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

 
data_mo_nj_wyt_52_2_0m 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C18 H19 N O3' 
_chemical_formula_weight          297.34 
 
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            ? 
_symmetry_space_group_name_H-M    "p-1" 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
 
_cell_length_a                    10.2117(11) 
_cell_length_b                    12.3644(11) 
_cell_length_c                    12.8781(11) 
_cell_angle_alpha                 93.100(3) 
_cell_angle_beta                  96.848(3) 
_cell_angle_gamma                 90.294(3) 
_cell_volume                      1611.9(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     273(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           ? 
_exptl_crystal_size_mid           ? 
_exptl_crystal_size_min           ? 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.225 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              632 
_exptl_absorpt_coefficient_mu     0.083 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       273(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   ? 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             15443 
_diffrn_reflns_av_R_equivalents   0.0502 
_diffrn_reflns_av_sigmaI/netI     0.0725 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        12 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -15 
_diffrn_reflns_limit_l_max        15 
_diffrn_reflns_theta_min          2.23 
_diffrn_reflns_theta_max          25.07 
_reflns_number_total              5704 
_reflns_number_gt                 3250 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_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)+(0.0714P)²+0.2259P] 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          5704 
_refine_ls_number_parameters      403 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1210 
_refine_ls_R_factor_gt            0.0557 
_refine_ls_wR_factor_ref          0.1526 
_refine_ls_wR_factor_gt           0.1263 
_refine_ls_goodness_of_fit_ref    1.008 
_refine_ls_restrained_S_all       1.008 
_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 
O5 O 0.23846(19) -0.12425(13) 0.18482(14) 0.0630(5) Uani 1 1 d . . . 
O2 O -0.00891(19) 0.30967(15) 0.56013(14) 0.0635(5) Uani 1 1 d . . . 
N1 N -0.1760(2) 0.59479(16) 0.94019(15) 0.0471(5) Uani 1 1 d . . . 
O3 O -0.19574(19) 0.67337(14) 1.01916(13) 0.0568(5) Uani 1 1 d . . . 
H3 H -0.2438 0.7208 0.9944 0.085 Uiso 1 1 calc R . . 
N2 N 0.6664(2) 0.49236(16) 0.09566(15) 0.0509(6) Uani 1 1 d . . . 
O6 O 0.6952(2) 0.42385(15) 0.01074(15) 0.0673(6) Uani 1 1 d . . . 
H6 H 0.6271 0.4095 -0.0282 0.101 Uiso 1 1 calc R . . 
O4 O 0.5013(2) 0.69347(16) 0.51983(14) 0.0707(6) Uani 1 1 d . . . 
C28 C 0.3985(2) 0.18590(18) 0.18609(18) 0.0398(6) Uani 1 1 d . . . 
C33 C 0.3893(3) 0.11878(19) 0.09576(19) 0.0485(7) Uani 1 1 d . . . 
H33 H 0.4196 0.1441 0.0361 0.058 Uiso 1 1 calc R . . 
C9 C -0.1064(2) 0.62817(19) 0.87064(18) 0.0417(6) Uani 1 1 d . . . 
O1 O 0.2852(2) 1.17280(14) 0.81059(16) 0.0663(6) Uani 1 1 d . . . 
C11 C -0.1044(3) 0.5598(2) 0.68374(19) 0.0483(7) Uani 1 1 d . . . 
H11 H -0.1372 0.6261 0.6621 0.058 Uiso 1 1 calc R . . 
C24 C 0.5617(2) 0.51537(18) 0.24733(18) 0.0391(6) Uani 1 1 d . . . 
C21 C 0.5138(3) 0.63561(19) 0.42765(18) 0.0476(7) Uani 1 1 d . . . 
C12 C -0.0823(3) 0.4804(2) 0.60997(19) 0.0499(7) Uani 1 1 d . . . 
H12 H -0.1021 0.4926 0.5392 0.060 Uiso 1 1 calc R . . 
C10 C -0.0791(2) 0.54389(19) 0.79019(18) 0.0413(6) Uani 1 1 d . . . 
