 
data_shelx 
  
_audit_creation_method            'SHELXL-2018/1' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety         'C18 H19 N O4' 
_chemical_formula_sum 
 'C18 H19 N O4' 
_chemical_formula_weight          313.34 
  
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' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            4 
_space_group_name_H-M_alt         'P 21' 
_space_group_name_Hall            'P 2yb' 
  
_shelx_space_group_comment 
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x, y+1/2, -z' 
  
_cell_length_a                    5.757(4) 
_cell_length_b                    12.135(8) 
_cell_length_c                    11.539(7) 
_cell_angle_alpha                 90 
_cell_angle_beta                  102.075(7) 
_cell_angle_gamma                 90 
_cell_volume                      788.3(9) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     296(2) 
_cell_measurement_reflns_used     9703 
_cell_measurement_theta_min       3.61 
_cell_measurement_theta_max       30.16 
  
_exptl_crystal_description        BLOCK 
_exptl_crystal_colour             yellow 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.320 
_exptl_crystal_F_000              332 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.210 
_exptl_crystal_size_mid           0.113 
_exptl_crystal_size_min           0.097 
_exptl_absorpt_coefficient_mu     0.093 
_shelx_estimated_absorpt_T_min    0.981 
_shelx_estimated_absorpt_T_max    0.991 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.7050 
_exptl_absorpt_correction_T_max   0.7461 
_exptl_absorpt_process_details    'SADABS-2012/1' 
_diffrn_ambient_temperature       296(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_monochromator   graphite
_diffrn_radiation_probe           x-ray
_diffrn_radiation_type            MoK\a 
_diffrn_source                    'rotating-anode X-ray tube' 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             33881 
_diffrn_reflns_av_unetI/netI      0.0114 
_diffrn_reflns_av_R_equivalents   0.0210 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -17 
_diffrn_reflns_limit_k_max        17 
_diffrn_reflns_limit_l_min        -16 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          3.611 
_diffrn_reflns_theta_max          30.560 
_diffrn_reflns_theta_full         25.242 
_diffrn_measured_fraction_theta_max   0.997 
_diffrn_measured_fraction_theta_full  0.998 
_diffrn_reflns_Laue_measured_fraction_max    0.997 
_diffrn_reflns_Laue_measured_fraction_full   0.998 
_diffrn_reflns_point_group_measured_fraction_max   0.997 
_diffrn_reflns_point_group_measured_fraction_full  0.998 
_reflns_number_total              4830 
_reflns_number_gt                 4480 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.917 
_reflns_Friedel_fraction_max      0.997 
_reflns_Friedel_fraction_full     0.999 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_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-2018/1 (Sheldrick, 2018)' 
_computing_molecular_graphics     'PLATON (Spek A.L.,2003 ' 
_computing_publication_material   'WinGX publication routines (Farrugia, 2012)' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0643P)²+0.0260P] 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      none 
_refine_ls_extinction_coef        . 
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2011 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
; 
_refine_ls_abs_structure_Flack    -0.19(14) 
_chemical_absolute_configuration  rm 
_refine_ls_number_reflns          4830 
_refine_ls_number_parameters      209 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0378 
_refine_ls_R_factor_gt            0.0347 
_refine_ls_wR_factor_ref          0.0990 
_refine_ls_wR_factor_gt           0.0960 
_refine_ls_goodness_of_fit_ref    1.039 
_refine_ls_restrained_S_all       1.039 
_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_site_symmetry_order 
 _atom_site_calc_flag 
 _atom_site_refinement_flags_posn 
 _atom_site_refinement_flags_adp 
 _atom_site_refinement_flags_occupancy 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.6448(2) 0.66407(12) 0.67992(14) 0.0615(3) Uani 1 1 d . . . . . 
O2 O 0.45754(18) 0.88521(8) 0.74922(10) 0.0443(2) Uani 1 1 d . . . . . 
O3 O 0.1858(5) 1.14813(17) 0.7242(2) 0.1115(8) Uani 1 1 d . . . . . 
O4 O 0.0337(2) 1.02730(13) 0.58787(15) 0.0649(4) Uani 1 1 d . . . . . 
N1 N 0.5043(2) 0.62648(11) 0.84847(12) 0.0455(3) Uani 1 1 d . . . . . 
C1 C 0.5176(2) 0.68468(12) 0.74885(14) 0.0425(3) Uani 1 1 d . . . . . 
C2 C 0.3382(2) 0.78135(11) 0.73892(12) 0.0377(3) Uani 1 1 d . . . . . 
C3 C 0.2300(2) 0.76309(12) 0.84476(13) 0.0415(3) Uani 1 1 d . . . . . 
C4 C 0.0524(3) 0.82021(19) 0.88275(16) 0.0571(4) Uani 1 1 d . . . . . 
H4 H -0.017961 0.881910 0.842113 0.068 Uiso 1 1 calc R U . . . 
C5 C -0.0179(4) 0.7822(3) 0.9840(2) 0.0730(6) Uani 1 1 d . . . . . 
H5 H -0.138046 0.818901 1.011082 0.088 Uiso 1 1 calc R U . . . 
C6 C 0.0868(4) 0.6919(2) 1.04449(17) 0.0729(7) Uani 1 1 d . . . . . 
H6 H 0.036900 0.668922 1.112220 0.087 Uiso 1 1 calc R U . . . 
C7 C 0.2655(4) 0.63371(18) 1.00724(15) 0.0585(4) Uani 1 1 d . . . . . 
H7 H 0.336399 0.572403 1.048438 0.070 Uiso 1 1 calc R U . . . 
C8 C 0.3335(3) 0.67121(13) 0.90572(13) 0.0428(3) Uani 1 1 d . . . . . 
C9 C 0.6345(3) 0.52515(16) 0.8830(2) 0.0598(4) Uani 1 1 d . . . . . 
H9A H 0.691557 0.525027 0.968248 0.072 Uiso 1 1 calc R U . . . 
H9B H 0.771832 0.522954 0.846591 0.072 Uiso 1 1 calc R U . . . 
C10 C 0.4881(4) 0.42427(15) 0.84795(18) 0.0616(4) Uani 1 1 d . . . . . 
H10 H 0.560649 0.356840 0.870112 0.074 Uiso 1 1 calc R U . . . 
C11 C 0.2702(4) 0.42150(19) 0.78984(16) 0.0648(5) Uani 1 1 d . . . . . 
H11A H 0.190039 0.486803 0.765728 0.078 Uiso 1 1 calc R U . . . 
H11B H 0.193764 0.354199 0.772145 0.078 Uiso 1 1 calc R U . . . 
C12 C 0.1670(3) 0.78416(13) 0.61805(13) 0.0444(3) Uani 1 1 d . . . . . 
H12A H 0.009274 0.805864 0.626591 0.053 Uiso 1 1 calc R U . . . 
H12B H 0.157185 0.712216 0.580701 0.053 Uiso 1 1 calc R U . . . 
C13 C 0.2697(3) 0.86935(12) 0.54387(13) 0.0414(3) Uani 1 1 d . . . . . 
C14 C 0.4755(2) 0.92258(12) 0.63389(14) 0.0422(3) Uani 1 1 d . . . . . 
H14 H 0.628204 0.899954 0.616752 0.051 Uiso 1 1 calc R U . . . 
C15 C 0.3582(5) 0.8194(2) 0.43990(19) 0.0723(6) Uani 1 1 d . . . . . 
H15A H 0.229155 0.782934 0.387901 0.108 Uiso 1 1 calc R U . . . 
H15B H 0.481799 0.767166 0.468941 0.108 Uiso 1 1 calc R U . . . 
H15C H 0.419295 0.876795 0.397343 0.108 Uiso 1 1 calc R U . . . 
C16 C 0.0861(3) 0.95751(16) 0.49638(16) 0.0558(4) Uani 1 1 d . . . . . 
H16A H 0.144576 1.002446 0.439097 0.067 Uiso 1 1 calc R U . . . 
H16B H -0.059174 0.922065 0.455609 0.067 Uiso 1 1 calc R U . . . 
C17 C 0.2198(4) 1.08013(15) 0.6540(2) 0.0636(5) Uani 1 1 d . . . . . 
C18 C 0.4592(3) 1.04722(13) 0.63513(18) 0.0540(4) Uani 1 1 d . . . . . 
H18A H 0.581608 1.076777 0.698228 0.065 Uiso 1 1 calc R U . . . 
H18B H 0.483409 1.076734 0.560435 0.065 Uiso 1 1 calc R U . . . 
  
