# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1897071'
loop_
_audit_author_name
_audit_author_address
'Magda Monari'
;University of Bologna
Italy
;
_audit_update_record             
;
2019-02-13 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H26 N2 O6'
_chemical_formula_weight         390.43

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      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'

_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, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   10.5551(8)
_cell_length_b                   10.5551(8)
_cell_length_c                   18.9321(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2109.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      28.24

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32476
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.209
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5178
_reflns_number_gt                3720
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.930
_reflns_Friedel_fraction_max     0.979
_reflns_Friedel_fraction_full    0.989

_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-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1069P)²+0.2437P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1370 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         5178
_refine_ls_number_parameters     249
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.1841
_refine_ls_wR_factor_gt          0.1686
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.035
_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
O5 O 0.5415(3) 0.4018(3) 0.07598(15) 0.0739(8) Uani 1 1 d . . . . .
O6 O 0.5932(3) 0.5225(3) 0.17106(16) 0.0789(10) Uani 1 1 d . . . . .
N2 N 0.4160(3) 0.4142(4) 0.17112(16) 0.0661(9) Uani 1 1 d . . . . .
N1 N 0.2527(3) 0.3021(3) 0.01700(14) 0.0500(7) Uani 1 1 d . . . . .
O1 O 0.0638(3) 0.5102(3) -0.08316(18) 0.0747(8) Uani 1 1 d . . . . .
C9 C 0.2125(3) 0.3609(3) -0.04865(17) 0.0522(8) Uani 1 1 d . . . . .
H9 H 0.2703 0.4298 -0.0616 0.063 Uiso 1 1 calc R U . . .
C14 C 0.3253(4) 0.3265(4) 0.14177(18) 0.0600(9) Uani 1 1 d . . . . .
H14 H 0.3667 0.2456 0.1312 0.072 Uiso 1 1 calc R U . . .
O4 O 0.2415(4) 0.4917(3) 0.06926(17) 0.0789(9) Uani 1 1 d . . . . .
C8 C 0.0794(4) 0.4094(4) -0.04226(19) 0.0559(8) Uani 1 1 d . . . . .
C15 C 0.5192(4) 0.4432(4) 0.13431(19) 0.0615(9) Uani 1 1 d . . . . .
O2 O -0.0020(3) 0.3613(4) -0.0084(2) 0.0906(10) Uani 1 1 d . . . . .
O3 O 0.2905(5) 0.1014(3) 0.0592(2) 0.1126(16) Uani 1 1 d . . . . .
C13 C 0.2709(4) 0.3829(4) 0.07488(19) 0.0541(8) Uani 1 1 d . . . . .
C1 C -0.0547(3) 0.7035(3) -0.07051(16) 0.0683(11) Uani 1 1 d G . . . .
C2 C 0.0034(4) 0.7444(3) -0.00869(16) 0.0893(15) Uani 1 1 d G . . . .
H2 H 0.0425 0.6861 0.0210 0.107 Uiso 1 1 calc R U . . .
C3 C 0.0032(4) 0.8723(3) 0.0087(2) 0.109(2) Uani 1 1 d G . . . .
H3 H 0.0421 0.8996 0.0501 0.131 Uiso 1 1 calc R U . . .
C4 C -0.0552(5) 0.9594(3) -0.0357(3) 0.1097(19) Uani 1 1 d G U . . .
H4 H -0.0554 1.0450 -0.0241 0.132 Uiso 1 1 calc R U . . .
C5 C -0.1133(5) 0.9185(3) -0.0975(2) 0.143(4) Uani 1 1 d G U . . .
H5 H -0.1524 0.9768 -0.1273 0.172 Uiso 1 1 calc R U . . .
C6 C -0.1131(4) 0.7906(4) -0.11494(16) 0.118(3) Uani 1 1 d G . . . .
H6 H -0.1520 0.7633 -0.1563 0.141 Uiso 1 1 calc R U . . .
C12 C 0.2702(5) 0.1724(4) 0.0114(2) 0.0705(11) Uani 1 1 d . . . . .
