data_mo_ZZX606_0a
_audit_creation_method             'SHELXL-2018/3'
_shelx_SHELXL_version_number       '2018/3'
_chemical_formula_moiety           'C18 H21 N O5'
_chemical_formula_sum              'C18 H21 N O5'
_chemical_formula_weight           331.36
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'

_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.
;
_space_group_crystal_system        monoclinic
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 21/n'
_space_group_name_Hall             '-P 2yn'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                     5.986(8)
_cell_length_b                     30.35(4)
_cell_length_c                     9.570(14)
_cell_angle_alpha                  90
_cell_angle_beta                   98.61(3)
_cell_angle_gamma                  90
_cell_volume                       1719(4)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      1706
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        19.84
_cell_measurement_theta_min        2.27
_shelx_estimated_absorpt_T_max     0.998
_shelx_estimated_absorpt_T_min     0.982
_exptl_absorpt_coefficient_mu      0.094
_exptl_absorpt_correction_T_max    0.9590
_exptl_absorpt_correction_T_min    0.8116
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_density_diffrn      1.280
_exptl_crystal_description         plate
_exptl_crystal_F_000               704
_exptl_crystal_size_max            0.200
_exptl_crystal_size_mid            0.100
_exptl_crystal_size_min            0.020
_diffrn_reflns_av_R_equivalents    0.0839
_diffrn_reflns_av_unetI/netI       0.0457
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  1.000
_diffrn_reflns_limit_h_max         7
_diffrn_reflns_limit_h_min         -7
_diffrn_reflns_limit_k_max         36
_diffrn_reflns_limit_k_min         -36
_diffrn_reflns_limit_l_max         11
_diffrn_reflns_limit_l_min         -11
_diffrn_reflns_number              31906
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  1.000
_diffrn_reflns_theta_full          24.998
_diffrn_reflns_theta_max           24.998
_diffrn_reflns_theta_min           2.255
_diffrn_ambient_temperature        100(2)
_diffrn_detector_area_resol_mean   7.41
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  1.000
_diffrn_measurement_device_type    'Bruker D8 Venture'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'sealed X-ray tube'
_reflns_number_gt                  2236
_reflns_number_total               3026
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'Bruker SAINT'
_computing_data_collection         'Bruker APEX2'
_computing_data_reduction          'Bruker SAINT'
_computing_molecular_graphics      'Bruker SHELXTL'
_computing_publication_material    'Bruker SHELXTL'
_computing_structure_refinement    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution      'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max           0.211
_refine_diff_density_min           -0.418
_refine_diff_density_rms           0.056
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.076
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       221
_refine_ls_number_reflns           3026
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0725
_refine_ls_R_factor_gt             0.0488
_refine_ls_restrained_S_all        1.076
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0759P)²+0.3963P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1262
_refine_ls_wR_factor_ref           0.1408
_refine_special_details
;
 Reflections at 2θ > 50° were ommited from the refinement as almost no data
 was onservable beyond this limit.  The 0 2 0 reflection has also been omitted 
 as it has a much lower measured intensity than predicted and it is assumed that 
 this reflection is obscured by the beamstop. Th 0 2 0 reflection has smaller 
 2θ than any other non-absent reflection in the dataset.
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       direct
_atom_sites_solution_secondary     diffmap
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
 C1 C 0.6359(3) 0.59176(6) 0.2516(2) 0.0247(5) Uani 1 1 d . . . . .
 C2 C 0.8102(3) 0.56188(6) 0.3420(2) 0.0240(5) Uani 1 1 d . . . . .
 C3 C 0.6811(3) 0.55320(6) 0.4713(2) 0.0241(5) Uani 1 1 d . . . . .
 H3A H 0.522673 0.543283 0.445865 0.029 Uiso 1 1 calc R U . . .
 H3B H 0.764898 0.535220 0.548141 0.029 Uiso 1 1 calc R U . . .
 C4 C 0.7121(3) 0.60397(6) 0.4898(2) 0.0247(5) Uani 1 1 d . . . . .
 C5 C 0.9443(3) 0.59863(7) 0.4389(2) 0.0265(5) Uani 1 1 d . . . . .
 H5A H 1.066846 0.587386 0.511110 0.032 Uiso 1 1 calc R U . . .
 H5B H 0.993456 0.624270 0.387244 0.032 Uiso 1 1 calc R U . . .
 C6 C 0.4594(3) 0.66053(7) 0.3412(2) 0.0237(5) Uani 1 1 d . . . . .
 C7 C 0.1937(4) 0.70328(7) 0.1700(2) 0.0300(5) Uani 1 1 d . . . . .
 C8 C 0.3746(4) 0.73492(8) 0.1340(3) 0.0474(7) Uani 1 1 d . . . . .
