# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_AG_01_082_0m
_database_code_depnum_ccdc_archive 'CCDC 1955735'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2019-09-25 deposited with the CCDC.	2019-12-06 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            'C16 H15 N O6'
_chemical_formula_weight         317.29

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                   6.8717(4)
_cell_length_b                   7.6590(4)
_cell_length_c                   14.4338(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.854(2)
_cell_angle_gamma                90
_cell_volume                     743.46(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9979
_cell_measurement_theta_min      3.0255
_cell_measurement_theta_max      36.3053

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6687
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube X-ray source'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24622
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.025
_diffrn_reflns_theta_max         33.138
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             5530
_reflns_number_gt                4726
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_max     0.951
_reflns_Friedel_fraction_full    0.979

_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       'Apex3 v2016.9-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2016/6 (Sheldrick, 2015, 2016), 
SHELXLE Rev714 (Hübschle et al., 2011)
;
_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)+(0.0736P)²+0.0171P] 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_abs_structure_details 
;
 Flack x determined using 1911 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         5530
_refine_ls_number_parameters     209
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_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 0.32963(18) 0.16666(17) 0.78719(8) 0.0187(2) Uani 1 1 d . . . . .
O2 O 0.2431(2) 0.36867(18) 0.88460(9) 0.0222(3) Uani 1 1 d . . . . .
O3 O -0.0924(2) 0.5919(2) 0.69051(10) 0.0284(3) Uani 1 1 d . . . . .
O4 O 0.2250(2) 0.6781(2) 0.70342(12) 0.0357(4) Uani 1 1 d . . . . .
O5 O 0.2433(2) -0.48680(18) 1.10025(11) 0.0303(3) Uani 1 1 d . . . . .
O6 O 0.1773(2) -0.29803(19) 1.20103(9) 0.0258(3) Uani 1 1 d . . . . .
N1 N 0.2171(2) -0.3367(2) 1.12433(10) 0.0182(3) Uani 1 1 d . . . . .
C1 C 0.1013(3) 0.5647(2) 0.69153(11) 0.0214(3) Uani 1 1 d . . . . .
C2 C 0.1369(2) 0.3751(2) 0.67216(11) 0.0170(3) Uani 1 1 d . . . . .
H2 H 0.032888 0.302707 0.693281 0.020 Uiso 1 1 calc R U . . .
C3 C 0.3448(2) 0.3055(2) 0.72027(11) 0.0172(3) Uani 1 1 d . . . . .
H3 H 0.433692 0.401777 0.750769 0.021 Uiso 1 1 calc R U . . .
C4 C 0.4240(3) 0.2210(3) 0.63778(12) 0.0232(4) Uani 1 1 d . . . . .
H4 H 0.532661 0.133001 0.655758 0.028 Uiso 1 1 calc R U . . .
C5 C 0.2298(3) 0.1552(3) 0.57482(13) 0.0243(4) Uani 1 1 d . . . . .
H5A H 0.249222 0.106967 0.513728 0.029 Uiso 1 1 calc R U . . .
H5B H 0.158509 0.070097 0.607379 0.029 Uiso 1 1 calc R U . . .
C6 C 0.1319(3) 0.3364(3) 0.56478(12) 0.0221(3) Uani 1 1 d . . . . .
H6 H -0.001604 0.343790 0.521425 0.027 Uiso 1 1 calc R U . . .
C7 C 0.2961(4) 0.4440(3) 0.53660(14) 0.0302(4) Uani 1 1 d . . . . .
H7 H 0.278685 0.542177 0.495523 0.036 Uiso 1 1 calc R U . . .
C8 C 0.4688(3) 0.3754(3) 0.58002(14) 0.0316(4) Uani 1 1 d . . . . .
H8 H 0.597209 0.416001 0.575573 0.038 Uiso 1 1 calc R U . . .
C9 C 0.2780(2) 0.2182(2) 0.86809(11) 0.0151(3) Uani 1 1 d . . . . .
C10 C 0.2675(2) 0.0698(2) 0.93368(11) 0.0137(3) Uani 1 1 d . . . . .