C10 C 0.2202(5) 0.2529(5) -0.1031(2) 0.0750(12) Uani 1 1 d . . . . .
H11A H 0.1386 0.2409 -0.1257 0.090 Uiso 1 1 calc R U . . .
H11B H 0.2823 0.2728 -0.1391 0.090 Uiso 1 1 calc R U . . .
C16 C 0.7111(4) 0.5767(6) 0.1412(3) 0.096(2) Uani 1 1 d . . . . .
C20 C 0.2188(5) 0.3062(7) 0.1948(3) 0.0990(19) Uani 1 1 d . . . . .
H20A H 0.2532 0.2726 0.2379 0.148 Uiso 1 1 calc R U . . .
H20C H 0.1583 0.2475 0.1757 0.148 Uiso 1 1 calc R U . . .
H20B H 0.1777 0.3855 0.2043 0.148 Uiso 1 1 calc R U . . .
C19 C 0.7592(6) 0.6532(8) 0.2039(5) 0.130(3) Uani 1 1 d . . . . .
H19C H 0.6934 0.7088 0.2202 0.195 Uiso 1 1 calc R U . . .
H19B H 0.8314 0.7023 0.1898 0.195 Uiso 1 1 calc R U . . .
H19A H 0.7830 0.5966 0.2413 0.195 Uiso 1 1 calc R U . . .
C7 C -0.0631(5) 0.5660(6) -0.0862(4) 0.0977(17) Uani 1 1 d . . . . .
H7A H -0.1179 0.5249 -0.0521 0.117 Uiso 1 1 calc R U . . .
H7B H -0.0990 0.5535 -0.1329 0.117 Uiso 1 1 calc R U . . .
C17 C 0.6793(7) 0.6595(7) 0.0798(4) 0.120(2) Uani 1 1 d . . . . .
H17B H 0.6546 0.6078 0.0404 0.179 Uiso 1 1 calc R U . . .
H17A H 0.7521 0.7091 0.0672 0.179 Uiso 1 1 calc R U . . .
H17C H 0.6107 0.7148 0.0924 0.179 Uiso 1 1 calc R U . . .
C11 C 0.2569(7) 0.1387(5) -0.0652(3) 0.0938(17) Uani 1 1 d . . . . .
H12B H 0.3367 0.1067 -0.0834 0.113 Uiso 1 1 calc R U . . .
H12A H 0.1929 0.0736 -0.0711 0.113 Uiso 1 1 calc R U . . .
C18 C 0.8036(6) 0.4689(8) 0.1244(5) 0.124(3) Uani 1 1 d . . . . .
H18B H 0.8188 0.4200 0.1663 0.185 Uiso 1 1 calc R U . . .
H18C H 0.8822 0.5038 0.1078 0.185 Uiso 1 1 calc R U . . .
H18A H 0.7679 0.4154 0.0885 0.185 Uiso 1 1 calc R U . . .
H2N H 0.408(4) 0.445(4) 0.212(3) 0.067(12) 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
O5 C15 1.211(4) . ?
O6 C15 1.340(5) . ?
O6 C16 1.481(6) . ?
N2 C15 1.329(5) . ?
N2 C14 1.443(5) . ?
N2 H2N 0.84(5) . ?
N1 C12 1.385(5) . ?
N1 C13 1.402(4) . ?
N1 C9 1.453(4) . ?
O1 C8 1.326(5) . ?
O1 C7 1.464(6) . ?
C9 C8 1.500(5) . ?
C9 C10 1.539(6) . ?
C9 H9 0.9800 . ?
C14 C13 1.512(5) . ?
C14 C20 1.522(6) . ?
C14 H14 0.9800 . ?
O4 C13 1.194(5) . ?
C8 O2 1.187(5) . ?
O3 C12 1.193(6) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C7 1.484(7) . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C12 C11 1.500(7) . ?
C10 C11 1.455(8) . ?
C10 H11A 0.9700 . ?
C10 H11B 0.9700 . ?
C16 C17 1.492(11) . ?
C16 C19 1.523(8) . ?
C16 C18 1.533(9) . ?
C20 H20A 0.9600 . ?
