# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_cu_hv026_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2310392'
loop_
_audit_author_name
_audit_author_address
'Edwin Otten'
;University of Groningen
Netherlands
;
_audit_update_record             
;
2023-11-26 deposited with the CCDC.	2024-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H15 N O6'
_chemical_formula_weight         233.22

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      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                   5.3370(2)
_cell_length_b                   26.3849(12)
_cell_length_c                   8.0130(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.970(2)
_cell_angle_gamma                90
_cell_volume                     1067.08(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8613
_cell_measurement_theta_min      6.08
_cell_measurement_theta_max      74.71

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.057
_exptl_absorpt_coefficient_mu    1.056
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6466
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   SADABS
_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       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16473
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.839
_diffrn_reflns_theta_max         74.696
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             4220
_reflns_number_gt                3943
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_max     0.939
_reflns_Friedel_fraction_full    0.976

_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0288P)²+0.5211P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1690 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4220
_refine_ls_number_parameters     305
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0824
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.0882(4) 0.60690(8) 0.0990(3) 0.0148(4) Uani 1 1 d . . . . .
N1 N 0.4958(7) 0.74911(11) -0.0302(4) 0.0340(8) Uani 1 1 d . . . . .
C1 C 0.2606(6) 0.64062(11) 0.2275(4) 0.0165(6) Uani 1 1 d . . . . .
H1A H 0.156033 0.658650 0.290965 0.020 Uiso 1 1 calc R U . . .
H1B H 0.333543 0.666288 0.165810 0.020 Uiso 1 1 calc R U . . .
O2 O 0.3810(4) 0.58071(8) 0.4643(3) 0.0177(5) Uani 1 1 d . . . . .
H21 H 0.508(6) 0.5711(13) 0.559(5) 0.027 Uiso 1 1 calc R U . . .
N2 N 1.0300(7) 0.25079(12) 0.5720(5) 0.0373(8) Uani 1 1 d . . . . .
C2 C 0.4873(6) 0.61275(11) 0.3602(4) 0.0147(6) Uani 1 1 d . . . . .
H2 H 0.610744 0.637902 0.438586 0.018 Uiso 1 1 calc R U . . .
O3 O 0.8398(4) 0.55228(8) 0.3862(3) 0.0171(5) Uani 1 1 d . . . . .
H23 H 0.984(8) 0.5612(11) 0.383(4) 0.026 Uiso 1 1 calc R U . . .
C3 C 0.6366(5) 0.58174(11) 0.2629(4) 0.0135(6) Uani 1 1 d . . . . .
H3 H 0.720051 0.605193 0.198224 0.016 Uiso 1 1 calc R U . . .
O4 O 0.5666(4) 0.51908(8) 0.0283(3) 0.0152(4) Uani 1 1 d . . . . .
H4A H 0.626(7) 0.4908(14) 0.081(3) 0.023 Uiso 1 1 calc R U . . .
C4 C 0.4428(6) 0.54695(11) 0.1307(4) 0.0132(6) Uani 1 1 d . . . . .
H4 H 0.363648 0.522804 0.195792 0.016 Uiso 1 1 calc R U . . .
C5 C 0.2211(5) 0.57847(11) 0.0032(4) 0.0125(6) Uani 1 1 d . . . . .
O5 O 0.3526(4) 0.61113(7) -0.0825(3) 0.0141(4) Uani 1 1 d . . . . .
O6 O -0.2283(4) 0.56893(8) -0.2110(3) 0.0169(5) Uani 1 1 d . . . . .
H6 H -0.316(6) 0.5666(13) -0.155(4) 0.025 Uiso 1 1 calc R U . . .
C6 C 0.0162(6) 0.54414(11) -0.1260(4) 0.0152(6) Uani 1 1 d . . . . .
H6A H 0.090272 0.531709 -0.216794 0.018 Uiso 1 1 calc R U . . .
H6B H -0.016964 0.514333 -0.061125 0.018 Uiso 1 1 calc R U . . .
C7 C 0.1883(6) 0.63999(12) -0.2284(4) 0.0171(6) Uani 1 1 d . . . . .
H7A H 0.045859 0.657305 -0.196301 0.020 Uiso 1 1 calc R U . . .
H7B H 0.106384 0.617741 -0.331193 0.020 Uiso 1 1 calc R U . . .
O7 O 0.2892(4) 0.37189(7) 0.4740(2) 0.0148(4) Uani 1 1 d . . . . .
C8 C 0.3699(6) 0.67837(11) -0.2709(4) 0.0193(7) Uani 1 1 d . . . . .
H8A H 0.530779 0.661030 -0.277688 0.023 Uiso 1 1 calc R U . . .
