# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_03457_Cu
_audit_block_doi                 10.5517/ccdc.csd.cc2dm7pz
_database_code_depnum_ccdc_archive 'CCDC 2223031'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles'
;Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2022-11-29 deposited with the CCDC.	2023-03-07 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 N2 O6'
_chemical_formula_iupac          ?
_chemical_formula_weight         384.38
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_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                   6.5537(2)
_cell_length_b                   14.9106(4)
_cell_length_c                   18.4935(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1807.18(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9866
_cell_measurement_theta_min      3.8081
_cell_measurement_theta_max      74.5204
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.084
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808

_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;


_diffrn_source                   'sealed tube'
_diffrn_source_type              'Incoatec Cu-IMS3.0'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 Venture Cu-IMS3.0'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            21276
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_theta_min         3.81
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_full        68.23
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             3302
_reflns_number_gt                3184
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0711
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_number_reflns         3302
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+0.4017P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.144
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1305 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(6)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1328)'
_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
C C1 0.2914(3) 0.41217(14) 0.70354(10) 0.0234(4) Uani d . . . 1 . .
C C2 0.1574(3) 0.35750(14) 0.73645(11) 0.0249(4) Uani d . . . 1 . .
H H2 0.150596 0.344841 0.786738 0.030000 Uiso calc U . R 1 . .
C C3 0.0271(3) 0.32200(15) 0.68154(11) 0.0238(4) Uani d . . . 1 . .
H H3 -0.082940 0.281359 0.688280 0.029000 Uiso calc U . R 1 . .
C C4 0.0901(3) 0.35716(14) 0.61860(11) 0.0209(4) Uani d . . . 1 . .
C C5 0.0205(3) 0.34935(14) 0.54207(10) 0.0215(4) Uani d . . . 1 . .
H H5 -0.074352 0.296962 0.538902 0.026000 Uiso calc U . R 1 . .
C C6 -0.0942(3) 0.43433(14) 0.50971(10) 0.0205(4) Uani d . . . 1 . .
H H6 -0.242742 0.422111 0.502275 0.025000 Uiso calc U . R 1 . .
C C7 -0.0609(3) 0.51754(14) 0.55399(10) 0.0204(4) Uani d . . . 1 . .
C C8 0.1420(3) 0.53686(14) 0.45240(10) 0.0215(4) Uani d . . . 1 . .
C C9 0.0149(3) 0.45328(13) 0.43766(10) 0.0207(4) Uani d . . . 1 . .
H H9 -0.085766 0.464208 0.397995 0.025000 Uiso calc U . R 1 . .
C C10 0.1437(3) 0.36679(13) 0.42252(10) 0.0207(4) Uani d . . . 1 . .
C C11 0.4640(3) 0.46748(15) 0.73059(11) 0.0248(4) Uani d . . . 1 . .
H H11A 0.459967 0.527013 0.706935 0.030000 Uiso calc U . R 1 . .
H H11B 0.448061 0.476739 0.783296 0.030000 Uiso calc U . R 1 . .
C C12 0.3445(3) 0.38685(13) 0.38387(10) 0.0208(4) Uani d . . . 1 . .
C C13 0.5065(4) 0.41227(17) 0.27244(12) 0.0332(5) Uani d . . . 1 . .
H H13A 0.475463 0.413673 0.220618 0.050000 Uiso calc U . R 1 . .
H H13B 0.609015 0.365905 0.281978 0.050000 Uiso calc U . R 1 . .
H H13C 0.559590 0.470785 0.287544 0.050000 Uiso calc U . R 1 . .
C C14 0.0119(3) 0.29936(15) 0.38084(11) 0.0252(4) Uani d . . . 1 . .
H H14A -0.018996 0.323364 0.332742 0.038000 Uiso calc U . R 1 . .
H H14B -0.115569 0.288981 0.407231 0.038000 Uiso calc U . R 1 . .
H H14C 0.086153 0.242631 0.375903 0.038000 Uiso calc U . R 1 . .
C C15 0.1857(3) 0.64454(14) 0.55547(10) 0.0217(4) Uani d . . . 1 . .
C C16 0.3820(3) 0.63363(14) 0.58166(11) 0.0256(4) Uani d . . . 1 . .
H H16 0.453225 0.578944 0.574121 0.031000 Uiso calc U . R 1 . .
C C17 0.4736(4) 0.70380(16) 0.61919(12) 0.0315(5) Uani d . . . 1 . .
H H17 0.608014 0.697208 0.637635 0.038000 Uiso calc U . R 1 . .
C C18 0.3680(4) 0.78334(16) 0.62958(12) 0.0326(5) Uani d . . . 1 . .
H H18 0.429365 0.830710 0.656182 0.039000 Uiso calc U . R 1 . .
C C19 0.1738(4) 0.79419(15) 0.60141(12) 0.0316(5) Uani d . . . 1 . .
H H19 0.104070 0.849511 0.607668 0.038000 Uiso calc U . R 1 . .
C C20 0.0801(3) 0.72431(14) 0.56393(11) 0.0265(5) Uani d . . . 1 . .