C20 H20C 0.9600 . ?
C20 H20B 0.9600 . ?
C19 H19C 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19A 0.9600 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C17 H17B 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17C 0.9600 . ?
C11 H12B 0.9700 . ?
C11 H12A 0.9700 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18 H18A 0.9600 . ?

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
C15 O6 C16 122.2(3) . . ?
C15 N2 C14 119.3(3) . . ?
C15 N2 H2N 119(3) . . ?
C14 N2 H2N 122(3) . . ?
C12 N1 C13 130.0(3) . . ?
C12 N1 C9 113.3(3) . . ?
C13 N1 C9 116.6(3) . . ?
C8 O1 C7 117.4(4) . . ?
N1 C9 C8 110.5(3) . . ?
N1 C9 C10 103.9(3) . . ?
C8 C9 C10 110.9(3) . . ?
N1 C9 H9 110.5 . . ?
C8 C9 H9 110.5 . . ?
C10 C9 H9 110.5 . . ?
N2 C14 C13 108.8(3) . . ?
N2 C14 C20 109.1(3) . . ?
C13 C14 C20 109.1(4) . . ?
N2 C14 H14 110.0 . . ?
C13 C14 H14 110.0 . . ?
C20 C14 H14 110.0 . . ?
O2 C8 O1 124.7(4) . . ?
O2 C8 C9 125.1(4) . . ?
O1 C8 C9 110.1(3) . . ?
O5 C15 N2 123.7(4) . . ?
O5 C15 O6 125.9(4) . . ?
N2 C15 O6 110.5(3) . . ?
O4 C13 N1 118.7(3) . . ?
O4 C13 C14 123.5(3) . . ?
N1 C13 C14 117.8(3) . . ?
C2 C1 C6 120.0 . . ?
C2 C1 C7 119.9(3) . . ?
C6 C1 C7 119.9(3) . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
O3 C12 N1 125.9(4) . . ?
O3 C12 C11 126.9(4) . . ?
N1 C12 C11 107.2(4) . . ?
C11 C10 C9 107.3(3) . . ?
C11 C10 H11A 110.2 . . ?
C9 C10 H11A 110.2 . . ?
C11 C10 H11B 110.2 . . ?
C9 C10 H11B 110.2 . . ?
H11A C10 H11B 108.5 . . ?
O6 C16 C17 109.6(5) . . ?
O6 C16 C19 100.8(4) . . ?
C17 C16 C19 111.8(6) . . ?
O6 C16 C18 109.1(5) . . ?
C17 C16 C18 114.6(6) . . ?
C19 C16 C18 110.0(6) . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
C14 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20C C20 H20B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19C C19 H19B 109.5 . . ?
C16 C19 H19A 109.5 . . ?
H19C C19 H19A 109.5 . . ?
H19B C19 H19A 109.5 . . ?
O1 C7 C1 109.3(4) . . ?
O1 C7 H7A 109.8 . . ?
C1 C7 H7A 109.8 . . ?
O1 C7 H7B 109.8 . . ?
C1 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17A 109.5 . . ?
H17B C17 H17A 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
C10 C11 C12 107.8(4) . . ?
C10 C11 H12B 110.2 . . ?
C12 C11 H12B 110.2 . . ?
C10 C11 H12A 110.2 . . ?
C12 C11 H12A 110.2 . . ?
H12B C11 H12A 108.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
H18B C18 H18A 109.5 . . ?
H18C C18 H18A 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 C9 C8 112.5(4) . . . . ?
C13 N1 C9 C8 -69.0(4) . . . . ?
C12 N1 C9 C10 -6.5(4) . . . . ?
C13 N1 C9 C10 172.0(3) . . . . ?
C15 N2 C14 C13 -62.9(5) . . . . ?
C15 N2 C14 C20 178.2(5) . . . . ?
C7 O1 C8 O2 0.3(6) . . . . ?
C7 O1 C8 C9 176.9(4) . . . . ?
N1 C9 C8 O2 -33.9(5) . . . . ?
C10 C9 C8 O2 80.8(5) . . . . ?
