# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_x4esxt-04aug043254_a
_database_code_depnum_ccdc_archive 'CCDC 2160976'
loop_
_audit_author_name
_audit_author_address
'Giovanni Pierri'
;University of Salerno
Italy
;
_audit_update_record             
;
2022-03-25 deposited with the CCDC.	2022-05-02 downloaded from the CCDC.
;
_audit_creation_date             2022-03-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C14 H20 N2 O3), 5(H2 O)'
_chemical_formula_sum            'C28 H50 N4 O11'
_chemical_formula_weight         618.72
_chemical_absolute_configuration syn
_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 0.0020 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 0.0039 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0075 0.0059 '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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   19.615(4)
_cell_length_b                   6.7520(14)
_cell_length_c                   13.402(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.86(3)
_cell_angle_gamma                90
_cell_volume                     1610.5(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13945
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.750
_cell_measurement_theta_min      2.162
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0107
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13945
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.750
_diffrn_reflns_theta_min         2.162
_diffrn_ambient_temperature      100.0
_diffrn_detector_type            'Pilatus 2M detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device       'Huber 4-circles kappa geometry'
_diffrn_measurement_device_type  'single axis'
_diffrn_measurement_method       'rotating crystal'
_diffrn_source_type              Synchrotron
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_source                   'Elettra XRD1 BL'
_diffrn_radiation_monochromator  Si(111)
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    0.925
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                4354
_reflns_number_total             4372
_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_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 1896 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4372
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0262
_refine_ls_restrained_S_all      1.065
_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)+(0.0489P)²+0.3528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0713
_refine_ls_wR_factor_ref         0.0714
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C1(H1), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C14(H14), C13(H13), C11(H11), C10(H10), C12(H12)
2.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C7(H7A,H7B,H7C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.82728(4) 0.18462(13) 0.69564(7) 0.01525(16) Uani 1 1 d . . . . .
O3 O 0.60194(4) 0.25299(14) 0.65329(7) 0.01823(18) Uani 1 1 d . . . . .
O2 O 0.65336(5) 0.31063(16) 0.53567(7) 0.02030(19) Uani 1 1 d . . . . .
N2 N 0.77718(5) 0.48962(14) 0.69172(7) 0.01225(17) Uani 1 1 d . . . . .
H2 H 0.779571 0.616081 0.677629 0.015 Uiso 1 1 calc R U . . .
N1 N 0.90485(5) 0.33633(14) 0.58198(7) 0.01390(18) Uani 1 1 d . . . . .
H1A H 0.861484 0.315605 0.520865 0.017 Uiso 1 1 calc R U . . .
H1B H 0.923561 0.218135 0.614633 0.017 Uiso 1 1 calc R U . . .
H1C H 0.938986 0.396648 0.562591 0.017 Uiso 1 1 calc R U . . .
C4 C 0.65287(6) 0.32031(16) 0.62890(9) 0.01370(19) Uani 1 1 d . . . . .
C8 C 0.69017(6) 0.60195(17) 0.76669(8) 0.01390(19) Uani 1 1 d . . . . .
H8A H 0.666217 0.698372 0.706288 0.017 Uiso 1 1 calc R U . . .
H8B H 0.651614 0.556515 0.791038 0.017 Uiso 1 1 calc R U . . .
C2 C 0.82750(5) 0.36570(17) 0.68323(8) 0.01185(19) Uani 1 1 d . . . . .
C14 C 0.78795(6) 0.60822(17) 0.96355(9) 0.0148(2) Uani 1 1 d . . . . .
H14 H 0.771289 0.480903 0.973816 0.018 Uiso 1 1 calc R U . . .
C7 C 0.94433(7) 0.6580(2) 0.83667(10) 0.0219(2) Uani 1 1 d . . . . .
H7A H 0.921564 0.775439 0.792080 0.033 Uiso 1 1 calc R U . . .
H7B H 0.991232 0.695624 0.898848 0.033 Uiso 1 1 calc R U . . .
H7C H 0.909532 0.601652 0.864285 0.033 Uiso 1 1 calc R U . . .
C13 C 0.84705(6) 0.70009(19) 1.05010(9) 0.0184(2) Uani 1 1 d . . . . .
H13 H 0.869624 0.636758 1.119744 0.022 Uiso 1 1 calc R U . . .
