# Electronic Supplementary Material (ESI) for Soft Matter.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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. 
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data_mo_dg14_rt_0m
_database_code_depnum_ccdc_archive 'CCDC 2053987'
loop_
_audit_author_name
_audit_author_address
'Claire Wilson'
;University of Glasgow
United Kingdom
;
_audit_update_record             
;
2021-01-05 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_audit_creation_date             2020-08-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 N2 O5, H2 O'
_chemical_formula_sum            'C18 H22 N2 O6'
_chemical_formula_weight         362.37
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.8565(7)
_cell_length_b                   8.6565(12)
_cell_length_c                   36.543(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1852.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2455
_cell_measurement_temperature    295
_cell_measurement_theta_max      21.08
_cell_measurement_theta_min      2.23
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1503 before and 0.0599 after correction. The Ratio of minimum to maximum transmission is 0.9051. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       lath
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0783
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8786
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.687
_diffrn_reflns_theta_min         2.229
_diffrn_ambient_temperature      295.0
_diffrn_detector_area_resol_mean 7.4074
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2274
_reflns_number_total             3499
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.9-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 682 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3499
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0947
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0281P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0992
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2B), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C6(H6A,H6B,H6C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.6176(5) 0.6416(3) 0.80162(8) 0.0599(8) Uani 1 1 d . . . . .
O2 O 0.6980(4) 0.8771(3) 0.78146(7) 0.0469(7) Uani 1 1 d . . . . .
H2 H 0.757980 0.885731 0.801633 0.070 Uiso 1 1 calc GR . . . .
O3 O 0.7427(4) 0.6234(3) 0.69323(7) 0.0578(8) Uani 1 1 d . . . . .
O4 O 0.3573(5) 0.6867(3) 0.62655(8) 0.0664(9) Uani 1 1 d . . . . .
O5 O 0.7918(4) 0.6139(3) 0.56175(7) 0.0524(7) Uani 1 1 d . . . . .
N1 N 0.5185(5) 0.8125(4) 0.71444(9) 0.0394(8) Uani 1 1 d . . . . .
H1 H 0.471(5) 0.905(4) 0.7120(9) 0.034(10) Uiso 1 1 d . . . . .
N2 N 0.7248(6) 0.7602(4) 0.62382(9) 0.0457(9) Uani 1 1 d . . . . .
H2A H 0.854(6) 0.755(4) 0.6114(10) 0.050(12) Uiso 1 1 d . . . . .
C1 C 0.5972(5) 0.7428(4) 0.77911(11) 0.0365(9) Uani 1 1 d . . . . .
C2 C 0.4433(6) 0.7261(4) 0.74614(10) 0.0372(9) Uani 1 1 d . . . . .
H2B H 0.437969 0.616492 0.739458 0.045 Uiso 1 1 calc R . . . .
C3 C 0.2030(6) 0.7763(5) 0.75679(11) 0.0555(12) Uani 1 1 d . . . . .
H3A H 0.099391 0.753130 0.737179 0.083 Uiso 1 1 calc GR . . . .
H3B H 0.201690 0.885447 0.761450 0.083 Uiso 1 1 calc GR . . . .
H3C H 0.156365 0.722011 0.778441 0.083 Uiso 1 1 calc GR . . . .
C4 C 0.6577(6) 0.7520(4) 0.68965(11) 0.0389(9) Uani 1 1 d . . . . .
C5 C 0.7127(6) 0.8538(4) 0.65663(10) 0.0407(9) Uani 1 1 d . . . . .
H5 H 0.590683 0.930238 0.653675 0.049 Uiso 1 1 calc R . . . .
C6 C 0.9381(6) 0.9384(4) 0.66260(11) 0.0591(12) Uani 1 1 d . . . . .
H6A H 0.965970 1.006780 0.642403 0.089 Uiso 1 1 calc GR . . . .
H6B H 1.059983 0.864665 0.664312 0.089 Uiso 1 1 calc GR . . . .
H6C H 0.930051 0.997143 0.684853 0.089 Uiso 1 1 calc GR . . . .
C7 C 0.5457(7) 0.6822(4) 0.61138(11) 0.0469(10) Uani 1 1 d . . . . .
C8 C 0.5754(7) 0.5875(5) 0.57759(11) 0.0564(12) Uani 1 1 d . . . . .
H8A H 0.559948 0.478884 0.583619 0.068 Uiso 1 1 calc R . . . .