N1 C9 C8 O1 149.6(3) . . . . ?
C10 C9 C8 O1 -95.7(4) . . . . ?
C14 N2 C15 O5 1.4(7) . . . . ?
C14 N2 C15 O6 -178.1(4) . . . . ?
C16 O6 C15 O5 4.2(8) . . . . ?
C16 O6 C15 N2 -176.3(5) . . . . ?
C12 N1 C13 O4 -175.0(4) . . . . ?
C9 N1 C13 O4 6.9(5) . . . . ?
C12 N1 C13 C14 4.2(6) . . . . ?
C9 N1 C13 C14 -174.0(3) . . . . ?
N2 C14 C13 O4 -41.9(5) . . . . ?
C20 C14 C13 O4 77.0(5) . . . . ?
N2 C14 C13 N1 139.0(3) . . . . ?
C20 C14 C13 N1 -102.2(5) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C7 C1 C2 C3 -175.3(4) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C7 C1 C6 C5 175.3(4) . . . . ?
C13 N1 C12 O3 9.8(8) . . . . ?
C9 N1 C12 O3 -172.0(5) . . . . ?
C13 N1 C12 C11 -171.1(4) . . . . ?
C9 N1 C12 C11 7.2(5) . . . . ?
N1 C9 C10 C11 3.1(5) . . . . ?
C8 C9 C10 C11 -115.7(5) . . . . ?
C15 O6 C16 C17 64.1(6) . . . . ?
C15 O6 C16 C19 -177.9(6) . . . . ?
C15 O6 C16 C18 -62.1(8) . . . . ?
C8 O1 C7 C1 127.3(5) . . . . ?
C2 C1 C7 O1 -54.3(6) . . . . ?
C6 C1 C7 O1 130.5(4) . . . . ?
C9 C10 C11 C12 0.9(6) . . . . ?
O3 C12 C11 C10 174.3(6) . . . . ?
N1 C12 C11 C10 -4.8(6) . . . . ?

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
N2 H2N O5 0.84(5) 2.16(6) 2.973(4) 161(4) 4_565
C14 H14 O3 0.98 2.20 2.868(5) 124.5 .
C10 H11B O4 0.97 2.53 3.380(6) 145.8 3_654
C17 H17B O5 0.96 2.57 3.085(7) 113.8 .
C18 H18A O5 0.96 2.41 3.000(8) 119.7 .
N2 H2N O5 0.84(5) 2.16(6) 2.973(4) 161(4) 4_565
C14 H14 O3 0.98 2.20 2.868(5) 124.5 .
C10 H11B O4 0.97 2.53 3.380(6) 145.8 3_654
C17 H17B O5 0.96 2.57 3.085(7) 113.8 .
C18 H18A O5 0.96 2.41 3.000(8) 119.7 .

_refine_diff_density_max         0.226
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1897072'
loop_
_audit_author_name
_audit_author_address
'Magda Monari'
;University of Bologna
Italy
;
_audit_update_record             
;
2019-02-13 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H26 N2 O6'
_chemical_formula_weight         390.43

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.3138(10)
_cell_length_b                   10.0679(6)
_cell_length_c                   11.1281(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.629(2)
_cell_angle_gamma                90
_cell_volume                     2002.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7526
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.39

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30766
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.279
_diffrn_reflns_theta_max         28.453
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5029
_reflns_number_gt                3419
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0823P)²+0.3338P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5029
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0674
_refine_ls_wR_factor_ref         0.1660
_refine_ls_wR_factor_gt          0.1498
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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 -0.48874(7) 0.29926(15) -0.44398(13) 0.0447(4) Uani 1 1 d . . . . .
O2 O -0.39510(9) 0.28121(15) -0.27659(13) 0.0514(4) Uani 1 1 d . . . . .
O3 O -0.20381(8) 0.08401(15) -0.30231(15) 0.0550(4) Uani 1 1 d . . . . .
O4 O -0.31475(8) 0.38927(14) -0.51283(14) 0.0489(4) Uani 1 1 d . . . . .