C3 C 0.71861(6) 0.42333(16) 0.72339(8) 0.01212(19) Uani 1 1 d . . . . .
H3 H 0.741339 0.326105 0.784893 0.015 Uiso 1 1 calc R U . . .
C1 C 0.88929(5) 0.46523(16) 0.66044(8) 0.01178(18) Uani 1 1 d . . . . .
H1 H 0.869826 0.595199 0.623729 0.014 Uiso 1 1 calc R U . . .
C9 C 0.75304(6) 0.70306(17) 0.86149(8) 0.01357(19) Uani 1 1 d . . . . .
C11 C 0.83912(7) 0.97873(19) 0.93379(10) 0.0203(2) Uani 1 1 d . . . . .
H11 H 0.856887 1.104230 0.923049 0.024 Uiso 1 1 calc R U . . .
C5 C 0.96099(6) 0.50423(17) 0.76613(9) 0.01454(19) Uani 1 1 d . . . . .
H5 H 0.999053 0.563311 0.743437 0.017 Uiso 1 1 calc R U . . .
C10 C 0.77865(6) 0.88880(18) 0.84784(9) 0.0169(2) Uani 1 1 d . . . . .
H10 H 0.754767 0.955258 0.779317 0.020 Uiso 1 1 calc R U . . .
C12 C 0.87314(6) 0.8844(2) 1.03484(10) 0.0200(2) Uani 1 1 d . . . . .
H12 H 0.914134 0.945365 1.093496 0.024 Uiso 1 1 calc R U . . .
C6 C 0.99579(7) 0.3176(2) 0.83246(10) 0.0242(3) Uani 1 1 d . . . . .
H6A H 1.043694 0.351149 0.893790 0.036 Uiso 1 1 calc R U . . .
H6B H 1.004486 0.220013 0.784909 0.036 Uiso 1 1 calc R U . . .
H6C H 0.961521 0.261784 0.861236 0.036 Uiso 1 1 calc R U . . .
O1W O 1.000000 0.52086(18) 0.500000 0.0144(2) Uani 1 2 d S T P . .
O2W O 0.74728(4) 0.36025(13) 0.43220(7) 0.01528(16) Uani 1 1 d . . . . .
O3W O 0.52861(5) 0.45855(15) 0.36578(8) 0.0245(2) Uani 1 1 d . . . . .
H2WA H 0.7303(11) 0.464(4) 0.3956(17) 0.030(5) Uiso 1 1 d . . . . .
H2WB H 0.7208(12) 0.349(4) 0.4702(19) 0.042(6) Uiso 1 1 d . . . . .
H3WA H 0.5624(14) 0.396(4) 0.421(2) 0.046(6) Uiso 1 1 d . . . . .
H3WB H 0.4845(12) 0.407(4) 0.3570(17) 0.032(5) Uiso 1 1 d . . . . .
H1W H 0.9676(12) 0.601(4) 0.4534(18) 0.044(6) 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 C2 1.2342(14) . ?
O3 C4 1.2593(13) . ?
O2 C4 1.2553(14) . ?
N2 H2 0.8800 . ?
N2 C2 1.3349(13) . ?
N2 C3 1.4526(13) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C1 1.4919(14) . ?
C4 C3 1.5419(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C3 1.5410(15) . ?
C8 C9 1.5111(15) . ?
C2 C1 1.5248(14) . ?
C14 H14 0.9500 . ?
C14 C13 1.3942(16) . ?
C14 C9 1.4008(15) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C5 1.5294(16) . ?
C13 H13 0.9500 . ?
C13 C12 1.3929(19) . ?
C3 H3 1.0000 . ?
C1 H1 1.0000 . ?
C1 C5 1.5422(15) . ?
C9 C10 1.3913(16) . ?
C11 H11 0.9500 . ?
C11 C10 1.3976(17) . ?
C11 C12 1.3875(19) . ?
C5 H5 1.0000 . ?
C5 C6 1.5280(17) . ?
C10 H10 0.9500 . ?
C12 H12 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
O1W H1W 0.87(2) . ?
O1W H1W 0.87(2) 2_756 ?
O2W H2WA 0.84(2) . ?
O2W H2WB 0.87(2) . ?
O3W H3WA 0.87(3) . ?
