# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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data_tm213-mod
_database_code_depnum_ccdc_archive 'CCDC 2269175'
loop_
_audit_author_name
_audit_author_address
'Elsa Van Elslande'
;CNRS
France
;
_audit_update_record             
;
2023-06-12 deposited with the CCDC.	2023-07-10 downloaded from the CCDC.
;
_audit_creation_date             2023-06-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
jean-francois.betzer@cnrs.fr
elsa.van-elslande@cnrs.fr
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 N2 O9'
_chemical_formula_sum            'C16 H16 N2 O9'
_chemical_formula_weight         380.31
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.3384(5)
_cell_length_b                   5.3232(2)
_cell_length_c                   16.2069(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.001(5)
_cell_angle_gamma                90
_cell_volume                     852.94(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14554
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      0.80070
_cell_measurement_theta_min      1.00000
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)

Empirical absorption correction using spherical harmonics,

implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_preparation       'liquid-liquid diffusion'
_exptl_crystal_recrystallization_method Dichloromethane/n-Hexane
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30178
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         3.785
_diffrn_ambient_temperature      100.15
_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_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.3 mm'
_diffrn_radiation_monochromator  
'Rigaku Integrated Confocal MaxFlux double bounce multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku micromax 003'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.802
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3318
_reflns_number_total             3502
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.175
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
Flack x determined using 1408 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_coef       0.007(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   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3370
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.079
_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)+(0.0298P)²+0.2477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0659
_refine_ls_wR_factor_ref         0.0674
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O6 O 0.90243(14) -0.3112(3) 0.47824(9) 0.0179(3) Uani 1 1 d . . . . .
O4 O 0.64328(15) 0.4034(3) 0.36611(9) 0.0192(3) Uani 1 1 d . . . . .
N1 N 0.93179(16) -0.2301(3) 0.55252(11) 0.0155(4) Uani 1 1 d . . . . .
O5 O 0.57053(14) 0.6792(3) 0.44935(9) 0.0200(3) Uani 1 1 d . . . . .
O7 O 1.02127(15) -0.3175(3) 0.61320(10) 0.0236(3) Uani 1 1 d . . . . .
O2 O 0.63661(15) 0.4126(3) 0.16068(10) 0.0219(3) Uani 1 1 d . . . . .
O1 O 0.94965(15) 1.1604(3) 0.20110(10) 0.0236(4) Uani 1 1 d . . . . .
O3 O 0.85113(17) 1.1084(3) 0.05903(10) 0.0249(4) Uani 1 1 d . . . . .
N2 N 0.79664(17) 0.3299(4) 0.75462(11) 0.0199(4) Uani 1 1 d . . . . .
C15 C 0.85317(19) -0.0166(4) 0.57025(14) 0.0153(4) Uani 1 1 d . . . . .
O8 O 0.86361(16) 0.2001(3) 0.81420(10) 0.0252(4) Uani 1 1 d . . . . .
O9 O 0.73400(17) 0.5189(3) 0.76392(11) 0.0288(4) Uani 1 1 d . . . . .
C10 C 0.62923(19) 0.4894(4) 0.44086(13) 0.0162(4) Uani 1 1 d . . . . .
C11 C 0.70335(19) 0.3239(4) 0.51425(13) 0.0150(4) Uani 1 1 d . . . . .
C16 C 0.7749(2) 0.1158(4) 0.49988(14) 0.0146(4) Uani 1 1 d . . . . .
C13 C 0.7893(2) 0.2536(4) 0.66579(13) 0.0161(4) Uani 1 1 d . . . . .
C14 C 0.8642(2) 0.0463(4) 0.65465(14) 0.0153(4) Uani 1 1 d . . . . .
C12 C 0.7093(2) 0.3932(4) 0.59808(13) 0.0153(4) Uani 1 1 d . . . . .
C3 C 0.7887(2) 0.7442(4) 0.22772(14) 0.0194(5) Uani 1 1 d . . . . .
H3 H 0.844822 0.826544 0.277332 0.023 Uiso 1 1 calc R U . . .
C2 C 0.7839(2) 0.8371(4) 0.15109(15) 0.0206(5) Uani 1 1 d . . . . .
C5 C 0.6073(2) 0.5715(4) 0.29197(14) 0.0185(5) Uani 1 1 d . . . . .
C1 C 0.8707(2) 1.0517(4) 0.14244(14) 0.0197(5) Uani 1 1 d . . . . .
C4 C 0.7116(2) 0.5187(4) 0.24119(14) 0.0190(4) Uani 1 1 d . . . . .
C7 C 0.5149(2) 0.3034(4) 0.17190(15) 0.0218(5) Uani 1 1 d . . . . .
C6 C 0.4725(2) 0.4947(5) 0.22846(15) 0.0212(5) Uani 1 1 d . . . . .