O5 O -0.12780(11) 0.48244(16) -0.29775(15) 0.0621(5) Uani 1 1 d . . . . .
O6 O -0.10982(8) 0.61942(13) -0.45113(12) 0.0417(4) Uani 1 1 d . . . . .
N1 N -0.30445(8) 0.18446(14) -0.43289(13) 0.0300(3) Uani 1 1 d . . . . .
N2 N -0.16375(10) 0.42465(18) -0.49743(18) 0.0463(5) Uani 1 1 d . . . . .
H2N H -0.1673(13) 0.449(2) -0.571(2) 0.056 Uiso 1 1 d . U . . .
C1 C -0.59482(10) 0.27802(18) -0.34744(18) 0.0349(4) Uani 1 1 d . . . . .
C2 C -0.66731(11) 0.2827(2) -0.41651(19) 0.0418(5) Uani 1 1 d . . . . .
H2 H -0.6796 0.3416 -0.4822 0.050 Uiso 1 1 calc R U . . .
C3 C -0.72149(13) 0.2004(3) -0.3885(2) 0.0554(6) Uani 1 1 d . . . . .
H3 H -0.7703 0.2044 -0.4350 0.066 Uiso 1 1 calc R U . . .
C4 C -0.70358(14) 0.1125(2) -0.2920(2) 0.0577(6) Uani 1 1 d . . . . .
H4 H -0.7400 0.0569 -0.2730 0.069 Uiso 1 1 calc R U . . .
C5 C -0.63151(14) 0.1072(2) -0.2240(2) 0.0547(6) Uani 1 1 d . . . . .
H5 H -0.6191 0.0473 -0.1591 0.066 Uiso 1 1 calc R U . . .
C6 C -0.57746(12) 0.1900(2) -0.2508(2) 0.0460(5) Uani 1 1 d . . . . .
H6 H -0.5289 0.1864 -0.2035 0.055 Uiso 1 1 calc R U . . .
C7 C -0.53650(12) 0.3699(2) -0.3750(2) 0.0478(5) Uani 1 1 d . . . . .
H7A H -0.5604 0.4446 -0.4231 0.057 Uiso 1 1 calc R U . . .
H7B H -0.5062 0.4039 -0.2987 0.057 Uiso 1 1 calc R U . . .
C8 C -0.42196(10) 0.25843(18) -0.38210(18) 0.0331(4) Uani 1 1 d . . . . .
C9 C -0.38571(9) 0.16984(19) -0.46268(17) 0.0321(4) Uani 1 1 d . . . . .
H9 H -0.4062 0.1875 -0.5501 0.039 Uiso 1 1 calc R U . . .
C10 C -0.39618(11) 0.0231(2) -0.4317(2) 0.0445(5) Uani 1 1 d . . . . .
H10A H -0.4420 0.0107 -0.4028 0.053 Uiso 1 1 calc R U . . .
H10B H -0.3977 -0.0329 -0.5031 0.053 Uiso 1 1 calc R U . . .
C11 C -0.32850(12) -0.00812(19) -0.3311(2) 0.0444(5) Uani 1 1 d . . . . .
H11A H -0.3396 0.0044 -0.2505 0.053 Uiso 1 1 calc R U . . .
H11B H -0.3124 -0.0991 -0.3378 0.053 Uiso 1 1 calc R U . . .
C12 C -0.26964(11) 0.08716(18) -0.35047(18) 0.0352(4) Uani 1 1 d . . . . .
C13 C -0.27362(10) 0.29902(17) -0.47226(17) 0.0310(4) Uani 1 1 d . . . . .
C14 C -0.19042(11) 0.29557(18) -0.4713(2) 0.0390(5) Uani 1 1 d . . . . .
H14 H -0.1633 0.2686 -0.3890 0.047 Uiso 1 1 calc R U . . .
C15 C -0.13325(11) 0.50778(19) -0.40579(19) 0.0395(5) Uani 1 1 d . . . . .
C16 C -0.06617(11) 0.71861(19) -0.36763(18) 0.0395(5) Uani 1 1 d . . . . .