H8B H 0.456967 0.613744 0.560099 0.068 Uiso 1 1 calc R . . . .
C9 C 0.8265(6) 0.5564(4) 0.52706(10) 0.0416(9) Uani 1 1 d . . . . .
C10 C 0.6823(6) 0.4610(4) 0.50880(10) 0.0437(10) Uani 1 1 d . . . . .
H10 H 0.547467 0.428704 0.519871 0.052 Uiso 1 1 calc R . . . .
C11 C 0.7361(6) 0.4102(4) 0.47291(11) 0.0413(9) Uani 1 1 d . . . . .
C12 C 0.5919(7) 0.3118(5) 0.45290(12) 0.0573(12) Uani 1 1 d . . . . .
H12 H 0.456488 0.277726 0.463484 0.069 Uiso 1 1 calc R . . . .
C13 C 0.6454(8) 0.2652(5) 0.41848(13) 0.0635(13) Uani 1 1 d . . . . .
H13 H 0.545786 0.200990 0.405768 0.076 Uiso 1 1 calc R . . . .
C14 C 0.8480(9) 0.3126(5) 0.40205(12) 0.0636(13) Uani 1 1 d . . . . .
H14 H 0.884007 0.280549 0.378459 0.076 Uiso 1 1 calc R . . . .
C15 C 0.9929(7) 0.4064(5) 0.42090(11) 0.0554(12) Uani 1 1 d . . . . .
H15 H 1.128747 0.437151 0.409927 0.066 Uiso 1 1 calc R . . . .
C16 C 0.9428(6) 0.4581(4) 0.45653(11) 0.0438(10) Uani 1 1 d . . . . .
C17 C 1.0875(6) 0.5576(5) 0.47665(12) 0.0528(11) Uani 1 1 d . . . . .
H17 H 1.224647 0.589823 0.466344 0.063 Uiso 1 1 calc R . . . .
C18 C 1.0305(6) 0.6069(5) 0.51062(11) 0.0489(11) Uani 1 1 d . . . . .
H18 H 1.126456 0.674412 0.523105 0.059 Uiso 1 1 calc R . . . .
O1W O 0.0793(6) 0.4575(4) 0.65986(10) 0.0591(9) Uani 1 1 d . . . . .
H1WA H 0.152(8) 0.524(6) 0.6492(13) 0.09(2) Uiso 1 1 d . . . . .
H1WB H -0.043(9) 0.516(7) 0.6680(15) 0.14(2) Uiso 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
O1 C1 1.208(4) . ?
O2 H2 0.8200 . ?
O2 C1 1.307(4) . ?
O3 C4 1.227(4) . ?
O4 C7 1.235(4) . ?
O5 C8 1.412(4) . ?
O5 C9 1.377(4) . ?
N1 H1 0.85(3) . ?
N1 C2 1.448(5) . ?
N1 C4 1.326(4) . ?
N2 H2A 0.89(4) . ?
N2 C5 1.449(4) . ?
N2 C7 1.328(5) . ?
C1 C2 1.512(5) . ?
C2 H2B 0.9800 . ?
C2 C3 1.524(5) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 C5 1.528(5) . ?
C5 H5 0.9800 . ?
C5 C6 1.525(5) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.492(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.357(5) . ?
C9 C18 1.407(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.419(5) . ?
C11 C12 1.405(5) . ?
C11 C16 1.413(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.357(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.362(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.408(5) . ?
C16 C17 1.414(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.354(5) . ?
C18 H18 0.9300 . ?
O1W H1WA 0.82(5) . ?
O1W H1WB 0.93(6) . ?

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
C1 O2 H2 109.5 . . ?
C9 O5 C8 116.8(3) . . ?
C2 N1 H1 118(2) . . ?
C4 N1 H1 120(2) . . ?
C4 N1 C2 122.0(3) . . ?
C5 N2 H2A 120(2) . . ?
C7 N2 H2A 118(2) . . ?
C7 N2 C5 121.9(3) . . ?
O1 C1 O2 123.8(3) . . ?
O1 C1 C2 122.1(3) . . ?
O2 C1 C2 114.0(3) . . ?
N1 C2 C1 114.0(3) . . ?
N1 C2 H2B 108.1 . . ?
N1 C2 C3 109.8(3) . . ?
C1 C2 H2B 108.1 . . ?
C1 C2 C3 108.6(3) . . ?
