# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

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

data_compound_3n
_database_code_depnum_ccdc_archive 'CCDC 1992288'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2020-03-23 deposited with the CCDC.	2020-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 N2 O9'
_chemical_formula_sum            'C16 H16 N2 O9'
_chemical_formula_weight         380.31

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.3667(3)
_cell_length_b                   6.84234(18)
_cell_length_c                   12.9093(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.345(3)
_cell_angle_gamma                90
_cell_volume                     858.56(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3377
_cell_measurement_theta_min      3.420
_cell_measurement_theta_max      26.0

_exptl_crystal_description       tab
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector                 'Dectris PILATUS3 R 200K-A area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'Hybrid Photon Counting area detector'

_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'

_diffrn_radiation_collimation    
'Rigaku Integrated Confocal MaxFlux double bounce multi-layer mirror optics'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          x-ray

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku micromax 003'
_diffrn_reflns_number            40844
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.420
_diffrn_reflns_theta_max         26.016
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3377
_reflns_number_gt                3234
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.842
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2015b)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0714P)²+0.1351P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.100(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
;
_chemical_absolute_configuration .
_refine_ls_number_reflns         3372
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1161
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
C1 C 0.6502(3) 0.2932(5) 0.7689(2) 0.0488(7) Uani 1 1 d . . . . .
H1 H 0.720123 0.261781 0.736328 0.059 Uiso 1 1 calc R U . . .
C2 C 0.6058(3) 0.4999(4) 0.7390(2) 0.0427(6) Uani 1 1 d . . . . .
C3 C 0.4860(3) 0.5505(4) 0.6661(2) 0.0426(6) Uani 1 1 d . . . . .
H3 H 0.461502 0.681776 0.656595 0.051 Uiso 1 1 calc R U . . .
C4 C 0.3887(3) 0.3981(4) 0.5981(2) 0.0450(6) Uani 1 1 d . . . . .
H4 H 0.362480 0.437619 0.520527 0.054 Uiso 1 1 calc R U . . .
C5 C 0.4646(3) 0.2048(5) 0.6105(3) 0.0553(7) Uani 1 1 d . . . . .
H5A H 0.399144 0.100920 0.578688 0.066 Uiso 1 1 calc R U . . .
H5B H 0.528243 0.210507 0.570428 0.066 Uiso 1 1 calc R U . . .
O6 O 0.5384(2) 0.1624(3) 0.72354(19) 0.0549(5) Uani 1 1 d . . . . .
C7 C 0.7121(3) 0.2562(6) 0.8915(3) 0.0603(8) Uani 1 1 d . . . . .
H7A H 0.728689 0.117483 0.905239 0.072 Uiso 1 1 calc R U . . .
H7B H 0.799414 0.324048 0.921763 0.072 Uiso 1 1 calc R U . . .
C8 C 0.6651(3) 0.3060(5) 1.0543(2) 0.0508(6) Uani 1 1 d . . . . .
C9 C 0.7828(3) 0.7189(5) 0.7476(2) 0.0496(6) Uani 1 1 d . . . . .
C10 C 0.2568(2) 0.3803(4) 0.6241(2) 0.0410(5) Uani 1 1 d . . . . .
C11 C 0.1309(3) 0.3760(4) 0.5381(2) 0.0442(6) Uani 1 1 d . . . . .
H11 H 0.127035 0.385679 0.465222 0.053 Uiso 1 1 calc R U . . .
O11 O 0.61886(18) 0.3250(3) 0.94391(15) 0.0494(5) Uani 1 1 d . . . . .
C12 C 0.0117(3) 0.3572(4) 0.5618(2) 0.0467(6) Uani 1 1 d . . . . .
O12 O 0.7746(3) 0.2339(6) 1.1031(2) 0.0940(11) Uani 1 1 d . . . . .
C13 C 0.0110(3) 0.3406(4) 0.6676(2) 0.0485(6) Uani 1 1 d . . . . .
H13 H -0.070409 0.329622 0.682215 0.058 Uiso 1 1 calc R U . . .
O13 O 0.7043(2) 0.6360(4) 0.79845(16) 0.0547(5) Uani 1 1 d . . . . .
C14 C 0.1373(3) 0.3411(4) 0.7508(2) 0.0459(6) Uani 1 1 d . . . . .
