# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2023

####################################################################### 
# 
# 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_tt2103
_database_code_depnum_ccdc_archive 'CCDC 2252827'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2023-05-11 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         'C7 H14 O6'
_chemical_formula_sum            'C7 H14 O6'
_chemical_formula_weight         194.18

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

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

_cell_length_a                   7.7218(2)
_cell_length_b                   8.4910(2)
_cell_length_c                   13.0382(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     854.86(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9946
_cell_measurement_theta_min      6.22
_cell_measurement_theta_max      69.45

_exptl_crystal_description       tablet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    1.152
_shelx_estimated_absorpt_T_min   0.800
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  .8544
_exptl_absorpt_correction_T_max  0.9599
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec micro-focus'
_diffrn_source_monochromator     'MONTEL Multi-layer'
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            16808
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         6.220
_diffrn_reflns_theta_max         69.451
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1598
_reflns_number_gt                1560
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_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       'Bruker APEX-4 (Bruker, 2021)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2011)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2011)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_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)+(0.0307P)²+0.1915P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 634 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(5)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         1598
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0219
_refine_ls_wR_factor_ref         0.0552
_refine_ls_wR_factor_gt          0.0549
_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_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 0.67480(15) 0.54197(14) 0.49023(9) 0.0178(3) Uani 1 1 d . . . . .
O2 O 0.35142(15) 0.41976(14) 0.56806(9) 0.0174(3) Uani 1 1 d . . . . .
H2O H 0.322(3) 0.424(3) 0.512(2) 0.025(6) Uiso 1 1 d . . . . .
O3 O 0.38309(15) 0.12344(15) 0.66999(10) 0.0184(3) Uani 1 1 d . . . . .
H3O H 0.366(4) 0.098(3) 0.612(2) 0.044(8) Uiso 1 1 d . . . . .
O4 O 0.73284(14) 0.05670(14) 0.62726(9) 0.0141(3) Uani 1 1 d . . . . .
H4O H 0.786(3) -0.011(3) 0.6586(17) 0.023(6) Uiso 1 1 d . . . . .
O5 O 0.82141(14) 0.38586(13) 0.60202(8) 0.0135(2) Uani 1 1 d . . . . .
O6 O 1.12102(15) 0.37875(14) 0.72888(9) 0.0174(3) Uani 1 1 d . . . . .
H6O H 1.183(3) 0.385(3) 0.675(2) 0.034(6) Uiso 1 1 d . . . . .
C1 C 0.6608(2) 0.46323(19) 0.58370(12) 0.0138(3) Uani 1 1 d . . . . .
H1 H 0.637(3) 0.535(2) 0.6374(15) 0.012(4) Uiso 1 1 d . . . . .
C2 C 0.5146(2) 0.34276(19) 0.57639(12) 0.0133(3) Uani 1 1 d . . . . .
H2 H 0.536(2) 0.280(2) 0.5179(15) 0.008(4) Uiso 1 1 d . . . . .
C3 C 0.5107(2) 0.2436(2) 0.67413(12) 0.0130(3) Uani 1 1 d . . . . .
H3 H 0.481(3) 0.312(2) 0.7291(16) 0.013(5) Uiso 1 1 d . . . . .
C4 C 0.6883(2) 0.17632(19) 0.70001(12) 0.0122(3) Uani 1 1 d . . . . .
H4 H 0.681(3) 0.129(2) 0.7676(15) 0.010(4) Uiso 1 1 d . . . . .
C5 C 0.8211(2) 0.30963(19) 0.70085(12) 0.0125(3) Uani 1 1 d . . . . .
H5 H 0.789(3) 0.391(2) 0.7532(15) 0.015(5) Uiso 1 1 d . . . . .
C6 C 1.0027(2) 0.2506(2) 0.72187(13) 0.0148(3) Uani 1 1 d . . . . .
H6A H 1.001(3) 0.196(2) 0.7862(15) 0.009(4) Uiso 1 1 d . . . . .
H6B H 1.038(2) 0.175(2) 0.6671(15) 0.013(5) Uiso 1 1 d . . . . .
C7 C 0.7725(3) 0.6848(2) 0.49834(15) 0.0263(4) Uani 1 1 d . . . . .
H7A H 0.766(3) 0.738(3) 0.433(2) 0.032(6) Uiso 1 1 d . . . . .
H7B H 0.891(4) 0.664(3) 0.519(2) 0.043(7) Uiso 1 1 d . . . . .
H7C H 0.722(3) 0.753(3) 0.550(2) 0.039(7) 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
O1 C1 1.3942(19) . ?
O1 C7 1.432(2) . ?
O2 C2 1.4236(19) . ?
O2 H2O 0.77(3) . ?
O3 C3 1.4194(19) . ?
O3 H3O 0.79(3) . ?
O4 C4 1.432(2) . ?
O4 H4O 0.82(3) . ?
O5 C1 1.4238(19) . ?
O5 C5 1.4419(19) . ?
O6 C6 1.424(2) . ?
O6 H6O 0.86(3) . ?
C1 C2 1.526(2) . ?
C1 H1 0.95(2) . ?
C2 C3 1.528(2) . ?
C2 H2 0.944(19) . ?
C3 C4 1.524(2) . ?
C3 H3 0.95(2) . ?
C4 C5 1.527(2) . ?
C4 H4 0.970(19) . ?
C5 C6 1.514(2) . ?
C5 H5 1.00(2) . ?
C6 H6A 0.96(2) . ?
C6 H6B 1.00(2) . ?
C7 H7A 0.96(3) . ?
C7 H7B 0.97(3) . ?
C7 H7C 0.96(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
C1 O1 C7 112.49(13) . . ?
C2 O2 H2O 110.8(17) . . ?
C3 O3 H3O 110(2) . . ?
C4 O4 H4O 107.0(15) . . ?
C1 O5 C5 110.84(12) . . ?
C6 O6 H6O 110.8(17) . . ?
O1 C1 O5 107.47(12) . . ?
O1 C1 C2 108.92(12) . . ?
O5 C1 C2 110.22(12) . . ?
O1 C1 H1 110.7(11) . . ?
O5 C1 H1 110.2(12) . . ?
C2 C1 H1 109.4(12) . . ?
O2 C2 C1 110.58(13) . . ?
O2 C2 C3 107.42(12) . . ?
C1 C2 C3 109.38(12) . . ?
O2 C2 H2 110.7(11) . . ?
C1 C2 H2 107.2(11) . . ?
C3 C2 H2 111.6(11) . . ?
O3 C3 C4 111.34(13) . . ?
O3 C3 C2 112.21(12) . . ?
C4 C3 C2 111.94(12) . . ?
O3 C3 H3 107.5(13) . . ?
C4 C3 H3 106.1(12) . . ?
C2 C3 H3 107.3(12) . . ?
O4 C4 C3 109.59(12) . . ?
O4 C4 C5 111.68(12) . . ?
C3 C4 C5 109.15(13) . . ?
O4 C4 H4 108.6(11) . . ?
C3 C4 H4 107.8(12) . . ?
C5 C4 H4 109.9(11) . . ?
O5 C5 C6 108.00(13) . . ?
O5 C5 C4 109.10(12) . . ?
C6 C5 C4 112.19(13) . . ?
O5 C5 H5 107.5(11) . . ?
C6 C5 H5 109.5(12) . . ?
C4 C5 H5 110.4(12) . . ?
O6 C6 C5 110.66(13) . . ?
O6 C6 H6A 108.7(12) . . ?
C5 C6 H6A 108.0(12) . . ?
O6 C6 H6B 111.3(11) . . ?
C5 C6 H6B 109.8(11) . . ?
H6A C6 H6B 108.3(16) . . ?
O1 C7 H7A 107.8(14) . . ?
O1 C7 H7B 111.2(17) . . ?
H7A C7 H7B 112(2) . . ?
O1 C7 H7C 110.2(16) . . ?
H7A C7 H7C 108(2) . . ?
H7B C7 H7C 107(2) . . ?

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
C7 O1 C1 O5 -77.18(17) . . . . ?
C7 O1 C1 C2 163.43(14) . . . . ?
C5 O5 C1 O1 176.32(13) . . . . ?
C5 O5 C1 C2 -65.12(15) . . . . ?
O1 C1 C2 O2 -67.98(16) . . . . ?
O5 C1 C2 O2 174.35(12) . . . . ?
O1 C1 C2 C3 173.92(13) . . . . ?
O5 C1 C2 C3 56.25(16) . . . . ?
O2 C2 C3 O3 63.05(16) . . . . ?
C1 C2 C3 O3 -176.89(13) . . . . ?
O2 C2 C3 C4 -170.91(13) . . . . ?
C1 C2 C3 C4 -50.86(17) . . . . ?
O3 C3 C4 O4 56.01(16) . . . . ?
C2 C3 C4 O4 -70.50(16) . . . . ?
O3 C3 C4 C5 178.61(12) . . . . ?
C2 C3 C4 C5 52.10(17) . . . . ?
C1 O5 C5 C6 -171.90(13) . . . . ?
C1 O5 C5 C4 65.90(15) . . . . ?
O4 C4 C5 O5 63.28(16) . . . . ?
C3 C4 C5 O5 -58.06(16) . . . . ?
O4 C4 C5 C6 -56.36(17) . . . . ?
C3 C4 C5 C6 -177.69(13) . . . . ?
O5 C5 C6 O6 63.60(16) . . . . ?
C4 C5 C6 O6 -176.13(12) . . . . ?

