# Electronic Supplementary Material (ESI) for Green 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_AX1727
_database_code_depnum_ccdc_archive 'CCDC 2022131'
loop_
_audit_author_name
_audit_author_address
'Anke Spannenberg'
;LIKAT
Germany
;
_audit_update_record             
;
2020-08-07 deposited with the CCDC.	2020-09-09 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 H12 O5'
_chemical_formula_weight         200.19

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'
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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.7742(5)
_cell_length_b                   7.0350(3)
_cell_length_c                   12.0329(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.6189(17)
_cell_angle_gamma                90
_cell_volume                     893.36(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      30.57

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.419
_exptl_crystal_size_mid          0.335
_exptl_crystal_size_min          0.156
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            16827
_diffrn_reflns_av_unetI/netI     0.0104
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.930
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2151
_reflns_number_gt                1993
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_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)+(0.0480P)²+0.3191P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2151
_refine_ls_number_parameters     135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0888
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
C1 C 0.55761(9) 0.21756(15) 0.58354(9) 0.0220(2) Uani 1 1 d . . . . .
H1A H 0.488340 0.263542 0.522512 0.026 Uiso 1 1 calc R U . . .
H1B H 0.544224 0.079986 0.593842 0.026 Uiso 1 1 calc R U . . .
C2 C 0.68038(9) 0.24519(14) 0.54782(8) 0.0186(2) Uani 1 1 d . . . . .
C3 C 0.71363(9) 0.33800(14) 0.45997(8) 0.0203(2) Uani 1 1 d . . . . .
H3 H 0.658311 0.403551 0.400900 0.024 Uiso 1 1 calc R U . . .
C4 C 0.84816(9) 0.31881(14) 0.47277(8) 0.0193(2) Uani 1 1 d . . . . .
H4 H 0.899683 0.368200 0.424118 0.023 Uiso 1 1 calc R U . . .
C5 C 0.88661(9) 0.21599(13) 0.56833(8) 0.0166(2) Uani 1 1 d . . . . .
C6 C 1.01305(8) 0.15199(13) 0.63099(8) 0.0164(2) Uani 1 1 d . . . . .
H6 H 1.015429 0.010269 0.637503 0.020 Uiso 1 1 calc R U . . .
C7 C 1.22804(9) 0.16769(15) 0.62296(8) 0.0195(2) Uani 1 1 d . . . . .
H7A H 1.288875 0.218221 0.578709 0.023 Uiso 1 1 calc R U . . .
H7B H 1.237631 0.027776 0.627287 0.023 Uiso 1 1 calc R U . . .
C8 C 1.25661(9) 0.25149(14) 0.74194(8) 0.0171(2) Uani 1 1 d . . . . .
H8 H 1.254816 0.393438 0.737494 0.020 Uiso 1 1 calc R U . . .
C9 C 1.15598(9) 0.18236(16) 0.80418(8) 0.0211(2) Uani 1 1 d . . . . .
H9A H 1.160844 0.042445 0.812751 0.025 Uiso 1 1 calc R U . . .
H9B H 1.169550 0.239950 0.880753 0.025 Uiso 1 1 calc R U . . .
O1 O 0.55103(7) 0.31493(12) 0.68670(7) 0.02539(19) Uani 1 1 d . . . . .
O2 O 0.78576(6) 0.16712(10) 0.61591(6) 0.01894(17) Uani 1 1 d . . . . .
O3 O 1.10163(6) 0.21526(11) 0.56753(6) 0.01933(17) Uani 1 1 d . . . . .
O4 O 1.03422(6) 0.23612(11) 0.73987(6) 0.02051(18) Uani 1 1 d . . . . .
O5 O 1.37773(6) 0.18930(11) 0.80300(6) 0.02092(17) Uani 1 1 d . . . . .
H1 H 0.5786(16) 0.428(3) 0.6844(14) 0.051(5) Uiso 1 1 d . . . . .
H5 H 1.4368(17) 0.238(3) 0.7683(16) 0.052(5) 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 O1 1.4320(12) . ?
C1 C2 1.4837(13) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.3508(14) . ?
C2 O2 1.3738(11) . ?
C3 C4 1.4328(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.3509(13) . ?
C4 H4 0.9500 . ?
C5 O2 1.3702(11) . ?
C5 C6 1.4877(12) . ?
C6 O3 1.4091(11) . ?
C6 O4 1.4137(11) . ?
C6 H6 1.0000 . ?
C7 O3 1.4304(11) . ?
C7 C8 1.5213(13) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O5 1.4311(11) . ?
C8 C9 1.5166(13) . ?
C8 H8 1.0000 . ?
C9 O4 1.4332(11) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
O1 H1 0.85(2) . ?
O5 H5 0.90(2) . ?