O3W H3WB 0.89(2) . ?

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 N2 H2 118.8 . . ?
C2 N2 C3 122.39(9) . . ?
C3 N2 H2 118.8 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
O3 C4 C3 115.50(9) . . ?
O2 C4 O3 125.35(10) . . ?
O2 C4 C3 119.15(9) . . ?
H8A C8 H8B 107.9 . . ?
C3 C8 H8A 109.2 . . ?
C3 C8 H8B 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C9 C8 C3 111.93(8) . . ?
O1 C2 N2 124.39(10) . . ?
O1 C2 C1 120.78(9) . . ?
N2 C2 C1 114.79(9) . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C9 120.21(11) . . ?
C9 C14 H14 119.9 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
C14 C13 H13 119.9 . . ?
C12 C13 C14 120.24(11) . . ?
C12 C13 H13 119.9 . . ?
N2 C3 C4 112.96(9) . . ?
N2 C3 C8 108.96(9) . . ?
N2 C3 H3 108.1 . . ?
C4 C3 H3 108.1 . . ?
C8 C3 C4 110.62(8) . . ?
C8 C3 H3 108.1 . . ?
N1 C1 C2 107.42(8) . . ?
N1 C1 H1 108.3 . . ?
N1 C1 C5 111.66(8) . . ?
C2 C1 H1 108.3 . . ?
C2 C1 C5 112.70(8) . . ?
C5 C1 H1 108.3 . . ?
C14 C9 C8 120.36(10) . . ?
C10 C9 C8 120.59(10) . . ?
C10 C9 C14 119.02(10) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C12 C11 C10 119.88(12) . . ?
C7 C5 C1 109.54(9) . . ?
C7 C5 H5 107.3 . . ?
C1 C5 H5 107.3 . . ?
C6 C5 C7 111.09(10) . . ?
C6 C5 C1 113.91(10) . . ?
C6 C5 H5 107.3 . . ?
C9 C10 C11 120.76(11) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C13 C12 H12 120.1 . . ?
C11 C12 C13 119.86(11) . . ?
C11 C12 H12 120.1 . . ?
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 . . ?
H1W O1W H1W 103(3) . 2_756 ?
H2WA O2W H2WB 103(2) . . ?
H3WA O3W H3WB 106(2) . . ?

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 C2 C1 N1 40.56(12) . . . . ?
O1 C2 C1 C5 -82.85(12) . . . . ?
O3 C4 C3 N2 177.31(10) . . . . ?
O3 C4 C3 C8 -60.26(13) . . . . ?
O2 C4 C3 N2 -3.17(14) . . . . ?
O2 C4 C3 C8 119.26(11) . . . . ?
N2 C2 C1 N1 -141.50(9) . . . . ?
N2 C2 C1 C5 95.08(10) . . . . ?
N1 C1 C5 C7 172.57(9) . . . . ?
N1 C1 C5 C6 -62.33(12) . . . . ?
C8 C9 C10 C11 -176.96(10) . . . . ?
C2 N2 C3 C4 -77.47(12) . . . . ?
C2 N2 C3 C8 159.18(9) . . . . ?
C2 C1 C5 C7 -66.41(12) . . . . ?
C2 C1 C5 C6 58.69(12) . . . . ?
C14 C13 C12 C11 1.36(17) . . . . ?
C14 C9 C10 C11 1.08(16) . . . . ?
C13 C14 C9 C8 178.56(9) . . . . ?
C13 C14 C9 C10 0.51(16) . . . . ?
C3 N2 C2 O1 3.76(16) . . . . ?
C3 N2 C2 C1 -174.09(8) . . . . ?
C3 C8 C9 C14 -69.17(13) . . . . ?
C3 C8 C9 C10 108.85(11) . . . . ?
C9 C8 C3 N2 -56.76(11) . . . . ?
C9 C8 C3 C4 178.50(9) . . . . ?
C9 C14 C13 C12 -1.73(17) . . . . ?
C10 C11 C12 C13 0.22(17) . . . . ?
C12 C11 C10 C9 -1.45(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_x4esxt-03aug213322_a
_database_code_depnum_ccdc_archive 'CCDC 2160978'
loop_
_audit_author_name
_audit_author_address
'Giovanni Pierri'
;University of Salerno
Italy
;
_audit_update_record             
;
2022-03-25 deposited with the CCDC.	2022-05-02 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_x4esxt-03aug213322_a 
;
PROBLEM: Short Inter D...A Contact  O2       ..O1W      .       2.42 Ang.