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 H2O O4 0.77(3) 1.95(3) 2.7136(16) 176(2) 4_456 yes
O3 H3O O1 0.79(3) 2.32(3) 2.9872(17) 142(3) 4_456 yes
O4 H4O O6 0.82(3) 1.88(3) 2.6598(16) 158(2) 3_746 yes
O6 H6O O2 0.86(3) 1.93(3) 2.7718(17) 170(2) 1_655 yes

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_tt2102
_database_code_depnum_ccdc_archive 'CCDC 2252829'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2023-05-11 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         'C7 H14 O6, H2 O'
_chemical_formula_sum            'C7 H16 O7'
_chemical_formula_weight         212.20

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

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

_cell_length_a                   6.1050(2)
_cell_length_b                   7.4158(2)
_cell_length_c                   21.1354(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     956.87(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9879
_cell_measurement_theta_min      6.32
_cell_measurement_theta_max      69.71

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    1.157
_shelx_estimated_absorpt_T_min   0.787
_shelx_estimated_absorpt_T_max   0.891
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8771
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec micro-focus'
_diffrn_source_monochromator     'MONTEL Multi-layer'
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            20791
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         6.325
_diffrn_reflns_theta_max         69.762
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1790
_reflns_number_gt                1777
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.664
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX-3 (Bruker, 2020)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2010)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2010)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_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)+(0.0308P)²+0.1737P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 709 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         1790
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0208
_refine_ls_R_factor_gt           0.0206
_refine_ls_wR_factor_ref         0.0548
_refine_ls_wR_factor_gt          0.0547
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_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 0.63694(16) 0.15266(14) 0.42332(5) 0.0145(2) Uani 1 1 d . . . . .
O2 O 0.88974(19) 0.03228(14) 0.32887(5) 0.0176(3) Uani 1 1 d . . . . .
H2O H 0.901(4) -0.017(3) 0.2934(11) 0.032(6) Uiso 1 1 d . . . . .
O3 O 1.09081(17) 0.36423(15) 0.28888(5) 0.0154(2) Uani 1 1 d . . . . .
H3O H 1.204(4) 0.377(3) 0.3070(11) 0.030(6) Uiso 1 1 d . . . . .
O4 O 0.69844(18) 0.56293(15) 0.27038(5) 0.0168(2) Uani 1 1 d . . . . .
H4O H 0.777(4) 0.626(3) 0.2539(12) 0.041(7) Uiso 1 1 d . . . . .
O5 O 0.45684(15) 0.36155(14) 0.35918(5) 0.0132(2) Uani 1 1 d . . . . .
O6 O 0.27031(18) 0.65735(15) 0.42385(6) 0.0198(2) Uani 1 1 d . . . . .
H6O H 0.319(4) 0.647(3) 0.4592(13) 0.036(6) Uiso 1 1 d . . . . .
C1 C 0.5687(2) 0.19315(19) 0.36163(6) 0.0132(3) Uani 1 1 d . . . . .
H1 H 0.465(3) 0.107(2) 0.3472(8) 0.012(4) Uiso 1 1 d . . . . .
C2 C 0.7719(2) 0.1952(2) 0.31926(7) 0.0131(3) Uani 1 1 d . . . . .
H2 H 0.723(3) 0.208(2) 0.2758(9) 0.009(4) Uiso 1 1 d . . . . .
C3 C 0.9159(2) 0.35755(19) 0.33431(6) 0.0127(3) Uani 1 1 d . . . . .
H3 H 0.981(3) 0.345(2) 0.3771(9) 0.011(4) Uiso 1 1 d . . . . .
C4 C 0.7824(2) 0.5320(2) 0.33229(7) 0.0136(3) Uani 1 1 d . . . . .
H4 H 0.873(3) 0.629(2) 0.3469(8) 0.015(4) Uiso 1 1 d . . . . .
C5 C 0.5905(2) 0.51364(18) 0.37786(6) 0.0131(3) Uani 1 1 d . . . . .
H5 H 0.644(3) 0.493(2) 0.4202(9) 0.011(4) Uiso 1 1 d . . . . .
C6 C 0.4426(3) 0.6775(2) 0.37911(7) 0.0167(3) Uani 1 1 d . . . . .
H6A H 0.533(3) 0.779(3) 0.3893(9) 0.018(4) Uiso 1 1 d . . . . .
H6B H 0.374(3) 0.694(3) 0.3359(9) 0.020(5) Uiso 1 1 d . . . . .
C7 C 0.4585(3) 0.1328(2) 0.46694(8) 0.0210(3) Uani 1 1 d . . . . .
H7A H 0.517(4) 0.071(3) 0.5037(11) 0.033(6) Uiso 1 1 d . . . . .
H7B H 0.343(4) 0.062(3) 0.4492(10) 0.028(5) Uiso 1 1 d . . . . .
H7C H 0.400(4) 0.250(3) 0.4778(9) 0.029(5) Uiso 1 1 d . . . . .
O1W O 0.4294(2) 0.6285(2) 0.54050(6) 0.0351(3) Uani 1 1 d . . . . .
H1WA H 0.388(5) 0.561(4) 0.5641(13) 0.043(7) Uiso 1 1 d . . . . .
H1WB H 0.535(5) 0.684(3) 0.5539(12) 0.041(7) 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
O1 C1 1.4014(17) . ?
O1 C7 1.4350(18) . ?
O2 C2 1.4209(17) . ?
O2 H2O 0.84(2) . ?
O3 C3 1.4370(16) . ?
O3 H3O 0.80(3) . ?
O4 C4 1.4240(18) . ?
O4 H4O 0.75(3) . ?
O5 C1 1.4241(17) . ?
O5 C5 1.4469(17) . ?
O6 C6 1.4221(19) . ?
O6 H6O 0.81(3) . ?
C1 C2 1.530(2) . ?
C1 H1 0.950(18) . ?
C2 C3 1.524(2) . ?
C2 H2 0.970(18) . ?
C3 C4 1.5295(19) . ?
C3 H3 0.993(18) . ?
C4 C5 1.5230(19) . ?
C4 H4 0.959(19) . ?
C5 C6 1.514(2) . ?
C5 H5 0.965(18) . ?
C6 H6A 0.95(2) . ?
C6 H6B 1.01(2) . ?
C7 H7A 0.97(2) . ?
C7 H7B 0.96(2) . ?
C7 H7C 0.97(2) . ?
O1W H1WA 0.75(3) . ?
O1W H1WB 0.82(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
C1 O1 C7 113.20(11) . . ?
C2 O2 H2O 106.7(16) . . ?
C3 O3 H3O 109.1(16) . . ?
C4 O4 H4O 107.2(19) . . ?
C1 O5 C5 113.79(10) . . ?
C6 O6 H6O 110.6(17) . . ?
O1 C1 O5 111.36(11) . . ?
O1 C1 C2 107.78(11) . . ?
O5 C1 C2 111.01(11) . . ?
O1 C1 H1 110.7(11) . . ?
O5 C1 H1 104.9(11) . . ?
C2 C1 H1 111.1(11) . . ?
O2 C2 C3 110.49(11) . . ?
O2 C2 C1 108.56(11) . . ?
C3 C2 C1 110.71(11) . . ?
O2 C2 H2 111.9(10) . . ?
C3 C2 H2 107.4(10) . . ?
C1 C2 H2 107.7(10) . . ?
O3 C3 C2 108.44(11) . . ?
O3 C3 C4 110.37(11) . . ?
C2 C3 C4 110.80(11) . . ?
O3 C3 H3 108.2(10) . . ?
C2 C3 H3 110.4(10) . . ?
C4 C3 H3 108.6(10) . . ?
O4 C4 C5 108.57(12) . . ?
O4 C4 C3 110.71(11) . . ?
C5 C4 C3 108.45(11) . . ?
O4 C4 H4 112.6(11) . . ?
C5 C4 H4 108.0(11) . . ?
C3 C4 H4 108.4(11) . . ?
O5 C5 C6 107.11(11) . . ?
O5 C5 C4 109.34(11) . . ?
C6 C5 C4 113.46(12) . . ?
O5 C5 H5 108.5(10) . . ?
C6 C5 H5 108.3(10) . . ?
C4 C5 H5 110.0(11) . . ?
O6 C6 C5 111.60(12) . . ?
O6 C6 H6A 111.0(11) . . ?
C5 C6 H6A 106.9(11) . . ?
O6 C6 H6B 107.9(11) . . ?
C5 C6 H6B 109.2(11) . . ?
H6A C6 H6B 110.2(15) . . ?
O1 C7 H7A 106.3(13) . . ?
O1 C7 H7B 111.4(13) . . ?
H7A C7 H7B 109.3(19) . . ?
O1 C7 H7C 110.0(13) . . ?
H7A C7 H7C 111.9(18) . . ?
H7B C7 H7C 108.0(19) . . ?
H1WA O1W H1WB 112(3) . . ?