C11 C 0.2893(2) -0.1034(2) 0.90723(11) 0.0167(3) Uani 1 1 d . . . . .
H11 H 0.315570 -0.129112 0.846596 0.020 Uiso 1 1 calc R U . . .
C12 C 0.2724(2) -0.2383(2) 0.96961(12) 0.0173(3) Uani 1 1 d . . . . .
H12 H 0.286066 -0.356760 0.952574 0.021 Uiso 1 1 calc R U . . .
C13 C 0.2349(2) -0.1941(2) 1.05769(11) 0.0144(3) Uani 1 1 d . . . . .
C14 C 0.2132(3) -0.0240(2) 1.08602(12) 0.0171(3) Uani 1 1 d . . . . .
H14 H 0.187320 0.000826 1.146828 0.020 Uiso 1 1 calc R U . . .
C15 C 0.2304(2) 0.1096(2) 1.02296(11) 0.0171(3) Uani 1 1 d . . . . .
H15 H 0.216845 0.227814 1.040542 0.020 Uiso 1 1 calc R U . . .
C16 C -0.1478(4) 0.7702(3) 0.70677(17) 0.0382(5) Uani 1 1 d . . . . .
H16A H -0.082772 0.806173 0.770827 0.057 Uiso 1 1 calc R U . . .
H16B H -0.292385 0.777674 0.700070 0.057 Uiso 1 1 calc R U . . .
H16C H -0.105647 0.847399 0.660419 0.057 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 C9 1.3473(19) . ?
O1 C3 1.455(2) . ?
O2 C9 1.211(2) . ?
O3 C1 1.344(2) . ?
O3 C16 1.450(3) . ?
O4 C1 1.203(3) . ?
O5 N1 1.225(2) . ?
O6 N1 1.2297(19) . ?
N1 C13 1.477(2) . ?
C1 C2 1.508(2) . ?
C2 C3 1.549(2) . ?
C2 C6 1.571(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.549(2) . ?
C3 H3 1.0000 . ?
C4 C8 1.514(3) . ?
C4 C5 1.537(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.536(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.519(3) . ?
C6 H6 1.0000 . ?
C7 C8 1.331(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.491(2) . ?
C10 C11 1.397(2) . ?
C10 C15 1.398(2) . ?
C11 C12 1.390(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(2) . ?
C14 C15 1.391(2) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C9 O1 C3 115.39(13) . . ?
C1 O3 C16 115.88(18) . . ?
O5 N1 O6 123.67(16) . . ?
O5 N1 C13 118.19(15) . . ?
O6 N1 C13 118.14(15) . . ?
O4 C1 O3 123.95(18) . . ?
O4 C1 C2 125.84(18) . . ?
O3 C1 C2 110.18(16) . . ?
C1 C2 C3 114.68(14) . . ?
C1 C2 C6 113.12(14) . . ?
C3 C2 C6 102.04(13) . . ?
C1 C2 H2 108.9 . . ?
C3 C2 H2 108.9 . . ?
C6 C2 H2 108.9 . . ?
O1 C3 C4 106.83(14) . . ?
O1 C3 C2 111.32(13) . . ?
C4 C3 C2 103.67(13) . . ?
O1 C3 H3 111.6 . . ?
C4 C3 H3 111.6 . . ?
C2 C3 H3 111.6 . . ?
C8 C4 C5 100.42(15) . . ?
C8 C4 C3 103.91(16) . . ?
C5 C4 C3 101.09(14) . . ?
C8 C4 H4 116.3 . . ?
C5 C4 H4 116.3 . . ?
C3 C4 H4 116.3 . . ?
C6 C5 C4 94.00(15) . . ?
C6 C5 H5A 112.9 . . ?
C4 C5 H5A 112.9 . . ?
C6 C5 H5B 112.9 . . ?
C4 C5 H5B 112.9 . . ?
H5A C5 H5B 110.3 . . ?
C7 C6 C5 100.38(16) . . ?
C7 C6 C2 107.15(15) . . ?