 H8A H 0.302216 0.761110 0.087427 0.071 Uiso 1 1 calc R U . . .
 H8B H 0.465221 0.720297 0.070392 0.071 Uiso 1 1 calc R U . . .
 H8C H 0.472526 0.743670 0.220899 0.071 Uiso 1 1 calc R U . . .
 C9 C 0.0555(4) 0.72218(7) 0.2769(3) 0.0350(6) Uani 1 1 d . . . . .
 H9A H -0.035530 0.746903 0.234198 0.052 Uiso 1 1 calc R U . . .
 H9B H 0.157311 0.732507 0.360225 0.052 Uiso 1 1 calc R U . . .
 H9C H -0.044331 0.699298 0.305032 0.052 Uiso 1 1 calc R U . . .
 C10 C 0.0378(4) 0.68745(9) 0.0380(3) 0.0478(7) Uani 1 1 d . . . . .
 H10A H -0.039271 0.712812 -0.010948 0.072 Uiso 1 1 calc R U . . .
 H10B H -0.074483 0.667025 0.065742 0.072 Uiso 1 1 calc R U . . .
 H10C H 0.127497 0.672395 -0.025196 0.072 Uiso 1 1 calc R U . . .
 C11 C 0.9256(3) 0.52686(6) 0.2683(2) 0.0236(5) Uani 1 1 d . . . . .
 C12 C 0.8401(3) 0.48389(7) 0.2531(2) 0.0281(5) Uani 1 1 d . . . . .
 H12 H 0.705699 0.476546 0.289516 0.034 Uiso 1 1 calc R U . . .
 C13 C 0.9509(4) 0.45180(7) 0.1847(2) 0.0310(5) Uani 1 1 d . . . . .
 H13 H 0.890785 0.422827 0.173980 0.037 Uiso 1 1 calc R U . . .
 C14 C 1.1502(4) 0.46212(7) 0.1320(2) 0.0312(5) Uani 1 1 d . . . . .
 H14 H 1.227490 0.440069 0.087484 0.037 Uiso 1 1 calc R U . . .
 C15 C 1.2347(3) 0.50501(7) 0.1450(2) 0.0291(5) Uani 1 1 d . . . . .
 H15 H 1.368860 0.512288 0.108200 0.035 Uiso 1 1 calc R U . . .
 C16 C 1.1228(3) 0.53717(7) 0.2120(2) 0.0269(5) Uani 1 1 d . . . . .
 H16 H 1.180462 0.566372 0.219703 0.032 Uiso 1 1 calc R U . . .
 C17 C 0.6823(3) 0.62781(6) 0.6246(2) 0.0245(5) Uani 1 1 d . . . . .
 C18 C 0.4182(4) 0.64680(7) 0.7769(2) 0.0322(5) Uani 1 1 d . . . . .
 H18A H 0.254503 0.650969 0.769365 0.048 Uiso 1 1 calc R U . . .
 H18B H 0.493109 0.675593 0.782342 0.048 Uiso 1 1 calc R U . . .
 H18C H 0.472622 0.629801 0.862323 0.048 Uiso 1 1 calc R U . . .
 N1 N 0.5618(3) 0.61890(5) 0.35746(19) 0.0248(4) Uani 1 1 d . . . . .
 O1 O 0.5038(2) 0.68975(5) 0.42814(16) 0.0317(4) Uani 1 1 d . . . . .
 O2 O 0.3068(2) 0.66104(4) 0.22441(16) 0.0277(4) Uani 1 1 d . . . . .
 O3 O 0.5806(2) 0.59367(5) 0.12431(17) 0.0308(4) Uani 1 1 d . . . . .
 O4 O 0.8335(2) 0.64665(5) 0.69938(16) 0.0313(4) Uani 1 1 d . . . . .
 O5 O 0.4696(2) 0.62298(5) 0.65267(16) 0.0290(4) 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 C2 1.545(3) . ?
 C1 N1 1.427(3) . ?
 C1 O3 1.215(3) . ?
 C2 C3 1.576(3) . ?
 C2 C5 1.589(3) . ?
 C2 C11 1.500(3) . ?
 C3 H3A 0.9900 . ?
 C3 H3B 0.9900 . ?
 C3 C4 1.559(3) . ?
 C4 C5 1.549(3) . ?
 C4 C17 1.513(4) . ?
 C4 N1 1.509(3) . ?
 C5 H5A 0.9900 . ?
 C5 H5B 0.9900 . ?
 C6 N1 1.403(3) . ?
 C6 O1 1.218(3) . ?
 C6 O2 1.333(3) . ?
 C7 C8 1.525(3) . ?
