# 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_jcn_npg11_4
_database_code_depnum_ccdc_archive 'CCDC 2177368'
loop_
_audit_author_name
_audit_author_address
'Tilo Soehnel'
;University of Auckland
New Zealand
;
_audit_update_record             
;
2022-06-06 deposited with the CCDC.	2022-07-26 downloaded from the CCDC.
;
_audit_creation_date             2022-06-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H11 N O5'
_chemical_formula_sum            'C8 H11 N O5'
_chemical_formula_weight         201.18
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C8H11NO5
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'

_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.
;
_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'
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                   6.0853(2)
_cell_length_b                   6.9127(2)
_cell_length_c                   21.3235(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     896.99(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4269
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      73.4970
_cell_measurement_theta_min      4.1440
_shelx_estimated_absorpt_T_max   0.900
_shelx_estimated_absorpt_T_min   0.881
_exptl_absorpt_coefficient_mu    1.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5090
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.733
_diffrn_reflns_theta_min         4.147
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     28.00  53.00   0.50    0.40    --  100.91 -61.00 120.00   50
  2  ω     29.00  55.00   0.50    0.40    --  100.91 -61.00-150.00   52
  3  ω     28.00  68.00   0.50    0.40    --  100.91 -61.00-120.00   80
  4  ω     23.00  48.00   0.50    0.40    --  100.91 -45.00 120.00   50
  5  ω     24.00  49.00   0.50    0.40    --  100.91 -45.00  60.00   50
  6  ω     23.00  48.00   0.50    0.40    --  100.91 -45.00 -30.00   50
  7  ω     25.00  51.00   0.50    0.40    --  100.91 -45.00  30.00   52
  8  ω     24.00  50.00   0.50    0.40    --  100.91 -45.00-120.00   52
  9  ω     25.00  51.00   0.50    0.40    --  100.91 -45.00 -60.00   52
 10  ω    102.00 178.00   0.50    0.40    --  100.91 111.00 -18.00  152
 11  ω    -26.00   0.00   0.50    0.10    --   47.23 -19.00 150.00   52
 12  ω     97.00 135.00   0.50    0.40    --  100.91  17.00 177.00   76
 13  ω     91.00 117.00   0.50    0.40    --  100.91-147.00  -1.00   52
 14  ω     62.00 104.00   0.50    0.40    --  100.91 -95.00-120.00   84
 15  ω    -43.00  26.00   0.50    0.10    --  -47.23  38.00 -60.00  138
 16  ω     -2.00  28.00   0.50    0.10    --  -47.23  17.00 177.00   60
 17  ω   -101.00 -54.00   0.50    0.40    --  -90.25  77.00-150.00   94
 18  ω    -62.00 -23.00   0.50    0.40    --  -90.25  61.00   0.00   78
 19  ω    -71.00 -41.00   0.50    0.40    --  -90.25  61.00 -30.00   60
 20  ω    -39.00 -14.00   0.50    0.40    --  -90.25  45.00  60.00   50
 21  ω    -47.00 -20.00   0.50    0.40    --  -90.25  45.00  90.00   54
 22  ω   -146.00 -85.00   0.50    0.40    --  -90.25-125.00 164.00  122
 23  ω   -111.00 -86.00   0.50    0.10    --  -47.23-125.00 -90.00   50
 24  ω   -120.00 -76.00   0.50    0.10    --  -47.23-125.00  30.00   88
 25  ω    -99.00 -74.00   0.50    0.10    --  -47.23 -17.00   8.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1023832000
_diffrn_orient_matrix_UB_12      -0.2037362000
_diffrn_orient_matrix_UB_13      -0.0007891000
_diffrn_orient_matrix_UB_21      -0.2257340000
_diffrn_orient_matrix_UB_22      -0.0885994000
_diffrn_orient_matrix_UB_23      0.0158510000
_diffrn_orient_matrix_UB_31      -0.0518346000
_diffrn_orient_matrix_UB_32      -0.0176098000
_diffrn_orient_matrix_UB_33      -0.0704606000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1558
_reflns_number_total             1620
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 
;
 Flack x determined using 600 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(14)
_refine_ls_extinction_coef       0.0042(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1620
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0356P)²+0.1955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0741
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), N(H)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
C1 C 0.1482(4) -0.0648(3) 0.71057(10) 0.0194(5) Uani 1 1 d . . . . .
H1A H -0.001971 -0.030043 0.700258 0.023 Uiso 1 1 calc R U . . .
H1B H 0.198061 -0.158802 0.679944 0.023 Uiso 1 1 calc R U . . .
C2 C 0.2923(4) 0.1142(3) 0.70688(10) 0.0168(5) Uani 1 1 d . . . . .
H2 H 0.254549 0.196385 0.742748 0.020 Uiso 1 1 calc R U . . .
C3 C 0.2493(4) 0.2328(3) 0.64727(9) 0.0175(5) Uani 1 1 d . . . . .
H3 H 0.093767 0.268659 0.644836 0.021 Uiso 1 1 calc R U . . .
C4 C 0.4692(4) 0.2107(3) 0.56072(9) 0.0165(5) Uani 1 1 d . . . . .
C5 C 0.3896(4) 0.4091(3) 0.64302(10) 0.0177(5) Uani 1 1 d . . . . .
H5 H 0.384915 0.513917 0.670346 0.021 Uiso 1 1 calc R U . . .
