# Electronic Supplementary Material (ESI) for Organic .
# This journal is © The Royal Society of Chemistry 2014

 
data_mo_dm11163_0m 
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C16 H25 N O5' 
_chemical_formula_weight          311.37 
  
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            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                    5.4633(8) 
_cell_length_b                    11.8774(17) 
_cell_length_c                    12.6900(18) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  93.632(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      821.8(2) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     133(2) 
_cell_measurement_reflns_used     5864 
_cell_measurement_theta_min       4.702 
_cell_measurement_theta_max       55.073 
  
_exptl_crystal_description        prismatic 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.315 
_exptl_crystal_size_mid           0.168 
_exptl_crystal_size_min           0.127 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.258 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              336 
_exptl_absorpt_coefficient_mu     0.093 
_exptl_absorpt_correction_type    empirical 
_exptl_absorpt_correction_T_min   0.6965 
_exptl_absorpt_correction_T_max   0.7456 
_exptl_absorpt_process_details    sadabs 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       133(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   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             5307 
_diffrn_reflns_av_R_equivalents   0.0156 
_diffrn_reflns_av_sigmaI/netI     0.0218 
_diffrn_reflns_limit_h_min        -5 
_diffrn_reflns_limit_h_max        6 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        14 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          1.61 
_diffrn_reflns_theta_max          26.00 
_reflns_number_total              3156 
_reflns_number_gt                 3141 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
  