 C7 C9 1.521(3) . ?
 C7 C10 1.531(4) . ?
 C7 O2 1.506(3) . ?
 C8 H8A 0.9800 . ?
 C8 H8B 0.9800 . ?
 C8 H8C 0.9800 . ?
 C9 H9A 0.9800 . ?
 C9 H9B 0.9800 . ?
 C9 H9C 0.9800 . ?
 C10 H10A 0.9800 . ?
 C10 H10B 0.9800 . ?
 C10 H10C 0.9800 . ?
 C11 C12 1.401(3) . ?
 C11 C16 1.404(3) . ?
 C12 H12 0.9500 . ?
 C12 C13 1.395(3) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.399(3) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.396(4) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.394(3) . ?
 C16 H16 0.9500 . ?
 C17 O4 1.210(3) . ?
 C17 O5 1.348(3) . ?
 C18 H18A 0.9800 . ?
 C18 H18B 0.9800 . ?
 C18 H18C 0.9800 . ?
 C18 O5 1.463(3) . ?

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
 N1 C1 C2 101.4(2) . . ?
 O3 C1 C2 130.44(19) . . ?
 O3 C1 N1 128.10(19) . . ?
 C1 C2 C3 99.68(18) . . ?
 C1 C2 C5 98.88(18) . . ?
 C3 C2 C5 85.60(17) . . ?
 C11 C2 C1 118.2(2) . . ?
 C11 C2 C3 124.41(18) . . ?
 C11 C2 C5 122.91(18) . . ?
 C2 C3 H3A 115.0 . . ?
 C2 C3 H3B 115.0 . . ?
 H3A C3 H3B 112.0 . . ?
 C4 C3 C2 81.95(15) . . ?
 C4 C3 H3A 115.0 . . ?
 C4 C3 H3B 115.0 . . ?
 C5 C4 C3 87.60(15) . . ?
 C17 C4 C3 122.84(18) . . ?
 C17 C4 C5 122.99(18) . . ?
 N1 C4 C3 98.95(16) . . ?
 N1 C4 C5 102.59(19) . . ?
 N1 C4 C17 116.13(18) . . ?
 C2 C5 H5A 115.0 . . ?
 C2 C5 H5B 115.0 . . ?
 C4 C5 C2 81.85(16) . . ?
 C4 C5 H5A 115.0 . . ?
 C4 C5 H5B 115.0 . . ?
 H5A C5 H5B 112.0 . . ?
 O1 C6 N1 122.2(2) . . ?
 O1 C6 O2 128.07(19) . . ?
 O2 C6 N1 109.67(18) . . ?
 C8 C7 C10 112.1(2) . . ?
 C9 C7 C8 113.0(2) . . ?
 C9 C7 C10 110.3(2) . . ?
 O2 C7 C8 108.47(19) . . ?
 O2 C7 C9 110.52(19) . . ?
 O2 C7 C10 101.81(18) . . ?
 C7 C8 H8A 109.5 . . ?
 C7 C8 H8B 109.5 . . ?
 C7 C8 H8C 109.5 . . ?
 H8A C8 H8B 109.5 . . ?
 H8A C8 H8C 109.5 . . ?
 H8B C8 H8C 109.5 . . ?
 C7 C9 H9A 109.5 . . ?
 C7 C9 H9B 109.5 . . ?
 C7 C9 H9C 109.5 . . ?
 H9A C9 H9B 109.5 . . ?
 H9A C9 H9C 109.5 . . ?
 H9B C9 H9C 109.5 . . ?
 C7 C10 H10A 109.5 . . ?
 C7 C10 H10B 109.5 . . ?
 C7 C10 H10C 109.5 . . ?
 H10A C10 H10B 109.5 . . ?
 H10A C10 H10C 109.5 . . ?
 H10B C10 H10C 109.5 . . ?
 C12 C11 C2 121.45(19) . . ?
 C12 C11 C16 118.86(18) . . ?
 C16 C11 C2 119.68(19) . . ?
 C11 C12 H12 119.8 . . ?
 C13 C12 C11 120.4(2) . . ?
 C13 C12 H12 119.8 . . ?
 C12 C13 H13 119.9 . . ?
 C12 C13 C14 120.3(2) . . ?
 C14 C13 H13 119.9 . . ?
 C13 C14 H14 120.2 . . ?
 C15 C14 C13 119.61(19) . . ?
 C15 C14 H14 120.2 . . ?
 C14 C15 H15 119.9 . . ?
 C16 C15 C14 120.1(2) . . ?
 C16 C15 H15 119.9 . . ?
 C11 C16 H16 119.7 . . ?
 C15 C16 C11 120.7(2) . . ?
