 
data_2006src1256 

#Dr P J Murphy
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C14 H25 N3 O5' 
_chemical_formula_weight          315.37 
 
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 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
 
_cell_length_a                    9.0231(6) 
_cell_length_b                    9.1863(6) 
_cell_length_c                    12.5757(9) 
_cell_angle_alpha                 106.174(4) 
_cell_angle_beta                  97.221(4) 
_cell_angle_gamma                 110.245(4) 
_cell_volume                      910.30(11) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     120(2) 
_cell_measurement_reflns_used     3912
_cell_measurement_theta_min       2.91 
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        Plate
_exptl_crystal_colour             Colourless 
_exptl_crystal_size_max           0.06 
_exptl_crystal_size_mid           0.04 
_exptl_crystal_size_min           0.01 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.151 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              340 
_exptl_absorpt_coefficient_mu     0.087 
_exptl_absorpt_correction_type    Multi-scan 
_exptl_absorpt_correction_T_min   0.9948 
_exptl_absorpt_correction_T_max   0.9991 
_exptl_absorpt_process_details    'SADABS V2.10 (Sheldrick, G.M., 2003)'
 
_exptl_special_details 
; 
SADABS was used to perform the Absorption correction 
Parameter refinement on 13558 reflections reduced R(int) from 0.1013 to 0.0564 
Ratio of minimum to maximum apparent transmission: 0.728378 
The given Tmin and Tmax were generated using the SHELX SIZE command 
 
; 
 
_diffrn_ambient_temperature       120(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   '10cm confocal mirrors' 
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on κ-goniostat'
_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             17747 
_diffrn_reflns_av_R_equivalents   0.0682 
_diffrn_reflns_av_sigmaI/netI     0.0727 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -11 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -16 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          3.10 
_diffrn_reflns_theta_max          27.48 
_reflns_number_total              4139 
_reflns_number_gt                 2743 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        
'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_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)+(0.0000P)²+1.5038P] 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        0.0088(18) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          4139 
_refine_ls_number_parameters      200 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1405 
_refine_ls_R_factor_gt            0.0883 
_refine_ls_wR_factor_ref          0.1583 
_refine_ls_wR_factor_gt           0.1374 
_refine_ls_goodness_of_fit_ref    1.145 
_refine_ls_restrained_S_all       1.145 
_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 
C1 C 0.7191(4) 0.8707(4) -0.4040(3) 0.0344(8) Uani 1 1 d . . . 
C2 C 0.8173(5) 0.7886(6) -0.4685(3) 0.0558(11) Uani 1 1 d . . . 
H22A H 0.8087 0.6896 -0.4501 0.084 Uiso 1 1 calc R . . 
H22B H 0.9318 0.8661 -0.4462 0.084 Uiso 1 1 calc R . . 
H22C H 0.7745 0.7573 -0.5509 0.084 Uiso 1 1 calc R . . 
C3 C 0.7286(5) 1.0240(4) -0.4305(3) 0.0464(9) Uani 1 1 d . . . 
H20A H 0.6643 1.0742 -0.3879 0.070 Uiso 1 1 calc R . . 
H20B H 0.6851 0.9938 -0.5126 0.070 Uiso 1 1 calc R . . 
H20C H 0.8425 1.1032 -0.4080 0.070 Uiso 1 1 calc R . . 
C4 C 0.5449(4) 0.7471(5) -0.4305(3) 0.0454(9) Uani 1 1 d . . . 
H18A H 0.5441 0.6494 -0.4130 0.068 Uiso 1 1 calc R . . 
H18B H 0.4934 0.7142 -0.5116 0.068 Uiso 1 1 calc R . . 
H18C H 0.4843 0.7977 -0.3840 0.068 Uiso 1 1 calc R . . 
C5 C 0.7491(4) 0.9919(4) -0.1976(3) 0.0267(7) Uani 1 1 d . . . 
C6 C 0.8132(3) 1.0848(3) -0.0004(2) 0.0252(7) Uani 1 1 d . . . 
C7 C 0.7061(4) 1.2085(4) 0.1378(3) 0.0292(7) Uani 1 1 d . . . 
H14A H 0.6015 1.1643 0.1587 0.035 Uiso 1 1 calc R . . 
H14B H 0.7440 1.3300 0.1595 0.035 Uiso 1 1 calc R . . 
C8 C 0.8355(4) 1.1607(4) 0.1948(3) 0.0267(7) Uani 1 1 d . . . 
H10 H 0.9192 1.2608 0.2571 0.032 Uiso 1 1 calc R . . 
C9 C 0.7674(4) 1.0245(4) 0.2422(3) 0.0286(7) Uani 1 1 d . . . 
H13A H 0.8543 0.9909 0.2687 0.034 Uiso 1 1 calc R . . 
H13B H 0.7239 1.0636 0.3079 0.034 Uiso 1 1 calc R . . 
C10 C 0.5498(4) 0.7670(4) 0.1885(3) 0.0270(7) Uani 1 1 d . . . 
C11 C 0.3085(4) 0.5067(4) 0.1094(3) 0.0324(7) Uani 1 1 d . . . 
C12 C 0.3913(4) 0.4018(4) 0.1408(3) 0.0417(9) Uani 1 1 d . . . 
H21A H 0.4608 0.4600 0.2187 0.063 Uiso 1 1 calc R . . 
H21B H 0.4581 0.3811 0.0875 0.063 Uiso 1 1 calc R . . 
H21C H 0.3086 0.2963 0.1367 0.063 Uiso 1 1 calc R . . 
C13 C 0.2157(4) 0.5599(4) 0.1956(3) 0.0422(9) Uani 1 1 d . . . 
H19A H 0.2890 0.6145 0.2723 0.063 Uiso 1 1 calc R . . 
H19B H 0.1240 0.4625 0.1941 0.063 Uiso 1 1 calc R . . 
H19C H 0.1744 0.6370 0.1756 0.063 Uiso 1 1 calc R . . 
C14 C 0.1995(4) 0.4216(4) -0.0108(3) 0.0383(8) Uani 1 1 d . . . 
H15A H 0.1478 0.4926 -0.0288 0.057 Uiso 1 1 calc R . . 
H15B H 0.1153 0.3163 -0.0162 0.057 Uiso 1 1 calc R . . 
H15C H 0.2650 0.4010 -0.0652 0.057 Uiso 1 1 calc R . . 
N1 N 0.8496(3) 1.0201(3) -0.0970(2) 0.0258(6) Uani 1 1 d . . . 
N2 N 0.6901(3) 1.1306(3) 0.0165(2) 0.0294(6) Uani 1 1 d . . . 
H2 H 0.6098 1.1157 -0.0385 0.035 Uiso 1 1 calc R . . 
N3 N 0.9081(3) 1.1127(3) 0.1005(2) 0.0267(6) Uani 1 1 d . . . 
H1 H 1.0023 1.1031 0.1087 0.032 Uiso 1 1 calc R . . 
O1 O 0.8027(2) 0.9156(3) -0.28391(17) 0.0322(5) Uani 1 1 d . . . 
O2 O 0.6291(3) 1.0238(3) -0.21328(18) 0.0326(5) Uani 1 1 d . . . 
O3 O 0.6389(2) 0.8862(2) 0.15265(17) 0.0266(5) Uani 1 1 d . . . 
O4 O 0.5773(3) 0.7642(3) 0.28342(18) 0.0366(6) Uani 1 1 d . . . 
O5 O 0.4315(2) 0.6561(2) 0.09831(17) 0.0276(5) Uani 1 1 d . . . 
 