C9 C 0.9316(3) 1.3145(5) 0.04304(16) 0.0282(6) Uani 1 1 d . . . . .
H9A H 0.913592 1.337381 -0.019303 0.042 Uiso 1 1 calc R U . . .
H9B H 1.027755 1.277277 0.069151 0.042 Uiso 1 1 calc R U . . .
H9C H 0.908039 1.468625 0.068434 0.042 Uiso 1 1 calc R U . . .
C8 C 0.4163(2) 0.2567(5) 0.08399(16) 0.0320(6) Uani 1 1 d . . . . .
H8A H 0.393507 0.416571 0.053161 0.048 Uiso 1 1 calc R U . . .
H8B H 0.333880 0.179546 0.090685 0.048 Uiso 1 1 calc R U . . .
H8C H 0.457493 0.143739 0.051083 0.048 Uiso 1 1 calc R U . . .
H14 H 0.922(2) -0.049(5) 0.7022(16) 0.019(6) Uiso 1 1 d . . . . .
H16 H 0.774(2) 0.060(5) 0.4437(16) 0.022(6) Uiso 1 1 d . . . . .
H5 H 0.610(2) 0.742(5) 0.3125(15) 0.021(6) Uiso 1 1 d . . . . .
H4 H 0.778(2) 0.393(5) 0.2758(15) 0.020(6) Uiso 1 1 d . . . . .
H12 H 0.665(2) 0.540(5) 0.6092(16) 0.020(6) Uiso 1 1 d . . . . .
H2 H 0.727(3) 0.767(5) 0.0983(17) 0.026(7) Uiso 1 1 d . . . . .
H6A H 0.407(3) 0.436(6) 0.2593(18) 0.035(7) Uiso 1 1 d . . . . .
H7 H 0.534(3) 0.141(6) 0.2021(16) 0.027(7) Uiso 1 1 d . . . . .
H6B H 0.432(3) 0.634(5) 0.1927(16) 0.027(7) 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
O6 N1 1.231(2) . ?
O4 C10 1.342(3) . ?
O4 C5 1.456(3) . ?
N1 O7 1.228(2) . ?
N1 C15 1.473(3) . ?
O5 C10 1.207(3) . ?
O2 C4 1.425(3) . ?
O2 C7 1.445(3) . ?
O1 C1 1.205(3) . ?
O3 C1 1.341(3) . ?
O3 C9 1.446(3) . ?
N2 O8 1.224(2) . ?
N2 O9 1.229(2) . ?
N2 C13 1.476(3) . ?
C15 C16 1.383(3) . ?
C15 C14 1.380(3) . ?
C10 C11 1.498(3) . ?
C11 C16 1.389(3) . ?
C11 C12 1.392(3) . ?
C16 H16 0.95(3) . ?
C13 C14 1.390(3) . ?
C13 C12 1.382(3) . ?
C14 H14 0.97(3) . ?
C12 H12 0.95(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.324(3) . ?
C3 C4 1.492(3) . ?
C2 C1 1.485(3) . ?
C2 H2 0.96(3) . ?
C5 C4 1.561(3) . ?
C5 C6 1.526(3) . ?
C5 H5 0.97(3) . ?
C4 H4 1.01(3) . ?
C7 C6 1.518(3) . ?
C7 C8 1.510(3) . ?
C7 H7 0.98(3) . ?
C6 H6A 1.00(3) . ?
C6 H6B 0.96(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
C10 O4 C5 117.79(17) . . ?
O6 N1 C15 117.98(16) . . ?
O7 N1 O6 124.26(18) . . ?
O7 N1 C15 117.75(17) . . ?
C4 O2 C7 107.75(16) . . ?
C1 O3 C9 115.24(17) . . ?
O8 N2 O9 124.18(18) . . ?
O8 N2 C13 118.03(18) . . ?
O9 N2 C13 117.79(18) . . ?
C16 C15 N1 117.09(18) . . ?
C14 C15 N1 119.34(18) . . ?
C14 C15 C16 123.5(2) . . ?
O4 C10 C11 110.54(18) . . ?
O5 C10 O4 125.4(2) . . ?
O5 C10 C11 124.00(19) . . ?
C16 C11 C10 120.64(19) . . ?
C16 C11 C12 120.09(19) . . ?
C12 C11 C10 119.04(19) . . ?
C15 C16 C11 118.69(19) . . ?
C15 C16 H16 117.9(16) . . ?
C11 C16 H16 123.4(16) . . ?
C14 C13 N2 118.26(19) . . ?
C12 C13 N2 118.33(19) . . ?
C12 C13 C14 123.41(19) . . ?
C15 C14 C13 115.70(19) . . ?
C15 C14 H14 120.9(15) . . ?
C13 C14 H14 123.4(15) . . ?
C11 C12 H12 121.2(15) . . ?
