# Electronic Supplementary Material (ESI) for ChemComm.
# 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_igl9219a
_database_code_depnum_ccdc_archive 'CCDC 1990722'
loop_
_audit_author_name
_audit_author_address
'Javier Iglesias-Siguenza'
;University of Seville
Spain
;
_audit_update_record             
;
2020-03-16 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 N2 O4'
_chemical_formula_weight         328.36

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   11.5787(4)
_cell_length_b                   16.5844(5)
_cell_length_c                   17.9315(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3443.3(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9670
_cell_measurement_theta_min      3.63
_cell_measurement_theta_max      64.99

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.470
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.742
_shelx_estimated_absorpt_T_min   0.708
_shelx_estimated_absorpt_T_max   0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5192
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_process_details   
; 
 SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical 
 X-ray Solutions, Madison, Wisconsin, USA. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            38255
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.630
_diffrn_reflns_theta_max         65.173
_diffrn_reflns_theta_full        65.173
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             5748
_reflns_number_gt                5715
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_max     0.964
_reflns_Friedel_fraction_full    0.964

_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-2018/1 (Sheldrick, 2018)'
_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)+(0.1000P)²+0.7023P] 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 2445 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5748
_refine_ls_number_parameters     451
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0741
_refine_ls_wR_factor_gt          0.0738
_refine_ls_goodness_of_fit_ref   0.626
_refine_ls_restrained_S_all      0.626
_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 0.67437(9) 0.31888(7) 0.14088(6) 0.0237(3) Uani 1 1 d . . . . .
O2 O 0.70496(9) 0.33998(7) 0.01726(6) 0.0216(2) Uani 1 1 d . . . . .
O3 O 0.33387(10) 0.48575(7) 0.06269(7) 0.0252(3) Uani 1 1 d . . . . .
O4 O 0.47549(10) 0.57279(6) 0.03468(6) 0.0220(2) Uani 1 1 d . . . . .
N1 N 0.52596(11) 0.35158(8) 0.07025(8) 0.0204(3) Uani 1 1 d . . . . .
N2 N 0.46653(11) 0.36323(8) 0.00252(7) 0.0182(3) Uani 1 1 d . . . . .
C1 C 0.93687(15) 0.29468(11) 0.25450(10) 0.0288(4) Uani 1 1 d . . . . .
H1 H 0.994552 0.291793 0.218509 0.035 Uiso 1 1 calc R U . . .
C2 C 0.96583(17) 0.28988(13) 0.32951(11) 0.0375(4) Uani 1 1 d . . . . .
H2 H 1.042656 0.284115 0.343663 0.045 Uiso 1 1 calc R U . . .
C3 C 0.8805(2) 0.29367(14) 0.38285(11) 0.0420(5) Uani 1 1 d . . . . .
H3 H 0.899835 0.291220 0.433139 0.050 Uiso 1 1 calc R U . . .
C4 C 0.76642(18) 0.30110(15) 0.36177(10) 0.0413(5) Uani 1 1 d . . . . .
H4 H 0.708933 0.302603 0.397967 0.050 Uiso 1 1 calc R U . . .
C5 C 0.73680(15) 0.30637(12) 0.28674(10) 0.0303(4) Uani 1 1 d . . . . .
H5 H 0.659753 0.311609 0.272920 0.036 Uiso 1 1 calc R U . . .
C6 C 0.82200(14) 0.30380(9) 0.23268(9) 0.0212(3) Uani 1 1 d . . . . .
C7 C 0.79738(13) 0.31198(10) 0.15083(9) 0.0216(3) Uani 1 1 d . . . . .
H7A H 0.835639 0.359472 0.131158 0.026 Uiso 1 1 calc R U . . .
H7B H 0.826126 0.265137 0.124284 0.026 Uiso 1 1 calc R U . . .
C8 C 0.64050(13) 0.33690(9) 0.07056(9) 0.0176(3) Uani 1 1 d . . . . .
C9 C 0.48134(13) 0.44564(9) -0.02573(9) 0.0192(3) Uani 1 1 d . . . . .
H9 H 0.563703 0.458948 -0.028337 0.023 Uiso 1 1 calc R U . . .
C10 C 0.42064(13) 0.50216(9) 0.02905(8) 0.0180(3) Uani 1 1 d . . . . .