RESPONSE: This is because of the presence of a disordered water molecule with 0.25 occupancy factor
;
_vrf_PLAT430_x4esxt-03aug213322_a_2 
;
PROBLEM: Short Inter D...A Contact  O2       ..O3W      .       2.81 Ang.
RESPONSE: This is because of the presence of a disordered water molecule with 0.25 occupancy factor
;
_vrf_PLAT430_x4esxt-03aug213322_a_3 
;
PROBLEM: Short Inter D...A Contact  O2       ..O4W      .       2.83 Ang.
RESPONSE: This is because of the presence of a disordered water molecule with 0.25 occupancy factor
;
# Added during the CSD deposition process: Friday 25 March 2022 01:46 PM
# end Validation Reply Form

_audit_creation_date             2022-03-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C14 H20 N2 O3), 4(H2O)'
_chemical_formula_sum            'C56 H88 N8 O16'
_chemical_formula_weight         1129.34
_chemical_absolute_configuration syn
_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 0.0020 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 0.0039 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0075 0.0059 '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      tetragonal
_space_group_IT_number           79
_space_group_name_H-M_alt        'I 4'
_space_group_name_Hall           'I 4'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'

_cell_length_a                   22.947(3)
_cell_length_b                   22.947(3)
_cell_length_c                   5.6120(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2955.1(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13478
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.743
_cell_measurement_theta_min      1.236
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0501
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            13478
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.743
_diffrn_reflns_theta_min         1.236
_diffrn_ambient_temperature      100.0
_diffrn_detector_type            'Pilatus 2M detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Huber 4-circles kappa geometry'
_diffrn_measurement_device_type  'single axis'
_diffrn_measurement_method       'rotating crystal'
_diffrn_source_type              Synchrotron
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.956
_reflns_number_gt                2954
_reflns_number_total             4314
_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_data_collection       'Elettra XRD1 Data Collection SW'
_computing_cell_refinement       'XDS (Kabsch, 2010)'
_computing_data_reduction        'XDS (Kabsch, 2010)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 974 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.9(10)
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         4314
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0661
_refine_ls_restrained_S_all      1.043
_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)+(0.0899P)²+2.4128P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1683
_refine_ls_wR_factor_ref         0.1921
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: O3W(0.25) O2W(0.25) O1W(0.25) O4W(0.25)
 Fixed Uiso: O1W(0.10247)
3.a Free rotating group:
 O1(O3,O2,N2,N1,C2,C4,C6,C3,C11,C1,C5,C10,C12,C7,C9,C8,C13,C14)
3.b Ternary CH refined with riding coordinates:
 C3(H3), C1(H1), C12(H12)
3.c Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
3.d Aromatic/amide H refined with riding coordinates:
 N2(H2), C11(H11), C10(H10), C7(H7), C9(H9), C8(H8)
3.e Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.46139(4) 0.69417(5) 0.3112(8) 0.0414(6) Uani 1 1 d G . . . .
O3 O 0.59527(6) 0.67586(6) -0.0310(8) 0.0445(7) Uani 1 1 d G . . . .
O2 O 0.58490(5) 0.61877(5) 0.2819(8) 0.0482(7) Uani 1 1 d G . . . .
N2 N 0.54015(4) 0.71117(4) 0.5408(8) 0.0362(7) Uani 1 1 d G . . . .
H2 H 0.553310 0.714289 0.687569 0.043 Uiso 1 1 calc R U . . .
N1 N 0.42362(6) 0.62628(5) 0.7124(8) 0.0451(8) Uani 1 1 d G . . . .
H1A H 0.411352 0.620519 0.559992 0.054 Uiso 1 1 calc R U . . .
H1B H 0.392727 0.623331 0.813337 0.054 Uiso 1 1 calc R U . . .
H1C H 0.450707 0.598881 0.750760 0.054 Uiso 1 1 calc R U . . .
C2 C 0.48519(4) 0.69657(4) 0.5043(8) 0.0351(7) Uani 1 1 d G . . . .