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
C7 O1 C1 O5 62.59(16) . . . . ?
C7 O1 C1 C2 -175.43(11) . . . . ?
C5 O5 C1 O1 61.89(14) . . . . ?
C5 O5 C1 C2 -58.20(14) . . . . ?
O1 C1 C2 O2 51.43(14) . . . . ?
O5 C1 C2 O2 173.63(11) . . . . ?
O1 C1 C2 C3 -70.02(14) . . . . ?
O5 C1 C2 C3 52.19(14) . . . . ?
O2 C2 C3 O3 65.95(14) . . . . ?
C1 C2 C3 O3 -173.76(10) . . . . ?
O2 C2 C3 C4 -172.78(11) . . . . ?
C1 C2 C3 C4 -52.48(14) . . . . ?
O3 C3 C4 O4 57.20(15) . . . . ?
C2 C3 C4 O4 -62.94(15) . . . . ?
O3 C3 C4 C5 176.21(11) . . . . ?
C2 C3 C4 C5 56.08(14) . . . . ?
C1 O5 C5 C6 -174.34(11) . . . . ?
C1 O5 C5 C4 62.33(14) . . . . ?
O4 C4 C5 O5 61.00(14) . . . . ?
C3 C4 C5 O5 -59.36(14) . . . . ?
O4 C4 C5 C6 -58.48(16) . . . . ?
C3 C4 C5 C6 -178.84(11) . . . . ?
O5 C5 C6 O6 61.35(15) . . . . ?
C4 C5 C6 O6 -177.90(12) . . . . ?

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 H2O O3 0.84(2) 1.95(2) 2.7857(15) 177(2) 3_745 yes
O3 H3O O5 0.80(3) 1.90(3) 2.6836(14) 168(2) 1_655 yes
O4 H4O O3 0.75(3) 2.14(3) 2.8664(16) 161(3) 3_755 yes
O6 H6O O1W 0.81(3) 1.85(3) 2.6584(17) 179(2) . yes
O1W H1WA O1 0.75(3) 2.22(3) 2.8493(18) 142(3) 4_456 yes
O1W H1WA O2 0.75(3) 2.37(3) 3.0171(17) 146(3) 4_456 yes
O1W H1WB O6 0.82(3) 1.92(3) 2.7245(18) 171(3) 4_566 yes

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_tt2101
_database_code_depnum_ccdc_archive 'CCDC 2252830'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT089_tt2101              
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       5.49 Note
RESPONSE: The structure is chiral that aryifically deflates the d:p ratio. The structure is correct.
;
# Added during the CSD deposition process: Wednesday 29 March 2023 09:57 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H14 O6'
_chemical_formula_sum            'C7 H14 O6'
_chemical_formula_weight         194.18

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

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

_cell_length_a                   5.2396(4)
_cell_length_b                   11.2244(7)
_cell_length_c                   14.6702(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     862.77(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      8.46
_cell_measurement_theta_max      69.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.191
_exptl_crystal_size_min          0.185
_exptl_absorpt_coefficient_mu    1.142
_shelx_estimated_absorpt_T_min   0.731
_shelx_estimated_absorpt_T_max   0.817
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7561
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Incoatec micro-focus'
_diffrn_radiation_monochromator  'MONTEL Multi-layer'
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            11638
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         8.457
_diffrn_reflns_theta_max         69.453
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             1594
_reflns_number_gt                1589
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.667
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.990

_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       'Bruker APEX-4 (Bruker, 2021)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2021)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2021)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_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)+(0.0409P)²+0.1510P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 635 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(4)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         1594
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0677
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.126
_refine_ls_shift/su_max          0.003
_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 0.3564(2) 0.59004(10) 0.57060(7) 0.0160(3) Uani 1 1 d . . . . .
O2 O 0.7369(2) 0.44262(10) 0.49672(8) 0.0168(3) Uani 1 1 d . . . . .
H2 H 0.607(6) 0.446(2) 0.4625(18) 0.030(6) Uiso 1 1 d . . . . .
O3 O 0.5393(2) 0.22869(11) 0.57369(8) 0.0176(3) Uani 1 1 d . . . . .
H3 H 0.423(6) 0.185(2) 0.5509(18) 0.034(7) Uiso 1 1 d . . . . .
O4 O 0.1534(3) 0.26543(11) 0.71827(8) 0.0223(3) Uani 1 1 d . . . . .
H4 H 0.187(6) 0.194(3) 0.7018(18) 0.040(7) Uiso 1 1 d . . . . .
O5 O 0.5011(2) 0.54596(10) 0.71860(7) 0.0150(3) Uani 1 1 d . . . . .
O6 O 0.1153(2) 0.56940(11) 0.86498(8) 0.0168(3) Uani 1 1 d . . . . .
H6 H 0.219(6) 0.624(2) 0.8766(18) 0.032(7) Uiso 1 1 d . . . . .
C1 C 0.5645(3) 0.55479(16) 0.62456(11) 0.0147(4) Uani 1 1 d . . . . .
H1 H 0.696(4) 0.6136(19) 0.6229(14) 0.017(5) Uiso 1 1 d . . . . .
C2 C 0.6541(3) 0.43419(14) 0.58850(10) 0.0146(3) Uani 1 1 d . . . . .
H2A H 0.801(4) 0.4094(18) 0.6247(14) 0.013(5) Uiso 1 1 d . . . . .
C3 C 0.4445(3) 0.34183(14) 0.60232(11) 0.0140(4) Uani 1 1 d . . . . .
H3A H 0.290(4) 0.3624(17) 0.5656(15) 0.015(5) Uiso 1 1 d . . . . .
C4 C 0.3718(3) 0.33801(14) 0.70299(11) 0.0151(3) Uani 1 1 d . . . . .
H4A H 0.520(5) 0.308(2) 0.7353(16) 0.017(5) Uiso 1 1 d . . . . .
C5 C 0.2996(3) 0.46249(14) 0.73678(11) 0.0141(4) Uani 1 1 d . . . . .
H5 H 0.147(5) 0.4905(19) 0.7057(14) 0.017(5) Uiso 1 1 d . . . . .
C6 C 0.2510(4) 0.46493(14) 0.83866(11) 0.0161(4) Uani 1 1 d . . . . .
H6A H 0.140(5) 0.399(2) 0.8534(16) 0.027(6) Uiso 1 1 d . . . . .
H6B H 0.407(5) 0.459(2) 0.8714(16) 0.023(6) Uiso 1 1 d . . . . .
C7 C 0.2619(4) 0.70548(16) 0.59314(12) 0.0203(4) Uani 1 1 d . . . . .
H7A H 0.136(6) 0.724(3) 0.5454(19) 0.042(7) Uiso 1 1 d . . . . .
H7B H 0.400(6) 0.765(2) 0.5951(18) 0.036(6) Uiso 1 1 d . . . . .
H7C H 0.184(5) 0.709(2) 0.6543(17) 0.025(6) 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
O1 C1 1.404(2) . ?
O1 C7 1.426(2) . ?
O2 C2 1.4179(19) . ?
O2 H2 0.85(3) . ?
O3 C3 1.4268(19) . ?
O3 H3 0.85(3) . ?
O4 C4 1.422(2) . ?
O4 H4 0.85(3) . ?
O5 C1 1.4225(19) . ?
O5 C5 1.436(2) . ?
O6 C6 1.425(2) . ?
O6 H6 0.84(3) . ?
C1 C2 1.527(2) . ?
C1 H1 0.95(2) . ?
C2 C3 1.524(2) . ?
C2 H2A 0.98(2) . ?
C3 C4 1.526(2) . ?
C3 H3A 1.00(2) . ?
C4 C5 1.530(2) . ?
C4 H4A 0.97(3) . ?
C5 C6 1.516(2) . ?
C5 H5 0.97(2) . ?
C6 H6A 0.96(3) . ?
C6 H6B 0.95(3) . ?
C7 H7A 0.99(3) . ?
C7 H7B 0.99(3) . ?
C7 H7C 0.99(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
C1 O1 C7 113.26(13) . . ?
C2 O2 H2 108.6(17) . . ?
C3 O3 H3 112.5(18) . . ?
C4 O4 H4 109(2) . . ?
C1 O5 C5 113.40(11) . . ?
C6 O6 H6 109.8(19) . . ?
O1 C1 O5 112.66(13) . . ?
O1 C1 C2 107.05(13) . . ?
O5 C1 C2 110.24(13) . . ?
O1 C1 H1 110.6(13) . . ?
O5 C1 H1 104.0(13) . . ?
C2 C1 H1 112.5(13) . . ?
O2 C2 C3 113.09(13) . . ?
O2 C2 C1 111.34(13) . . ?
C3 C2 C1 109.59(13) . . ?
O2 C2 H2A 107.1(12) . . ?
C3 C2 H2A 107.6(12) . . ?
C1 C2 H2A 107.9(12) . . ?
O3 C3 C2 108.40(13) . . ?
O3 C3 C4 110.29(12) . . ?
C2 C3 C4 109.14(13) . . ?
O3 C3 H3A 109.2(11) . . ?
C2 C3 H3A 110.9(12) . . ?
C4 C3 H3A 109.0(12) . . ?
O4 C4 C3 111.69(13) . . ?
O4 C4 C5 105.85(14) . . ?
C3 C4 C5 110.46(12) . . ?
O4 C4 H4A 111.7(14) . . ?
C3 C4 H4A 106.5(13) . . ?
C5 C4 H4A 110.7(14) . . ?
O5 C5 C6 107.13(13) . . ?
O5 C5 C4 110.72(13) . . ?
C6 C5 C4 112.16(13) . . ?
O5 C5 H5 107.9(13) . . ?
C6 C5 H5 108.5(13) . . ?
C4 C5 H5 110.3(12) . . ?
O6 C6 C5 111.45(13) . . ?
O6 C6 H6A 105.5(15) . . ?
C5 C6 H6A 108.0(14) . . ?
O6 C6 H6B 110.4(14) . . ?
C5 C6 H6B 110.7(14) . . ?
H6A C6 H6B 111(2) . . ?
O1 C7 H7A 105.3(17) . . ?
O1 C7 H7B 111.8(16) . . ?
H7A C7 H7B 111(2) . . ?
O1 C7 H7C 113.0(14) . . ?
H7A C7 H7C 111(2) . . ?
H7B C7 H7C 104(2) . . ?