O14 O 0.7657(3) 0.6889(7) 0.6531(2) 0.1052(14) Uani 1 1 d . . . . .
C15 C 0.2601(2) 0.3621(4) 0.7319(2) 0.0430(6) Uani 1 1 d . . . . .
H15 H 0.343433 0.364070 0.790550 0.052 Uiso 1 1 calc R U . . .
O15 O 0.2488(3) 0.2832(7) 0.9366(2) 0.0933(11) Uani 1 1 d . . . . .
N16 N 0.1397(3) 0.3172(5) 0.8647(2) 0.0616(7) Uani 1 1 d . . . . .
O16 O 0.0314(3) 0.3321(6) 0.8806(2) 0.0905(10) Uani 1 1 d . . . . .
N17 N -0.1222(3) 0.3549(4) 0.4709(3) 0.0612(7) Uani 1 1 d . . . . .
O17 O -0.2245(2) 0.3183(5) 0.4937(3) 0.0836(9) Uani 1 1 d . . . . .
O18 O -0.1237(3) 0.3866(5) 0.3780(3) 0.0894(9) Uani 1 1 d . . . . .
C19 C 0.5664(4) 0.3757(6) 1.1051(3) 0.0645(8) Uani 1 1 d . . . . .
H19A H 0.612777 0.392537 1.183094 0.097 Uiso 1 1 calc R U . . .
H19B H 0.493850 0.281608 1.092689 0.097 Uiso 1 1 calc R U . . .
H19C H 0.528182 0.498368 1.072621 0.097 Uiso 1 1 calc R U . . .
C20 C 0.8966(3) 0.8363(6) 0.8236(3) 0.0682(9) Uani 1 1 d . . . . .
H20A H 0.910465 0.951023 0.785997 0.102 Uiso 1 1 calc R U . . .
H20B H 0.979331 0.759772 0.847447 0.102 Uiso 1 1 calc R U . . .
H20C H 0.873594 0.874216 0.886694 0.102 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
C1 O6 1.419(4) . ?
C1 C2 1.496(4) . ?
C1 C7 1.509(4) . ?
C1 H1 0.9800 . ?
C2 C3 1.317(4) . ?
C2 O13 1.398(3) . ?
C3 C4 1.504(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.519(4) . ?
C4 C10 1.521(3) . ?
C4 H4 0.9800 . ?
C5 O6 1.422(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 O11 1.438(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O12 1.197(4) . ?
C8 O11 1.342(3) . ?
C8 C19 1.474(4) . ?
C9 O14 1.188(4) . ?
C9 O13 1.337(3) . ?
C9 C20 1.481(4) . ?
C10 C15 1.386(3) . ?
C10 C11 1.389(3) . ?
C11 C12 1.379(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.373(4) . ?
C12 N17 1.473(3) . ?
C13 C14 1.374(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(3) . ?
C14 N16 1.471(4) . ?
C15 H15 0.9300 . ?
O15 N16 1.211(4) . ?
N16 O16 1.213(3) . ?
N17 O18 1.213(5) . ?
N17 O17 1.221(4) . ?
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
O6 C1 C2 110.9(2) . . ?
O6 C1 C7 108.4(2) . . ?
C2 C1 C7 114.2(3) . . ?
O6 C1 H1 107.7 . . ?
C2 C1 H1 107.7 . . ?
C7 C1 H1 107.7 . . ?
C3 C2 O13 123.0(3) . . ?
C3 C2 C1 124.2(3) . . ?
O13 C2 C1 112.8(2) . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 108.9(2) . . ?
C3 C4 C10 113.5(2) . . ?
C5 C4 C10 112.3(2) . . ?
C3 C4 H4 107.3 . . ?
C5 C4 H4 107.3 . . ?
C10 C4 H4 107.3 . . ?
O6 C5 C4 111.1(2) . . ?
O6 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
O6 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C1 O6 C5 111.4(2) . . ?
O11 C7 C1 109.2(2) . . ?
O11 C7 H7A 109.8 . . ?
C1 C7 H7A 109.8 . . ?
O11 C7 H7B 109.8 . . ?
C1 C7 H7B 109.8 . . ?
H7A C7 H7B 108.3 . . ?
O12 C8 O11 121.5(3) . . ?
O12 C8 C19 125.3(3) . . ?
O11 C8 C19 113.2(2) . . ?
O14 C9 O13 122.1(3) . . ?
O14 C9 C20 125.1(3) . . ?
O13 C9 C20 112.7(3) . . ?
C15 C10 C11 119.3(2) . . ?
C15 C10 C4 121.2(2) . . ?
C11 C10 C4 119.5(2) . . ?
C12 C11 C10 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C8 O11 C7 114.7(2) . . ?
C13 C12 C11 122.9(2) . . ?
C13 C12 N17 117.6(3) . . ?
C11 C12 N17 119.5(3) . . ?
C12 C13 C14 116.4(2) . . ?
C12 C13 H13 121.8 . . ?
C14 C13 H13 121.8 . . ?
C9 O13 C2 117.8(2) . . ?
C13 C14 C15 123.2(2) . . ?
C13 C14 N16 117.5(2) . . ?
C15 C14 N16 119.4(2) . . ?
C14 C15 C10 118.9(2) . . ?
C14 C15 H15 120.6 . . ?
C10 C15 H15 120.6 . . ?
O15 N16 O16 124.0(3) . . ?
O15 N16 C14 118.3(2) . . ?
O16 N16 C14 117.7(3) . . ?
O18 N17 O17 124.1(3) . . ?
O18 N17 C12 118.1(3) . . ?
O17 N17 C12 117.8(3) . . ?
C8 C19 H19A 109.5 . . ?
C8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 C20 H20A 109.5 . . ?
C9 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C9 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.079