  
_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 C1 1.215(2) . ? 
O2 C2 1.4286(18) . ? 
O2 C14 1.430(2) . ? 
O3 C17 1.201(3) . ? 
O4 C17 1.341(3) . ? 
O4 C16 1.434(3) . ? 
N1 C1 1.365(2) . ? 
N1 C8 1.404(2) . ? 
N1 C9 1.452(2) . ? 
C1 C2 1.552(2) . ? 
C2 C3 1.499(2) . ? 
C2 C12 1.531(2) . ? 
C3 C4 1.381(2) . ? 
C3 C8 1.385(2) . ? 
C4 C5 1.392(3) . ? 
C4 H4 0.9300 . ? 
C5 C6 1.370(4) . ? 
C5 H5 0.9300 . ? 
C6 C7 1.388(4) . ? 
C6 H6 0.9300 . ? 
C7 C8 1.387(2) . ? 
C7 H7 0.9300 . ? 
C9 C10 1.493(3) . ? 
C9 H9A 0.9700 . ? 
C9 H9B 0.9700 . ? 
C10 C11 1.293(3) . ? 
C10 H10 0.9300 . ? 
C11 H11A 0.9300 . ? 
C11 H11B 0.9300 . ? 
C12 C13 1.537(2) . ? 
C12 H12A 0.9700 . ? 
C12 H12B 0.9700 . ? 
C13 C16 1.523(2) . ? 
C13 C15 1.524(2) . ? 
C13 C14 1.544(2) . ? 
C14 C18 1.516(2) . ? 
C14 H14 0.9800 . ? 
C15 H15A 0.9600 . ? 
C15 H15B 0.9600 . ? 
C15 H15C 0.9600 . ? 
C16 H16A 0.9700 . ? 
C16 H16B 0.9700 . ? 
C17 C18 1.494(3) . ? 
C18 H18A 0.9700 . ? 
C18 H18B 0.9700 . ? 
  
