# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_elgr3_en2
_database_code_depnum_ccdc_archive 'CCDC 710420'
_audit_update_record             
;
2008-11-20 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H11 N O5'
_chemical_formula_weight         213.19

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.300(2)
_cell_length_b                   6.2591(6)
_cell_length_c                   9.340(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.02(2)
_cell_angle_gamma                90.00
_cell_volume                     461.42(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    80(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             224
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      80(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD Saphire 3 Xcalibur'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 19.64
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6188
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.98
_diffrn_reflns_theta_max         27.00
_reflns_number_total             1983
_reflns_number_gt                1706
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlis CCD, Oxford Diffraction Ltd.,Version 1.171.26'
_computing_cell_refinement       
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.26'
_computing_data_reduction        
'CrysAlis RED, Oxford Diffraction Ltd.,Version 1.171.26'

_computing_structure_solution    'SIR-97_(Altomare & al., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON_(Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0490P)²+0.0000P] 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 H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(9)
_refine_ls_number_reflns         1983
_refine_ls_number_parameters     136
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0760
_refine_ls_wR_factor_gt          0.0742
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21627(14) 0.85779(18) -0.00057(11) 0.0200(3) Uani 1 1 d . . .
O2 O -0.06015(13) 0.86805(18) -0.01523(11) 0.0190(3) Uani 1 1 d . . .
O3 O 0.09077(15) 1.0638(2) 0.48688(12) 0.0273(3) Uani 1 1 d . . .
O4 O 0.56215(15) 0.89989(19) 0.27080(13) 0.0249(3) Uani 1 1 d . . .
O5 O 0.42992(14) 0.58124(18) 0.25186(12) 0.0195(3) Uani 1 1 d . . .
N1 N 0.13035(17) 0.81808(19) 0.21057(14) 0.0158(3) Uani 1 1 d . . .
C1 C 0.1069(2) 0.8493(2) 0.06083(16) 0.0162(3) Uani 1 1 d . . .
C2 C -0.15817(19) 0.8600(3) 0.09000(16) 0.0182(3) Uani 1 1 d . . .
H2A H -0.2276 0.7284 0.0748 0.022 Uiso 1 1 calc R . .
H2B H -0.2340 0.9854 0.0766 0.022 Uiso 1 1 calc R . .
C3 C -0.02606(19) 0.8614(3) 0.24747(16) 0.0168(3) Uani 1 1 d . . .
H3 H -0.0493 0.7420 0.3094 0.020 Uiso 1 1 calc R . .
C4 C -0.0157(2) 1.0714(3) 0.33096(17) 0.0219(4) Uani 1 1 d . . .
H4 H -0.1233 1.1550 0.3096 0.026 Uiso 1 1 calc R . .
C5 C 0.1425(2) 1.1944(3) 0.37891(18) 0.0238(4) Uani 1 1 d . . .
H5 H 0.1308 1.3525 0.3872 0.029 Uiso 1 1 calc R . .
C6 C 0.2993(2) 1.1172(3) 0.34460(19) 0.0210(4) Uani 1 1 d . . .
H6A H 0.4011 1.1542 0.4293 0.025 Uiso 1 1 calc R . .
H6B H 0.3079 1.1897 0.2531 0.025 Uiso 1 1 calc R . .
C7 C 0.29243(19) 0.8762(3) 0.32025(16) 0.0175(3) Uani 1 1 d . . .
H7 H 0.2971 0.8075 0.4181 0.021 Uiso 1 1 calc R . .
C8 C 0.4425(2) 0.7927(3) 0.27538(18) 0.0189(4) Uani 1 1 d . . .
C9 C 0.5599(2) 0.4861(3) 0.1985(2) 0.0234(4) Uani 1 1 d . . .
H9A H 0.5396 0.3321 0.1847 0.035 Uiso 1 1 calc R . .
H9B H 0.6713 0.5106 0.2725 0.035 Uiso 1 1 calc R . .
H9C H 0.5568 0.5512 0.1023 0.035 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0226(6) 0.0189(6) 0.0222(5) -0.0004(5) 0.0124(5) -0.0005(5)
O2 0.0177(6) 0.0216(6) 0.0180(5) 0.0027(5) 0.0057(5) -0.0014(5)
O3 0.0275(7) 0.0371(8) 0.0172(6) -0.0049(5) 0.0068(5) 0.0028(6)
O4 0.0191(6) 0.0218(7) 0.0350(7) -0.0009(5) 0.0102(5) -0.0029(5)
O5 0.0177(6) 0.0164(6) 0.0267(6) -0.0013(5) 0.0104(5) 0.0008(5)
N1 0.0146(7) 0.0164(7) 0.0176(6) -0.0006(5) 0.0067(5) 0.0003(5)
C1 0.0188(8) 0.0107(8) 0.0186(7) -0.0010(7) 0.0052(6) -0.0013(7)
C2 0.0169(8) 0.0182(8) 0.0213(7) -0.0008(7) 0.0086(6) -0.0006(7)
C3 0.0168(8) 0.0162(8) 0.0193(7) 0.0018(7) 0.0083(6) 0.0011(7)
C4 0.0220(9) 0.0250(9) 0.0185(8) -0.0015(7) 0.0059(7) 0.0066(7)
C5 0.0280(10) 0.0197(9) 0.0227(8) -0.0048(7) 0.0062(8) 0.0014(8)
C6 0.0205(9) 0.0201(9) 0.0214(8) -0.0053(6) 0.0052(7) -0.0013(7)
C7 0.0159(8) 0.0192(8) 0.0168(7) 0.0004(6) 0.0041(6) 0.0024(6)
C8 0.0168(9) 0.0197(9) 0.0185(8) 0.0007(6) 0.0029(7) 0.0014(7)
C9 0.0182(8) 0.0223(9) 0.0325(10) -0.0018(7) 0.0117(8) 0.0035(7)