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
C7 O1 C1 O5 62.25(18) . . . . ?
C7 O1 C1 C2 -176.42(13) . . . . ?
C5 O5 C1 O1 59.08(17) . . . . ?
C5 O5 C1 C2 -60.42(17) . . . . ?
O1 C1 C2 O2 61.61(17) . . . . ?
O5 C1 C2 O2 -175.54(12) . . . . ?
O1 C1 C2 C3 -64.26(17) . . . . ?
O5 C1 C2 C3 58.59(17) . . . . ?
O2 C2 C3 O3 58.93(17) . . . . ?
C1 C2 C3 O3 -176.21(12) . . . . ?
O2 C2 C3 C4 179.08(13) . . . . ?
C1 C2 C3 C4 -56.05(17) . . . . ?
O3 C3 C4 O4 -69.05(17) . . . . ?
C2 C3 C4 O4 171.96(14) . . . . ?
O3 C3 C4 C5 173.43(13) . . . . ?
C2 C3 C4 C5 54.44(17) . . . . ?
C1 O5 C5 C6 -178.92(13) . . . . ?
C1 O5 C5 C4 58.49(16) . . . . ?
O4 C4 C5 O5 -175.85(12) . . . . ?
C3 C4 C5 O5 -54.79(17) . . . . ?
O4 C4 C5 C6 64.54(17) . . . . ?
C3 C4 C5 C6 -174.40(14) . . . . ?
O5 C5 C6 O6 75.19(17) . . . . ?
C4 C5 C6 O6 -163.12(14) . . . . ?

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 O6 0.85(3) 1.85(3) 2.6754(18) 164(2) 2_564 yes
O3 H3 O2 0.85(3) 1.87(3) 2.6970(17) 165(3) 4_456 yes
O4 H4 O6 0.85(3) 2.33(3) 2.8834(17) 123(2) 3_546 yes
O6 H6 O3 0.84(3) 1.87(3) 2.6986(18) 167(3) 3_656 yes
O4 H4 O5 0.85(3) 2.61(3) 3.1944(17) 127(2) 3_646 yes

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_tt2202
_database_code_depnum_ccdc_archive 'CCDC 2252831'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT089_tt2202              
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       5.50 Note
RESPONSE: The structure is chiral that aryifically deflates the d:p ratio. The structure is correct.
;
# Added during the CSD deposition process: Wednesday 29 March 2023 09:57 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H14 O6'
_chemical_formula_sum            'C7 H14 O6'
_chemical_formula_weight         194.18

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

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

_cell_length_a                   5.2406(2)
_cell_length_b                   11.2187(4)
_cell_length_c                   14.6715(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     862.58(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6615
_cell_measurement_theta_min      6.03
_cell_measurement_theta_max      69.56

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.179
_exptl_absorpt_coefficient_mu    1.142
_shelx_estimated_absorpt_T_min   0.772
_shelx_estimated_absorpt_T_max   0.822
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8017
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Incoatec micro-focus'
_diffrn_radiation_monochromator  'MONTEL Multi-layer'
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            7159
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         6.032
_diffrn_reflns_theta_max         69.579
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             1573
_reflns_number_gt                1553
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.644
_reflns_Friedel_fraction_max     0.952
_reflns_Friedel_fraction_full    0.969

_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       'Bruker APEX-4 (Bruker, 2021)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2021)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2021)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_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)+(0.0440P)²+0.1364P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 611 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         1573
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0682
_refine_ls_wR_factor_gt          0.0680
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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 0.6436(2) 0.40988(10) 0.57066(8) 0.0161(3) Uani 1 1 d . . . . .
O2 O 0.2629(2) 0.55736(11) 0.49663(8) 0.0168(3) Uani 1 1 d . . . . .
H2O H 0.395(6) 0.554(2) 0.4616(18) 0.033(7) Uiso 1 1 d . . . . .
O3 O 0.4606(2) 0.77116(11) 0.57370(8) 0.0176(3) Uani 1 1 d . . . . .
H3O H 0.575(6) 0.814(3) 0.5506(18) 0.037(7) Uiso 1 1 d . . . . .
O4 O 0.8466(3) 0.73455(12) 0.71827(9) 0.0222(3) Uani 1 1 d . . . . .
H4O H 0.816(6) 0.805(3) 0.7024(18) 0.038(7) Uiso 1 1 d . . . . .
O5 O 0.4986(2) 0.45395(10) 0.71864(7) 0.0147(3) Uani 1 1 d . . . . .
O6 O 0.8850(3) 0.43063(11) 0.86501(8) 0.0167(3) Uani 1 1 d . . . . .
H6O H 0.786(5) 0.376(2) 0.8761(17) 0.029(6) Uiso 1 1 d . . . . .
C1 C 0.4355(3) 0.44517(16) 0.62451(11) 0.0146(4) Uani 1 1 d . . . . .
H1 H 0.306(4) 0.3873(19) 0.6234(13) 0.014(5) Uiso 1 1 d . . . . .
C2 C 0.3458(3) 0.56569(15) 0.58853(11) 0.0145(4) Uani 1 1 d . . . . .
H2 H 0.198(4) 0.5917(19) 0.6244(14) 0.013(5) Uiso 1 1 d . . . . .
C3 C 0.5553(3) 0.65804(15) 0.60237(11) 0.0141(4) Uani 1 1 d . . . . .
H3 H 0.712(5) 0.6362(18) 0.5657(15) 0.021(5) Uiso 1 1 d . . . . .
C4 C 0.6281(4) 0.66187(14) 0.70299(11) 0.0151(4) Uani 1 1 d . . . . .
H4 H 0.481(5) 0.693(2) 0.7361(16) 0.020(5) Uiso 1 1 d . . . . .
C5 C 0.7003(3) 0.53752(15) 0.73674(11) 0.0141(4) Uani 1 1 d . . . . .
H5 H 0.855(5) 0.5103(19) 0.7050(15) 0.019(5) Uiso 1 1 d . . . . .
C6 C 0.7490(4) 0.53505(15) 0.83862(11) 0.0159(4) Uani 1 1 d . . . . .
H6A H 0.855(5) 0.601(2) 0.8535(14) 0.023(6) Uiso 1 1 d . . . . .
H6B H 0.590(5) 0.541(2) 0.8719(15) 0.024(6) Uiso 1 1 d . . . . .
C7 C 0.7384(4) 0.29436(16) 0.59317(13) 0.0202(4) Uani 1 1 d . . . . .
H7A H 0.865(6) 0.274(2) 0.5453(18) 0.041(7) Uiso 1 1 d . . . . .
H7B H 0.599(5) 0.236(2) 0.5957(17) 0.034(6) Uiso 1 1 d . . . . .
H7C H 0.820(5) 0.291(2) 0.6533(16) 0.026(6) 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
O1 C1 1.403(2) . ?
O1 C7 1.427(2) . ?
O2 C2 1.4195(19) . ?
O2 H2O 0.86(3) . ?
O3 C3 1.426(2) . ?
O3 H3O 0.84(3) . ?
O4 C4 1.423(2) . ?
O4 H4O 0.84(3) . ?
O5 C1 1.4235(19) . ?
O5 C5 1.438(2) . ?
O6 C6 1.425(2) . ?
O6 H6O 0.82(3) . ?
C1 C2 1.526(2) . ?
C1 H1 0.94(2) . ?
C2 C3 1.523(2) . ?
C2 H2 0.98(2) . ?
C3 C4 1.525(2) . ?
C3 H3 1.01(2) . ?
C4 C5 1.528(2) . ?
C4 H4 0.98(3) . ?
C5 C6 1.517(2) . ?
C5 H5 0.98(2) . ?
C6 H6A 0.95(3) . ?
C6 H6B 0.97(3) . ?
C7 H7A 0.99(3) . ?
C7 H7B 0.98(3) . ?
C7 H7C 0.98(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
C1 O1 C7 113.36(13) . . ?
C2 O2 H2O 108.8(17) . . ?
C3 O3 H3O 112.6(19) . . ?
C4 O4 H4O 110(2) . . ?
C1 O5 C5 113.27(12) . . ?
C6 O6 H6O 110.8(18) . . ?
O1 C1 O5 112.66(14) . . ?
O1 C1 C2 107.14(13) . . ?
O5 C1 C2 110.24(14) . . ?
O1 C1 H1 111.0(12) . . ?
O5 C1 H1 103.4(12) . . ?
C2 C1 H1 112.5(12) . . ?
O2 C2 C3 113.07(14) . . ?
O2 C2 C1 111.38(14) . . ?
C3 C2 C1 109.54(14) . . ?
O2 C2 H2 106.7(12) . . ?
C3 C2 H2 107.2(12) . . ?
C1 C2 H2 108.8(12) . . ?
O3 C3 C2 108.35(14) . . ?
O3 C3 C4 110.34(13) . . ?
C2 C3 C4 109.17(13) . . ?
O3 C3 H3 109.9(12) . . ?
C2 C3 H3 110.5(12) . . ?
C4 C3 H3 108.6(13) . . ?
O4 C4 C3 111.70(13) . . ?
O4 C4 C5 105.84(14) . . ?
C3 C4 C5 110.48(12) . . ?
O4 C4 H4 110.6(14) . . ?
C3 C4 H4 107.0(14) . . ?
C5 C4 H4 111.3(14) . . ?
O5 C5 C6 107.08(13) . . ?
O5 C5 C4 110.70(13) . . ?
C6 C5 C4 112.19(13) . . ?
O5 C5 H5 108.3(13) . . ?
C6 C5 H5 108.9(13) . . ?
C4 C5 H5 109.5(13) . . ?
O6 C6 C5 111.52(14) . . ?
O6 C6 H6A 106.9(14) . . ?
C5 C6 H6A 108.0(13) . . ?
O6 C6 H6B 110.7(14) . . ?
C5 C6 H6B 110.6(14) . . ?
H6A C6 H6B 109.1(19) . . ?
O1 C7 H7A 106.3(16) . . ?
O1 C7 H7B 110.7(15) . . ?
H7A C7 H7B 112(2) . . ?
O1 C7 H7C 113.0(14) . . ?
H7A C7 H7C 110(2) . . ?
H7B C7 H7C 106(2) . . ?