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
O1 C1 C2 113.02(8) . . ?
O1 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
O1 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 O2 110.02(8) . . ?
C3 C2 C1 133.04(9) . . ?
O2 C2 C1 116.93(8) . . ?
C2 C3 C4 107.00(8) . . ?
C2 C3 H3 126.5 . . ?
C4 C3 H3 126.5 . . ?
C5 C4 C3 105.79(9) . . ?
C5 C4 H4 127.1 . . ?
C3 C4 H4 127.1 . . ?
C4 C5 O2 110.92(8) . . ?
C4 C5 C6 133.31(9) . . ?
O2 C5 C6 115.75(8) . . ?
O3 C6 O4 111.68(7) . . ?
O3 C6 C5 106.31(7) . . ?
O4 C6 C5 107.66(7) . . ?
O3 C6 H6 110.4 . . ?
O4 C6 H6 110.4 . . ?
C5 C6 H6 110.4 . . ?
O3 C7 C8 109.96(7) . . ?
O3 C7 H7A 109.7 . . ?
C8 C7 H7A 109.7 . . ?
O3 C7 H7B 109.7 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
O5 C8 C9 108.49(8) . . ?
O5 C8 C7 110.82(8) . . ?
C9 C8 C7 108.13(8) . . ?
O5 C8 H8 109.8 . . ?
C9 C8 H8 109.8 . . ?
C7 C8 H8 109.8 . . ?
O4 C9 C8 108.44(8) . . ?
O4 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
O4 C9 H9B 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
C1 O1 H1 109.9(11) . . ?
C5 O2 C2 106.27(7) . . ?
C6 O3 C7 111.02(7) . . ?
C6 O4 C9 110.44(7) . . ?
C8 O5 H5 107.6(11) . . ?

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
O1 C1 C2 C3 -111.59(13) . . . . ?
O1 C1 C2 O2 66.77(12) . . . . ?
O2 C2 C3 C4 -0.21(11) . . . . ?
C1 C2 C3 C4 178.23(10) . . . . ?
C2 C3 C4 C5 -0.30(11) . . . . ?
C3 C4 C5 O2 0.71(11) . . . . ?
C3 C4 C5 C6 -177.60(10) . . . . ?
C4 C5 C6 O3 -2.22(14) . . . . ?
O2 C5 C6 O3 179.53(7) . . . . ?
C4 C5 C6 O4 117.59(11) . . . . ?
O2 C5 C6 O4 -60.66(10) . . . . ?
O3 C7 C8 O5 174.03(7) . . . . ?
O3 C7 C8 C9 55.24(10) . . . . ?
O5 C8 C9 O4 -177.02(7) . . . . ?
C7 C8 C9 O4 -56.77(10) . . . . ?
C4 C5 O2 C2 -0.84(11) . . . . ?
C6 C5 O2 C2 177.79(8) . . . . ?
C3 C2 O2 C5 0.64(11) . . . . ?
C1 C2 O2 C5 -178.09(8) . . . . ?
O4 C6 O3 C7 60.47(10) . . . . ?
C5 C6 O3 C7 177.63(7) . . . . ?
C8 C7 O3 C6 -56.89(10) . . . . ?
O3 C6 O4 C9 -62.70(10) . . . . ?
C5 C6 O4 C9 -179.04(7) . . . . ?
C8 C9 O4 C6 60.63(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O5 0.85(2) 1.89(2) 2.7390(11) 170.3(16) 2_756 yes
O5 H5 O1 0.90(2) 1.80(2) 2.6978(10) 173.3(18) 1_655 yes

_refine_diff_density_max         0.318
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.047