H H20 -0.053275 0.731252 0.544609 0.032000 Uiso calc U . R 1 . .
N N1 0.1945(3) 0.33161(12) 0.49416(9) 0.0219(4) Uani d . . . 1 . .
H H1N 0.301(4) 0.3605(18) 0.5108(13) 0.026000 Uiso d U . . 1 . .
N N2 0.0886(3) 0.56937(12) 0.52071(8) 0.0207(4) Uani d . . . 1 . .
O O1 0.2537(2) 0.41348(9) 0.63012(7) 0.0219(3) Uani d . . . 1 . .
O O2 -0.1448(2) 0.53771(10) 0.61028(7) 0.0248(3) Uani d . . . 1 . .
O O3 0.2650(2) 0.57105(10) 0.41289(8) 0.0280(3) Uani d . . . 1 . .
O O4 0.3217(2) 0.39215(10) 0.31277(7) 0.0244(3) Uani d . . . 1 . .
O O5 0.5052(2) 0.39581(11) 0.41481(8) 0.0301(3) Uani d . . . 1 . .
O O6 0.6548(2) 0.42695(12) 0.71698(9) 0.0347(4) Uani d . . . 1 . .
H H6O 0.715(5) 0.456(2) 0.6778(16) 0.042000 Uiso d U . . 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
C1 C2 . 1.344(3) ?
C1 O1 . 1.380(2) ?
C1 C11 . 1.487(3) ?
C2 C3 . 1.429(3) ?
C3 C4 . 1.342(3) ?
C4 O1 . 1.379(2) ?
C4 C5 . 1.491(3) ?
C5 N1 . 1.468(3) ?
C5 C6 . 1.590(3) ?
C6 C7 . 1.502(3) ?
C6 C9 . 1.538(3) ?
C7 O2 . 1.215(2) ?
C7 N2 . 1.391(3) ?
C8 O3 . 1.201(2) ?
C8 N2 . 1.398(2) ?
C8 C9 . 1.524(3) ?
C9 C10 . 1.566(3) ?
C10 N1 . 1.463(3) ?
C10 C12 . 1.527(3) ?
C10 C14 . 1.533(3) ?
C11 O6 . 1.412(3) ?
C12 O5 . 1.206(3) ?
C12 O4 . 1.326(2) ?
C13 O4 . 1.453(2) ?
C15 C16 . 1.384(3) ?
C15 C20 . 1.385(3) ?
C15 N2 . 1.440(3) ?
C16 C17 . 1.392(3) ?
C17 C18 . 1.386(3) ?
C18 C19 . 1.385(4) ?
C19 C20 . 1.394(3) ?

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 C1 O1 . . 109.72(17) ?
C2 C1 C11 . . 132.94(18) ?
O1 C1 C11 . . 117.33(17) ?
C1 C2 C3 . . 107.06(18) ?
C4 C3 C2 . . 106.74(19) ?
C3 C4 O1 . . 110.08(17) ?
C3 C4 C5 . . 134.31(19) ?
O1 C4 C5 . . 115.59(16) ?
N1 C5 C4 . . 110.43(17) ?
N1 C5 C6 . . 106.48(15) ?
C4 C5 C6 . . 116.07(16) ?
C7 C6 C9 . . 104.65(16) ?
C7 C6 C5 . . 112.60(15) ?
C9 C6 C5 . . 104.63(15) ?
O2 C7 N2 . . 124.06(19) ?
O2 C7 C6 . . 127.27(18) ?
N2 C7 C6 . . 108.66(16) ?
O3 C8 N2 . . 124.79(19) ?
O3 C8 C9 . . 127.23(18) ?
N2 C8 C9 . . 107.97(16) ?
C8 C9 C6 . . 104.44(15) ?
C8 C9 C10 . . 114.26(16) ?
C6 C9 C10 . . 104.71(15) ?
N1 C10 C12 . . 107.32(16) ?
N1 C10 C14 . . 110.39(17) ?
C12 C10 C14 . . 112.23(16) ?
N1 C10 C9 . . 104.84(15) ?
C12 C10 C9 . . 112.74(16) ?
C14 C10 C9 . . 109.05(16) ?
O6 C11 C1 . . 112.14(17) ?
O5 C12 O4 . . 124.20(19) ?
O5 C12 C10 . . 123.52(17) ?
O4 C12 C10 . . 112.28(16) ?
C16 C15 C20 . . 121.7(2) ?
C16 C15 N2 . . 118.39(18) ?
C20 C15 N2 . . 119.86(18) ?
C15 C16 C17 . . 119.1(2) ?
C18 C17 C16 . . 119.8(2) ?
C19 C18 C17 . . 120.4(2) ?
C18 C19 C20 . . 120.3(2) ?
C15 C20 C19 . . 118.6(2) ?
C10 N1 C5 . . 107.74(15) ?
C7 N2 C8 . . 112.55(17) ?
C7 N2 C15 . . 123.09(16) ?
C8 N2 C15 . . 124.24(16) ?
C4 O1 C1 . . 106.40(15) ?
C12 O4 C13 . . 115.31(17) ?