C4 C 0.58538(5) 0.66688(5) 0.1841(8) 0.0375(8) Uani 1 1 d G . . . .
C6 C 0.42401(5) 0.79009(5) 0.7573(8) 0.0383(8) Uani 1 1 d G . . . .
C3 C 0.57924(4) 0.72217(4) 0.3415(8) 0.0356(8) Uani 1 1 d G . . . .
H3 H 0.562535 0.754268 0.242219 0.043 Uiso 1 1 calc R U . . .
C11 C 0.45600(6) 0.80948(6) 0.9498(8) 0.0415(8) Uani 1 1 d G . . . .
H11 H 0.463089 0.785022 1.083246 0.050 Uiso 1 1 calc R U . . .
C1 C 0.44924(5) 0.68385(5) 0.7332(8) 0.0373(8) Uani 1 1 d G . . . .
H1 H 0.475108 0.685593 0.876415 0.045 Uiso 1 1 calc R U . . .
C5 C 0.39979(5) 0.72881(6) 0.7568(8) 0.0403(8) Uani 1 1 d G . . . .
H5A H 0.372262 0.724262 0.622221 0.048 Uiso 1 1 calc R U . . .
H5B H 0.378131 0.721795 0.906614 0.048 Uiso 1 1 calc R U . . .
C10 C 0.47838(7) 0.86843(6) 0.9411(8) 0.0476(10) Uani 1 1 d G . . . .
H10 H 0.501214 0.883206 1.068730 0.057 Uiso 1 1 calc R U . . .
C12 C 0.64018(4) 0.74297(6) 0.4448(8) 0.0421(8) Uani 1 1 d G . . . .
H12 H 0.653555 0.713767 0.565191 0.051 Uiso 1 1 calc R U . . .
C7 C 0.41296(6) 0.82689(5) 0.5606(8) 0.0465(9) Uani 1 1 d G . . . .
H7 H 0.389841 0.813364 0.431498 0.056 Uiso 1 1 calc R U . . .
C9 C 0.46642(8) 0.90265(5) 0.7480(8) 0.0581(12) Uani 1 1 d G . . . .
H9 H 0.479831 0.941817 0.746659 0.070 Uiso 1 1 calc R U . . .
C8 C 0.43566(7) 0.88217(5) 0.5562(8) 0.0577(12) Uani 1 1 d G . . . .
H8 H 0.430065 0.906236 0.420389 0.069 Uiso 1 1 calc R U . . .
C13 C 0.63235(5) 0.80130(6) 0.5693(8) 0.0526(11) Uani 1 1 d G . . . .
H13A H 0.618974 0.830415 0.453811 0.079 Uiso 1 1 calc R U . . .
H13B H 0.669627 0.813752 0.637599 0.079 Uiso 1 1 calc R U . . .
H13C H 0.603404 0.797327 0.696627 0.079 Uiso 1 1 calc R U . . .
C14 C 0.68537(5) 0.74731(7) 0.2542(8) 0.0518(10) Uani 1 1 d G . . . .
H14A H 0.691285 0.708902 0.181782 0.078 Uiso 1 1 calc R U . . .
H14B H 0.722093 0.760951 0.323754 0.078 Uiso 1 1 calc R U . . .
H14C H 0.672395 0.774924 0.132024 0.078 Uiso 1 1 calc R U . . .
O3W O 0.5239(5) 0.5535(5) 0.939(2) 0.044(2) Uiso 0.25 1 d . . P A 2
O2W O 0.5095(7) 0.5468(7) 0.559(3) 0.070(4) Uiso 0.25 1 d . . P B 1
O1W O 0.5044(10) 0.5609(10) 0.428(5) 0.102 Uiso 0.25 1 d . U P C 2
O4W O 0.4901(7) 0.5635(7) 1.052(3) 0.072(4) Uiso 0.25 1 d . . P D 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2151 . ?
O3 C4 1.2453 . ?
O2 C4 1.2330 . ?
N2 H2 0.8800 . ?
N2 C2 1.3209 . ?
N2 C3 1.4559 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C1 1.4507 . ?
C2 C1 1.5541 . ?
C4 C3 1.5524 . ?
C6 C11 1.3797 . ?
C6 C5 1.5120 . ?
C6 C7 1.4129 . ?
C3 H3 1.0000 . ?
