# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1964616'
loop_
_audit_author_name
_audit_author_address
'Simon Lawrence'
;University College Cork
Republic of Ireland
;
_audit_update_record             
;
2019-11-08 deposited with the CCDC.	2019-12-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H23 N3 O5'
_chemical_formula_sum            'C19 H23 N3 O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         373.40

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_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                   6.8732(3)
_cell_length_b                   16.6383(7)
_cell_length_c                   16.3749(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.7080(10)
_cell_angle_gamma                90
_cell_volume                     1871.77(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9060
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      24.90
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.054
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792

_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.75

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              Bruker

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker ACS Kappa APEX II DUO diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            57684
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_full        26.44
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             3863
_reflns_number_gt                3030
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1241
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.263
_refine_ls_number_reflns         3863
_refine_ls_number_parameters     251
_refine_ls_number_restraints     30
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0596P)²+0.5094P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.184
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2009, 7, 0, 0'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.7236(2) 1.00173(8) 0.42538(10) 0.0793(4) Uani d U . . 1 . .
C C2 0.7902(3) 0.98280(12) 0.34686(13) 0.0712(6) Uani d . . . 1 . .
H H2A 0.8277 1.0319 0.3195 0.085 Uiso calc U . R 1 . .
H H2B 0.6851 0.9583 0.3148 0.085 Uiso calc U . R 1 . .
C C3 0.9600(3) 0.92663(10) 0.35112(11) 0.0558(4) Uani d . . . 1 . .
H H3A 1.0 0.9141 0.2963 0.067 Uiso calc U . R 1 . .
H H3B 1.0685 0.9524 0.3799 0.067 Uiso calc U . R 1 . .
N N4 0.90993(18) 0.85287(7) 0.39306(8) 0.0418(3) Uani d . . . 1 . .
C C5 0.8446(3) 0.87316(11) 0.47416(11) 0.0630(5) Uani d . . . 1 . .
H H5A 0.9503 0.898 0.5056 0.076 Uiso calc U . R 1 . .
H H5B 0.806 0.8247 0.5023 0.076 Uiso calc U . R 1 . .
C C6 0.6760(4) 0.92989(13) 0.46726(16) 0.0855(7) Uani d U . . 1 . .
H H6A 0.5685 0.9035 0.4384 0.103 Uiso calc U . R 1 . .
H H6B 0.6338 0.9433 0.5216 0.103 Uiso calc U . R 1 . .
C C7 1.0701(2) 0.79570(9) 0.39413(10) 0.0476(4) Uani d . . . 1 . .
H H7A 1.1727 0.8149 0.4311 0.057 Uiso calc U . R 1 . .
H H7B 1.1225 0.7923 0.3399 0.057 Uiso calc U . R 1 . .
C C8 1.0067(2) 0.71270(9) 0.42084(10) 0.0462(4) Uani d . . . 1 . .
H H8A 1.109 0.674 0.4112 0.055 Uiso calc U . R 1 . .
H H8B 0.9812 0.7129 0.4788 0.055 Uiso calc U . R 1 . .
N N9 0.83218(19) 0.69077(8) 0.37460(8) 0.0431(3) Uani d . . . 1 . .
H H9 0.765(3) 0.7302(11) 0.3539(11) 0.053(5) Uiso d . . . 1 . .
C C10 0.7417(2) 0.62020(8) 0.38079(8) 0.0382(3) Uani d . . . 1 . .
C C11 0.8126(2) 0.55435(9) 0.42126(9) 0.0435(4) Uani d . . . 1 . .
H H11 0.9325 0.5577 0.4489 0.052 Uiso calc U . R 1 . .
C C12 0.7078(2) 0.48065(8) 0.42227(9) 0.0439(4) Uani d . . . 1 . .
C C13 0.5147(2) 0.47531(8) 0.37670(8) 0.0373(3) Uani d . . . 1 . .
C C14 0.4369(2) 0.54227(8) 0.33537(8) 0.0380(3) Uani d . . . 1 . .