C11 C 0.42606(15) 0.62882(10) 0.08873(9) 0.0245(3) Uani 1 1 d . . . . .
H11A H 0.413030 0.601733 0.135927 0.029 Uiso 1 1 calc R U . . .
H11B H 0.352746 0.649353 0.070705 0.029 Uiso 1 1 calc R U . . .
C12 C 0.51029(18) 0.69664(11) 0.09862(10) 0.0347(4) Uani 1 1 d . . . . .
H12A H 0.585781 0.675032 0.108148 0.052 Uiso 1 1 calc R U . . .
H12B H 0.486760 0.729561 0.139951 0.052 Uiso 1 1 calc R U . . .
H12C H 0.512274 0.728754 0.054095 0.052 Uiso 1 1 calc R U . . .
C13 C 0.42774(14) 0.45128(9) -0.10298(9) 0.0205(3) Uani 1 1 d . . . . .
C14 C 0.32671(14) 0.40956(10) -0.11959(10) 0.0237(3) Uani 1 1 d . . . . .
H14 H 0.289709 0.379827 -0.082678 0.028 Uiso 1 1 calc R U . . .
C15 C 0.28091(16) 0.41219(11) -0.19127(10) 0.0286(4) Uani 1 1 d . . . . .
H15 H 0.215072 0.382448 -0.202490 0.034 Uiso 1 1 calc R U . . .
C16 C 0.33240(17) 0.45863(12) -0.24594(10) 0.0326(4) Uani 1 1 d . . . . .
H16 H 0.300947 0.460689 -0.293628 0.039 Uiso 1 1 calc R U . . .
C17 C 0.4309(2) 0.50192(13) -0.22924(11) 0.0401(5) Uani 1 1 d . . . . .
H17 H 0.464844 0.534240 -0.265493 0.048 Uiso 1 1 calc R U . . .
C18 C 0.47975(17) 0.49741(11) -0.15806(10) 0.0311(4) Uani 1 1 d . . . . .
H18 H 0.547398 0.525448 -0.147613 0.037 Uiso 1 1 calc R U . . .
O5 O 0.55536(9) 0.22687(6) 0.91385(6) 0.0216(2) Uani 1 1 d . . . . .
O6 O 0.61238(10) 0.12438(7) 0.98990(7) 0.0260(3) Uani 1 1 d . . . . .
O7 O 0.78100(10) 0.18412(7) 0.69515(6) 0.0218(2) Uani 1 1 d . . . . .
O8 O 0.91294(10) 0.15741(7) 0.78317(6) 0.0258(3) Uani 1 1 d . . . . .
N3 N 0.74198(11) 0.18272(8) 0.91777(7) 0.0206(3) Uani 1 1 d . . . . .
N4 N 0.79179(12) 0.25183(8) 0.88502(7) 0.0194(3) Uani 1 1 d . . . . .
C19 C 0.34756(16) -0.00083(12) 1.00686(14) 0.0403(5) Uani 1 1 d . . . . .
H19 H 0.303487 0.029336 1.040052 0.048 Uiso 1 1 calc R U . . .
C20 C 0.30601(19) -0.07343(13) 0.98051(16) 0.0511(6) Uani 1 1 d . . . . .
H20 H 0.233066 -0.091143 0.994764 0.061 Uiso 1 1 calc R U . . .
C21 C 0.3724(2) -0.11994(14) 0.93300(16) 0.0535(6) Uani 1 1 d . . . . .
H21 H 0.344810 -0.169230 0.915841 0.064 Uiso 1 1 calc R U . . .
C22 C 0.4799(2) -0.09272(14) 0.91122(14) 0.0465(5) Uani 1 1 d . . . . .
H22 H 0.525167 -0.124142 0.879754 0.056 Uiso 1 1 calc R U . . .
C23 C 0.52085(16) -0.01872(12) 0.93598(10) 0.0324(4) Uani 1 1 d . . . . .
H23 H 0.592658 -0.000292 0.920192 0.039 Uiso 1 1 calc R U . . .
C24 C 0.45528(14) 0.02758(11) 0.98398(10) 0.0263(4) Uani 1 1 d . . . . .