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
C7 O1 C1 O5 62.18(18) . . . . ?
C7 O1 C1 C2 -176.42(14) . . . . ?
C5 O5 C1 O1 59.09(18) . . . . ?
C5 O5 C1 C2 -60.54(17) . . . . ?
O1 C1 C2 O2 61.61(17) . . . . ?
O5 C1 C2 O2 -175.47(12) . . . . ?
O1 C1 C2 C3 -64.22(17) . . . . ?
O5 C1 C2 C3 58.70(17) . . . . ?
O2 C2 C3 O3 58.87(17) . . . . ?
C1 C2 C3 O3 -176.27(12) . . . . ?
O2 C2 C3 C4 179.07(13) . . . . ?
C1 C2 C3 C4 -56.07(17) . . . . ?
O3 C3 C4 O4 -69.03(18) . . . . ?
C2 C3 C4 O4 172.00(14) . . . . ?
O3 C3 C4 C5 173.44(13) . . . . ?
C2 C3 C4 C5 54.47(18) . . . . ?
C1 O5 C5 C6 -178.87(13) . . . . ?
C1 O5 C5 C4 58.55(17) . . . . ?
O4 C4 C5 O5 -175.92(12) . . . . ?
C3 C4 C5 O5 -54.84(18) . . . . ?
O4 C4 C5 C6 64.53(17) . . . . ?
C3 C4 C5 C6 -174.39(14) . . . . ?
O5 C5 C6 O6 75.30(17) . . . . ?
C4 C5 C6 O6 -163.06(14) . . . . ?

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 H2O O6 0.86(3) 1.83(3) 2.6742(18) 164(2) 2_664 yes
O3 H3O O2 0.84(3) 1.88(3) 2.6975(17) 165(3) 4_566 yes
O4 H4O O5 0.84(3) 2.62(3) 3.1917(18) 127(2) 3_656 yes
O4 H4O O6 0.84(3) 2.33(3) 2.8828(18) 124(2) 3_756 yes
O6 H6O O3 0.82(3) 1.90(3) 2.6998(18) 166(2) 3_646 yes

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_tt2104
_database_code_depnum_ccdc_archive 'CCDC 2252828'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2023-05-11 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         '2(C7 H14 O6), H2 O'
_chemical_formula_sum            'C14 H30 O13'
_chemical_formula_weight         406.38

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'

_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+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   7.3491(2)
_cell_length_b                   7.3491(2)
_cell_length_c                   34.1307(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1843.37(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9905
_cell_measurement_theta_min      6.16
_cell_measurement_theta_max      69.40

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.108
_exptl_absorpt_coefficient_mu    1.135
_shelx_estimated_absorpt_T_min   0.804
_shelx_estimated_absorpt_T_max   0.887
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8540
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec micro-focus'
_diffrn_source_monochromator     'MONTEL Multi-layer'
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            35600
_diffrn_reflns_av_unetI/netI     0.0097
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         6.160
_diffrn_reflns_theta_max         69.366
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1716
_reflns_number_gt                1693
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.557
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX-4 (Bruker, 2021)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2021)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2021)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_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)+(0.0346P)²+0.3453P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 607 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(4)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         1716
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0215
_refine_ls_R_factor_gt           0.0213
_refine_ls_wR_factor_ref         0.0579
_refine_ls_wR_factor_gt          0.0577
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_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 0.64313(13) 0.28506(14) 0.66589(3) 0.0149(2) Uani 1 1 d . . . . .
O2 O 0.97592(14) 0.20712(14) 0.62803(3) 0.0156(2) Uani 1 1 d . . . . .
H2O H 0.904(3) 0.172(3) 0.6110(6) 0.040(6) Uiso 1 1 d . . . . .
O3 O 1.20828(15) 0.50912(14) 0.61876(3) 0.0162(2) Uani 1 1 d . . . . .
H3O H 1.300(3) 0.572(3) 0.6231(6) 0.036(6) Uiso 1 1 d . . . . .
O4 O 1.20546(14) 0.75951(14) 0.68535(3) 0.0152(2) Uani 1 1 d . . . . .
H4O H 1.243(3) 0.839(3) 0.6692(6) 0.027(5) Uiso 1 1 d . . . . .
O5 O 0.75039(13) 0.56087(14) 0.68612(3) 0.0131(2) Uani 1 1 d . . . . .
O6 O 0.71658(16) 0.83513(15) 0.74749(3) 0.0203(2) Uani 1 1 d . . . . .
H6O H 0.625(3) 0.766(3) 0.7435(6) 0.038(6) Uiso 1 1 d . . . . .
C1 C 0.79974(19) 0.37737(19) 0.67599(4) 0.0125(3) Uani 1 1 d . . . . .
H1 H 0.860(2) 0.324(2) 0.6989(5) 0.013(4) Uiso 1 1 d . . . . .
C2 C 0.9263(2) 0.38547(19) 0.64065(4) 0.0126(3) Uani 1 1 d . . . . .
H2 H 0.863(3) 0.450(2) 0.6195(5) 0.017(4) Uiso 1 1 d . . . . .
C3 C 1.09641(19) 0.4894(2) 0.65263(4) 0.0130(3) Uani 1 1 d . . . . .
H3 H 1.165(3) 0.416(2) 0.6731(5) 0.015(4) Uiso 1 1 d . . . . .
C4 C 1.04696(19) 0.67624(19) 0.66925(4) 0.0126(3) Uani 1 1 d . . . . .
H4 H 0.998(2) 0.747(2) 0.6484(5) 0.012(4) Uiso 1 1 d . . . . .
C5 C 0.90351(19) 0.6603(2) 0.70142(4) 0.0127(3) Uani 1 1 d . . . . .
H5 H 0.952(2) 0.596(2) 0.7241(5) 0.013(4) Uiso 1 1 d . . . . .
C6 C 0.8321(2) 0.8447(2) 0.71426(4) 0.0158(3) Uani 1 1 d . . . . .
H6A H 0.932(3) 0.918(3) 0.7218(5) 0.019(4) Uiso 1 1 d . . . . .
H6B H 0.764(3) 0.899(3) 0.6922(5) 0.017(4) Uiso 1 1 d . . . . .
C7 C 0.5298(2) 0.2458(2) 0.69933(4) 0.0183(3) Uani 1 1 d . . . . .
H7A H 0.419(3) 0.185(3) 0.6898(5) 0.026(5) Uiso 1 1 d . . . . .
H7B H 0.490(3) 0.355(3) 0.7113(5) 0.025(5) Uiso 1 1 d . . . . .
H7C H 0.600(3) 0.171(3) 0.7186(6) 0.032(5) Uiso 1 1 d . . . . .
O1W O 1.37693(15) 0.62307(15) 0.750000 0.0220(4) Uani 1 2 d S T P . .
H1W H 1.330(3) 0.680(3) 0.7690(6) 0.036(6) 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
O1 C1 1.3797(17) . ?
O1 C7 1.4421(17) . ?
O2 C2 1.4271(16) . ?
O2 H2O 0.83(3) . ?
O3 C3 1.4259(16) . ?
O3 H3O 0.83(3) . ?
O4 C4 1.4259(16) . ?
O4 H4O 0.85(2) . ?
O5 C1 1.4386(17) . ?
O5 C5 1.4399(17) . ?
O6 C6 1.4181(17) . ?
O6 H6O 0.86(3) . ?
C1 C2 1.5243(18) . ?
C1 H1 0.983(18) . ?
C2 C3 1.521(2) . ?
C2 H2 0.978(18) . ?
C3 C4 1.5297(19) . ?
C3 H3 1.016(18) . ?
C4 C5 1.5267(18) . ?
C4 H4 0.953(17) . ?
C5 C6 1.5179(19) . ?
C5 H5 0.976(16) . ?
C6 H6A 0.95(2) . ?
C6 H6B 0.987(18) . ?
C7 H7A 0.98(2) . ?
C7 H7B 0.95(2) . ?
C7 H7C 1.00(2) . ?
O1W H1W 0.84(2) . ?
O1W H1W 0.84(2) 8_776 ?