H8B H 0.278501 0.693893 -0.387313 0.023 Uiso 1 1 calc R U . . .
O8 O 0.2104(4) 0.40168(8) 0.1112(3) 0.0173(4) Uani 1 1 d . . . . .
H8 H 0.228(5) 0.4086(13) 0.013(5) 0.026 Uiso 1 1 calc R U . . .
C9 C 0.4464(6) 0.71816(12) -0.1358(4) 0.0221(7) Uani 1 1 d . . . . .
O9 O 0.7490(4) 0.42966(8) 0.1852(3) 0.0168(4) Uani 1 1 d . . . . .
H9 H 0.884(8) 0.4212(11) 0.185(4) 0.025 Uiso 1 1 calc R U . . .
C10 C 0.3309(6) 0.33923(11) 0.3413(4) 0.0159(6) Uani 1 1 d . . . . .
H10A H 0.163784 0.321278 0.278743 0.019 Uiso 1 1 calc R U . . .
H10B H 0.466129 0.313460 0.398978 0.019 Uiso 1 1 calc R U . . .
O10 O 0.8353(4) 0.46023(8) 0.5454(3) 0.0166(4) Uani 1 1 d . . . . .
H10 H 0.835(4) 0.4883(15) 0.500(4) 0.025 Uiso 1 1 calc R U . . .
C11 C 0.4212(6) 0.36870(11) 0.2087(4) 0.0153(6) Uani 1 1 d . . . . .
H11 H 0.463551 0.344497 0.125573 0.018 Uiso 1 1 calc R U . . .
O11 O 0.7341(4) 0.36710(8) 0.6521(3) 0.0152(4) Uani 1 1 d . . . . .
C12 C 0.6690(6) 0.39903(11) 0.3066(4) 0.0131(6) Uani 1 1 d . . . . .
H12 H 0.815488 0.375075 0.367324 0.016 Uiso 1 1 calc R U . . .
O12 O 0.2775(4) 0.40725(8) 0.7861(3) 0.0178(4) Uani 1 1 d . . . . .
H12A H 0.120(8) 0.4073(13) 0.719(4) 0.027 Uiso 1 1 calc R U . . .
C13 C 0.6097(6) 0.43245(11) 0.4437(4) 0.0135(6) Uani 1 1 d . . . . .
H13 H 0.465611 0.456785 0.382297 0.016 Uiso 1 1 calc R U . . .
C14 C 0.5166(5) 0.39978(11) 0.5703(4) 0.0137(6) Uani 1 1 d . . . . .
C15 C 0.4405(6) 0.43276(12) 0.7034(4) 0.0168(6) Uani 1 1 d . . . . .
H15A H 0.604167 0.444289 0.795382 0.020 Uiso 1 1 calc R U . . .
H15B H 0.345809 0.463195 0.642143 0.020 Uiso 1 1 calc R U . . .
C16 C 0.6975(6) 0.33153(12) 0.7769(4) 0.0191(7) Uani 1 1 d . . . . .
H16A H 0.538319 0.310475 0.722177 0.023 Uiso 1 1 calc R U . . .
H16B H 0.675815 0.349376 0.880049 0.023 Uiso 1 1 calc R U . . .
C17 C 0.9457(6) 0.29875(12) 0.8329(4) 0.0203(7) Uani 1 1 d . . . . .
H17A H 1.100894 0.320529 0.890311 0.024 Uiso 1 1 calc R U . . .
H17B H 0.930618 0.273757 0.921256 0.024 Uiso 1 1 calc R U . . .
C18 C 0.9917(7) 0.27165(12) 0.6860(5) 0.0237(7) Uani 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 C5 1.417(3) . ?
O1 C1 1.443(3) . ?
N1 C9 1.144(4) . ?
C1 C2 1.516(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
O2 C2 1.428(4) . ?
O2 H21 0.87(4) . ?
N2 C18 1.140(5) . ?
C2 C3 1.522(4) . ?
C2 H2 1.0000 . ?
O3 C3 1.435(3) . ?
O3 H23 0.81(4) . ?
C3 C4 1.524(4) . ?
C3 H3 1.0000 . ?
O4 C4 1.415(3) . ?
O4 H4A 0.86(4) . ?
C4 C5 1.533(4) . ?
C4 H4 1.0000 . ?
C5 O5 1.422(3) . ?
C5 C6 1.534(4) . ?
O5 C7 1.431(3) . ?
O6 C6 1.420(4) . ?
O6 H6 0.74(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.515(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O7 C14 1.414(3) . ?
O7 C10 1.441(4) . ?
C8 C9 1.467(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
O8 C11 1.436(3) . ?
O8 H8 0.84(4) . ?
O9 C12 1.433(3) . ?
O9 H9 0.75(4) . ?