_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)+(0.0492P)²+0.0740P] 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        0.056(5) 
_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    0.3(5) 
_chemical_absolute_configuration  ad 
_refine_ls_number_reflns          3156 
_refine_ls_number_parameters      204 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0251 
_refine_ls_R_factor_gt            0.0250 
_refine_ls_wR_factor_ref          0.0712 
_refine_ls_wR_factor_gt           0.0709 
_refine_ls_goodness_of_fit_ref    1.052 
_refine_ls_restrained_S_all       1.052 
_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 
N1 N 0.17134(16) 0.70907(8) 0.36377(7) 0.0205(2) Uani 1 1 d . . . 
O1 O 0.48591(15) 0.84105(7) 0.39324(6) 0.02606(18) Uani 1 1 d . . . 
O2 O 0.46977(16) 0.68438(8) 0.49008(7) 0.0297(2) Uani 1 1 d . . . 
O3 O -0.17093(14) 0.70557(7) 0.25652(6) 0.02327(18) Uani 1 1 d . . . 
O4 O -0.08197(13) 0.88471(6) 0.14049(6) 0.02124(18) Uani 1 1 d . . . 
O5 O 0.00123(13) 0.81553(7) 0.05393(6) 0.02137(18) Uani 1 1 d . . . 
C1 C 0.1064(2) 0.60035(9) 0.41133(9) 0.0222(2) Uani 1 1 d . . . 
H1 H -0.0644 0.6049 0.4352 0.027 Uiso 1 1 calc R . . 
C2 C 0.2891(3) 0.59867(11) 0.50856(10) 0.0334(3) Uani 1 1 d . . . 
H2A H 0.2044 0.6156 0.5734 0.040 Uiso 1 1 calc R . . 
H2B H 0.3680 0.5239 0.5166 0.040 Uiso 1 1 calc R . . 
C3 C 0.3847(2) 0.75432(10) 0.41217(8) 0.0220(2) Uani 1 1 d . . . 
C4 C 0.01724(18) 0.75449(9) 0.28187(8) 0.0182(2) Uani 1 1 d . . . 
C5 C 0.09472(18) 0.86354(9) 0.22677(8) 0.0186(2) Uani 1 1 d . . . 
C6 C 0.33861(18) 0.84761(9) 0.17356(8) 0.0193(2) Uani 1 1 d . . . 
H6A H 0.4505 0.9119 0.1890 0.023 Uiso 1 1 calc R . . 
H6B H 0.4215 0.7773 0.1978 0.023 Uiso 1 1 calc R . . 
C7 C 0.26022(18) 0.84170(9) 0.05515(8) 0.0196(2) Uani 1 1 d . . . 
C8 C 0.3043(2) 0.95162(10) -0.00021(9) 0.0260(2) Uani 1 1 d . . . 
H8 H 0.4692 0.9771 -0.0001 0.031 Uiso 1 1 calc R . . 
C9 C 0.1358(3) 1.01524(11) -0.04843(10) 0.0338(3) Uani 1 1 d . . . 
H9A H -0.0316 0.9932 -0.0505 0.041 Uiso 1 1 calc R . . 
H9B H 0.1812 1.0834 -0.0812 0.041 Uiso 1 1 calc R . . 
C10 C 0.3773(2) 0.74232(11) 0.00007(9) 0.0269(2) Uani 1 1 d . . . 
H10A H 0.5567 0.7546 0.0012 0.032 Uiso 1 1 calc R . . 
H10B H 0.3490 0.6729 0.0407 0.032 Uiso 1 1 calc R . . 
C11 C 0.2796(3) 0.72458(14) -0.11369(12) 0.0431(3) Uani 1 1 d . . . 
H11A H 0.1008 0.7164 -0.1162 0.065 Uiso 1 1 calc R . . 
H11B H 0.3525 0.6563 -0.1418 0.065 Uiso 1 1 calc R . . 
H11C H 0.3226 0.7896 -0.1564 0.065 Uiso 1 1 calc R . . 
C12 C 0.0622(2) 0.96549(9) 0.29983(9) 0.0251(2) Uani 1 1 d . . . 
H12A H -0.1135 0.9866 0.2961 0.030 Uiso 1 1 calc R . . 
H12B H 0.1081 0.9425 0.3734 0.030 Uiso 1 1 calc R . . 
C13 C 0.2115(3) 1.06854(10) 0.27410(11) 0.0324(3) Uani 1 1 d . . . 
H13A H 0.3863 1.0524 0.2884 0.049 Uiso 1 1 calc R . . 
H13B H 0.1643 1.1319 0.3179 0.049 Uiso 1 1 calc R . . 
H13C H 0.1801 1.0878 0.1994 0.049 Uiso 1 1 calc R . . 
C14 C 0.1244(2) 0.50011(10) 0.33576(10) 0.0268(2) Uani 1 1 d . . . 
H14 H 0.0047 0.5133 0.2741 0.032 Uiso 1 1 calc R . . 
C15 C 0.3781(3) 0.48810(14) 0.29326(15) 0.0502(4) Uani 1 1 d . . . 
H15A H 0.4996 0.4744 0.3520 0.075 Uiso 1 1 calc R . . 
H15B H 0.4199 0.5575 0.2566 0.075 Uiso 1 1 calc R . . 
H15C H 0.3778 0.4247 0.2438 0.075 Uiso 1 1 calc R . . 
C16 C 0.0474(3) 0.39182(11) 0.39060(11) 0.0354(3) Uani 1 1 d . . . 
H16A H 0.1657 0.3749 0.4498 0.053 Uiso 1 1 calc R . . 
H16B H 0.0432 0.3294 0.3400 0.053 Uiso 1 1 calc R . . 
H16C H -0.1158 0.4020 0.4170 0.053 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 C3 1.3906(14) . ? 
N1 C4 1.4032(13) . ? 
N1 C1 1.4782(14) . ? 
O1 C3 1.2006(15) . ? 
O2 C3 1.3512(14) . ? 
O2 C2 1.4475(15) . ? 
O3 C4 1.2066(14) . ? 
O4 C5 1.4352(12) . ? 
O4 O5 1.4668(10) . ? 
O5 C7 1.4478(12) . ? 
C1 C2 1.5373(16) . ? 
C1 C14 1.5359(16) . ? 
C1 H1 1.0000 . ? 
C2 H2A 0.9900 . ? 
C2 H2B 0.9900 . ? 
C4 C5 1.5438(14) . ? 
C5 C12 1.5422(14) . ? 
C5 C6 1.5431(13) . ? 
C6 C7 1.5378(14) . ? 
C6 H6A 0.9900 . ? 
C6 H6B 0.9900 . ? 
C7 C8 1.5092(15) . ? 
C7 C10 1.5321(15) . ? 
C8 C9 1.3121(19) . ? 
C8 H8 0.9500 . ? 
C9 H9A 0.9500 . ? 
C9 H9B 0.9500 . ? 
C10 C11 1.5218(18) . ? 
C10 H10A 0.9900 . ? 
C10 H10B 0.9900 . ? 
C11 H11A 0.9800 . ? 
C11 H11B 0.9800 . ? 
C11 H11C 0.9800 . ? 
C12 C13 1.5177(17) . ? 
C12 H12A 0.9900 . ? 
C12 H12B 0.9900 . ? 
C13 H13A 0.9800 . ? 
C13 H13B 0.9800 . ? 
C13 H13C 0.9800 . ? 
C14 C15 1.5254(19) . ? 
C14 C16 1.5338(17) . ? 
C14 H14 1.0000 . ? 
C15 H15A 0.9800 . ? 
C15 H15B 0.9800 . ? 
C15 H15C 0.9800 . ? 
C16 H16A 0.9800 . ? 
C16 H16B 0.9800 . ? 
C16 H16C 0.9800 . ? 
  