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 O1 C7 112.49(10) . . ?
C2 O2 H2O 109.9(17) . . ?
C3 O3 H3O 112.4(15) . . ?
C4 O4 H4O 108.2(14) . . ?
C1 O5 C5 111.47(10) . . ?
C6 O6 H6O 111.9(15) . . ?
O1 C1 O5 108.10(11) . . ?
O1 C1 C2 109.30(11) . . ?
O5 C1 C2 107.90(11) . . ?
O1 C1 H1 112.2(11) . . ?
O5 C1 H1 107.3(10) . . ?
C2 C1 H1 111.8(10) . . ?
O2 C2 C3 109.39(12) . . ?
O2 C2 C1 111.04(11) . . ?
C3 C2 C1 107.96(11) . . ?
O2 C2 H2 109.9(10) . . ?
C3 C2 H2 110.2(11) . . ?
C1 C2 H2 108.3(11) . . ?
O3 C3 C2 107.89(11) . . ?
O3 C3 C4 110.25(11) . . ?
C2 C3 C4 110.80(11) . . ?
O3 C3 H3 109.0(10) . . ?
C2 C3 H3 108.8(11) . . ?
C4 C3 H3 110.0(10) . . ?
O4 C4 C5 108.65(10) . . ?
O4 C4 C3 109.52(11) . . ?
C5 C4 C3 111.22(11) . . ?
O4 C4 H4 111.2(11) . . ?
C5 C4 H4 108.7(10) . . ?
C3 C4 H4 107.7(10) . . ?
O5 C5 C6 106.72(11) . . ?
O5 C5 C4 108.52(10) . . ?
C6 C5 C4 112.22(12) . . ?
O5 C5 H5 109.1(10) . . ?
C6 C5 H5 109.3(10) . . ?
C4 C5 H5 110.9(10) . . ?
O6 C6 C5 113.18(12) . . ?
O6 C6 H6A 106.0(10) . . ?
C5 C6 H6A 108.6(12) . . ?
O6 C6 H6B 109.2(10) . . ?
C5 C6 H6B 108.4(11) . . ?
H6A C6 H6B 111.4(16) . . ?
O1 C7 H7A 107.9(11) . . ?
O1 C7 H7B 110.4(12) . . ?
H7A C7 H7B 105.8(16) . . ?
O1 C7 H7C 109.3(12) . . ?
H7A C7 H7C 113.4(17) . . ?
H7B C7 H7C 109.9(16) . . ?
H1W O1W H1W 101(3) . 8_776 ?

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
C7 O1 C1 O5 -72.30(13) . . . . ?
C7 O1 C1 C2 170.51(11) . . . . ?
C5 O5 C1 O1 173.24(10) . . . . ?
C5 O5 C1 C2 -68.67(13) . . . . ?
O1 C1 C2 O2 -60.60(15) . . . . ?
O5 C1 C2 O2 -177.92(11) . . . . ?
O1 C1 C2 C3 179.48(11) . . . . ?
O5 C1 C2 C3 62.16(13) . . . . ?
O2 C2 C3 O3 63.50(13) . . . . ?
C1 C2 C3 O3 -175.56(11) . . . . ?
O2 C2 C3 C4 -175.72(10) . . . . ?
C1 C2 C3 C4 -54.78(14) . . . . ?
O3 C3 C4 O4 -68.92(13) . . . . ?
C2 C3 C4 O4 171.71(10) . . . . ?
O3 C3 C4 C5 170.97(11) . . . . ?
C2 C3 C4 C5 51.60(15) . . . . ?
C1 O5 C5 C6 -175.19(10) . . . . ?
C1 O5 C5 C4 63.67(13) . . . . ?
O4 C4 C5 O5 -174.62(10) . . . . ?
C3 C4 C5 O5 -53.99(14) . . . . ?
O4 C4 C5 C6 67.70(14) . . . . ?
C3 C4 C5 C6 -171.68(11) . . . . ?
O5 C5 C6 O6 68.96(14) . . . . ?
C4 C5 C6 O6 -172.29(12) . . . . ?

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 H2O O5 0.83(3) 2.13(2) 2.9520(14) 172(2) 5_646 yes
O3 H3O O2 0.83(3) 1.92(3) 2.7415(14) 168(2) 5_756 yes
O4 H4O O3 0.85(2) 1.83(2) 2.6789(14) 172(2) 5_756 yes
O6 H6O O1W 0.86(3) 2.11(3) 2.9439(12) 163(2) 1_455 yes
O1W H1W O4 0.84(2) 1.89(2) 2.7318(14) 175(2) 8_776 yes

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_tt2203
_database_code_depnum_ccdc_archive 'CCDC 2252833'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2023-05-11 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         'C7 H14 O6, 0.5(H2 O)'
_chemical_formula_sum            'C7 H15 O6.50'
_chemical_formula_weight         203.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'

_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+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   7.3472(2)
_cell_length_b                   7.3472(2)
_cell_length_c                   34.1458(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1843.24(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9615
_cell_measurement_theta_min      6.16
_cell_measurement_theta_max      69.81