 
_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 
C1 O1 1.473(4) . ? 
C1 C3 1.512(5) . ? 
C1 C4 1.514(5) . ? 
C1 C2 1.522(5) . ? 
C2 H22A 0.9800 . ? 
C2 H22B 0.9800 . ? 
C2 H22C 0.9800 . ? 
C3 H20A 0.9800 . ? 
C3 H20B 0.9800 . ? 
C3 H20C 0.9800 . ? 
C4 H18A 0.9800 . ? 
C4 H18B 0.9800 . ? 
C4 H18C 0.9800 . ? 
C5 O2 1.224(3) . ? 
C5 O1 1.358(4) . ? 
C5 N1 1.362(4) . ? 
C6 N1 1.331(4) . ? 
C6 N2 1.337(4) . ? 
C6 N3 1.343(4) . ? 
C7 N2 1.459(4) . ? 
C7 C8 1.545(4) . ? 
C7 H14A 0.9900 . ? 
C7 H14B 0.9900 . ? 
C8 N3 1.461(4) . ? 
C8 C9 1.508(4) . ? 
C8 H10 1.0000 . ? 
C9 O3 1.443(3) . ? 
C9 H13A 0.9900 . ? 
C9 H13B 0.9900 . ? 
C10 O4 1.197(3) . ? 
C10 O5 1.328(4) . ? 
C10 O3 1.344(3) . ? 
C11 O5 1.492(3) . ? 
C11 C12 1.509(5) . ? 
C11 C14 1.516(5) . ? 
C11 C13 1.527(4) . ? 
C12 H21A 0.9800 . ? 
C12 H21B 0.9800 . ? 
C12 H21C 0.9800 . ? 
C13 H19A 0.9800 . ? 
C13 H19B 0.9800 . ? 
C13 H19C 0.9800 . ? 
C14 H15A 0.9800 . ? 
C14 H15B 0.9800 . ? 
C14 H15C 0.9800 . ? 
N2 H2 0.8800 . ? 
N3 H1 0.8800 . ? 
 
