.2341(3) 0.8129(5) 0.4218(5) 0.0540(17) Uani 1 1 d . . . 
H1F H 0.2686 0.7610 0.4215 0.081 Uiso 1 1 calc R . . 
H1G H 0.2557 0.8767 0.4354 0.081 Uiso 1 1 calc R . . 
H1H H 0.2104 0.8150 0.3560 0.081 Uiso 1 1 calc R . . 
C14 C 0.2187(4) 0.7879(5) 0.6079(5) 0.0545(17) Uani 1 1 d . . . 
H1I H 0.1858 0.7705 0.6589 0.082 Uiso 1 1 calc R . . 
H1J H 0.2381 0.8528 0.6234 0.082 Uiso 1 1 calc R . . 
H1K H 0.2548 0.7383 0.6079 0.082 Uiso 1 1 calc R . . 
N4 N 0.4490(2) 0.6604(3) 0.9353(3) 0.0330(11) Uani 1 1 d . . . 
N5 N 0.4492(2) 0.7290(3) 1.0891(4) 0.0397(12) Uani 1 1 d . . . 
N6 N 0.3920(2) 0.5716(3) 1.0676(3) 0.0354(11) Uani 1 1 d . . . 
O6 O 0.5861(2) 0.6284(3) 1.0140(3) 0.0477(11) Uani 1 1 d . . . 
H6 H 0.5943 0.5708 0.9950 0.072 Uiso 1 1 calc R . . 
O7 O 0.45845(19) 0.6309(3) 0.7654(3) 0.0409(10) Uani 1 1 d . . . 
O8 O 0.37808(18) 0.5482(3) 0.8554(3) 0.0340(9) Uani 1 1 d . . . 
O9 O 0.3858(3) 0.6360(4) 1.2336(3) 0.0768(16) Uani 1 1 d . . . 
O10 O 0.3383(2) 0.4901(3) 1.1899(3) 0.0544(12) Uani 1 1 d . . . 
C15 C 0.5738(3) 0.6904(4) 0.9273(4) 0.0414(14) Uani 1 1 d . . . 
H1L H 0.5769 0.6505 0.8652 0.050 Uiso 1 1 calc R . . 
H1M H 0.6088 0.7426 0.9254 0.050 Uiso 1 1 calc R . . 
C16 C 0.5033(3) 0.7382(4) 0.9312(4) 0.0365(14) Uani 1 1 d . . . 
H16 H 0.4953 0.7818 0.8713 0.044 Uiso 1 1 calc R . . 
C17 C 0.4916(3) 0.7966(4) 1.0297(4) 0.0418(14) Uani 1 1 d . . . 
H1N H 0.5350 0.8108 1.0657 0.050 Uiso 1 1 calc R . . 
H1O H 0.4678 0.8595 1.0155 0.050 Uiso 1 1 calc R . . 
C18 C 0.4269(3) 0.6496(4) 1.0359(4) 0.0338(13) Uani 1 1 d . . . 
C19 C 0.4297(3) 0.6115(4) 0.8446(4) 0.0353(13) Uani 1 1 d . . . 
C20 C 0.3524(3) 0.4887(4) 0.7657(4) 0.0392(14) Uani 1 1 d . . . 
C21 C 0.3227(3) 0.5581(5) 0.6840(4) 0.0480(15) Uani 1 1 d . . . 
H2A H 0.2916 0.6048 0.7147 0.072 Uiso 1 1 calc R . . 
H2B H 0.2983 0.5191 0.6326 0.072 Uiso 1 1 calc R . . 
H2C H 0.3595 0.5945 0.6528 0.072 Uiso 1 1 calc R . . 
C22 C 0.2953(3) 0.4262(4) 0.8126(4) 0.0458(15) Uani 1 1 d . . . 
H2D H 0.3138 0.3895 0.8707 0.069 Uiso 1 1 calc R . . 
H2E H 0.2771 0.3798 0.7622 0.069 Uiso 1 1 calc R . . 
