# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_good
_database_code_depnum_ccdc_archive 'CCDC 1565939'
_audit_update_record             
;
2017-08-01 deposited with the CCDC.	2020-12-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 N2 O6'
_chemical_formula_weight         345.32

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                   8.1209(12)
_cell_length_b                   10.5753(16)
_cell_length_c                   11.3680(18)
_cell_angle_alpha                113.295(7)
_cell_angle_beta                 93.648(8)
_cell_angle_gamma                107.911(7)
_cell_volume                     833.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2920
_cell_measurement_theta_min      2.263
_cell_measurement_theta_max      25.008

_exptl_crystal_description       bar
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             362
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8606
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.263
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_full        25.008
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2920
_reflns_number_gt                2574
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0649P)²+0.3333P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.217(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2920
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1385
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
N1 N 0.8955(2) 1.00843(19) 0.35873(16) 0.0625(5) Uani 1 1 d . . . . .
H1A H 0.995314 1.036598 0.410015 0.075 Uiso 1 1 calc R U . . .
C20 C 0.5743(2) 0.89077(18) 0.30217(16) 0.0442(4) Uani 1 1 d . . . . .
H20A H 0.525486 0.966171 0.348644 0.053 Uiso 1 1 calc R U . . .
O1 O 0.7647(2) 0.88262(19) 0.46660(15) 0.0835(6) Uani 1 1 d . . . . .
O2 O 0.6109(2) 0.66845(14) -0.01681(14) 0.0729(5) Uani 1 1 d . . . . .
N2 N 0.47810(19) 0.64521(15) 0.14858(14) 0.0478(4) Uani 1 1 d . . . . .
H2A H 0.448680 0.551189 0.119893 0.057 Uiso 1 1 calc R U . . .
O4 O 0.4853(3) 0.57043(18) 0.34917(17) 0.0832(5) Uani 1 1 d . . . . .
O7 O 0.1341(2) 0.5997(2) 0.2038(2) 0.0940(6) Uani 1 1 d . . . . .
C1 C 0.7526(3) 0.9248(2) 0.38182(17) 0.0547(5) Uani 1 1 d . . . . .
C2 C 0.8977(3) 1.05459(19) 0.25835(18) 0.0508(5) Uani 1 1 d . . . . .
C3 C 1.0495(3) 1.1607(2) 0.2597(2) 0.0685(6) Uani 1 1 d . . . . .
H3A H 1.147373 1.203891 0.328323 0.082 Uiso 1 1 calc R U . . .
C4 C 1.0549(3) 1.2019(3) 0.1595(3) 0.0736(7) Uani 1 1 d . . . . .
H4A H 1.156747 1.273243 0.160090 0.088 Uiso 1 1 calc R U . . .
C5 C 0.9102(3) 1.1380(3) 0.0581(2) 0.0699(6) Uani 1 1 d . . . . .
H5A H 0.915174 1.164799 -0.010602 0.084 Uiso 1 1 calc R U . . .
C6 C 0.7575(3) 1.0341(2) 0.0581(2) 0.0561(5) Uani 1 1 d . . . . .
H6A H 0.659366 0.992335 -0.010083 0.067 Uiso 1 1 calc R U . . .
C7 C 0.7495(2) 0.99173(18) 0.15893(17) 0.0441(4) Uani 1 1 d . . . . .
C8 C 0.5872(2) 0.88127(17) 0.16442(16) 0.0415(4) Uani 1 1 d . . . . .
H8A H 0.484191 0.896609 0.131149 0.050 Uiso 1 1 calc R U . . .
C9 C 0.5637(2) 0.72002(18) 0.08552(17) 0.0469(4) Uani 1 1 d . . . . .
C10 C 0.4394(2) 0.73568(18) 0.26871(16) 0.0431(4) Uani 1 1 d . . . . .
C11 C 0.4467(3) 0.6743(2) 0.3685(2) 0.0583(5) Uani 1 1 d . . . . .
C14 C 0.2501(3) 0.7340(3) 0.2431(2) 0.0617(5) Uani 1 1 d . . . . .