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 
C2 O2 C14 109.24(11) . . ? 
C17 O4 C16 115.79(15) . . ? 
C1 N1 C8 111.39(12) . . ? 
C1 N1 C9 123.54(15) . . ? 
C8 N1 C9 124.81(14) . . ? 
O1 C1 N1 126.36(15) . . ? 
O1 C1 C2 126.21(14) . . ? 
N1 C1 C2 107.43(12) . . ? 
O2 C2 C3 109.71(12) . . ? 
O2 C2 C12 105.25(11) . . ? 
C3 C2 C12 116.60(12) . . ? 
O2 C2 C1 111.07(11) . . ? 
C3 C2 C1 102.23(11) . . ? 
C12 C2 C1 112.09(12) . . ? 
C4 C3 C8 120.77(16) . . ? 
C4 C3 C2 130.25(16) . . ? 
C8 C3 C2 108.97(13) . . ? 
C3 C4 C5 117.7(2) . . ? 
C3 C4 H4 121.2 . . ? 
C5 C4 H4 121.2 . . ? 
C6 C5 C4 121.2(2) . . ? 
C6 C5 H5 119.4 . . ? 
C4 C5 H5 119.4 . . ? 
C5 C6 C7 121.65(18) . . ? 
C5 C6 H6 119.2 . . ? 
C7 C6 H6 119.2 . . ? 
C8 C7 C6 116.9(2) . . ? 
C8 C7 H7 121.5 . . ? 
C6 C7 H7 121.5 . . ? 
C3 C8 C7 121.72(16) . . ? 
C3 C8 N1 109.97(13) . . ? 
C7 C8 N1 128.30(16) . . ? 
N1 C9 C10 112.97(15) . . ? 
N1 C9 H9A 109.0 . . ? 
C10 C9 H9A 109.0 . . ? 
N1 C9 H9B 109.0 . . ? 
C10 C9 H9B 109.0 . . ? 
H9A C9 H9B 107.8 . . ? 
C11 C10 C9 126.38(18) . . ? 
C11 C10 H10 116.8 . . ? 
C9 C10 H10 116.8 . . ? 
C10 C11 H11A 120.0 . . ? 
C10 C11 H11B 120.0 . . ? 
H11A C11 H11B 120.0 . . ? 
C2 C12 C13 105.84(12) . . ? 
C2 C12 H12A 110.6 . . ? 
C13 C12 H12A 110.6 . . ? 
C2 C12 H12B 110.6 . . ? 
C13 C12 H12B 110.6 . . ? 
H12A C12 H12B 108.7 . . ? 
C16 C13 C15 108.48(16) . . ? 
C16 C13 C12 110.71(13) . . ? 
C15 C13 C12 113.71(15) . . ? 
C16 C13 C14 108.98(13) . . ? 
C15 C13 C14 111.12(15) . . ? 
C12 C13 C14 103.72(12) . . ? 
O2 C14 C18 106.92(13) . . ? 
O2 C14 C13 107.39(11) . . ? 
C18 C14 C13 112.55(13) . . ? 
O2 C14 H14 110.0 . . ? 
C18 C14 H14 110.0 . . ? 
C13 C14 H14 110.0 . . ? 
C13 C15 H15A 109.5 . . ? 
C13 C15 H15B 109.5 . . ? 
H15A C15 H15B 109.5 . . ? 
C13 C15 H15C 109.5 . . ? 
H15A C15 H15C 109.5 . . ? 
H15B C15 H15C 109.5 . . ? 
O4 C16 C13 112.77(14) . . ? 
O4 C16 H16A 109.0 . . ? 
C13 C16 H16A 109.0 . . ? 
O4 C16 H16B 109.0 . . ? 
C13 C16 H16B 109.0 . . ? 
H16A C16 H16B 107.8 . . ? 
O3 C17 O4 119.3(2) . . ? 
O3 C17 C18 124.6(3) . . ? 
O4 C17 C18 116.16(17) . . ? 
C17 C18 C14 109.20(14) . . ? 
C17 C18 H18A 109.8 . . ? 
C14 C18 H18A 109.8 . . ? 
C17 C18 H18B 109.8 . . ? 
C14 C18 H18B 109.8 . . ? 
H18A C18 H18B 108.3 . . ? 
  