C C15 0.5460(2) 0.61875(8) 0.33786(9) 0.0422(3) Uani d . . . 1 . .
O O16 0.4840(2) 0.68030(7) 0.30715(9) 0.0745(4) Uani d U . . 1 . .
O O17 0.7677(2) 0.42048(7) 0.45904(8) 0.0679(4) Uani d U . . 1 . .
C C18 0.2610(2) 0.53315(9) 0.29049(9) 0.0428(3) Uani d . . . 1 . .
N N19 0.16138(19) 0.46401(8) 0.29130(9) 0.0488(3) Uani d . . . 1 . .
C C20 0.2327(2) 0.40074(9) 0.33260(10) 0.0456(4) Uani d . . . 1 . .
C C21 0.4134(2) 0.40328(9) 0.37431(9) 0.0410(3) Uani d . . . 1 . .
C C22 0.4924(2) 0.32634(9) 0.41014(10) 0.0452(4) Uani d . . . 1 . .
O O23 0.4511(2) 0.29788(8) 0.47437(8) 0.0736(4) Uani d U . . 1 . .
O O24 0.60074(16) 0.28937(6) 0.35559(7) 0.0482(3) Uani d . . . 1 . .
C C25 0.6828(3) 0.21375(10) 0.38057(12) 0.0586(5) Uani d . . . 1 . .
H H25A 0.7732 0.222 0.4256 0.088 Uiso calc U . R 1 . .
H H25B 0.7494 0.1902 0.3358 0.088 Uiso calc U . R 1 . .
H H25C 0.5808 0.1784 0.3971 0.088 Uiso calc U . R 1 . .
C C26 0.1092(3) 0.32650(11) 0.32940(13) 0.0645(5) Uani d . . . 1 . .
H H26A -0.0001 0.3334 0.3638 0.097 Uiso calc U . R 1 . .
H H26B 0.1851 0.2813 0.3481 0.097 Uiso calc U . R 1 . .
H H26C 0.0637 0.3173 0.2742 0.097 Uiso calc U . R 1 . .
C C27 0.1729(3) 0.59616(11) 0.23518(12) 0.0590(5) Uani d . . . 1 . .
H H27A 0.0673 0.5732 0.2034 0.088 Uiso calc U . R 1 . .
H H27B 0.27 0.6159 0.1993 0.088 Uiso calc U . R 1 . .
H H27C 0.1252 0.6397 0.2674 0.088 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.413(2) ?
O1 C6 . 1.421(2) ?
C2 C3 . 1.495(3) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
C3 N4 . 1.4527(19) ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
N4 C5 . 1.454(2) ?
N4 C7 . 1.454(2) ?
C5 C6 . 1.497(3) ?
C5 H5A . 0.97 ?
C5 H5B . 0.97 ?
C6 H6A . 0.97 ?
C6 H6B . 0.97 ?
C7 C8 . 1.516(2) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C8 N9 . 1.446(2) ?
C8 H8A . 0.97 ?
C8 H8B . 0.97 ?
N9 C10 . 1.3340(19) ?
N9 H9 . 0.865(19) ?
C10 C11 . 1.363(2) ?
C10 C15 . 1.499(2) ?
C11 C12 . 1.423(2) ?
C11 H11 . 0.93 ?
C12 O17 . 1.2327(18) ?
C12 C13 . 1.506(2) ?
C13 C21 . 1.386(2) ?
C13 C14 . 1.4012(19) ?
C14 C18 . 1.404(2) ?
C14 C15 . 1.477(2) ?
C15 O16 . 1.2129(18) ?
C18 N19 . 1.339(2) ?
C18 C27 . 1.501(2) ?
N19 C20 . 1.337(2) ?
C20 C21 . 1.400(2) ?
C20 C26 . 1.499(2) ?
C21 C22 . 1.503(2) ?
C22 O23 . 1.1954(19) ?
C22 O24 . 1.3305(18) ?
