# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_E-245
_database_code_depnum_ccdc_archive 'CCDC 1995768'
loop_
_audit_author_name
_audit_author_address
'Mikhail Minyaev'
;N D Zelinsky Institute of Organic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2020-04-08 deposited with the CCDC.	2021-04-12 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         'C16 H20 O7'
_chemical_formula_sum            'C16 H20 O7'
_chemical_formula_weight         324.32

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.9357(3)
_cell_length_b                   10.0298(3)
_cell_length_c                   10.1554(3)
_cell_angle_alpha                62.7143(8)
_cell_angle_beta                 65.4279(8)
_cell_angle_gamma                63.8808(8)
_cell_volume                     777.98(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7419
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      33.15

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.22
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8155
_exptl_absorpt_correction_T_max  0.8499
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-Ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            20219
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.566
_diffrn_reflns_theta_max         33.167
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5947
_reflns_number_gt                4756
_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       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    
;
SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)
;
_computing_structure_refinement  
;
SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)
;
_computing_molecular_graphics    'SHELXTL (Bruker, 2018)'
_computing_publication_material  'SHELXTL (Bruker, 2018)'

_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     
'w=1/[σ²(Fo²)+(0.0488P)²+0.2556P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5947
_refine_ls_number_parameters     215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1136
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.41276(9) 0.16742(9) 0.16619(10) 0.02085(16) Uani 1 1 d . . . . .
C1 C 0.50677(11) 0.23804(11) 0.10652(12) 0.01541(17) Uani 1 1 d . . . . .
O2 O 0.57545(9) 0.27421(10) -0.04425(9) 0.02107(16) Uani 1 1 d . . . . .
C2 C 0.55322(11) 0.28682(11) 0.19664(11) 0.01325(16) Uani 1 1 d . . . . .
H2 H 0.634(2) 0.329(2) -0.069(2) 0.037(5) Uiso 1 1 d . . . . .
C3 C 0.57529(13) 0.16215(13) 0.35304(12) 0.0216(2) Uani 1 1 d . . . . .
H3A H 0.561424 0.059686 0.381067 0.026 Uiso 1 1 calc R U . . .
H3B H 0.656551 0.155804 0.389889 0.026 Uiso 1 1 calc R U . . .
C4 C 0.43579(12) 0.30201(14) 0.34839(12) 0.0209(2) Uani 1 1 d . . . . .
H4A H 0.429937 0.382644 0.382780 0.025 Uiso 1 1 calc R U . . .
H4B H 0.334867 0.286583 0.373963 0.025 Uiso 1 1 calc R U . . .
C5 C 0.65660(10) 0.38717(11) 0.11293(11) 0.01279(16) Uani 1 1 d . . . . .
O3 O 0.71559(9) 0.42577(9) -0.02619(8) 0.01722(14) Uani 1 1 d . . . . .
O4 O 0.68107(8) 0.43020(9) 0.20438(8) 0.01495(14) Uani 1 1 d . . . . .
C6 C 0.78629(11) 0.52323(11) 0.13037(11) 0.01418(16) Uani 1 1 d . . . . .