C10 C11 1.516(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
O10 C13 1.419(3) . ?
O10 H10 0.82(4) . ?
C11 C12 1.527(4) . ?
C11 H11 1.0000 . ?
O11 C14 1.423(3) . ?
O11 C16 1.431(3) . ?
C12 C13 1.520(4) . ?
C12 H12 1.0000 . ?
O12 C15 1.422(4) . ?
O12 H12A 0.84(4) . ?
C13 C14 1.531(4) . ?
C13 H13 1.0000 . ?
C14 C15 1.530(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.523(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.464(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?

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
C5 O1 C1 113.5(2) . . ?
O1 C1 C2 112.3(2) . . ?
O1 C1 H1A 109.1 . . ?
C2 C1 H1A 109.1 . . ?
O1 C1 H1B 109.1 . . ?
C2 C1 H1B 109.1 . . ?
H1A C1 H1B 107.9 . . ?
C2 O2 H21 109.5 . . ?
O2 C2 C1 108.6(2) . . ?
O2 C2 C3 110.8(2) . . ?
C1 C2 C3 109.5(2) . . ?
O2 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
C3 C2 H2 109.3 . . ?
C3 O3 H23 109.5 . . ?
O3 C3 C2 110.1(2) . . ?
O3 C3 C4 110.0(2) . . ?
C2 C3 C4 109.3(2) . . ?
O3 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C4 O4 H4A 109.5 . . ?
O4 C4 C3 112.1(2) . . ?
O4 C4 C5 107.5(2) . . ?
C3 C4 C5 109.8(2) . . ?
O4 C4 H4 109.1 . . ?
C3 C4 H4 109.1 . . ?
C5 C4 H4 109.1 . . ?
O1 C5 O5 110.7(2) . . ?
O1 C5 C4 109.9(2) . . ?
O5 C5 C4 104.8(2) . . ?
O1 C5 C6 107.8(2) . . ?
O5 C5 C6 112.8(2) . . ?
C4 C5 C6 110.9(2) . . ?
C5 O5 C7 116.7(2) . . ?
C6 O6 H6 109.5 . . ?
O6 C6 C5 113.2(2) . . ?
O6 C6 H6A 108.9 . . ?
C5 C6 H6A 108.9 . . ?
O6 C6 H6B 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.8 . . ?
O5 C7 C8 105.8(2) . . ?
O5 C7 H7A 110.6 . . ?
C8 C7 H7A 110.6 . . ?
O5 C7 H7B 110.6 . . ?
C8 C7 H7B 110.6 . . ?
H7A C7 H7B 108.7 . . ?
C14 O7 C10 113.8(2) . . ?
C9 C8 C7 110.9(3) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.0 . . ?
C11 O8 H8 109.5 . . ?
N1 C9 C8 177.2(4) . . ?
C12 O9 H9 109.5 . . ?
O7 C10 C11 111.8(2) . . ?
O7 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
O7 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C13 O10 H10 109.5 . . ?
O8 C11 C10 108.7(2) . . ?
O8 C11 C12 110.9(2) . . ?
C10 C11 C12 109.2(2) . . ?
O8 C11 H11 109.4 . . ?
C10 C11 H11 109.4 . . ?
C12 C11 H11 109.4 . . ?
C14 O11 C16 116.3(2) . . ?
O9 C12 C13 110.0(2) . . ?
O9 C12 C11 110.3(2) . . ?
C13 C12 C11 109.1(2) . . ?
O9 C12 H12 109.2 . . ?
C13 C12 H12 109.2 . . ?
C11 C12 H12 109.2 . . ?
C15 O12 H12A 109.5 . . ?
O10 C13 C12 112.2(2) . . ?
O10 C13 C14 107.9(2) . . ?
C12 C13 C14 109.9(2) . . ?
O10 C13 H13 108.9 . . ?
C12 C13 H13 108.9 . . ?
C14 C13 H13 108.9 . . ?
O7 C14 O11 111.3(2) . . ?
O7 C14 C15 107.5(2) . . ?
O11 C14 C15 112.6(2) . . ?
O7 C14 C13 109.7(2) . . ?
O11 C14 C13 104.7(2) . . ?
C15 C14 C13 111.0(2) . . ?
O12 C15 C14 113.4(2) . . ?
O12 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
O12 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
O11 C16 C17 106.0(2) . . ?
O11 C16 H16A 110.5 . . ?
C17 C16 H16A 110.5 . . ?
O11 C16 H16B 110.5 . . ?
C17 C16 H16B 110.5 . . ?
H16A C16 H16B 108.7 . . ?
C18 C17 C16 113.4(3) . . ?
C18 C17 H17A 108.9 . . ?
C16 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
N2 C18 C17 179.3(4) . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.047