H2F H 0.2591 0.4700 0.8344 0.069 Uiso 1 1 calc R . . 
C23 C 0.4084(3) 0.4220(5) 0.7276(5) 0.0524(16) Uani 1 1 d . . . 
H2G H 0.4437 0.4626 0.6978 0.079 Uiso 1 1 calc R . . 
H2H H 0.3896 0.3768 0.6765 0.079 Uiso 1 1 calc R . . 
H2I H 0.4280 0.3839 0.7839 0.079 Uiso 1 1 calc R . . 
C24 C 0.3737(3) 0.5720(4) 1.1688(4) 0.0371(14) Uani 1 1 d . . . 
C25 C 0.3158(4) 0.4682(5) 1.2953(5) 0.0557(18) Uani 1 1 d . . . 
C26 C 0.2632(4) 0.5367(9) 1.3259(6) 0.118(4) Uani 1 1 d . . . 
H2J H 0.2822 0.6032 1.3325 0.176 Uiso 1 1 calc R . . 
H2K H 0.2456 0.5158 1.3908 0.176 Uiso 1 1 calc R . . 
H2L H 0.2264 0.5372 1.2750 0.176 Uiso 1 1 calc R . . 
C27 C 0.2885(13) 0.3650(11) 1.2819(10) 0.331(17) Uani 1 1 d . . . 
H2M H 0.3019 0.3248 1.3405 0.497 Uiso 1 1 calc R . . 
H2N H 0.3068 0.3358 1.2209 0.497 Uiso 1 1 calc R . . 
H2O H 0.2391 0.3673 1.2755 0.497 Uiso 1 1 calc R . . 
C28 C 0.3741(5) 0.4685(12) 1.3678(7) 0.177(7) Uani 1 1 d . . . 
H2P H 0.3877 0.5367 1.3822 0.266 Uiso 1 1 calc R . . 
H2Q H 0.4120 0.4328 1.3388 0.266 Uiso 1 1 calc R . . 
H2R H 0.3612 0.4361 1.4304 0.266 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 C5 1.391(7) . ? 
N1 C4 1.396(7) . ? 
N1 C2 1.487(7) . ? 
N2 C4 1.329(6) . ? 
N2 C3 1.457(7) . ? 
N3 C4 1.319(6) . ? 
N3 C10 1.377(7) . ? 
O1 C1 1.407(6) . ? 
O2 C5 1.213(6) . ? 
O3 C5 1.320(6) . ? 
O3 C6 1.483(6) . ? 
O4 C10 1.219(6) . ? 
O5 C10 1.348(6) . ? 
O5 C11 1.484(6) . ? 
C1 C2 1.501(8) . ? 
C2 C3 1.526(8) . ? 
C6 C7 1.499(8) . ? 
C6 C8 1.508(8) . ? 
C6 C9 1.508(8) . ? 
C11 C14 1.500(8) . ? 
C11 C13 1.502(8) . ? 
C11 C12 1.524(8) . ? 
N4 C19 1.388(7) . ? 
N4 C18 1.396(7) . ? 
N4 C16 1.477(7) . ? 
N5 C18 1.327(7) . ? 
N5 C17 1.453(7) . ? 
N6 C18 1.310(7) . ? 
N6 C24 1.372(7) . ? 
O6 C15 1.410(6) . ? 
O7 C19 1.213(6) . ? 
O8 C19 1.317(6) . ? 
O8 C20 1.483(6) . ? 
O9 C24 1.216(7) . ? 
O10 C24 1.319(6) . ? 
O10 C25 1.480(7) . ? 
C15 C16 1.510(8) . ? 
C16 C17 1.519(8) . ? 
C20 C23 1.496(8) . ? 
C20 C21 1.508(8) . ? 
C20 C22 1.523(8) . ? 
C25 C26 1.432(10) . ? 
C25 C28 1.452(12) . ? 
C25 C27 1.478(12) . ? 
 
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 N1 C4 132.3(4) . . ? 
C5 N1 C2 118.2(4) . . ? 