C15 C -0.066(3) 0.614(2) 0.196(3) 0.106(5) Uani 0.361(13) 1 d . . P A 1
H15A H -0.082820 0.672041 0.282192 0.127 Uiso 0.361(13) 1 calc R U P A 1
H15B H -0.087406 0.654619 0.136804 0.127 Uiso 0.361(13) 1 calc R U P A 1
C16 C -0.1704(12) 0.4659(14) 0.1487(13) 0.112(5) Uani 0.361(13) 1 d . . P A 1
H16A H -0.293041 0.454828 0.138649 0.168 Uiso 0.361(13) 1 calc R U P A 1
H16B H -0.147590 0.411464 0.065256 0.168 Uiso 0.361(13) 1 calc R U P A 1
H16C H -0.143055 0.428689 0.209001 0.168 Uiso 0.361(13) 1 calc R U P A 1
C15A C -0.0492(12) 0.5649(14) 0.1763(16) 0.125(4) Uani 0.639(13) 1 d . . P A 2
H15C H -0.074192 0.634753 0.149620 0.150 Uiso 0.639(13) 1 calc R U P A 2
H15D H -0.105201 0.466895 0.104600 0.150 Uiso 0.639(13) 1 calc R U P A 2
C16A C -0.1162(12) 0.5695(14) 0.2829(14) 0.188(7) Uani 0.639(13) 1 d . . P A 2
H16D H -0.241740 0.545391 0.262500 0.281 Uiso 0.639(13) 1 calc R U P A 2
H16E H -0.092749 0.499358 0.308507 0.281 Uiso 0.639(13) 1 calc R U P A 2
H16F H -0.061796 0.666910 0.353445 0.281 Uiso 0.639(13) 1 calc R U P A 2
O6A O 0.223(4) 0.846(3) 0.280(8) 0.114(7) Uani 0.41(9) 1 d . . P B 1
O6 O 0.2095(17) 0.8312(17) 0.2394(14) 0.081(3) Uani 0.59(9) 1 d . . P B 2
O5 O 0.3668(6) 0.7474(4) 0.4698(4) 0.0548(9) Uani 0.648(7) 1 d . . P C 1
C12 C 0.3353(7) 0.6885(5) 0.5658(4) 0.0722(13) Uani 0.648(7) 1 d . . P C 1
H12A H 0.228703 0.700312 0.594383 0.087 Uiso 0.648(7) 1 calc R U P C 1
H12D H 0.311326 0.583239 0.521698 0.087 Uiso 0.648(7) 1 calc R U P C 1
C13 C 0.4685(6) 0.7491(5) 0.6767(4) 0.0880(16) Uani 0.648(7) 1 d . . P C 1
H13A H 0.431781 0.701095 0.731856 0.132 Uiso 0.648(7) 1 calc R U P C 1
H13B H 0.574408 0.735260 0.651005 0.132 Uiso 0.648(7) 1 calc R U P C 1
H13C H 0.491456 0.852798 0.723979 0.132 Uiso 0.648(7) 1 calc R U P C 1
O5A O 0.4310(10) 0.7306(10) 0.4735(8) 0.0649(18) Uani 0.352(7) 1 d . . P C 2
C12A C 0.4429(13) 0.6633(11) 0.5643(8) 0.080(3) Uani 0.352(7) 1 d . . P C 2
H12B H 0.499168 0.736560 0.653625 0.096 Uiso 0.352(7) 1 calc R U P C 2
H12C H 0.501880 0.592666 0.535533 0.096 Uiso 0.352(7) 1 calc R U P C 2
C13A C 0.222(2) 0.5810(17) 0.5451(18) 0.185(8) Uani 0.352(7) 1 d . . P C 2
H13D H 0.200607 0.528759 0.598339 0.278 Uiso 0.352(7) 1 calc R U P C 2
H13E H 0.169301 0.654712 0.571186 0.278 Uiso 0.352(7) 1 calc R U P C 2
H13F H 0.171976 0.512806 0.454726 0.278 Uiso 0.352(7) 1 calc R U P C 2


_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
N1 C1 1.337(2) . ?
N1 C2 1.407(2) . ?
N1 H1A 0.8600 . ?
C20 C1 1.517(3) . ?
C20 C8 1.541(2) . ?
C20 C10 1.544(2) . ?
C20 H20A 0.9800 . ?
O1 C1 1.222(2) . ?
O2 C9 1.217(2) . ?
N2 C9 1.340(2) . ?
N2 C10 1.444(2) . ?
N2 H2A 0.8600 . ?
O4 C11 1.176(3) . ?
O7 C14 1.313(3) . ?
O7 C15A 1.401(9) . ?
O7 C15 1.678(17) . ?
C2 C7 1.381(3) . ?
C2 C3 1.383(3) . ?
C3 C4 1.370(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.381(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.384(2) . ?
C6 H6A 0.9300 . ?
C7 C8 1.493(2) . ?
C8 C9 1.522(2) . ?
C8 H8A 0.9800 . ?
C10 C11 1.519(2) . ?
C10 C14 1.540(3) . ?
C11 O5A 1.140(8) . ?
C11 O5 1.430(4) . ?
C14 O6A 1.18(2) . ?
C14 O6 1.186(12) . ?
C15 C16 1.38(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15A C16A 1.349(18) . ?
C15A H15C 0.9700 . ?