_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 1.2157(18) . ?
O2 C1 1.3532(19) . ?
O2 C2 1.4578(17) . ?
O3 C4 1.452(2) . ?
O3 C5 1.462(2) . ?
O4 C8 1.210(2) . ?
O5 C8 1.340(2) . ?
O5 C9 1.4492(18) . ?
N1 C1 1.3652(19) . ?
N1 C7 1.463(2) . ?
N1 C3 1.4678(19) . ?
C2 C3 1.539(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.517(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.468(2) . ?
C4 H4 1.0000 . ?
C5 C6 1.512(2) . ?
C5 H5 1.0000 . ?
C6 C7 1.524(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.524(2) . ?
C7 H7 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
C1 O2 C2 109.75(11) . . ?
C4 O3 C5 60.49(11) . . ?
C8 O5 C9 115.69(12) . . ?
C1 N1 C7 119.39(13) . . ?
C1 N1 C3 110.97(13) . . ?
C7 N1 C3 118.57(11) . . ?
O1 C1 O2 122.81(13) . . ?
O1 C1 N1 126.79(15) . . ?
O2 C1 N1 110.39(12) . . ?
O2 C2 C3 105.24(11) . . ?
O2 C2 H2A 110.7 . . ?
C3 C2 H2A 110.7 . . ?
O2 C2 H2B 110.7 . . ?
C3 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
N1 C3 C4 111.56(13) . . ?
N1 C3 C2 101.24(11) . . ?
C4 C3 C2 113.99(14) . . ?
N1 C3 H3 109.9 . . ?
C4 C3 H3 109.9 . . ?
C2 C3 H3 109.9 . . ?
O3 C4 C5 60.10(11) . . ?
O3 C4 C3 114.02(13) . . ?
C5 C4 C3 120.92(14) . . ?
O3 C4 H4 116.5 . . ?
C5 C4 H4 116.5 . . ?
C3 C4 H4 116.5 . . ?
O3 C5 C4 59.41(10) . . ?
O3 C5 C6 115.05(14) . . ?
C4 C5 C6 121.03(15) . . ?
O3 C5 H5 116.3 . . ?
C4 C5 H5 116.3 . . ?
C6 C5 H5 116.3 . . ?
C5 C6 C7 110.67(14) . . ?
C5 C6 H6A 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
N1 C7 C6 109.55(13) . . ?
N1 C7 C8 112.01(12) . . ?
C6 C7 C8 112.63(13) . . ?
N1 C7 H7 107.5 . . ?
C6 C7 H7 107.5 . . ?
C8 C7 H7 107.5 . . ?
O4 C8 O5 124.39(15) . . ?
O4 C8 C7 124.66(15) . . ?
O5 C8 C7 110.79(13) . . ?
O5 C9 H9A 109.5 . . ?
O5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
C2 O2 C1 O1 -177.69(14) . . . . ?
C2 O2 C1 N1 3.05(17) . . . . ?
C7 N1 C1 O1 24.8(2) . . . . ?
C3 N1 C1 O1 168.24(15) . . . . ?
C7 N1 C1 O2 -156.01(13) . . . . ?
C3 N1 C1 O2 -12.53(17) . . . . ?
C1 O2 C2 C3 6.89(17) . . . . ?
C1 N1 C3 C4 -105.94(15) . . . . ?
C7 N1 C3 C4 37.87(18) . . . . ?
C1 N1 C3 C2 15.68(16) . . . . ?
C7 N1 C3 C2 159.49(14) . . . . ?
O2 C2 C3 N1 -13.08(15) . . . . ?
O2 C2 C3 C4 106.82(14) . . . . ?
C5 O3 C4 C3 113.12(16) . . . . ?
N1 C3 C4 O3 -74.40(16) . . . . ?
C2 C3 C4 O3 171.69(12) . . . . ?
N1 C3 C4 C5 -6.1(2) . . . . ?
C2 C3 C4 C5 -119.98(16) . . . . ?
C4 O3 C5 C6 -112.62(16) . . . . ?
C3 C4 C5 O3 -101.71(16) . . . . ?
O3 C4 C5 C6 102.62(17) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?
O3 C5 C6 C7 44.44(18) . . . . ?
C4 C5 C6 C7 -23.6(2) . . . . ?
C1 N1 C7 C6 78.33(16) . . . . ?
C3 N1 C7 C6 -62.41(17) . . . . ?
C1 N1 C7 C8 -47.40(19) . . . . ?
C3 N1 C7 C8 171.86(13) . . . . ?
C5 C6 C7 N1 50.95(16) . . . . ?
C5 C6 C7 C8 176.33(13) . . . . ?
C9 O5 C8 O4 -8.4(2) . . . . ?
C9 O5 C8 C7 175.96(13) . . . . ?
N1 C7 C8 O4 129.70(17) . . . . ?
C6 C7 C8 O4 5.7(2) . . . . ?
N1 C7 C8 O5 -54.62(17) . . . . ?
C6 C7 C8 O5 -178.65(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.043