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 
O1 C1 C3 110.4(3) . . ? 
O1 C1 C4 110.8(3) . . ? 
C3 C1 C4 112.0(3) . . ? 
O1 C1 C2 102.3(2) . . ? 
C3 C1 C2 111.1(3) . . ? 
C4 C1 C2 109.7(3) . . ? 
C1 C2 H22A 109.5 . . ? 
C1 C2 H22B 109.5 . . ? 
H22A C2 H22B 109.5 . . ? 
C1 C2 H22C 109.5 . . ? 
H22A C2 H22C 109.5 . . ? 
H22B C2 H22C 109.5 . . ? 
C1 C3 H20A 109.5 . . ? 
C1 C3 H20B 109.5 . . ? 
H20A C3 H20B 109.5 . . ? 
C1 C3 H20C 109.5 . . ? 
H20A C3 H20C 109.5 . . ? 
H20B C3 H20C 109.5 . . ? 
C1 C4 H18A 109.5 . . ? 
C1 C4 H18B 109.5 . . ? 
H18A C4 H18B 109.5 . . ? 
C1 C4 H18C 109.5 . . ? 
H18A C4 H18C 109.5 . . ? 
H18B C4 H18C 109.5 . . ? 
O2 C5 O1 123.3(3) . . ? 
O2 C5 N1 128.8(3) . . ? 
O1 C5 N1 107.9(2) . . ? 
N1 C6 N2 130.3(3) . . ? 
N1 C6 N3 119.8(3) . . ? 
N2 C6 N3 109.9(3) . . ? 
N2 C7 C8 102.5(2) . . ? 
N2 C7 H14A 111.3 . . ? 
C8 C7 H14A 111.3 . . ? 
N2 C7 H14B 111.3 . . ? 
C8 C7 H14B 111.3 . . ? 
H14A C7 H14B 109.2 . . ? 
N3 C8 C9 112.7(2) . . ? 
N3 C8 C7 101.4(2) . . ? 
C9 C8 C7 114.4(2) . . ? 
N3 C8 H10 109.4 . . ? 
C9 C8 H10 109.4 . . ? 
C7 C8 H10 109.4 . . ? 
O3 C9 C8 108.1(2) . . ? 
O3 C9 H13A 110.1 . . ? 
C8 C9 H13A 110.1 . . ? 
O3 C9 H13B 110.1 . . ? 
C8 C9 H13B 110.1 . . ? 
H13A C9 H13B 108.4 . . ? 
O4 C10 O5 128.4(3) . . ? 
O4 C10 O3 125.2(3) . . ? 
O5 C10 O3 106.3(2) . . ? 
O5 C11 C12 109.8(3) . . ? 
O5 C11 C14 101.3(2) . . ? 
C12 C11 C14 111.4(3) . . ? 
O5 C11 C13 109.5(3) . . ? 
C12 C11 C13 112.9(3) . . ? 
C14 C11 C13 111.3(3) . . ? 
C11 C12 H21A 109.5 . . ? 
C11 C12 H21B 109.5 . . ? 
H21A C12 H21B 109.5 . . ? 
C11 C12 H21C 109.5 . . ? 
H21A C12 H21C 109.5 . . ? 
H21B C12 H21C 109.5 . . ? 
C11 C13 H19A 109.5 . . ? 
C11 C13 H19B 109.5 . . ? 
H19A C13 H19B 109.5 . . ? 
C11 C13 H19C 109.5 . . ? 
H19A C13 H19C 109.5 . . ? 
H19B C13 H19C 109.5 . . ? 
C11 C14 H15A 109.5 . . ? 
C11 C14 H15B 109.5 . . ? 
H15A C14 H15B 109.5 . . ? 
C11 C14 H15C 109.5 . . ? 
H15A C14 H15C 109.5 . . ? 
H15B C14 H15C 109.5 . . ? 
C6 N1 C5 118.1(3) . . ? 
C6 N2 C7 111.2(2) . . ? 
C6 N2 H2 124.4 . . ? 
C7 N2 H2 124.4 . . ? 
C6 N3 C8 111.5(2) . . ? 
C6 N3 H1 124.3 . . ? 
C8 N3 H1 124.3 . . ? 
C5 O1 C1 120.6(2) . . ? 
C10 O3 C9 114.1(2) . . ? 
C10 O5 C11 120.1(2) . . ? 
 
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 
N2 H2 O2  0.88 2.18 2.694(3) 117.2 . 
N3 H1 N1  0.88 2.02 2.847(3) 155.5 2_775 


_diffrn_measured_fraction_theta_max    0.992 
_diffrn_reflns_theta_full              27.48 
_diffrn_measured_fraction_theta_full   0.992 
_refine_diff_density_max    0.311 
_refine_diff_density_min   -0.288 
_refine_diff_density_rms    0.059 