C15A H15D 0.9700 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?
O5 C12 1.456(5) . ?
C12 C13 1.391(6) . ?
C12 H12A 0.9700 . ?
C12 H12D 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O5A C12A 1.481(10) . ?
C12A C13A 1.689(19) . ?
C12A H12B 0.9700 . ?
C12A H12C 0.9700 . ?
C13A H13D 0.9600 . ?
C13A H13E 0.9600 . ?
C13A H13F 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
C1 N1 C2 126.05(16) . . ?
C1 N1 H1A 117.0 . . ?
C2 N1 H1A 117.0 . . ?
C1 C20 C8 111.93(14) . . ?
C1 C20 C10 113.39(14) . . ?
C8 C20 C10 101.45(13) . . ?
C1 C20 H20A 109.9 . . ?
C8 C20 H20A 109.9 . . ?
C10 C20 H20A 109.9 . . ?
C9 N2 C10 114.39(14) . . ?
C9 N2 H2A 122.8 . . ?
C10 N2 H2A 122.8 . . ?
C14 O7 C15A 123.1(5) . . ?
C14 O7 C15 106.3(7) . . ?
O1 C1 N1 121.52(18) . . ?
O1 C1 C20 121.57(17) . . ?
N1 C1 C20 116.86(15) . . ?
C7 C2 C3 121.01(18) . . ?
C7 C2 N1 119.62(16) . . ?
C3 C2 N1 119.36(18) . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3A 120.2 . . ?
C2 C3 H3A 120.2 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C5 C6 C7 120.4(2) . . ?
C5 C6 H6A 119.8 . . ?
C7 C6 H6A 119.8 . . ?
C2 C7 C6 118.58(17) . . ?
C2 C7 C8 118.86(15) . . ?
C6 C7 C8 122.56(17) . . ?
C7 C8 C9 115.57(14) . . ?
C7 C8 C20 115.04(14) . . ?
C9 C8 C20 102.30(13) . . ?
C7 C8 H8A 107.8 . . ?
C9 C8 H8A 107.8 . . ?
C20 C8 H8A 107.8 . . ?
O2 C9 N2 126.51(16) . . ?
O2 C9 C8 126.39(15) . . ?
N2 C9 C8 107.09(14) . . ?
N2 C10 C11 110.51(15) . . ?
N2 C10 C14 110.15(15) . . ?
C11 C10 C14 106.68(15) . . ?
N2 C10 C20 102.00(13) . . ?
C11 C10 C20 117.91(14) . . ?
C14 C10 C20 109.49(15) . . ?
O5A C11 O4 112.4(5) . . ?
O4 C11 O5 129.3(2) . . ?
O5A C11 C10 124.0(5) . . ?
O4 C11 C10 123.2(2) . . ?
O5 C11 C10 106.4(2) . . ?
O6A C14 O7 127.8(12) . . ?
O6 C14 O7 122.2(7) . . ?
O6A C14 C10 120.5(19) . . ?
O6 C14 C10 126.7(7) . . ?
O7 C14 C10 110.19(18) . . ?
C16 C15 O7 99.1(9) . . ?
C16 C15 H15A 111.9 . . ?
O7 C15 H15A 111.9 . . ?
C16 C15 H15B 111.9 . . ?
O7 C15 H15B 111.9 . . ?
H15A C15 H15B 109.6 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C16A C15A O7 110.5(11) . . ?
C16A C15A H15C 109.6 . . ?
O7 C15A H15C 109.6 . . ?
C16A C15A H15D 109.6 . . ?
O7 C15A H15D 109.6 . . ?
H15C C15A H15D 108.1 . . ?
C15A C16A H16D 109.5 . . ?
C15A C16A H16E 109.5 . . ?
H16D C16A H16E 109.5 . . ?
C15A C16A H16F 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C11 O5 C12 115.3(3) . . ?
C13 C12 O5 117.6(4) . . ?
C13 C12 H12A 107.9 . . ?
O5 C12 H12A 107.9 . . ?
C13 C12 H12D 107.9 . . ?
O5 C12 H12D 107.9 . . ?
H12A C12 H12D 107.2 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 O5A C12A 120.0(8) . . ?
O5A C12A C13A 96.1(8) . . ?
O5A C12A H12B 112.5 . . ?
C13A C12A H12B 112.5 . . ?
O5A C12A H12C 112.5 . . ?
C13A C12A H12C 112.5 . . ?
H12B C12A H12C 110.0 . . ?
C12A C13A H13D 109.5 . . ?
C12A C13A H13E 109.5 . . ?
H13D C13A H13E 109.5 . . ?
C12A C13A H13F 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?

_refine_diff_density_max         0.348
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.040