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 N1 C4 128.70(9) . . ? 
C3 N1 C1 111.94(9) . . ? 
C4 N1 C1 119.33(8) . . ? 
C3 O2 C2 110.14(9) . . ? 
C5 O4 O5 104.35(7) . . ? 
C7 O5 O4 102.75(7) . . ? 
N1 C1 C2 100.28(8) . . ? 
N1 C1 C14 113.31(9) . . ? 
C2 C1 C14 115.28(10) . . ? 
N1 C1 H1 109.2 . . ? 
C2 C1 H1 109.2 . . ? 
C14 C1 H1 109.2 . . ? 
O2 C2 C1 106.01(9) . . ? 
O2 C2 H2A 110.5 . . ? 
C1 C2 H2A 110.5 . . ? 
O2 C2 H2B 110.5 . . ? 
C1 C2 H2B 110.5 . . ? 
H2A C2 H2B 108.7 . . ? 
O1 C3 O2 122.16(10) . . ? 
O1 C3 N1 128.84(10) . . ? 
O2 C3 N1 108.99(10) . . ? 
O3 C4 N1 118.26(10) . . ? 
O3 C4 C5 122.46(9) . . ? 
N1 C4 C5 119.28(9) . . ? 
O4 C5 C12 102.92(8) . . ? 
O4 C5 C6 104.20(8) . . ? 
C12 C5 C6 119.67(9) . . ? 
O4 C5 C4 107.58(8) . . ? 
C12 C5 C4 109.94(8) . . ? 
C6 C5 C4 111.37(8) . . ? 
C7 C6 C5 103.79(7) . . ? 
C7 C6 H6A 111.0 . . ? 
C5 C6 H6A 111.0 . . ? 
C7 C6 H6B 111.0 . . ? 
C5 C6 H6B 111.0 . . ? 
H6A C6 H6B 109.0 . . ? 
O5 C7 C8 111.44(9) . . ? 
O5 C7 C10 105.41(8) . . ? 
C8 C7 C10 111.75(9) . . ? 
O5 C7 C6 103.40(8) . . ? 
C8 C7 C6 111.88(9) . . ? 
C10 C7 C6 112.49(9) . . ? 
C9 C8 C7 125.97(11) . . ? 
C9 C8 H8 117.0 . . ? 
C7 C8 H8 117.0 . . ? 
C8 C9 H9A 120.0 . . ? 
C8 C9 H9B 120.0 . . ? 
H9A C9 H9B 120.0 . . ? 
C11 C10 C7 114.07(10) . . ? 
C11 C10 H10A 108.7 . . ? 
C7 C10 H10A 108.7 . . ? 
C11 C10 H10B 108.7 . . ? 
C7 C10 H10B 108.7 . . ? 
H10A C10 H10B 107.6 . . ? 
C10 C11 H11A 109.5 . . ? 
C10 C11 H11B 109.5 . . ? 
H11A C11 H11B 109.5 . . ? 
C10 C11 H11C 109.5 . . ? 
H11A C11 H11C 109.5 . . ? 
H11B C11 H11C 109.5 . . ? 
C13 C12 C5 114.83(10) . . ? 
C13 C12 H12A 108.6 . . ? 
C5 C12 H12A 108.6 . . ? 
C13 C12 H12B 108.6 . . ? 
C5 C12 H12B 108.6 . . ? 
H12A C12 H12B 107.5 . . ? 
C12 C13 H13A 109.5 . . ? 
C12 C13 H13B 109.5 . . ? 
H13A C13 H13B 109.5 . . ? 
C12 C13 H13C 109.5 . . ? 
H13A C13 H13C 109.5 . . ? 
H13B C13 H13C 109.5 . . ? 
C15 C14 C16 111.31(11) . . ? 
C15 C14 C1 112.89(11) . . ? 
C16 C14 C1 109.66(10) . . ? 
C15 C14 H14 107.6 . . ? 
C16 C14 H14 107.6 . . ? 
C1 C14 H14 107.6 . . ? 
C14 C15 H15A 109.5 . . ? 
C14 C15 H15B 109.5 . . ? 
H15A C15 H15B 109.5 . . ? 
C14 C15 H15C 109.5 . . ? 
H15A C15 H15C 109.5 . . ? 
H15B C15 H15C 109.5 . . ? 
C14 C16 H16A 109.5 . . ? 
C14 C16 H16B 109.5 . . ? 
H16A C16 H16B 109.5 . . ? 
C14 C16 H16C 109.5 . . ? 
H16A C16 H16C 109.5 . . ? 
H16B C16 H16C 109.5 . . ? 
  
