# 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_002MGL14
_database_code_depnum_ccdc_archive 'CCDC 1540568'
loop_
_audit_author_name
_audit_author_address
'Ruben Alfredo Toscano'
;Instituto de Quimica, UNAM
Mexico
;
_audit_update_record             
;
2022-02-08 deposited with the CCDC.	2022-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N2 O6'
_chemical_formula_sum            'C22 H20 N2 O6'
_chemical_formula_weight         408.40

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.3790(13)
_cell_length_b                   10.2477(16)
_cell_length_c                   12.547(2)
_cell_angle_alpha                94.605(3)
_cell_angle_beta                 108.730(4)
_cell_angle_gamma                98.534(4)
_cell_volume                     999.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3997
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      27.13

_exptl_crystal_description       platy
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9661
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_process_details   '(Sheldrick, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            12191
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.730
_diffrn_reflns_theta_max         27.567
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4597
_reflns_number_gt                2909
_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       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'

_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)+(0.0756P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4597
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1607
_refine_ls_wR_factor_gt          0.1340
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.1822(2) -0.00799(15) 0.00257(13) 0.0555(5) Uani 1 1 d . . . . .
O2 O 0.2095(2) 0.07511(14) 0.72830(12) 0.0430(4) Uani 1 1 d . . . . .
O3 O 0.0666(2) 0.27704(14) 0.67291(12) 0.0477(4) Uani 1 1 d . . . . .
O4 O 0.0266(2) 0.29994(15) 0.26024(12) 0.0479(4) Uani 1 1 d . . . . .
O5 O 0.3297(2) 0.51915(13) 0.26921(12) 0.0453(4) Uani 1 1 d . . . . .
O6 O 0.3120(2) 0.64144(14) 0.07897(13) 0.0618(5) Uani 1 1 d . . . . .
C1 C 0.2159(3) 0.0910(2) 0.07123(18) 0.0401(5) Uani 1 1 d . . . . .
N1 N 0.2462(2) 0.09027(15) 0.18615(14) 0.0361(4) Uani 1 1 d . . . . .
N2 N 0.5843(3) 0.2828(2) 0.40176(18) 0.0598(6) Uani 1 1 d . . . . .
C2 C 0.2771(3) 0.22430(18) 0.24781(16) 0.0326(4) Uani 1 1 d . . . . .
C3 C 0.2729(3) 0.31153(19) 0.15503(16) 0.0343(5) Uani 1 1 d . . . . .
C4 C 0.3012(3) 0.44808(19) 0.16591(17) 0.0367(5) Uani 1 1 d . . . . .
C5 C 0.2882(3) 0.5060(2) 0.06613(19) 0.0434(5) Uani 1 1 d . . . . .
C6 C 0.2532(3) 0.4265(2) -0.0362(2) 0.0535(6) Uani 1 1 d . . . . .
H6 H 0.2473 0.4665 -0.1010 0.064 Uiso 1 1 calc R U . . .
C7 C 0.2269(3) 0.2889(2) -0.04453(18) 0.0494(6) Uani 1 1 d . . . . .
H7 H 0.2032 0.2363 -0.1136 0.059 Uiso 1 1 calc R U . . .
C8 C 0.2370(3) 0.2326(2) 0.05320(17) 0.0392(5) Uani 1 1 d . . . . .
C9 C 0.1895(3) -0.02835(19) 0.23124(17) 0.0402(5) Uani 1 1 d . . . . .
H9A H 0.2110 -0.1059 0.1921 0.048 Uiso 1 1 calc R U . . .
H9B H 0.0668 -0.0391 0.2156 0.048 Uiso 1 1 calc R U . . .
C10 C 0.2786(3) -0.0226(2) 0.35810(17) 0.0391(5) Uani 1 1 d . . . . .
H10A H 0.2615 -0.1124 0.3771 0.047 Uiso 1 1 calc R U . . .
H10B H 0.4006 0.0058 0.3744 0.047 Uiso 1 1 calc R U . . .
C11 C 0.2236(2) 0.06704(18) 0.43650(16) 0.0322(4) Uani 1 1 d . . . . .
C12 C 0.2395(2) 0.02984(19) 0.54393(16) 0.0335(5) Uani 1 1 d . . . . .
H12 H 0.2844 -0.0460 0.5635 0.040 Uiso 1 1 calc R U . . .
C13 C 0.1906(3) 0.10231(19) 0.62144(16) 0.0324(4) Uani 1 1 d . . . . .
C14 C 0.1140(3) 0.21395(19) 0.59118(16) 0.0337(5) Uani 1 1 d . . . . .
C15 C 0.0943(3) 0.25017(19) 0.48605(17) 0.0352(5) Uani 1 1 d . . . . .
H15 H 0.0418 0.3224 0.4650 0.042 Uiso 1 1 calc R U . . .
C16 C 0.1523(3) 0.18008(18) 0.40875(16) 0.0323(4) Uani 1 1 d . . . . .
C17 C 0.1374(3) 0.23820(19) 0.30319(16) 0.0336(5) Uani 1 1 d . . . . .
C18 C 0.4505(3) 0.2564(2) 0.33618(18) 0.0381(5) Uani 1 1 d . . . . .
C19 C 0.3022(3) -0.0279(2) 0.76836(19) 0.0547(7) Uani 1 1 d . . . . .
H19A H 0.3056 -0.0370 0.8446 0.082 Uiso 1 1 calc R U . . .