H6A H 0.744035 0.624561 0.054312 0.017 Uiso 1 1 calc R U . . .
H6B H 0.889003 0.465565 0.076653 0.017 Uiso 1 1 calc R U . . .
C7 C 0.80167(10) 0.55235(11) 0.25809(11) 0.01266(16) Uani 1 1 d . . . . .
O5 O 0.65886(8) 0.63941(8) 0.33399(8) 0.01520(14) Uani 1 1 d . . . . .
O6 O 0.91079(8) 0.63719(8) 0.17553(8) 0.01505(14) Uani 1 1 d . . . . .
C8 C 0.59090(12) 0.79589(12) 0.24072(12) 0.01899(19) Uani 1 1 d . . . . .
H8A H 0.501563 0.851955 0.306351 0.028 Uiso 1 1 calc R U . . .
H8B H 0.556307 0.790461 0.166418 0.028 Uiso 1 1 calc R U . . .
H8C H 0.668347 0.852315 0.185592 0.028 Uiso 1 1 calc R U . . .
C9 C 0.94656(13) 0.68485(13) 0.26716(13) 0.01972(19) Uani 1 1 d . . . . .
H9A H 1.008534 0.757108 0.199801 0.030 Uiso 1 1 calc R U . . .
H9B H 1.005895 0.591719 0.335278 0.030 Uiso 1 1 calc R U . . .
H9C H 0.849724 0.738313 0.329083 0.030 Uiso 1 1 calc R U . . .
C10 C 0.85959(10) 0.39853(11) 0.38012(11) 0.01275(16) Uani 1 1 d . . . . .
C11 C 0.75928(11) 0.33722(11) 0.51810(11) 0.01487(17) Uani 1 1 d . . . . .
H11 H 0.650935 0.392262 0.537385 0.018 Uiso 1 1 calc R U . . .
C12 C 0.81494(11) 0.19590(12) 0.62915(11) 0.01541(17) Uani 1 1 d . . . . .
H12 H 0.745148 0.155533 0.723577 0.018 Uiso 1 1 calc R U . . .
C13 C 0.97334(11) 0.11476(11) 0.60038(11) 0.01448(17) Uani 1 1 d . . . . .
C14 C 1.07464(11) 0.17264(12) 0.45996(11) 0.01524(17) Uani 1 1 d . . . . .
H14 H 1.182407 0.115445 0.438888 0.018 Uiso 1 1 calc R U . . .
C15 C 1.01811(11) 0.31341(12) 0.35137(11) 0.01454(17) Uani 1 1 d . . . . .
H15 H 1.087730 0.352696 0.256216 0.017 Uiso 1 1 calc R U . . .
O7 O 1.04055(9) -0.02139(9) 0.70278(9) 0.01913(15) Uani 1 1 d . . . . .
C16 C 0.94059(14) -0.08150(13) 0.84868(12) 0.0228(2) Uani 1 1 d . . . . .
H16A H 1.002012 -0.178881 0.911429 0.034 Uiso 1 1 calc R U . . .
H16B H 0.862015 -0.103760 0.834165 0.034 Uiso 1 1 calc R U . . .
H16C H 0.888997 -0.003224 0.900799 0.034 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 C1 1.2082(12) . ?
C1 O2 1.3347(13) . ?
C1 C2 1.5001(13) . ?
O2 H2 0.858(18) . ?
C2 C5 1.4800(13) . ?
C2 C4 1.5241(14) . ?
C2 C3 1.5368(14) . ?
C3 C4 1.4740(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O3 1.2243(12) . ?
C5 O4 1.3250(11) . ?
O4 C6 1.4459(11) . ?
C6 C7 1.5305(13) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O5 1.4095(11) . ?
C7 O6 1.4159(11) . ?
C7 C10 1.5184(13) . ?
O5 C8 1.4326(12) . ?
O6 C9 1.4330(12) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.3867(13) . ?
C10 C15 1.3989(13) . ?
C11 C12 1.3964(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.3901(13) . ?
C12 H12 0.9500 . ?
C13 O7 1.3655(12) . ?
C13 C14 1.3948(13) . ?
C14 C15 1.3836(14) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
O7 C16 1.4246(13) . ?
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
O1 C1 O2 120.54(9) . . ?
O1 C1 C2 122.31(9) . . ?
O2 C1 C2 117.15(8) . . ?
C1 O2 H2 108.9(12) . . ?
C5 C2 C1 118.92(8) . . ?
C5 C2 C4 118.63(8) . . ?
C1 C2 C4 115.59(8) . . ?
C5 C2 C3 116.95(8) . . ?
C1 C2 C3 114.50(8) . . ?
C4 C2 C3 57.57(7) . . ?
C4 C3 C2 60.78(7) . . ?
C4 C3 H3A 117.7 . . ?
C2 C3 H3A 117.7 . . ?
C4 C3 H3B 117.7 . . ?