C3 C12 1.5872 . ?
C11 H11 0.9500 . ?
C11 C10 1.4477 . ?
C1 H1 1.0000 . ?
C1 C5 1.5393 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C10 H10 0.9500 . ?
C10 C9 1.3661 . ?
C12 H12 1.0000 . ?
C12 C13 1.5205 . ?
C12 C14 1.4929 . ?
C7 H7 0.9500 . ?
C7 C8 1.3715 . ?
C9 H9 0.9500 . ?
C9 C8 1.3702 . ?
C8 H8 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O2W O2W 1.55(2) 4_565 ?
O2W O2W 1.55(2) 3_655 ?

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 N2 H2 119.6 . . ?
C2 N2 C3 120.9 . . ?
C3 N2 H2 119.6 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
O1 C2 N2 125.4 . . ?
O1 C2 C1 119.4 . . ?
N2 C2 C1 115.2 . . ?
O3 C4 C3 115.6 . . ?
O2 C4 O3 125.5 . . ?
O2 C4 C3 118.5 . . ?
C11 C6 C5 119.8 . . ?
C11 C6 C7 121.0 . . ?
C7 C6 C5 119.2 . . ?
N2 C3 C4 110.6 . . ?
N2 C3 H3 108.6 . . ?
N2 C3 C12 108.3 . . ?
C4 C3 H3 108.6 . . ?
C4 C3 C12 111.9 . . ?
C12 C3 H3 108.6 . . ?
C6 C11 H11 121.2 . . ?
C6 C11 C10 117.6 . . ?
C10 C11 H11 121.2 . . ?
N1 C1 C2 108.6 . . ?
N1 C1 H1 110.0 . . ?
N1 C1 C5 108.6 . . ?
C2 C1 H1 110.0 . . ?
C5 C1 C2 109.7 . . ?
C5 C1 H1 110.0 . . ?
C6 C5 C1 110.6 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C11 C10 H10 120.2 . . ?
C9 C10 C11 119.5 . . ?
C9 C10 H10 120.2 . . ?
C3 C12 H12 108.4 . . ?
C13 C12 C3 109.2 . . ?
C13 C12 H12 108.4 . . ?
C14 C12 C3 111.7 . . ?
C14 C12 H12 108.4 . . ?
C14 C12 C13 110.6 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 119.9 . . ?
C8 C7 H7 120.0 . . ?
C10 C9 H9 119.0 . . ?
C10 C9 C8 122.0 . . ?
C8 C9 H9 119.0 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 119.9 . . ?
C9 C8 H8 120.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2W O2W O2W 89.998(10) 4_565 3_655 ?

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 C2 C1 N1 56.8 . . . . ?
O1 C2 C1 C5 -61.7 . . . . ?
O3 C4 C3 N2 150.4 . . . . ?
O3 C4 C3 C12 -88.8 . . . . ?
O2 C4 C3 N2 -35.4 . . . . ?
O2 C4 C3 C12 85.5 . . . . ?
N2 C2 C1 N1 -125.2 . . . . ?
N2 C2 C1 C5 116.3 . . . . ?
N2 C3 C12 C13 -65.2 . . . . ?
N2 C3 C12 C14 172.1 . . . . ?
N1 C1 C5 C6 -175.0 . . . . ?
C2 N2 C3 C4 -61.0 . . . . ?
C2 N2 C3 C12 176.0 . . . . ?
C2 C1 C5 C6 -56.5 . . . . ?
C4 C3 C12 C13 172.7 . . . . ?
C4 C3 C12 C14 49.9 . . . . ?
C6 C11 C10 C9 1.2 . . . . ?
C6 C7 C8 C9 -3.4 . . . . ?
C3 N2 C2 O1 -4.4 . . . . ?
C3 N2 C2 C1 177.8 . . . . ?
C11 C6 C5 C1 -69.5 . . . . ?
C11 C6 C7 C8 2.0 . . . . ?
C11 C10 C9 C8 -2.7 . . . . ?
C5 C6 C11 C10 179.8 . . . . ?
C5 C6 C7 C8 -178.6 . . . . ?
C10 C9 C8 C7 3.8 . . . . ?
C7 C6 C11 C10 -0.8 . . . . ?
C7 C6 C5 C1 111.1 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