H19B H 0.4170 -0.0053 0.7673 0.082 Uiso 1 1 calc R U . . .
H19C H 0.2461 -0.1105 0.7200 0.082 Uiso 1 1 calc R U . . .
C20 C -0.0075(4) 0.3924(2) 0.6470(2) 0.0596(7) Uani 1 1 d . . . . .
H20A H -0.0368 0.4271 0.7102 0.089 Uiso 1 1 calc R U . . .
H20B H -0.1089 0.3689 0.5810 0.089 Uiso 1 1 calc R U . . .
H20C H 0.0736 0.4589 0.6323 0.089 Uiso 1 1 calc R U . . .
C21 C 0.4874(4) 0.6126(3) 0.3166(2) 0.0736(8) Uani 1 1 d . . . . .
H21A H 0.4980 0.6513 0.3914 0.110 Uiso 1 1 calc R U . . .
H21B H 0.4885 0.6816 0.2692 0.110 Uiso 1 1 calc R U . . .
H21C H 0.5817 0.5678 0.3210 0.110 Uiso 1 1 calc R U . . .
C22 C 0.2965(5) 0.7054(3) -0.0200(2) 0.0849(10) Uani 1 1 d . . . . .
H22A H 0.3183 0.8002 0.0008 0.127 Uiso 1 1 calc R U . . .
H22B H 0.1826 0.6772 -0.0737 0.127 Uiso 1 1 calc R U . . .
H22C H 0.3780 0.6817 -0.0536 0.127 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 C1 1.212(2) . ?
O2 C13 1.355(2) . ?
O2 C19 1.431(2) . ?
O3 C14 1.363(2) . ?
O3 C20 1.428(3) . ?
O4 C17 1.209(2) . ?
O5 C4 1.366(2) . ?
O5 C21 1.430(3) . ?
O6 C5 1.361(2) . ?
O6 C22 1.428(3) . ?
C1 N1 1.382(3) . ?
C1 C8 1.480(3) . ?
N1 C9 1.461(2) . ?
N1 C2 1.465(2) . ?
N2 C18 1.135(3) . ?
C2 C18 1.488(3) . ?
C2 C3 1.518(3) . ?
C2 C17 1.559(3) . ?
C3 C4 1.372(3) . ?
C3 C8 1.376(3) . ?
C4 C5 1.408(3) . ?
C5 C6 1.385(3) . ?
C6 C7 1.384(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.380(3) . ?
C7 H7 0.9300 . ?
C9 C10 1.518(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.515(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.399(3) . ?
C11 C12 1.401(3) . ?
C12 C13 1.377(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.413(3) . ?
C14 C15 1.365(3) . ?
C15 C16 1.410(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.472(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C13 O2 C19 118.07(16) . . ?
C14 O3 C20 117.16(16) . . ?
C4 O5 C21 116.67(18) . . ?
C5 O6 C22 117.80(19) . . ?
O1 C1 N1 124.55(19) . . ?
O1 C1 C8 129.02(19) . . ?
N1 C1 C8 106.42(16) . . ?
C1 N1 C9 121.82(16) . . ?
C1 N1 C2 112.58(16) . . ?
C9 N1 C2 121.79(15) . . ?
N1 C2 C18 111.01(16) . . ?
N1 C2 C3 102.18(15) . . ?
C18 C2 C3 108.94(16) . . ?
N1 C2 C17 110.76(15) . . ?
C18 C2 C17 110.07(16) . . ?
C3 C2 C17 113.66(16) . . ?
C4 C3 C8 122.82(18) . . ?
C4 C3 C2 127.58(18) . . ?
C8 C3 C2 109.59(16) . . ?
O5 C4 C3 119.20(18) . . ?
O5 C4 C5 123.90(18) . . ?
C3 C4 C5 116.78(18) . . ?
O6 C5 C6 124.25(19) . . ?
O6 C5 C4 115.44(19) . . ?
C6 C5 C4 120.31(19) . . ?
C7 C6 C5 121.7(2) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C8 C7 C6 117.7(2) . . ?
C8 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
C3 C8 C7 120.64(19) . . ?
C3 C8 C1 109.11(17) . . ?
C7 C8 C1 130.24(19) . . ?
N1 C9 C10 113.21(17) . . ?
N1 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
N1 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 117.35(17) . . ?
C11 C10 H10A 108.0 . . ?
C9 C10 H10A 108.0 . . ?
C11 C10 H10B 108.0 . . ?
C9 C10 H10B 108.0 . . ?
H10A C10 H10B 107.2 . . ?
C16 C11 C12 117.67(17) . . ?
C16 C11 C10 125.44(17) . . ?
C12 C11 C10 116.83(16) . . ?
C13 C12 C11 121.94(18) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
O2 C13 C12 124.85(17) . . ?
O2 C13 C14 115.32(16) . . ?
C12 C13 C14 119.83(17) . . ?
O3 C14 C15 125.70(18) . . ?
O3 C14 C13 115.28(17) . . ?
C15 C14 C13 119.01(17) . . ?
C14 C15 C16 121.18(18) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C11 C16 C15 120.25(17) . . ?
C11 C16 C17 124.70(17) . . ?
C15 C16 C17 115.01(17) . . ?
O4 C17 C16 123.31(18) . . ?
O4 C17 C2 118.80(17) . . ?
C16 C17 C2 117.82(16) . . ?
N2 C18 C2 178.2(2) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C21 H21A 109.5 . . ?
O5 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O5 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O6 C22 H22A 109.5 . . ?
O6 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O6 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
C9 H9B O2 0.97 2.61 3.510(3) 153.8 2_556
C19 H19A O1 0.96 2.53 3.398(3) 150.5 1_556
C21 H21B O6 0.96 2.33 2.931(3) 119.7 .
C22 H22A O1 0.96 2.42 3.240(3) 143.7 1_565
C22 H22B O4 0.96 2.49 3.333(4) 147.0 2_565

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