C4 N1 C2 109.4(4) . . ? 
C4 N2 C3 113.1(4) . . ? 
C4 N3 C10 115.6(4) . . ? 
C5 O3 C6 120.0(4) . . ? 
C10 O5 C11 120.4(4) . . ? 
O1 C1 C2 110.6(4) . . ? 
N1 C2 C1 111.2(4) . . ? 
N1 C2 C3 102.2(4) . . ? 
C1 C2 C3 113.2(5) . . ? 
N2 C3 C2 103.4(4) . . ? 
N3 C4 N2 128.9(5) . . ? 
N3 C4 N1 122.6(5) . . ? 
N2 C4 N1 108.5(4) . . ? 
O2 C5 O3 126.9(5) . . ? 
O2 C5 N1 120.3(5) . . ? 
O3 C5 N1 112.8(5) . . ? 
O3 C6 C7 109.7(4) . . ? 
O3 C6 C8 110.5(4) . . ? 
C7 C6 C8 112.7(5) . . ? 
O3 C6 C9 102.7(4) . . ? 
C7 C6 C9 111.4(5) . . ? 
C8 C6 C9 109.4(5) . . ? 
O4 C10 O5 123.4(5) . . ? 
O4 C10 N3 128.3(5) . . ? 
O5 C10 N3 108.3(4) . . ? 
O5 C11 C14 103.0(4) . . ? 
O5 C11 C13 110.1(5) . . ? 
C14 C11 C13 110.7(5) . . ? 
O5 C11 C12 109.5(4) . . ? 
C14 C11 C12 109.8(5) . . ? 
C13 C11 C12 113.3(5) . . ? 
C19 N4 C18 131.8(4) . . ? 
C19 N4 C16 118.1(4) . . ? 
C18 N4 C16 110.1(4) . . ? 
C18 N5 C17 113.3(4) . . ? 
C18 N6 C24 116.6(5) . . ? 
C19 O8 C20 119.7(4) . . ? 
C24 O10 C25 121.6(5) . . ? 
O6 C15 C16 110.6(5) . . ? 
N4 C16 C15 110.7(4) . . ? 
N4 C16 C17 101.8(4) . . ? 
C15 C16 C17 113.5(5) . . ? 
N5 C17 C16 103.5(4) . . ? 
N6 C18 N5 128.9(5) . . ? 
N6 C18 N4 123.4(5) . . ? 
N5 C18 N4 107.6(5) . . ? 
O7 C19 O8 126.4(5) . . ? 
O7 C19 N4 120.2(5) . . ? 
O8 C19 N4 113.3(5) . . ? 
O8 C20 C23 110.2(4) . . ? 
O8 C20 C21 110.0(4) . . ? 
C23 C20 C21 113.2(5) . . ? 
O8 C20 C22 101.9(4) . . ? 
C23 C20 C22 110.6(5) . . ? 
C21 C20 C22 110.4(5) . . ? 
O9 C24 O10 121.5(5) . . ? 
O9 C24 N6 128.2(5) . . ? 
O10 C24 N6 110.2(5) . . ? 
C26 C25 C28 111.5(8) . . ? 
C26 C25 C27 111.5(12) . . ? 
C28 C25 C27 110.4(13) . . ? 
C26 C25 O10 111.3(6) . . ? 
C28 C25 O10 111.0(6) . . ? 
C27 C25 O10 100.7(6) . . ? 
 
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
O1 H1 N3  0.82 2.09 2.904(5) 171.4 3_566 
O1 H1 O3  0.82 2.60 3.025(5) 113.4 3_566 
O6 H6 N6  0.82 2.08 2.895(6) 173.5 3_667 
O6 H6 O8  0.82 2.55 2.967(5) 112.7 3_667 
 
_diffrn_measured_fraction_theta_max    0.890 
_diffrn_reflns_theta_full              25.03 
_diffrn_measured_fraction_theta_full   0.890 
_refine_diff_density_max    0.601 
_refine_diff_density_min   -0.501 
_refine_diff_density_rms    0.069 