C3 C2 H2B 108.1 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O3 C4 N1 122.3(4) . . ?
O3 C4 C5 121.5(3) . . ?
N1 C4 C5 116.2(3) . . ?
N2 C5 C4 110.0(3) . . ?
N2 C5 H5 108.8 . . ?
N2 C5 C6 110.2(3) . . ?
C4 C5 H5 108.8 . . ?
C6 C5 C4 110.3(3) . . ?
C6 C5 H5 108.8 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O4 C7 N2 122.4(4) . . ?
O4 C7 C8 119.5(4) . . ?
N2 C7 C8 118.1(4) . . ?
O5 C8 C7 110.8(3) . . ?
O5 C8 H8A 109.5 . . ?
O5 C8 H8B 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
O5 C9 C18 114.0(3) . . ?
C10 C9 O5 125.5(3) . . ?
C10 C9 C18 120.5(4) . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.3(3) . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 122.4(3) . . ?
C12 C11 C16 118.2(4) . . ?
C16 C11 C10 119.4(3) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 C11 121.6(4) . . ?
C13 C12 H12 119.2 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.6(4) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.3(4) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 119.1 . . ?
C14 C15 C16 121.9(4) . . ?
C16 C15 H15 119.1 . . ?
C11 C16 C17 118.2(3) . . ?
C15 C16 C11 118.5(4) . . ?
C15 C16 C17 123.4(4) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.4(4) . . ?
C18 C17 H17 119.3 . . ?
C9 C18 H18 119.9 . . ?
C17 C18 C9 120.2(4) . . ?
C17 C18 H18 119.9 . . ?
H1WA O1W H1WB 100(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1W H1WB O3 0.93(6) 1.81(6) 2.727(4) 168(5) 1_455 yes

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
O1 C1 C2 N1 -150.5(3) . . . . ?
O1 C1 C2 C3 86.7(4) . . . . ?
O2 C1 C2 N1 31.6(4) . . . . ?
O2 C1 C2 C3 -91.1(4) . . . . ?
O3 C4 C5 N2 39.6(5) . . . . ?
O3 C4 C5 C6 -82.0(4) . . . . ?
O4 C7 C8 O5 172.0(4) . . . . ?
O5 C9 C10 C11 179.5(3) . . . . ?
O5 C9 C18 C17 179.1(3) . . . . ?
N1 C4 C5 N2 -142.1(3) . . . . ?
N1 C4 C5 C6 96.2(4) . . . . ?
N2 C7 C8 O5 -7.3(5) . . . . ?
C2 N1 C4 O3 -4.8(5) . . . . ?
C2 N1 C4 C5 176.9(3) . . . . ?
C4 N1 C2 C1 90.0(4) . . . . ?
C4 N1 C2 C3 -147.8(3) . . . . ?
C5 N2 C7 O4 1.3(6) . . . . ?
C5 N2 C7 C8 -179.3(3) . . . . ?
C7 N2 C5 C4 62.4(4) . . . . ?
C7 N2 C5 C6 -175.9(4) . . . . ?
C8 O5 C9 C10 -8.7(5) . . . . ?
C8 O5 C9 C18 170.5(3) . . . . ?
C9 O5 C8 C7 -168.5(3) . . . . ?
C9 C10 C11 C12 -179.8(4) . . . . ?
C9 C10 C11 C16 0.9(5) . . . . ?
C10 C9 C18 C17 -1.6(6) . . . . ?
C10 C11 C12 C13 179.5(4) . . . . ?
C10 C11 C16 C15 -180.0(3) . . . . ?
C10 C11 C16 C17 -0.9(5) . . . . ?
C11 C12 C13 C14 0.8(7) . . . . ?
C11 C16 C17 C18 -0.3(6) . . . . ?
C12 C11 C16 C15 0.7(5) . . . . ?
C12 C11 C16 C17 179.8(3) . . . . ?
C12 C13 C14 C15 0.1(7) . . . . ?
C13 C14 C15 C16 -0.5(6) . . . . ?
C14 C15 C16 C11 0.1(6) . . . . ?
C14 C15 C16 C17 -178.9(4) . . . . ?
C15 C16 C17 C18 178.7(4) . . . . ?
C16 C11 C12 C13 -1.2(6) . . . . ?
C16 C17 C18 C9 1.6(6) . . . . ?
C18 C9 C10 C11 0.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