C25 C 0.49508(15) 0.10826(11) 1.01229(10) 0.0295(4) Uani 1 1 d . . . . .
H25A H 0.444857 0.150131 0.992924 0.035 Uiso 1 1 calc R U . . .
H25B H 0.489976 0.109191 1.066278 0.035 Uiso 1 1 calc R U . . .
C26 C 0.62967(13) 0.18248(9) 0.93836(8) 0.0180(3) Uani 1 1 d . . . . .
C27 C 0.76591(13) 0.25940(9) 0.80533(8) 0.0175(3) Uani 1 1 d . . . . .
H27 H 0.682528 0.254106 0.797312 0.021 Uiso 1 1 calc R U . . .
C28 C 0.82938(13) 0.19405(9) 0.76204(8) 0.0180(3) Uani 1 1 d . . . . .
C29 C 0.83359(15) 0.12398(10) 0.64658(9) 0.0252(3) Uani 1 1 d . . . . .
H29A H 0.823653 0.070421 0.667345 0.030 Uiso 1 1 calc R U . . .
H29B H 0.915575 0.134418 0.641060 0.030 Uiso 1 1 calc R U . . .
C30 C 0.77389(17) 0.13016(12) 0.57239(10) 0.0336(4) Uani 1 1 d . . . . .
H30A H 0.692442 0.121990 0.578982 0.050 Uiso 1 1 calc R U . . .
H30B H 0.803907 0.089788 0.539284 0.050 Uiso 1 1 calc R U . . .
H30C H 0.787166 0.182653 0.551519 0.050 Uiso 1 1 calc R U . . .
C31 C 0.80578(14) 0.34215(9) 0.78005(9) 0.0203(3) Uani 1 1 d . . . . .
C32 C 0.92115(14) 0.36451(10) 0.78633(9) 0.0234(3) Uani 1 1 d . . . . .
H32 H 0.974919 0.328082 0.805016 0.028 Uiso 1 1 calc R U . . .
C33 C 0.95628(15) 0.44128(11) 0.76472(10) 0.0286(4) Uani 1 1 d . . . . .
H33 H 1.033345 0.456154 0.769648 0.034 Uiso 1 1 calc R U . . .
C34 C 0.87830(19) 0.49495(12) 0.73630(13) 0.0426(5) Uani 1 1 d . . . . .
H34 H 0.902182 0.546091 0.721630 0.051 Uiso 1 1 calc R U . . .
C35 C 0.7638(2) 0.47279(14) 0.72948(19) 0.0619(7) Uani 1 1 d . . . . .
H35 H 0.710804 0.509018 0.709622 0.074 Uiso 1 1 calc R U . . .
C36 C 0.72730(17) 0.39698(12) 0.75201(14) 0.0432(5) Uani 1 1 d . . . . .
H36 H 0.649724 0.383039 0.748210 0.052 Uiso 1 1 calc R U . . .
H2N H 0.4920(17) 0.3285(12) -0.0323(11) 0.019(4) Uiso 1 1 d . . . . .
H1N H 0.4861(18) 0.3409(12) 0.1113(11) 0.022(5) Uiso 1 1 d . . . . .
H3N H 0.7899(19) 0.1519(13) 0.9402(12) 0.027(5) Uiso 1 1 d . . . . .
H4N H 0.7647(18) 0.2950(13) 0.9088(11) 0.026(5) 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
O1 C8 1.354(2) . ?
O1 C7 1.4400(18) . ?
O2 C8 1.214(2) . ?
O3 C10 1.203(2) . ?
O4 C10 1.3363(19) . ?
O4 C11 1.4597(19) . ?
N1 C8 1.348(2) . ?
N1 N2 1.4092(18) . ?
N2 C9 1.468(2) . ?
C1 C2 1.388(3) . ?
C1 C6 1.395(2) . ?
C2 C3 1.376(3) . ?
C3 C4 1.380(3) . ?
C4 C5 1.391(3) . ?
C5 C6 1.384(2) . ?
C6 C7 1.501(2) . ?
C9 C13 1.521(2) . ?
C9 C10 1.529(2) . ?
C11 C12 1.499(2) . ?
C13 C18 1.387(2) . ?
C13 C14 1.391(2) . ?
C14 C15 1.391(2) . ?
C15 C16 1.382(3) . ?