O24 C25 . 1.4335(19) ?
C25 H25A . 0.96 ?
C25 H25B . 0.96 ?
C25 H25C . 0.96 ?
C26 H26A . 0.96 ?
C26 H26B . 0.96 ?
C26 H26C . 0.96 ?
C27 H27A . 0.96 ?
C27 H27B . 0.96 ?
C27 H27C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C6 . . 109.69(16) ?
O1 C2 C3 . . 111.74(16) ?
O1 C2 H2A . . 109.3 ?
C3 C2 H2A . . 109.3 ?
O1 C2 H2B . . 109.3 ?
C3 C2 H2B . . 109.3 ?
H2A C2 H2B . . 107.9 ?
N4 C3 C2 . . 110.77(15) ?
N4 C3 H3A . . 109.5 ?
C2 C3 H3A . . 109.5 ?
N4 C3 H3B . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.1 ?
C3 N4 C5 . . 108.63(13) ?
C3 N4 C7 . . 111.62(12) ?
C5 N4 C7 . . 113.25(13) ?
N4 C5 C6 . . 109.69(17) ?
N4 C5 H5A . . 109.7 ?
C6 C5 H5A . . 109.7 ?
N4 C5 H5B . . 109.7 ?
C6 C5 H5B . . 109.7 ?
H5A C5 H5B . . 108.2 ?
O1 C6 C5 . . 112.20(17) ?
O1 C6 H6A . . 109.2 ?
C5 C6 H6A . . 109.2 ?
O1 C6 H6B . . 109.2 ?
C5 C6 H6B . . 109.2 ?
H6A C6 H6B . . 107.9 ?
N4 C7 C8 . . 112.05(13) ?
N4 C7 H7A . . 109.2 ?
C8 C7 H7A . . 109.2 ?
N4 C7 H7B . . 109.2 ?
C8 C7 H7B . . 109.2 ?
H7A C7 H7B . . 107.9 ?
N9 C8 C7 . . 108.64(13) ?
N9 C8 H8A . . 110.0 ?
C7 C8 H8A . . 110.0 ?
N9 C8 H8B . . 110.0 ?
C7 C8 H8B . . 110.0 ?
H8A C8 H8B . . 108.3 ?
C10 N9 C8 . . 124.30(13) ?
C10 N9 H9 . . 116.9(12) ?
C8 N9 H9 . . 116.0(12) ?
N9 C10 C11 . . 125.71(14) ?
N9 C10 C15 . . 113.10(12) ?
C11 C10 C15 . . 121.19(13) ?
C10 C11 C12 . . 121.64(14) ?
C10 C11 H11 . . 119.2 ?
C12 C11 H11 . . 119.2 ?
O17 C12 C11 . . 122.94(15) ?
O17 C12 C13 . . 118.09(14) ?
C11 C12 C13 . . 118.97(12) ?
C21 C13 C14 . . 119.35(14) ?
C21 C13 C12 . . 119.97(13) ?
C14 C13 C12 . . 120.68(13) ?
C13 C14 C18 . . 118.47(13) ?
C13 C14 C15 . . 119.06(13) ?
C18 C14 C15 . . 122.42(13) ?
O16 C15 C14 . . 122.95(14) ?
O16 C15 C10 . . 118.72(14) ?
C14 C15 C10 . . 118.33(12) ?
N19 C18 C14 . . 121.35(14) ?
N19 C18 C27 . . 114.13(14) ?
C14 C18 C27 . . 124.45(14) ?
C20 N19 C18 . . 120.12(13) ?
N19 C20 C21 . . 121.98(14) ?
N19 C20 C26 . . 115.65(15) ?
C21 C20 C26 . . 122.35(15) ?
C13 C21 C20 . . 118.51(14) ?
C13 C21 C22 . . 123.38(14) ?
C20 C21 C22 . . 118.02(13) ?
O23 C22 O24 . . 124.05(15) ?
O23 C22 C21 . . 126.04(15) ?