C13 C12 C11 118.55(19) . . ?
C13 C12 H12 120.1(15) . . ?
C2 C3 H3 117.9 . . ?
C2 C3 C4 124.2(2) . . ?
C4 C3 H3 117.9 . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2 122.5(16) . . ?
C1 C2 H2 116.3(16) . . ?
O4 C5 C4 105.97(17) . . ?
O4 C5 C6 110.75(18) . . ?
O4 C5 H5 108.6(15) . . ?
C4 C5 H5 113.6(15) . . ?
C6 C5 C4 103.38(18) . . ?
C6 C5 H5 114.2(14) . . ?
O1 C1 O3 123.7(2) . . ?
O1 C1 C2 125.7(2) . . ?
O3 C1 C2 110.56(18) . . ?
O2 C4 C3 110.85(18) . . ?
O2 C4 C5 106.21(16) . . ?
O2 C4 H4 110.4(14) . . ?
C3 C4 C5 114.38(18) . . ?
C3 C4 H4 108.0(14) . . ?
C5 C4 H4 107.0(13) . . ?
O2 C7 C6 102.82(17) . . ?
O2 C7 C8 108.66(18) . . ?
O2 C7 H7 111.0(16) . . ?
C6 C7 H7 109.9(15) . . ?
C8 C7 C6 116.5(2) . . ?
C8 C7 H7 107.9(16) . . ?
C5 C6 H6A 111.3(16) . . ?
C5 C6 H6B 110.4(16) . . ?
C7 C6 C5 102.66(18) . . ?
C7 C6 H6A 116.7(18) . . ?
C7 C6 H6B 107.7(16) . . ?
H6A C6 H6B 108(2) . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
O6 N1 C15 C16 -15.2(3) . . . . ?
O6 N1 C15 C14 166.99(18) . . . . ?
O4 C10 C11 C16 0.6(2) . . . . ?
O4 C10 C11 C12 175.17(17) . . . . ?
O4 C5 C4 O2 113.93(19) . . . . ?
O4 C5 C4 C3 -123.48(19) . . . . ?
O4 C5 C6 C7 -87.5(2) . . . . ?
N1 C15 C16 C11 -177.65(16) . . . . ?
N1 C15 C14 C13 178.48(16) . . . . ?
O5 C10 C11 C16 -176.37(19) . . . . ?
O5 C10 C11 C12 -1.8(3) . . . . ?
O7 N1 C15 C16 165.78(18) . . . . ?
O7 N1 C15 C14 -12.1(3) . . . . ?
O2 C7 C6 C5 -40.0(2) . . . . ?
N2 C13 C14 C15 179.87(18) . . . . ?
N2 C13 C12 C11 179.18(18) . . . . ?
O8 N2 C13 C14 -3.2(3) . . . . ?
O8 N2 C13 C12 177.32(18) . . . . ?
O9 N2 C13 C14 177.38(18) . . . . ?
O9 N2 C13 C12 -2.1(3) . . . . ?
C10 O4 C5 C4 143.37(17) . . . . ?
C10 O4 C5 C6 -105.2(2) . . . . ?
C10 C11 C16 C15 173.42(18) . . . . ?
C10 C11 C12 C13 -173.44(18) . . . . ?
C16 C15 C14 C13 0.8(3) . . . . ?
C16 C11 C12 C13 1.1(3) . . . . ?
C14 C15 C16 C11 0.1(3) . . . . ?
C14 C13 C12 C11 -0.2(3) . . . . ?
C12 C11 C16 C15 -1.1(3) . . . . ?
C12 C13 C14 C15 -0.7(3) . . . . ?
C3 C2 C1 O1 -0.8(3) . . . . ?
C3 C2 C1 O3 178.3(2) . . . . ?
C2 C3 C4 O2 2.1(3) . . . . ?
C2 C3 C4 C5 -117.9(2) . . . . ?
C5 O4 C10 O5 11.9(3) . . . . ?
C5 O4 C10 C11 -165.07(17) . . . . ?
C4 O2 C7 C6 40.1(2) . . . . ?
C4 O2 C7 C8 164.08(19) . . . . ?
C4 C3 C2 C1 -175.71(19) . . . . ?
C4 C5 C6 C7 25.7(2) . . . . ?
C7 O2 C4 C3 -148.09(18) . . . . ?
C7 O2 C4 C5 -23.3(2) . . . . ?
C6 C5 C4 O2 -2.6(2) . . . . ?
C6 C5 C4 C3 120.0(2) . . . . ?
C9 O3 C1 O1 -0.5(3) . . . . ?
C9 O3 C1 C2 -179.61(18) . . . . ?
C8 C7 C6 C5 -158.7(2) . . . . ?

_olex2_exptl_crystal_mounting_method Cryoloop
_olex2_submission_special_instructions 'No special instructions were received'