C16 C17 1.380(3) . ?
C17 C18 1.398(3) . ?
O5 C26 1.215(2) . ?
O6 C26 1.350(2) . ?
O6 C25 1.441(2) . ?
O7 C28 1.3340(19) . ?
O7 C29 1.4574(19) . ?
O8 C28 1.204(2) . ?
N3 C26 1.352(2) . ?
N3 N4 1.4112(19) . ?
N4 C27 1.4653(19) . ?
C19 C20 1.380(3) . ?
C19 C24 1.395(3) . ?
C20 C21 1.382(4) . ?
C21 C22 1.380(3) . ?
C22 C23 1.389(3) . ?
C23 C24 1.381(3) . ?
C24 C25 1.503(3) . ?
C27 C31 1.517(2) . ?
C27 C28 1.522(2) . ?
C29 C30 1.503(2) . ?
C31 C36 1.380(3) . ?
C31 C32 1.391(2) . ?
C32 C33 1.392(2) . ?
C33 C34 1.366(3) . ?
C34 C35 1.381(3) . ?
C35 C36 1.387(3) . ?

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 114.80(12) . . ?
C10 O4 C11 114.95(12) . . ?
C8 N1 N2 120.57(13) . . ?
N1 N2 C9 111.60(12) . . ?
C2 C1 C6 120.55(17) . . ?
C3 C2 C1 119.82(18) . . ?
C2 C3 C4 120.06(18) . . ?
C3 C4 C5 120.43(19) . . ?
C6 C5 C4 119.99(17) . . ?
C5 C6 C1 119.13(16) . . ?
C5 C6 C7 123.14(15) . . ?
C1 C6 C7 117.72(15) . . ?
O1 C7 C6 108.43(13) . . ?
O2 C8 N1 126.44(15) . . ?
O2 C8 O1 124.37(14) . . ?
N1 C8 O1 109.19(13) . . ?
N2 C9 C13 108.91(12) . . ?
N2 C9 C10 107.18(12) . . ?
C13 C9 C10 111.09(12) . . ?
O3 C10 O4 123.87(14) . . ?
O3 C10 C9 124.57(14) . . ?
O4 C10 C9 111.56(12) . . ?
O4 C11 C12 107.52(14) . . ?
C18 C13 C14 119.13(16) . . ?
C18 C13 C9 120.36(14) . . ?
C14 C13 C9 120.50(14) . . ?
C15 C14 C13 120.18(16) . . ?
C16 C15 C14 120.56(17) . . ?
C17 C16 C15 119.49(17) . . ?
C16 C17 C18 120.31(17) . . ?
C13 C18 C17 120.25(17) . . ?
C26 O6 C25 117.57(13) . . ?
C28 O7 C29 116.51(12) . . ?
C26 N3 N4 120.61(13) . . ?
N3 N4 C27 113.07(12) . . ?
C20 C19 C24 120.4(2) . . ?
C19 C20 C21 120.3(2) . . ?
C22 C21 C20 119.5(2) . . ?
C21 C22 C23 120.4(2) . . ?
C24 C23 C22 120.20(18) . . ?
C23 C24 C19 119.15(18) . . ?
C23 C24 C25 122.47(16) . . ?
C19 C24 C25 118.38(17) . . ?
O6 C25 C24 111.09(14) . . ?
O5 C26 O6 125.12(14) . . ?
O5 C26 N3 125.51(15) . . ?
O6 C26 N3 109.37(13) . . ?
N4 C27 C31 107.85(12) . . ?
N4 C27 C28 109.73(12) . . ?
C31 C27 C28 110.16(12) . . ?
O8 C28 O7 123.94(14) . . ?
O8 C28 C27 125.93(14) . . ?
O7 C28 C27 110.10(12) . . ?
O7 C29 C30 106.86(14) . . ?
C36 C31 C32 119.09(16) . . ?
C36 C31 C27 120.29(15) . . ?
C32 C31 C27 120.61(14) . . ?
C31 C32 C33 120.14(16) . . ?
C34 C33 C32 120.44(17) . . ?
C33 C34 C35 119.59(18) . . ?
C34 C35 C36 120.6(2) . . ?
C31 C36 C35 120.16(18) . . ?

_refine_diff_density_max         0.108
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.035