C17 C -0.11463(16) 0.7796(3) -0.2884(2) 0.0635(7) Uani 1 1 d . . . . .
H17A H -0.0868 0.8469 -0.2367 0.095 Uiso 1 1 calc R U . . .
H17B H -0.1297 0.7120 -0.2380 0.095 Uiso 1 1 calc R U . . .
H17C H -0.1582 0.8186 -0.3401 0.095 Uiso 1 1 calc R U . . .
C18 C 0.00426(13) 0.6565(3) -0.2932(3) 0.0631(7) Uani 1 1 d . . . . .
H18A H 0.0299 0.6104 -0.3472 0.095 Uiso 1 1 calc R U . . .
H18B H -0.0085 0.5949 -0.2352 0.095 Uiso 1 1 calc R U . . .
H18C H 0.0362 0.7246 -0.2497 0.095 Uiso 1 1 calc R U . . .
C19 C -0.04693(16) 0.8202(2) -0.4560(2) 0.0634(7) Uani 1 1 d . . . . .
H19A H -0.0158 0.8880 -0.4104 0.095 Uiso 1 1 calc R U . . .
H19B H -0.0921 0.8596 -0.5024 0.095 Uiso 1 1 calc R U . . .
H19C H -0.0207 0.7775 -0.5112 0.095 Uiso 1 1 calc R U . . .
C20 C -0.17606(15) 0.1925(2) -0.5634(3) 0.0641(7) Uani 1 1 d . . . . .
H20A H -0.2043 0.2149 -0.6441 0.096 Uiso 1 1 calc R U . . .
H20B H -0.1911 0.1066 -0.5404 0.096 Uiso 1 1 calc R U . . .
H20C H -0.1237 0.1912 -0.5639 0.096 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 C8 1.331(2) . ?
O1 C7 1.467(2) . ?
O2 C8 1.192(2) . ?
O3 C12 1.208(2) . ?
O4 C13 1.203(2) . ?
O5 C15 1.212(2) . ?
O6 C15 1.340(2) . ?
O6 C16 1.475(2) . ?
N1 C13 1.396(2) . ?
N1 C12 1.397(2) . ?
N1 C9 1.460(2) . ?
N2 C15 1.343(3) . ?
N2 C14 1.440(2) . ?
N2 H2N 0.84(3) . ?
C1 C6 1.376(3) . ?
C1 C2 1.382(3) . ?
C1 C7 1.495(3) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.517(3) . ?
C9 C10 1.539(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.510(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.493(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 C14 1.522(3) . ?
C14 C20 1.521(3) . ?
C14 H14 0.9800 . ?
C16 C18 1.508(3) . ?
C16 C17 1.512(3) . ?
C16 C19 1.513(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

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
C8 O1 C7 117.69(16) . . ?
C15 O6 C16 120.31(15) . . ?
C13 N1 C12 128.86(15) . . ?
C13 N1 C9 118.31(14) . . ?
C12 N1 C9 112.01(14) . . ?
C15 N2 C14 120.81(18) . . ?
C15 N2 H2N 119.3(17) . . ?
C14 N2 H2N 119.9(17) . . ?
C6 C1 C2 119.10(19) . . ?
C6 C1 C7 120.40(19) . . ?
C2 C1 C7 120.48(18) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 119.5(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 C7 C1 109.98(16) . . ?
O1 C7 H7A 109.7 . . ?
C1 C7 H7A 109.7 . . ?
O1 C7 H7B 109.7 . . ?
C1 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
O2 C8 O1 125.80(18) . . ?
O2 C8 C9 123.77(17) . . ?
O1 C8 C9 110.32(16) . . ?
N1 C9 C8 111.26(14) . . ?
N1 C9 C10 102.52(15) . . ?
C8 C9 C10 109.86(15) . . ?
N1 C9 H9 111.0 . . ?
C8 C9 H9 111.0 . . ?
C10 C9 H9 111.0 . . ?
C11 C10 C9 104.12(15) . . ?
C11 C10 H10A 110.9 . . ?
C9 C10 H10A 110.9 . . ?
C11 C10 H10B 110.9 . . ?