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 
C8 N1 C1 O1 -178.17(16) . . . . ? 
C9 N1 C1 O1 -3.8(3) . . . . ? 
C8 N1 C1 C2 1.18(16) . . . . ? 
C9 N1 C1 C2 175.54(14) . . . . ? 
C14 O2 C2 C3 -156.84(11) . . . . ? 
C14 O2 C2 C12 -30.64(14) . . . . ? 
C14 O2 C2 C1 90.88(13) . . . . ? 
O1 C1 C2 O2 -64.7(2) . . . . ? 
N1 C1 C2 O2 115.95(13) . . . . ? 
O1 C1 C2 C3 178.34(16) . . . . ? 
N1 C1 C2 C3 -1.01(14) . . . . ? 
O1 C1 C2 C12 52.7(2) . . . . ? 
N1 C1 C2 C12 -126.62(13) . . . . ? 
O2 C2 C3 C4 64.3(2) . . . . ? 
C12 C2 C3 C4 -55.2(2) . . . . ? 
C1 C2 C3 C4 -177.79(16) . . . . ? 
O2 C2 C3 C8 -117.43(13) . . . . ? 
C12 C2 C3 C8 123.11(14) . . . . ? 
C1 C2 C3 C8 0.51(14) . . . . ? 
C8 C3 C4 C5 0.1(3) . . . . ? 
C2 C3 C4 C5 178.22(16) . . . . ? 
C3 C4 C5 C6 0.5(3) . . . . ? 
C4 C5 C6 C7 -0.5(3) . . . . ? 
C5 C6 C7 C8 0.0(3) . . . . ? 
C4 C3 C8 C7 -0.7(2) . . . . ? 
C2 C3 C8 C7 -179.17(13) . . . . ? 
C4 C3 C8 N1 178.64(14) . . . . ? 
C2 C3 C8 N1 0.15(16) . . . . ? 
C6 C7 C8 C3 0.6(2) . . . . ? 
C6 C7 C8 N1 -178.55(16) . . . . ? 
C1 N1 C8 C3 -0.87(17) . . . . ? 
C9 N1 C8 C3 -175.15(15) . . . . ? 
C1 N1 C8 C7 178.39(15) . . . . ? 
C9 N1 C8 C7 4.1(2) . . . . ? 
C1 N1 C9 C10 -98.14(19) . . . . ? 
C8 N1 C9 C10 75.5(2) . . . . ? 
N1 C9 C10 C11 2.1(3) . . . . ? 
O2 C2 C12 C13 23.17(15) . . . . ? 
C3 C2 C12 C13 145.01(13) . . . . ? 
C1 C2 C12 C13 -97.68(14) . . . . ? 
C2 C12 C13 C16 -124.77(14) . . . . ? 
C2 C12 C13 C15 112.81(17) . . . . ? 
C2 C12 C13 C14 -8.00(15) . . . . ? 
C2 O2 C14 C18 146.78(13) . . . . ? 
C2 O2 C14 C13 25.76(14) . . . . ? 
C16 C13 C14 O2 108.11(14) . . . . ? 
C15 C13 C14 O2 -132.40(15) . . . . ? 
C12 C13 C14 O2 -9.86(15) . . . . ? 
C16 C13 C14 C18 -9.29(18) . . . . ? 
C15 C13 C14 C18 110.20(17) . . . . ? 
C12 C13 C14 C18 -127.26(14) . . . . ? 
C17 O4 C16 C13 57.2(2) . . . . ? 
C15 C13 C16 O4 -165.95(16) . . . . ? 
C12 C13 C16 O4 68.63(19) . . . . ? 
C14 C13 C16 O4 -44.84(19) . . . . ? 
C16 O4 C17 O3 172.6(2) . . . . ? 
C16 O4 C17 C18 -8.4(2) . . . . ? 
O3 C17 C18 C14 132.4(2) . . . . ? 
O4 C17 C18 C14 -46.5(2) . . . . ? 
O2 C14 C18 C17 -64.07(18) . . . . ? 
C13 C14 C18 C17 53.6(2) . . . . ? 
  
_refine_diff_density_max    0.188 
_refine_diff_density_min   -0.142 
_refine_diff_density_rms    0.028 
  
  
  