C2 C3 H3B 117.7 . . ?
H3A C3 H3B 114.8 . . ?
C3 C4 C2 61.65(7) . . ?
C3 C4 H4A 117.6 . . ?
C2 C4 H4A 117.6 . . ?
C3 C4 H4B 117.6 . . ?
C2 C4 H4B 117.6 . . ?
H4A C4 H4B 114.7 . . ?
O3 C5 O4 122.89(9) . . ?
O3 C5 C2 124.03(8) . . ?
O4 C5 C2 113.07(8) . . ?
C5 O4 C6 115.79(7) . . ?
O4 C6 C7 106.40(7) . . ?
O4 C6 H6A 110.4 . . ?
C7 C6 H6A 110.4 . . ?
O4 C6 H6B 110.4 . . ?
C7 C6 H6B 110.4 . . ?
H6A C6 H6B 108.6 . . ?
O5 C7 O6 112.05(7) . . ?
O5 C7 C10 106.82(7) . . ?
O6 C7 C10 112.26(7) . . ?
O5 C7 C6 112.35(8) . . ?
O6 C7 C6 101.95(7) . . ?
C10 C7 C6 111.53(8) . . ?
C7 O5 C8 115.72(8) . . ?
C7 O6 C9 114.71(7) . . ?
O5 C8 H8A 109.5 . . ?
O5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O6 C9 H9A 109.5 . . ?
O6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 118.75(9) . . ?
C11 C10 C7 121.95(8) . . ?
C15 C10 C7 119.28(8) . . ?
C10 C11 C12 121.07(9) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 119.44(9) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
O7 C13 C12 124.21(9) . . ?
O7 C13 C14 115.81(9) . . ?
C12 C13 C14 119.97(9) . . ?
C15 C14 C13 119.97(9) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 120.74(9) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
C13 O7 C16 117.15(8) . . ?
O7 C16 H16A 109.5 . . ?
O7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O7 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
O1 C1 C2 C5 -173.73(9) . . . . ?
O2 C1 C2 C5 7.09(13) . . . . ?
O1 C1 C2 C4 -23.09(14) . . . . ?
O2 C1 C2 C4 157.73(9) . . . . ?
O1 C1 C2 C3 41.11(13) . . . . ?
O2 C1 C2 C3 -138.07(9) . . . . ?
C5 C2 C3 C4 108.30(9) . . . . ?
C1 C2 C3 C4 -105.83(9) . . . . ?
C5 C2 C4 C3 -105.36(10) . . . . ?
C1 C2 C4 C3 103.92(9) . . . . ?
C1 C2 C5 O3 -4.78(14) . . . . ?
C4 C2 C5 O3 -154.52(10) . . . . ?
C3 C2 C5 O3 139.54(10) . . . . ?
C1 C2 C5 O4 176.01(8) . . . . ?
C4 C2 C5 O4 26.27(12) . . . . ?
C3 C2 C5 O4 -39.67(12) . . . . ?
O3 C5 O4 C6 -1.63(13) . . . . ?
C2 C5 O4 C6 177.59(7) . . . . ?
C5 O4 C6 C7 -177.63(7) . . . . ?
O4 C6 C7 O5 -62.30(10) . . . . ?
O4 C6 C7 O6 177.57(7) . . . . ?
O4 C6 C7 C10 57.60(9) . . . . ?
O6 C7 O5 C8 51.26(11) . . . . ?
C10 C7 O5 C8 174.58(8) . . . . ?
C6 C7 O5 C8 -62.82(10) . . . . ?
O5 C7 O6 C9 58.38(10) . . . . ?
C10 C7 O6 C9 -61.82(10) . . . . ?
C6 C7 O6 C9 178.72(8) . . . . ?
O5 C7 C10 C11 23.58(12) . . . . ?
O6 C7 C10 C11 146.77(9) . . . . ?
C6 C7 C10 C11 -99.53(10) . . . . ?
O5 C7 C10 C15 -158.25(8) . . . . ?
O6 C7 C10 C15 -35.06(11) . . . . ?
C6 C7 C10 C15 78.64(10) . . . . ?
C15 C10 C11 C12 2.10(14) . . . . ?
C7 C10 C11 C12 -179.72(9) . . . . ?
C10 C11 C12 C13 -0.50(15) . . . . ?
C11 C12 C13 O7 177.77(9) . . . . ?
C11 C12 C13 C14 -1.61(14) . . . . ?
O7 C13 C14 C15 -177.34(9) . . . . ?
C12 C13 C14 C15 2.09(14) . . . . ?
C13 C14 C15 C10 -0.46(14) . . . . ?
C11 C10 C15 C14 -1.61(14) . . . . ?
C7 C10 C15 C14 -179.84(9) . . . . ?
C12 C13 O7 C16 -0.85(14) . . . . ?
C14 C13 O7 C16 178.55(9) . . . . ?

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
O2 H2 O3 0.858(18) 1.778(19) 2.5719(11) 152.9(17) . yes

_refine_diff_density_max         0.465
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.061