_exptl_crystal_description       tablet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.177
_exptl_crystal_size_min          0.084
_exptl_absorpt_coefficient_mu    1.135
_shelx_estimated_absorpt_T_min   0.805
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8394
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Incoatec micro-focus'
_diffrn_radiation_monochromator  'MONTEL Multi-layer'
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            43262
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         6.161
_diffrn_reflns_theta_max         69.733
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1727
_reflns_number_gt                1703
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.556
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX-4 (Bruker, 2021)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2021)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2021)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_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)+(0.0354P)²+0.3452P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 611 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         1727
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_ref         0.0586
_refine_ls_wR_factor_gt          0.0583
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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 0.64302(13) 0.71498(14) 0.58410(3) 0.0156(2) Uani 1 1 d . . . . .
O2 O 0.97582(14) 0.79296(14) 0.62198(3) 0.0162(2) Uani 1 1 d . . . . .
H2O H 0.904(3) 0.828(3) 0.6389(6) 0.032(6) Uiso 1 1 d . . . . .
O3 O 1.20821(15) 0.49087(14) 0.63123(3) 0.0168(2) Uani 1 1 d . . . . .
H3O H 1.300(3) 0.426(3) 0.6269(6) 0.036(6) Uiso 1 1 d . . . . .
O4 O 1.20551(14) 0.24043(14) 0.56465(3) 0.0159(2) Uani 1 1 d . . . . .
H4O H 1.243(3) 0.161(3) 0.5807(6) 0.026(5) Uiso 1 1 d . . . . .
O5 O 0.75027(13) 0.43911(14) 0.56391(3) 0.0137(2) Uani 1 1 d . . . . .
O6 O 0.71654(16) 0.16470(15) 0.50251(3) 0.0211(3) Uani 1 1 d . . . . .
H6O H 0.626(3) 0.234(3) 0.5071(6) 0.037(6) Uiso 1 1 d . . . . .
C1 C 0.79970(19) 0.62263(19) 0.57404(4) 0.0130(3) Uani 1 1 d . . . . .
H1 H 0.861(2) 0.677(2) 0.5511(5) 0.015(4) Uiso 1 1 d . . . . .
C2 C 0.9263(2) 0.61455(19) 0.60934(4) 0.0133(3) Uani 1 1 d . . . . .
H2 H 0.864(3) 0.549(2) 0.6303(5) 0.015(4) Uiso 1 1 d . . . . .
C3 C 1.09643(19) 0.5107(2) 0.59740(4) 0.0137(3) Uani 1 1 d . . . . .
H3 H 1.164(3) 0.584(2) 0.5771(5) 0.015(4) Uiso 1 1 d . . . . .
C4 C 1.04690(19) 0.32377(19) 0.58075(4) 0.0133(3) Uani 1 1 d . . . . .
H4 H 0.999(2) 0.253(2) 0.6017(5) 0.011(4) Uiso 1 1 d . . . . .
C5 C 0.90338(19) 0.3396(2) 0.54858(4) 0.0136(3) Uani 1 1 d . . . . .
H5 H 0.952(2) 0.404(2) 0.5260(5) 0.013(4) Uiso 1 1 d . . . . .
C6 C 0.8320(2) 0.1552(2) 0.53575(4) 0.0167(3) Uani 1 1 d . . . . .
H6A H 0.933(3) 0.080(3) 0.5284(5) 0.018(4) Uiso 1 1 d . . . . .
H6B H 0.767(2) 0.100(2) 0.5580(5) 0.014(4) Uiso 1 1 d . . . . .
C7 C 0.5298(2) 0.7541(2) 0.55068(4) 0.0192(3) Uani 1 1 d . . . . .
H7A H 0.419(3) 0.816(3) 0.5607(5) 0.026(5) Uiso 1 1 d . . . . .
H7B H 0.490(3) 0.643(3) 0.5384(6) 0.026(5) Uiso 1 1 d . . . . .
H7C H 0.598(3) 0.830(3) 0.5313(6) 0.031(5) Uiso 1 1 d . . . . .
O1W O 1.37686(15) 0.37686(15) 0.500000 0.0227(4) Uani 1 2 d S T P . .
H1W H 1.321(3) 0.331(3) 0.5193(6) 0.035(6) 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
O1 C1 1.3797(17) . ?
O1 C7 1.4409(17) . ?
O2 C2 1.4273(17) . ?
O2 H2O 0.83(2) . ?
O3 C3 1.4248(16) . ?
O3 H3O 0.84(3) . ?
O4 C4 1.4266(16) . ?
O4 H4O 0.84(2) . ?
O5 C1 1.4386(17) . ?
O5 C5 1.4402(17) . ?
O6 C6 1.4186(17) . ?
O6 H6O 0.85(3) . ?
C1 C2 1.5233(19) . ?
C1 H1 0.988(18) . ?
C2 C3 1.5203(19) . ?
C2 H2 0.975(18) . ?
C3 C4 1.5305(19) . ?
C3 H3 1.007(18) . ?
C4 C5 1.5272(18) . ?
C4 H4 0.952(17) . ?
C5 C6 1.517(2) . ?
C5 H5 0.972(17) . ?
C6 H6A 0.956(19) . ?
C6 H6B 0.984(18) . ?
C7 H7A 1.00(2) . ?
C7 H7B 0.96(2) . ?
C7 H7C 1.00(2) . ?
O1W H1W 0.85(2) . ?
O1W H1W 0.85(2) 7_646 ?

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 O1 C7 112.51(10) . . ?
C2 O2 H2O 109.8(16) . . ?
C3 O3 H3O 112.4(15) . . ?
C4 O4 H4O 108.2(14) . . ?
C1 O5 C5 111.48(11) . . ?
C6 O6 H6O 110.4(15) . . ?
O1 C1 O5 108.07(11) . . ?
O1 C1 C2 109.36(11) . . ?
O5 C1 C2 107.93(11) . . ?
O1 C1 H1 112.4(11) . . ?
O5 C1 H1 107.7(10) . . ?
C2 C1 H1 111.2(10) . . ?
O2 C2 C3 109.39(12) . . ?
O2 C2 C1 111.05(11) . . ?
C3 C2 C1 108.03(11) . . ?
O2 C2 H2 110.5(10) . . ?
C3 C2 H2 109.6(11) . . ?
C1 C2 H2 108.2(11) . . ?
O3 C3 C2 107.95(11) . . ?
O3 C3 C4 110.26(11) . . ?
C2 C3 C4 110.75(12) . . ?
O3 C3 H3 109.3(10) . . ?
C2 C3 H3 108.6(11) . . ?
C4 C3 H3 110.0(10) . . ?
O4 C4 C5 108.63(11) . . ?
O4 C4 C3 109.52(12) . . ?
C5 C4 C3 111.29(11) . . ?
O4 C4 H4 111.0(10) . . ?
C5 C4 H4 109.0(10) . . ?
C3 C4 H4 107.4(10) . . ?
O5 C5 C6 106.76(11) . . ?
O5 C5 C4 108.45(10) . . ?
C6 C5 C4 112.24(12) . . ?
O5 C5 H5 109.3(10) . . ?
C6 C5 H5 109.3(10) . . ?
C4 C5 H5 110.7(11) . . ?
O6 C6 C5 113.19(12) . . ?
O6 C6 H6A 106.3(10) . . ?
C5 C6 H6A 108.9(12) . . ?
O6 C6 H6B 110.3(10) . . ?
C5 C6 H6B 108.1(10) . . ?
H6A C6 H6B 110.0(15) . . ?
O1 C7 H7A 107.1(11) . . ?
O1 C7 H7B 110.6(12) . . ?
H7A C7 H7B 106.8(16) . . ?
O1 C7 H7C 110.2(12) . . ?
H7A C7 H7C 112.6(17) . . ?
H7B C7 H7C 109.5(16) . . ?
H1W O1W H1W 103(3) . 7_646 ?

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
C7 O1 C1 O5 -72.25(14) . . . . ?
C7 O1 C1 C2 170.50(11) . . . . ?
C5 O5 C1 O1 173.14(10) . . . . ?
C5 O5 C1 C2 -68.69(13) . . . . ?
O1 C1 C2 O2 -60.54(15) . . . . ?
O5 C1 C2 O2 -177.87(11) . . . . ?
O1 C1 C2 C3 179.50(11) . . . . ?
O5 C1 C2 C3 62.17(14) . . . . ?
O2 C2 C3 O3 63.49(14) . . . . ?
C1 C2 C3 O3 -175.51(11) . . . . ?
O2 C2 C3 C4 -175.71(10) . . . . ?
C1 C2 C3 C4 -54.71(14) . . . . ?
O3 C3 C4 O4 -68.92(13) . . . . ?
C2 C3 C4 O4 171.67(11) . . . . ?
O3 C3 C4 C5 170.96(11) . . . . ?
C2 C3 C4 C5 51.55(15) . . . . ?
C1 O5 C5 C6 -175.22(10) . . . . ?
C1 O5 C5 C4 63.64(13) . . . . ?
O4 C4 C5 O5 -174.62(11) . . . . ?
C3 C4 C5 O5 -53.97(14) . . . . ?
O4 C4 C5 C6 67.68(14) . . . . ?
C3 C4 C5 C6 -171.66(11) . . . . ?
O5 C5 C6 O6 69.04(14) . . . . ?
C4 C5 C6 O6 -172.26(12) . . . . ?

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 H2O O5 0.83(2) 2.13(2) 2.9505(14) 172(2) 5_656 yes
O3 H3O O2 0.84(3) 1.92(3) 2.7414(14) 168(2) 5_746 yes
O4 H4O O3 0.84(2) 1.84(2) 2.6793(14) 172(2) 5_746 yes
O6 H6O O1W 0.85(3) 2.12(3) 2.9438(13) 161(2) 1_455 yes
O1W H1W O4 0.85(2) 1.89(2) 2.7319(14) 176(2) . yes

_refine_diff_density_max         0.263
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.115

####################################################################### 
# 
# 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_tt2201
_database_code_depnum_ccdc_archive 'CCDC 2252832'
loop_
_audit_author_name
_audit_author_address
'Allen Oliver'
;University of Notre Dame
United States of America
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2023-05-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT089_tt2201              
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       5.48 Note
RESPONSE: The structure is chiral that aryifically deflates the d:p ratio. The structure is correct.
;
# Added during the CSD deposition process: Wednesday 29 March 2023 09:57 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H14 O6'
_chemical_formula_sum            'C7 H14 O6'
_chemical_formula_weight         194.18

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

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

_cell_length_a                   9.2620(2)
_cell_length_b                   9.3748(2)
_cell_length_c                   9.9796(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     866.52(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    127(2)
_cell_measurement_reflns_used    9852
_cell_measurement_theta_min      6.48
_cell_measurement_theta_max      69.69

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.143
_exptl_absorpt_coefficient_mu    1.137
_shelx_estimated_absorpt_T_min   0.757
_shelx_estimated_absorpt_T_max   0.854
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8090
_exptl_absorpt_correction_T_max  0.9965
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      127(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Incoatec micro-focus'
_diffrn_radiation_monochromator  'MONTEL Multi-layer'
_diffrn_measurement_device_type  'Bruker PHOTON-II'
_diffrn_measurement_method       'combination of ω and φ-scans '
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            33032
_diffrn_reflns_av_unetI/netI     0.0081
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         6.478
_diffrn_reflns_theta_max         69.674
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1607
_reflns_number_gt                1606
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.686
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.994