O24 C22 C21 . . 109.55(13) ?
C22 O24 C25 . . 115.94(13) ?
O24 C25 H25A . . 109.5 ?
O24 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
O24 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
C20 C26 H26A . . 109.5 ?
C20 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C20 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C18 C27 H27A . . 109.5 ?
C18 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C18 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 O1 C2 C3 . . . . -56.5(2) ?
O1 C2 C3 N4 . . . . 58.0(2) ?
C2 C3 N4 C5 . . . . -57.4(2) ?
C2 C3 N4 C7 . . . . 177.03(15) ?
C3 N4 C5 C6 . . . . 57.3(2) ?
C7 N4 C5 C6 . . . . -178.11(15) ?
C2 O1 C6 C5 . . . . 57.3(3) ?
N4 C5 C6 O1 . . . . -58.6(3) ?
C3 N4 C7 C8 . . . . -167.60(14) ?
C5 N4 C7 C8 . . . . 69.42(18) ?
N4 C7 C8 N9 . . . . 48.94(18) ?
C7 C8 N9 C10 . . . . 177.45(14) ?
C8 N9 C10 C11 . . . . -10.4(2) ?
C8 N9 C10 C15 . . . . 169.50(14) ?
N9 C10 C11 C12 . . . . -177.93(14) ?
C15 C10 C11 C12 . . . . 2.2(2) ?
C10 C11 C12 O17 . . . . -179.27(16) ?
C10 C11 C12 C13 . . . . 0.6(2) ?
O17 C12 C13 C21 . . . . -2.5(2) ?
C11 C12 C13 C21 . . . . 177.60(14) ?
O17 C12 C13 C14 . . . . 178.50(15) ?
C11 C12 C13 C14 . . . . -1.4(2) ?
C21 C13 C14 C18 . . . . -2.1(2) ?
C12 C13 C14 C18 . . . . 176.94(13) ?
C21 C13 C14 C15 . . . . -179.72(13) ?
C12 C13 C14 C15 . . . . -0.7(2) ?
C13 C14 C15 O16 . . . . -176.19(16) ?
C18 C14 C15 O16 . . . . 6.2(2) ?
C13 C14 C15 C10 . . . . 3.4(2) ?
C18 C14 C15 C10 . . . . -174.15(13) ?
N9 C10 C15 O16 . . . . -4.5(2) ?
C11 C10 C15 O16 . . . . 175.36(16) ?
N9 C10 C15 C14 . . . . 175.86(13) ?
C11 C10 C15 C14 . . . . -4.3(2) ?
C13 C14 C18 N19 . . . . 4.7(2) ?
C15 C14 C18 N19 . . . . -177.77(14) ?
C13 C14 C18 C27 . . . . -172.24(15) ?
C15 C14 C18 C27 . . . . 5.3(2) ?
C14 C18 N19 C20 . . . . -2.8(2) ?
C27 C18 N19 C20 . . . . 174.36(14) ?
C18 N19 C20 C21 . . . . -1.6(2) ?
C18 N19 C20 C26 . . . . 179.99(14) ?
C14 C13 C21 C20 . . . . -2.1(2) ?
C12 C13 C21 C20 . . . . 178.89(13) ?
C14 C13 C21 C22 . . . . 174.34(13) ?
C12 C13 C21 C22 . . . . -4.7(2) ?
N19 C20 C21 C13 . . . . 4.1(2) ?
C26 C20 C21 C13 . . . . -177.63(15) ?
N19 C20 C21 C22 . . . . -172.54(14) ?
C26 C20 C21 C22 . . . . 5.7(2) ?
C13 C21 C22 O23 . . . . 100.8(2) ?
C20 C21 C22 O23 . . . . -82.8(2) ?
C13 C21 C22 O24 . . . . -85.93(17) ?
C20 C21 C22 O24 . . . . 90.52(16) ?
O23 C22 O24 C25 . . . . -5.2(2) ?
C21 C22 O24 C25 . . . . -178.62(13) ?