C9 C10 H10B 110.9 . . ?
H10A C10 H10B 109.0 . . ?
C12 C11 C10 105.11(16) . . ?
C12 C11 H11A 110.7 . . ?
C10 C11 H11A 110.7 . . ?
C12 C11 H11B 110.7 . . ?
C10 C11 H11B 110.7 . . ?
H11A C11 H11B 108.8 . . ?
O3 C12 N1 125.29(17) . . ?
O3 C12 C11 126.94(18) . . ?
N1 C12 C11 107.75(16) . . ?
O4 C13 N1 118.58(16) . . ?
O4 C13 C14 124.31(16) . . ?
N1 C13 C14 116.87(15) . . ?
N2 C14 C20 111.28(17) . . ?
N2 C14 C13 111.18(16) . . ?
C20 C14 C13 109.34(17) . . ?
N2 C14 H14 108.3 . . ?
C20 C14 H14 108.3 . . ?
C13 C14 H14 108.3 . . ?
O5 C15 O6 125.90(19) . . ?
O5 C15 N2 123.55(18) . . ?
O6 C15 N2 110.55(17) . . ?
O6 C16 C18 110.24(17) . . ?
O6 C16 C17 109.64(17) . . ?
C18 C16 C17 112.9(2) . . ?
O6 C16 C19 102.68(16) . . ?
C18 C16 C19 110.18(19) . . ?
C17 C16 C19 110.8(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.2(3) . . . . ?
C7 C1 C2 C3 -178.09(19) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 -0.8(3) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C7 C1 C6 C5 178.71(19) . . . . ?
C8 O1 C7 C1 -101.1(2) . . . . ?
C6 C1 C7 O1 80.1(2) . . . . ?
C2 C1 C7 O1 -101.6(2) . . . . ?
C7 O1 C8 O2 -5.0(3) . . . . ?
C7 O1 C8 C9 171.29(15) . . . . ?
C13 N1 C9 C8 -75.0(2) . . . . ?
C12 N1 C9 C8 95.59(18) . . . . ?
C13 N1 C9 C10 167.66(15) . . . . ?
C12 N1 C9 C10 -21.79(19) . . . . ?
O2 C8 C9 N1 -36.2(2) . . . . ?
O1 C8 C9 N1 147.43(15) . . . . ?
O2 C8 C9 C10 76.7(2) . . . . ?
O1 C8 C9 C10 -99.74(18) . . . . ?
N1 C9 C10 C11 28.63(19) . . . . ?
C8 C9 C10 C11 -89.74(18) . . . . ?
C9 C10 C11 C12 -25.9(2) . . . . ?
C13 N1 C12 O3 -3.5(3) . . . . ?
C9 N1 C12 O3 -172.77(19) . . . . ?
C13 N1 C12 C11 175.06(17) . . . . ?
C9 N1 C12 C11 5.8(2) . . . . ?
C10 C11 C12 O3 -168.2(2) . . . . ?
C10 C11 C12 N1 13.3(2) . . . . ?
C12 N1 C13 O4 -158.00(19) . . . . ?
C9 N1 C13 O4 10.7(3) . . . . ?
C12 N1 C13 C14 27.4(3) . . . . ?
C9 N1 C13 C14 -163.89(16) . . . . ?
C15 N2 C14 C20 -143.9(2) . . . . ?
C15 N2 C14 C13 94.0(2) . . . . ?
O4 C13 C14 N2 13.7(3) . . . . ?
N1 C13 C14 N2 -172.07(16) . . . . ?
O4 C13 C14 C20 -109.6(2) . . . . ?
N1 C13 C14 C20 64.7(2) . . . . ?
C16 O6 C15 O5 6.9(3) . . . . ?
C16 O6 C15 N2 -172.53(17) . . . . ?
C14 N2 C15 O5 -1.9(3) . . . . ?
C14 N2 C15 O6 177.57(17) . . . . ?
C15 O6 C16 C18 58.5(2) . . . . ?
C15 O6 C16 C17 -66.4(2) . . . . ?
C15 O6 C16 C19 175.85(19) . . . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.044