C31 C 0.2905(2) -0.02371(18) 0.17941(19) 0.0440(6) Uani 1 1 d . . . 
C13 C -0.0311(2) 0.3824(2) 0.63972(19) 0.0459(6) Uani 1 1 d . . . 
C25 C 0.5866(2) 0.44901(18) 0.15196(18) 0.0413(6) Uani 1 1 d . . . 
C19 C 0.6629(3) 0.5430(2) 0.32524(19) 0.0508(7) Uani 1 1 d . . . 
H19 H 0.7483 0.5211 0.3174 0.061 Uiso 1 1 calc R . . 
C23 C 0.4370(3) 0.54941(19) 0.26217(19) 0.0470(7) Uani 1 1 d . . . 
H23 H 0.3673 0.5310 0.2109 0.056 Uiso 1 1 calc R . . 
C15 C -0.0299(3) 0.4443(2) 0.81836(19) 0.0511(7) Uani 1 1 d . . . 
H15 H -0.0129 0.4310 0.8891 0.061 Uiso 1 1 calc R . . 
C27 C 0.4581(2) 0.29370(18) 0.19708(18) 0.0417(6) Uani 1 1 d . . . 
H27 H 0.4475 0.3337 0.2587 0.050 Uiso 1 1 calc R . . 
C30 C 0.2961(3) 0.0424(2) 0.2692(2) 0.0520(7) Uani 1 1 d . . . 
H30 H 0.2640 0.0172 0.3282 0.062 Uiso 1 1 calc R . . 
C6 C 0.1075(2) 0.87034(19) 0.81899(19) 0.0449(6) Uani 1 1 d . . . 
C32 C 0.3364(3) 0.01530(19) 0.09176(19) 0.0491(7) Uani 1 1 d . . . 
H32 H 0.3318 -0.0281 0.0301 0.059 Uiso 1 1 calc R . . 
C26 C 0.5260(3) 0.34275(19) 0.13059(19) 0.0472(7) Uani 1 1 d . . . 
H26 H 0.5350 0.3066 0.0666 0.057 Uiso 1 1 calc R . . 
C7 C 0.0478(3) 0.7641(2) 0.8220(2) 0.0501(7) Uani 1 1 d . . . 
H7 H 0.0868 0.7075 0.7869 0.060 Uiso 1 1 calc R . . 
C8 C -0.0566(3) 0.7382(2) 0.86928(19) 0.0471(7) Uani 1 1 d . . . 
H8 H -0.0996 0.7935 0.9030 0.056 Uiso 1 1 calc R . . 
C20 C 0.6394(3) 0.6023(2) 0.4144(2) 0.0580(8) Uani 1 1 d . . . 
H20 H 0.7088 0.6201 0.4661 0.070 Uiso 1 1 calc R . . 
C5 C 0.0533(3) 0.9656(2) 0.8557(2) 0.0527(7) Uani 1 1 d . . . 
H5 H -0.0262 0.9626 0.8839 0.063 Uiso 1 1 calc R . . 
C14 C -0.0054(3) 0.3643(2) 0.7451(2) 0.0544(7) Uani 1 1 d . . . 
H14 H 0.0284 0.2983 0.7663 0.065 Uiso 1 1 calc R . . 
C3 C 0.2327(3) 1.0710(2) 0.8108(2) 0.0479(7) Uani 1 1 d . . . 
C4 C 0.1144(3) 1.0637(2) 0.8514(2) 0.0568(7) Uani 1 1 d . . . 
H4 H 0.0755 1.1263 0.8763 0.068 Uiso 1 1 calc R . . 
C1 C 0.2268(3) 0.8798(2) 0.7789(2) 0.0593(8) Uani 1 1 d . . . 
H1 H 0.2664 0.8175 0.7545 0.071 Uiso 1 1 calc R . . 
C29 C 0.3483(3) 0.14489(19) 0.27285(19) 0.0483(7) Uani 1 1 d . . . 
H29 H 0.3505 0.1883 0.3343 0.058 Uiso 1 1 calc R . . 