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
O1 C1 C2 C3 . . . . -0.1(2) ?
C11 C1 C2 C3 . . . . -179.4(2) ?
C1 C2 C3 C4 . . . . 0.1(2) ?
C2 C3 C4 O1 . . . . -0.1(2) ?
C2 C3 C4 C5 . . . . -179.0(2) ?
C3 C4 C5 N1 . . . . -131.9(2) ?
O1 C4 C5 N1 . . . . 49.2(2) ?
C3 C4 C5 C6 . . . . 106.8(3) ?
O1 C4 C5 C6 . . . . -72.1(2) ?
N1 C5 C6 C7 . . . . -106.80(18) ?
C4 C5 C6 C7 . . . . 16.6(2) ?
N1 C5 C6 C9 . . . . 6.3(2) ?
C4 C5 C6 C9 . . . . 129.64(18) ?
C9 C6 C7 O2 . . . . 168.26(19) ?
C5 C6 C7 O2 . . . . -78.7(2) ?
C9 C6 C7 N2 . . . . -13.0(2) ?
C5 C6 C7 N2 . . . . 100.10(18) ?
O3 C8 C9 C6 . . . . 173.2(2) ?
N2 C8 C9 C6 . . . . -7.9(2) ?
O3 C8 C9 C10 . . . . 59.4(3) ?
N2 C8 C9 C10 . . . . -121.67(17) ?
C7 C6 C9 C8 . . . . 12.30(19) ?
C5 C6 C9 C8 . . . . -106.31(17) ?
C7 C6 C9 C10 . . . . 132.72(16) ?
C5 C6 C9 C10 . . . . 14.11(19) ?
C8 C9 C10 N1 . . . . 83.59(19) ?
C6 C9 C10 N1 . . . . -30.06(19) ?
C8 C9 C10 C12 . . . . -32.8(2) ?
C6 C9 C10 C12 . . . . -146.49(16) ?
C8 C9 C10 C14 . . . . -158.20(16) ?
C6 C9 C10 C14 . . . . 88.15(18) ?
C2 C1 C11 O6 . . . . 102.2(3) ?
O1 C1 C11 O6 . . . . -77.1(2) ?
N1 C10 C12 O5 . . . . -18.9(3) ?
C14 C10 C12 O5 . . . . -140.3(2) ?
C9 C10 C12 O5 . . . . 96.1(2) ?
N1 C10 C12 O4 . . . . 160.37(16) ?
C14 C10 C12 O4 . . . . 38.9(2) ?
C9 C10 C12 O4 . . . . -84.7(2) ?
C20 C15 C16 C17 . . . . 1.8(3) ?
N2 C15 C16 C17 . . . . -176.21(19) ?
C15 C16 C17 C18 . . . . -0.2(3) ?
C16 C17 C18 C19 . . . . -1.5(3) ?
C17 C18 C19 C20 . . . . 1.7(3) ?
C16 C15 C20 C19 . . . . -1.5(3) ?
N2 C15 C20 C19 . . . . 176.39(18) ?
C18 C19 C20 C15 . . . . -0.2(3) ?
C12 C10 N1 C5 . . . . 155.26(16) ?
C14 C10 N1 C5 . . . . -82.1(2) ?
C9 C10 N1 C5 . . . . 35.2(2) ?
C4 C5 N1 C10 . . . . -152.87(17) ?
C6 C5 N1 C10 . . . . -26.1(2) ?
O2 C7 N2 C8 . . . . -172.63(18) ?
C6 C7 N2 C8 . . . . 8.5(2) ?
O2 C7 N2 C15 . . . . 11.2(3) ?
C6 C7 N2 C15 . . . . -167.62(17) ?
O3 C8 N2 C7 . . . . 178.75(19) ?
C9 C8 N2 C7 . . . . -0.2(2) ?
O3 C8 N2 C15 . . . . -5.1(3) ?
C9 C8 N2 C15 . . . . 175.92(17) ?
C16 C15 N2 C7 . . . . 103.7(2) ?
C20 C15 N2 C7 . . . . -74.3(2) ?
C16 C15 N2 C8 . . . . -72.0(2) ?
C20 C15 N2 C8 . . . . 110.0(2) ?
C3 C4 O1 C1 . . . . 0.1(2) ?
C5 C4 O1 C1 . . . . 179.17(17) ?
C2 C1 O1 C4 . . . . 0.0(2) ?
C11 C1 O1 C4 . . . . 179.46(17) ?
O5 C12 O4 C13 . . . . -1.5(3) ?
C10 C12 O4 C13 . . . . 179.25(17) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C5 H5 N1 4_456 1.000000 2.520000 3.506(3) 169.300000 ?
C6 H6 O5 1_455 1.000000 2.350000 3.210(2) 144.200000 ?
C13 H13A O2 2_564 0.980000 2.430000 3.220(2) 137.000000 ?
N1 H1N O1 . 0.87(3) 2.36(2) 2.822(2) 112.9(19) ?
O6 H6O O2 1_655 0.93(3) 1.97(3) 2.889(2) 168.(3) ?