C5 C6 C2 99.02(14) . . ?
C7 C6 H6 116.0 . . ?
C5 C6 H6 116.0 . . ?
C2 C6 H6 116.0 . . ?
C8 C7 C6 107.44(19) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C7 C8 C4 107.73(17) . . ?
C7 C8 H8 126.1 . . ?
C4 C8 H8 126.1 . . ?
O2 C9 O1 123.21(16) . . ?
O2 C9 C10 124.29(14) . . ?
O1 C9 C10 112.49(14) . . ?
C11 C10 C15 120.60(15) . . ?
C11 C10 C9 121.93(13) . . ?
C15 C10 C9 117.46(14) . . ?
C12 C11 C10 120.04(14) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 117.85(15) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C14 C13 C12 123.47(16) . . ?
C14 C13 N1 118.41(14) . . ?
C12 C13 N1 118.12(15) . . ?
C13 C14 C15 118.11(15) . . ?
C13 C14 H14 120.9 . . ?
C15 C14 H14 120.9 . . ?
C14 C15 C10 119.93(15) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C16 O3 C1 O4 -1.2(3) . . . . ?
C16 O3 C1 C2 -179.07(16) . . . . ?
O4 C1 C2 C3 32.7(2) . . . . ?
O3 C1 C2 C3 -149.41(14) . . . . ?
O4 C1 C2 C6 -83.7(2) . . . . ?
O3 C1 C2 C6 94.11(17) . . . . ?
C9 O1 C3 C4 174.82(13) . . . . ?
C9 O1 C3 C2 -72.65(17) . . . . ?
C1 C2 C3 O1 117.62(15) . . . . ?
C6 C2 C3 O1 -119.69(14) . . . . ?
C1 C2 C3 C4 -127.87(16) . . . . ?
C6 C2 C3 C4 -5.18(17) . . . . ?
O1 C3 C4 C8 -170.79(14) . . . . ?
C2 C3 C4 C8 71.54(17) . . . . ?
O1 C3 C4 C5 85.42(16) . . . . ?
C2 C3 C4 C5 -32.25(17) . . . . ?
C8 C4 C5 C6 -49.66(16) . . . . ?
C3 C4 C5 C6 56.91(16) . . . . ?
C4 C5 C6 C7 49.69(15) . . . . ?
C4 C5 C6 C2 -59.74(15) . . . . ?
C1 C2 C6 C7 60.6(2) . . . . ?
C3 C2 C6 C7 -63.11(18) . . . . ?
C1 C2 C6 C5 164.51(15) . . . . ?
C3 C2 C6 C5 40.77(16) . . . . ?
C5 C6 C7 C8 -33.1(2) . . . . ?
C2 C6 C7 C8 69.8(2) . . . . ?
C6 C7 C8 C4 0.1(2) . . . . ?
C5 C4 C8 C7 33.0(2) . . . . ?
C3 C4 C8 C7 -71.3(2) . . . . ?
C3 O1 C9 O2 1.1(2) . . . . ?
C3 O1 C9 C10 -179.35(12) . . . . ?
O2 C9 C10 C11 173.30(16) . . . . ?
O1 C9 C10 C11 -6.2(2) . . . . ?
O2 C9 C10 C15 -5.3(2) . . . . ?
O1 C9 C10 C15 175.16(13) . . . . ?
C15 C10 C11 C12 0.5(2) . . . . ?
C9 C10 C11 C12 -178.04(15) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
C11 C12 C13 C14 0.2(2) . . . . ?
C11 C12 C13 N1 -179.92(14) . . . . ?
O5 N1 C13 C14 -177.46(16) . . . . ?
O6 N1 C13 C14 2.3(2) . . . . ?
O5 N1 C13 C12 2.6(2) . . . . ?
O6 N1 C13 C12 -177.61(15) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
N1 C13 C14 C15 179.93(14) . . . . ?
C13 C14 C15 C10 0.3(2) . . . . ?
C11 C10 C15 C14 -0.5(2) . . . . ?
C9 C10 C15 C14 178.12(15) . . . . ?

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.056