 C15 C16 H16 119.7 . . ?
 O4 C17 C4 123.85(19) . . ?
 O4 C17 O5 125.4(2) . . ?
 O5 C17 C4 110.70(17) . . ?
 H18A C18 H18B 109.5 . . ?
 H18A C18 H18C 109.5 . . ?
 H18B C18 H18C 109.5 . . ?
 O5 C18 H18A 109.5 . . ?
 O5 C18 H18B 109.5 . . ?
 O5 C18 H18C 109.5 . . ?
 C1 N1 C4 102.27(18) . . ?
 C6 N1 C1 128.19(19) . . ?
 C6 N1 C4 124.02(17) . . ?
 C6 O2 C7 121.02(16) . . ?
 C17 O5 C18 115.34(16) . . ?

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
 C1 C2 C3 C4 -63.60(16) . . . . ?
 C1 C2 C5 C4 64.18(17) . . . . ?
 C1 C2 C11 C12 -92.7(2) . . . . ?
 C1 C2 C11 C16 86.7(2) . . . . ?
 C2 C1 N1 C4 4.21(18) . . . . ?
 C2 C1 N1 C6 158.30(18) . . . . ?
 C2 C3 C4 C5 -35.64(14) . . . . ?
 C2 C3 C4 C17 -164.06(19) . . . . ?
 C2 C3 C4 N1 66.73(18) . . . . ?
 C2 C11 C12 C13 -179.71(19) . . . . ?
 C2 C11 C16 C15 179.04(19) . . . . ?
 C3 C2 C5 C4 -34.95(14) . . . . ?
 C3 C2 C11 C12 34.1(3) . . . . ?
 C3 C2 C11 C16 -146.5(2) . . . . ?
 C3 C4 C5 C2 35.31(15) . . . . ?
 C3 C4 C17 O4 115.3(2) . . . . ?
 C3 C4 C17 O5 -61.4(2) . . . . ?
 C3 C4 N1 C1 -48.48(18) . . . . ?
 C3 C4 N1 C6 156.00(17) . . . . ?
 C4 C17 O5 C18 -176.75(16) . . . . ?
 C5 C2 C3 C4 34.68(14) . . . . ?
 C5 C2 C11 C12 143.5(2) . . . . ?
 C5 C2 C11 C16 -37.1(3) . . . . ?
 C5 C4 C17 O4 4.2(3) . . . . ?
 C5 C4 C17 O5 -172.44(17) . . . . ?
 C5 C4 N1 C1 41.05(18) . . . . ?
 C5 C4 N1 C6 -114.48(19) . . . . ?
 C8 C7 O2 C6 61.6(3) . . . . ?
 C9 C7 O2 C6 -62.8(2) . . . . ?
 C10 C7 O2 C6 179.96(18) . . . . ?
 C11 C2 C3 C4 162.11(19) . . . . ?
 C11 C2 C5 C4 -163.66(19) . . . . ?
 C11 C12 C13 C14 0.7(3) . . . . ?
 C12 C11 C16 C15 -1.5(3) . . . . ?
 C12 C13 C14 C15 -1.5(3) . . . . ?
 C13 C14 C15 C16 0.9(3) . . . . ?
 C14 C15 C16 C11 0.6(3) . . . . ?
 C16 C11 C12 C13 0.8(3) . . . . ?
 C17 C4 C5 C2 163.61(19) . . . . ?
 C17 C4 N1 C1 178.01(16) . . . . ?
 C17 C4 N1 C6 22.5(3) . . . . ?
 N1 C1 C2 C3 40.47(18) . . . . ?
 N1 C1 C2 C5 -46.54(18) . . . . ?
 N1 C1 C2 C11 178.38(16) . . . . ?
 N1 C4 C5 C2 -63.32(17) . . . . ?
 N1 C4 C17 O4 -123.2(2) . . . . ?
 N1 C4 C17 O5 60.1(2) . . . . ?
 N1 C6 O2 C7 -171.56(16) . . . . ?
 O1 C6 N1 C1 -141.0(2) . . . . ?
 O1 C6 N1 C4 8.0(3) . . . . ?
 O1 C6 O2 C7 11.7(3) . . . . ?
 O2 C6 N1 C1 42.0(3) . . . . ?
 O2 C6 N1 C4 -168.95(16) . . . . ?
 O3 C1 C2 C3 -142.4(2) . . . . ?
 O3 C1 C2 C5 130.6(2) . . . . ?
 O3 C1 C2 C11 -4.5(3) . . . . ?
 O3 C1 N1 C4 -173.0(2) . . . . ?
 O3 C1 N1 C6 -18.9(3) . . . . ?
 O4 C17 O5 C18 6.6(3) . . . . ?