_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       'Bruker APEX-4 (Bruker, 2021)'
_computing_cell_refinement       'Bruker SAINT (Bruker, 2021)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2021)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  'CIFTAB (Sheldrick, 2008)'
_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)+(0.0282P)²+0.1779P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 652 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.046(18)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         1607
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0213
_refine_ls_R_factor_gt           0.0213
_refine_ls_wR_factor_ref         0.0540
_refine_ls_wR_factor_gt          0.0540
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.147
_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 0.14274(11) 0.88826(12) 0.66272(11) 0.0155(2) Uani 1 1 d . . . . .
O2 O 0.47238(12) 0.79593(11) 0.50001(12) 0.0154(3) Uani 1 1 d . . . . .
H2O H 0.500(3) 0.725(3) 0.454(2) 0.029(6) Uiso 1 1 d . . . . .
O3 O 0.34737(11) 0.52114(11) 0.50628(11) 0.0142(2) Uani 1 1 d . . . . .
H3O H 0.290(3) 0.519(3) 0.442(2) 0.031(6) Uiso 1 1 d . . . . .
O4 O 0.34087(12) 0.48242(11) 0.79197(11) 0.0140(2) Uani 1 1 d . . . . .
H4O H 0.417(3) 0.430(3) 0.789(3) 0.047(7) Uiso 1 1 d . . . . .
O5 O 0.37390(11) 0.87096(11) 0.75759(10) 0.0130(2) Uani 1 1 d . . . . .
O6 O 0.58717(12) 0.73724(12) 0.92412(12) 0.0198(3) Uani 1 1 d . . . . .
H6O H 0.616(3) 0.823(3) 0.930(2) 0.035(6) Uiso 1 1 d . . . . .
C1 C 0.29238(16) 0.89229(16) 0.63871(15) 0.0122(3) Uani 1 1 d . . . . .
H1 H 0.3208(18) 0.985(2) 0.6097(17) 0.008(4) Uiso 1 1 d . . . . .
C2 C 0.32507(16) 0.77648(16) 0.53655(15) 0.0119(3) Uani 1 1 d . . . . .
H2 H 0.262(2) 0.7920(19) 0.4579(18) 0.006(4) Uiso 1 1 d . . . . .
C3 C 0.29990(15) 0.62917(16) 0.59735(15) 0.0113(3) Uani 1 1 d . . . . .
H3 H 0.201(2) 0.6175(18) 0.6159(17) 0.007(4) Uiso 1 1 d . . . . .
C4 C 0.38326(16) 0.61286(15) 0.72758(15) 0.0114(3) Uani 1 1 d . . . . .
H4 H 0.4831(19) 0.6092(18) 0.7096(17) 0.005(4) Uiso 1 1 d . . . . .
C5 C 0.34724(15) 0.73566(16) 0.82244(14) 0.0122(3) Uani 1 1 d . . . . .
H5 H 0.246(2) 0.7299(19) 0.8476(19) 0.011(4) Uiso 1 1 d . . . . .
C6 C 0.43633(18) 0.73540(17) 0.94992(15) 0.0175(3) Uani 1 1 d . . . . .
H6A H 0.411(2) 0.817(2) 1.0059(19) 0.016(5) Uiso 1 1 d . . . . .
H6B H 0.411(2) 0.642(2) 0.996(2) 0.024(5) Uiso 1 1 d . . . . .
C7 C 0.09514(19) 0.99472(19) 0.75624(17) 0.0218(4) Uani 1 1 d . . . . .
H7A H -0.002(3) 0.998(2) 0.750(2) 0.032(6) Uiso 1 1 d . . . . .
H7B H 0.137(2) 1.087(3) 0.731(2) 0.034(6) Uiso 1 1 d . . . . .
H7C H 0.122(2) 0.967(2) 0.851(2) 0.026(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
O1 C1 1.4070(17) . ?
O1 C7 1.4358(19) . ?
O2 C2 1.4240(18) . ?
O2 H2O 0.85(2) . ?
O3 C3 1.4300(18) . ?
O3 H3O 0.83(2) . ?
O4 C4 1.4361(17) . ?
O4 H4O 0.86(3) . ?
O5 C1 1.4204(17) . ?
O5 C5 1.4452(17) . ?
O6 C6 1.421(2) . ?
O6 H6O 0.85(3) . ?
C1 C2 1.520(2) . ?
C1 H1 0.951(19) . ?
C2 C3 1.526(2) . ?
C2 H2 0.987(18) . ?
C3 C4 1.519(2) . ?
C3 H3 0.939(18) . ?
C4 C5 1.5273(19) . ?
C4 H4 0.943(17) . ?
C5 C6 1.516(2) . ?
C5 H5 0.971(19) . ?
C6 H6A 0.975(19) . ?
C6 H6B 1.01(2) . ?
C7 H7A 0.90(3) . ?
C7 H7B 0.98(3) . ?
C7 H7C 1.01(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
C1 O1 C7 113.23(12) . . ?
C2 O2 H2O 109.3(16) . . ?
C3 O3 H3O 107.8(17) . . ?
C4 O4 H4O 104.2(18) . . ?
C1 O5 C5 114.00(11) . . ?
C6 O6 H6O 107.7(17) . . ?
O1 C1 O5 112.19(12) . . ?
O1 C1 C2 106.93(12) . . ?
O5 C1 C2 110.72(12) . . ?
O1 C1 H1 110.4(10) . . ?
O5 C1 H1 103.6(11) . . ?
C2 C1 H1 113.1(11) . . ?
O2 C2 C1 105.73(12) . . ?
O2 C2 C3 111.35(11) . . ?
C1 C2 C3 110.44(12) . . ?
O2 C2 H2 110.0(11) . . ?
C1 C2 H2 108.1(10) . . ?
C3 C2 H2 111.0(10) . . ?
O3 C3 C4 108.43(11) . . ?
O3 C3 C2 109.95(11) . . ?
C4 C3 C2 110.70(12) . . ?
O3 C3 H3 110.0(11) . . ?
C4 C3 H3 108.3(10) . . ?
C2 C3 H3 109.4(11) . . ?
O4 C4 C3 109.24(12) . . ?
O4 C4 C5 107.74(11) . . ?
C3 C4 C5 110.08(12) . . ?
O4 C4 H4 108.8(10) . . ?
C3 C4 H4 109.9(10) . . ?
C5 C4 H4 111.1(10) . . ?
O5 C5 C6 106.50(12) . . ?
O5 C5 C4 110.28(11) . . ?
C6 C5 C4 113.58(12) . . ?
O5 C5 H5 109.3(11) . . ?
C6 C5 H5 107.9(11) . . ?
C4 C5 H5 109.2(11) . . ?
O6 C6 C5 112.53(12) . . ?
O6 C6 H6A 109.5(12) . . ?
C5 C6 H6A 110.3(12) . . ?
O6 C6 H6B 108.6(12) . . ?
C5 C6 H6B 104.8(12) . . ?
H6A C6 H6B 111.0(16) . . ?
O1 C7 H7A 106.3(14) . . ?
O1 C7 H7B 108.7(14) . . ?
H7A C7 H7B 110.4(18) . . ?
O1 C7 H7C 110.8(12) . . ?
H7A C7 H7C 108.5(19) . . ?
H7B C7 H7C 111.9(19) . . ?

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
C7 O1 C1 O5 59.58(16) . . . . ?
C7 O1 C1 C2 -178.84(12) . . . . ?
C5 O5 C1 O1 60.09(15) . . . . ?
C5 O5 C1 C2 -59.28(15) . . . . ?
O1 C1 C2 O2 172.01(11) . . . . ?
O5 C1 C2 O2 -65.50(14) . . . . ?
O1 C1 C2 C3 -67.42(14) . . . . ?
O5 C1 C2 C3 55.07(15) . . . . ?
O2 C2 C3 O3 -55.90(15) . . . . ?
C1 C2 C3 O3 -173.05(12) . . . . ?
O2 C2 C3 C4 63.88(15) . . . . ?
C1 C2 C3 C4 -53.27(15) . . . . ?
O3 C3 C4 O4 -67.77(14) . . . . ?
C2 C3 C4 O4 171.54(11) . . . . ?
O3 C3 C4 C5 174.11(11) . . . . ?
C2 C3 C4 C5 53.42(15) . . . . ?
C1 O5 C5 C6 -176.96(12) . . . . ?
C1 O5 C5 C4 59.38(15) . . . . ?
O4 C4 C5 O5 -174.17(11) . . . . ?
C3 C4 C5 O5 -55.14(15) . . . . ?
O4 C4 C5 C6 66.38(15) . . . . ?
C3 C4 C5 C6 -174.59(12) . . . . ?
O5 C5 C6 O6 -65.40(15) . . . . ?
C4 C5 C6 O6 56.18(17) . . . . ?

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 H2O O1 0.85(2) 2.05(3) 2.8476(16) 155(2) 4_566 yes
O3 H3O O4 0.83(2) 1.93(3) 2.7596(15) 179(2) 2_564 yes
O4 H4O O5 0.86(3) 2.07(3) 2.8837(15) 158(2) 3_646 yes
O6 H6O O3 0.85(3) 1.99(3) 2.8166(16) 163(2) 3_656 yes

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.042