C2 C 0.2893(3) 0.9788(2) 0.7740(2) 0.0574(7) Uani 1 1 d . . . 
H2 H 0.3690 0.9825 0.7460 0.069 Uiso 1 1 calc R . . 
C22 C 0.4118(3) 0.6100(2) 0.35081(19) 0.0488(7) Uani 1 1 d . . . 
H22 H 0.3267 0.6332 0.3583 0.059 Uiso 1 1 calc R . . 
C34 C 0.2310(3) -0.1971(2) 0.0960(2) 0.0768(9) Uani 1 1 d . . . 
H34A H 0.1798 -0.1657 0.0380 0.115 Uiso 1 1 calc R . . 
H34B H 0.1899 -0.2635 0.1110 0.115 Uiso 1 1 calc R . . 
H34C H 0.3183 -0.2115 0.0786 0.115 Uiso 1 1 calc R . . 
C18 C 0.4083(3) 1.1843(2) 0.7722(3) 0.0927(12) Uani 1 1 d . . . 
H18A H 0.4740 1.1452 0.8141 0.139 Uiso 1 1 calc R . . 
H18B H 0.4328 1.2596 0.7756 0.139 Uiso 1 1 calc R . . 
H18C H 0.4016 1.1561 0.7008 0.139 Uiso 1 1 calc R . . 
C16 C 0.0487(3) 0.2085(2) 0.5863(2) 0.0725(9) Uani 1 1 d . . . 
H16A H -0.0110 0.1665 0.6219 0.087 Uiso 1 1 calc R . . 
H16B H 0.1303 0.2204 0.6325 0.087 Uiso 1 1 calc R . . 
C35 C 0.3753(3) 0.7362(3) 0.5362(2) 0.0761(10) Uani 1 1 d . . . 
H35A H 0.3719 0.7500 0.6107 0.091 Uiso 1 1 calc R . . 
H35B H 0.3074 0.6830 0.5105 0.091 Uiso 1 1 calc R . . 
C17 C 0.0753(4) 0.1492(3) 0.4867(3) 0.1023(13) Uani 1 1 d . . . 
H17A H -0.0051 0.1418 0.4399 0.153 Uiso 1 1 calc R . . 
H17B H 0.1089 0.0787 0.5019 0.153 Uiso 1 1 calc R . . 
H17C H 0.1391 0.1890 0.4546 0.153 Uiso 1 1 calc R . . 
C36 C 0.3481(4) 0.8381(3) 0.4821(3) 0.1084(13) Uani 1 1 d . . . 
H36A H 0.4175 0.8898 0.5048 0.163 Uiso 1 1 calc R . . 
H36B H 0.2656 0.8669 0.4988 0.163 Uiso 1 1 calc R . . 
H36C H 0.3438 0.8236 0.4078 0.163 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 
O5 C31 1.358(3) . ? 
O5 C34 1.411(3) . ? 
O2 C13 1.367(3) . ? 
O2 C16 1.424(3) . ? 
N1 C9 1.291(3) . ? 
N1 O3 1.401(2) . ? 
N2 C25 1.287(3) . ? 
N2 O6 1.407(2) . ? 
O4 C21 1.372(3) . ? 
O4 C35 1.427(3) . ? 
C28 C33 1.386(3) . ? 
C28 C29 1.401(3) . ? 
C28 C27 1.456(3) . ? 
C33 C32 1.382(3) . ? 
C9 C8 1.452(3) . ? 
C9 C10 1.481(3) . ? 
O1 C3 1.366(3) . ? 
O1 C18 1.413(3) . ? 
C11 C12 1.368(3) . ? 
C11 C10 1.389(3) . ? 
C24 C23 1.375(3) . ? 
C24 C19 1.379(3) . ? 
C24 C25 1.488(3) . ? 
C21 C22 1.372(3) . ? 
C21 C20 1.375(4) . ? 
C12 C13 1.377(3) . ? 
C10 C15 1.383(3) . ? 
C31 C30 1.375(3) . ? 
C31 C32 1.382(3) . ? 
C13 C14 1.382(3) . ? 