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C5 O4 O5 C7 -47.79(9) . . . . ? 
C3 N1 C1 C2 9.72(12) . . . . ? 
C4 N1 C1 C2 -168.52(10) . . . . ? 
C3 N1 C1 C14 -113.70(10) . . . . ? 
C4 N1 C1 C14 68.07(12) . . . . ? 
C3 O2 C2 C1 16.32(14) . . . . ? 
N1 C1 C2 O2 -14.98(12) . . . . ? 
C14 C1 C2 O2 107.05(11) . . . . ? 
C2 O2 C3 O1 168.96(11) . . . . ? 
C2 O2 C3 N1 -10.27(13) . . . . ? 
C4 N1 C3 O1 -1.47(18) . . . . ? 
C1 N1 C3 O1 -179.50(10) . . . . ? 
C4 N1 C3 O2 177.69(10) . . . . ? 
C1 N1 C3 O2 -0.34(12) . . . . ? 
C3 N1 C4 O3 -174.21(10) . . . . ? 
C1 N1 C4 O3 3.70(14) . . . . ? 
C3 N1 C4 C5 6.52(15) . . . . ? 
C1 N1 C4 C5 -175.57(9) . . . . ? 
O5 O4 C5 C12 160.05(7) . . . . ? 
O5 O4 C5 C6 34.47(9) . . . . ? 
O5 O4 C5 C4 -83.86(8) . . . . ? 
O3 C4 C5 O4 -4.77(13) . . . . ? 
N1 C4 C5 O4 174.46(8) . . . . ? 
O3 C4 C5 C12 106.60(11) . . . . ? 
N1 C4 C5 C12 -74.16(11) . . . . ? 
O3 C4 C5 C6 -118.38(11) . . . . ? 
N1 C4 C5 C6 60.86(11) . . . . ? 
O4 C5 C6 C7 -9.65(11) . . . . ? 
C12 C5 C6 C7 -123.82(10) . . . . ? 
C4 C5 C6 C7 106.05(9) . . . . ? 
O4 O5 C7 C8 -80.46(9) . . . . ? 
O4 O5 C7 C10 158.13(7) . . . . ? 
O4 O5 C7 C6 39.87(10) . . . . ? 
C5 C6 C7 O5 -18.74(11) . . . . ? 
C5 C6 C7 C8 101.30(10) . . . . ? 
C5 C6 C7 C10 -131.96(9) . . . . ? 
O5 C7 C8 C9 -2.94(16) . . . . ? 
C10 C7 C8 C9 114.71(14) . . . . ? 
C6 C7 C8 C9 -118.15(14) . . . . ? 
O5 C7 C10 C11 60.60(12) . . . . ? 
C8 C7 C10 C11 -60.61(13) . . . . ? 
C6 C7 C10 C11 172.58(10) . . . . ? 
O4 C5 C12 C13 -86.46(11) . . . . ? 
C6 C5 C12 C13 28.40(14) . . . . ? 
C4 C5 C12 C13 159.16(10) . . . . ? 
N1 C1 C14 C15 56.77(14) . . . . ? 
C2 C1 C14 C15 -57.96(14) . . . . ? 
N1 C1 C14 C16 -178.50(9) . . . . ? 
C2 C1 C14 C16 66.77(13) . . . . ? 
  
_diffrn_measured_fraction_theta_max    0.995 
_diffrn_reflns_theta_full              26.00 
_diffrn_measured_fraction_theta_full   0.995 
_refine_diff_density_max    0.248 
_refine_diff_density_min   -0.185 
_refine_diff_density_rms    0.040 