C6 C 0.5226(4) 0.3924(3) 0.59385(10) 0.0165(5) Uani 1 1 d . . . . .
C7 C 0.7335(4) 0.6907(3) 0.58995(9) 0.0178(5) Uani 1 1 d . . . . .
C8 C 0.9174(4) 0.7900(4) 0.55556(11) 0.0245(5) Uani 1 1 d . . . . .
H8A H 0.910828 0.926601 0.563386 0.037 Uiso 1 1 calc R U . . .
H8B H 0.902914 0.766458 0.511379 0.037 Uiso 1 1 calc R U . . .
H8C H 1.055722 0.740187 0.569952 0.037 Uiso 1 1 calc R U . . .
N N 0.6898(3) 0.5079(3) 0.57003(8) 0.0174(4) Uani 1 1 d . . . . .
H H 0.770914 0.460726 0.540775 0.021 Uiso 1 1 calc R U . . .
O1 O 0.1535(3) -0.1493(3) 0.77117(7) 0.0237(4) Uani 1 1 d . . . . .
O2 O 0.5195(3) 0.0668(2) 0.71231(7) 0.0168(4) Uani 1 1 d . . . . .
O3 O 0.3108(3) 0.1177(2) 0.59265(6) 0.0178(4) Uani 1 1 d . . . . .
O4 O 0.5461(3) 0.1488(2) 0.51253(7) 0.0213(4) Uani 1 1 d . . . . .
O5 O 0.6283(3) 0.7663(2) 0.63239(7) 0.0235(4) Uani 1 1 d . . . . .
H2A H 0.544(5) -0.021(5) 0.6854(14) 0.031(8) Uiso 1 1 d . . . . .
H1 H 0.273(7) -0.230(5) 0.7720(15) 0.046(9) 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
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.519(3) . ?
C1 O1 1.418(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.535(3) . ?
C2 O2 1.426(3) . ?
C3 H3 0.9800 . ?
C3 C5 1.491(3) . ?
C3 O3 1.459(3) . ?
C4 C6 1.477(3) . ?
C4 O3 1.344(3) . ?
C4 O4 1.208(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.329(3) . ?
C6 N 1.390(3) . ?
C7 C8 1.503(3) . ?
C7 N 1.359(3) . ?
C7 O5 1.225(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
N H 0.8600 . ?
O1 H1 0.92(4) . ?
O2 H2A 0.85(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
H1A C1 H1B 107.9 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
O1 C1 H1A 109.3 . . ?
O1 C1 H1B 109.3 . . ?
O1 C1 C2 111.70(18) . . ?
C1 C2 H2 107.3 . . ?
C1 C2 C3 112.33(18) . . ?
C3 C2 H2 107.3 . . ?
O2 C2 C1 111.64(18) . . ?
O2 C2 H2 107.3 . . ?
O2 C2 C3 110.79(17) . . ?
C2 C3 H3 110.1 . . ?
C5 C3 C2 112.93(18) . . ?
C5 C3 H3 110.1 . . ?
O3 C3 C2 109.02(17) . . ?
O3 C3 H3 110.1 . . ?
O3 C3 C5 104.51(17) . . ?
O3 C4 C6 108.80(18) . . ?
O4 C4 C6 128.5(2) . . ?
O4 C4 O3 122.7(2) . . ?
C3 C5 H5 125.5 . . ?
C6 C5 C3 109.0(2) . . ?
C6 C5 H5 125.5 . . ?
C5 C6 C4 108.5(2) . . ?
C5 C6 N 133.1(2) . . ?
N C6 C4 118.37(19) . . ?
N C7 C8 114.7(2) . . ?
O5 C7 C8 123.7(2) . . ?
O5 C7 N 121.7(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 N H 117.9 . . ?
C7 N C6 124.30(19) . . ?
C7 N H 117.9 . . ?
C1 O1 H1 107(2) . . ?
C2 O2 H2A 106(2) . . ?
C4 O3 C3 109.11(17) . . ?

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
C1 C2 C3 C5 179.97(18) . . . . ?
C1 C2 C3 O3 -64.3(2) . . . . ?
C2 C3 C5 C6 115.6(2) . . . . ?
C2 C3 O3 C4 -119.98(18) . . . . ?
C3 C5 C6 C4 3.3(3) . . . . ?
C3 C5 C6 N -176.9(2) . . . . ?
C4 C6 N C7 169.6(2) . . . . ?
C5 C3 O3 C4 1.0(2) . . . . ?
C5 C6 N C7 -10.1(4) . . . . ?
C6 C4 O3 C3 0.9(2) . . . . ?
C8 C7 N C6 -177.9(2) . . . . ?
O1 C1 C2 C3 -167.11(18) . . . . ?
O1 C1 C2 O2 67.7(2) . . . . ?
O2 C2 C3 C5 -54.4(2) . . . . ?
O2 C2 C3 O3 61.3(2) . . . . ?
O3 C3 C5 C6 -2.8(2) . . . . ?
O3 C4 C6 C5 -2.7(3) . . . . ?
O3 C4 C6 N 177.44(18) . . . . ?
O4 C4 C6 C5 176.3(2) . . . . ?
O4 C4 C6 N -3.6(4) . . . . ?
O4 C4 O3 C3 -178.2(2) . . . . ?
O5 C7 N C6 1.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.264
_oxdiff_exptl_absorpt_empirical_full_min 0.793