C25 C26 1.448(3) . ? 
C19 C20 1.375(3) . ? 
C23 C22 1.382(3) . ? 
C15 C14 1.374(3) . ? 
C27 C26 1.332(3) . ? 
C30 C29 1.369(3) . ? 
C6 C1 1.386(3) . ? 
C6 C5 1.387(3) . ? 
C6 C7 1.449(3) . ? 
C7 C8 1.335(3) . ? 
C5 C4 1.368(3) . ? 
C3 C2 1.368(3) . ? 
C3 C4 1.377(3) . ? 
C1 C2 1.385(4) . ? 
C16 C17 1.496(4) . ? 
C35 C36 1.484(4) . ? 
 
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 
C31 O5 C34 119.1(2) . . ? 
C13 O2 C16 118.4(2) . . ? 
C9 N1 O3 114.1(2) . . ? 
C25 N2 O6 113.15(19) . . ? 
C21 O4 C35 118.7(2) . . ? 
C33 C28 C29 116.7(2) . . ? 
C33 C28 C27 124.7(2) . . ? 
C29 C28 C27 118.5(2) . . ? 
C32 C33 C28 121.9(2) . . ? 
N1 C9 C8 124.2(2) . . ? 
N1 C9 C10 114.4(2) . . ? 
C8 C9 C10 121.4(2) . . ? 
C3 O1 C18 118.2(2) . . ? 
C12 C11 C10 121.5(2) . . ? 
C23 C24 C19 117.6(2) . . ? 
C23 C24 C25 121.4(2) . . ? 
C19 C24 C25 121.0(2) . . ? 
C22 C21 O4 124.7(2) . . ? 
C22 C21 C20 119.6(2) . . ? 
O4 C21 C20 115.7(2) . . ? 
C11 C12 C13 120.5(2) . . ? 
C15 C10 C11 117.1(2) . . ? 
C15 C10 C9 121.0(2) . . ? 
C11 C10 C9 121.9(2) . . ? 
O5 C31 C30 115.9(2) . . ? 
O5 C31 C32 125.0(2) . . ? 
C30 C31 C32 119.1(2) . . ? 
O2 C13 C12 116.0(2) . . ? 
O2 C13 C14 124.9(2) . . ? 
C12 C13 C14 119.2(2) . . ? 
N2 C25 C26 125.1(2) . . ? 
N2 C25 C24 114.9(2) . . ? 
C26 C25 C24 120.0(2) . . ? 
C20 C19 C24 121.0(2) . . ? 
C24 C23 C22 122.2(2) . . ? 
C14 C15 C10 122.0(2) . . ? 
C26 C27 C28 128.6(2) . . ? 
C29 C30 C31 120.8(2) . . ? 
C1 C6 C5 116.6(2) . . ? 
C1 C6 C7 119.5(2) . . ? 
C5 C6 C7 124.0(2) . . ? 
C31 C32 C33 120.0(2) . . ? 
C27 C26 C25 123.9(2) . . ? 
C8 C7 C6 127.5(2) . . ? 
C7 C8 C9 123.3(2) . . ? 
C21 C20 C19 120.5(2) . . ? 
C4 C5 C6 121.5(2) . . ? 
C15 C14 C13 119.7(2) . . ? 
O1 C3 C2 124.6(2) . . ? 
O1 C3 C4 116.0(2) . . ? 
C2 C3 C4 119.4(2) . . ? 
C5 C4 C3 120.8(2) . . ? 
C2 C1 C6 122.4(2) . . ? 
C30 C29 C28 121.5(2) . . ? 
C3 C2 C1 119.3(3) . . ? 
C21 C22 C23 119.1(2) . . ? 
O2 C16 C17 107.9(3) . . ? 
O4 C35 C36 111.9(3) . . ? 
 
_diffrn_measured_fraction_theta_max    0.998 
_diffrn_reflns_theta_full              25.07 
_diffrn_measured_fraction_theta_full   0.998 
_refine_diff_density_max    0.337 
_refine_diff_density_min   -0.310 
_refine_diff_density_rms    0.042 
