data_global

#==============================================================================

# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic      2022-09-08
_journal_date_to_coeditor         ?
_journal_date_from_coeditor       ?
_journal_date_accepted     2023-02-14
_journal_date_printers_first      ?
_journal_date_printers_final      ?
_journal_date_proofs_out          ?
_journal_date_proofs_in           ?
_journal_coeditor_name            ?
_journal_coeditor_code      EI5091SUP1
_journal_coeditor_notes
; ?
;
_journal_paper_category      FA
_journal_techeditor_code      J230137
_iucr_compatibility_tag          ACTA95
_journal_techeditor_notes  
;
;
_journal_coden_ASTM               ?
_journal_name_full                ?
_journal_year                     ?
_journal_volume                   ?
_journal_issue                    ?
_journal_page_first               ?
_journal_page_last                ?
_journal_suppl_publ_number        ?
_journal_suppl_publ_pages         ?

#==============================================================================

data_298K

_audit_creation_date               2020-09-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic
;
 ? 
;
_chemical_formula_moiety           'C6 H10 O5'
_chemical_formula_sum              'C6 H10 O5'
_chemical_formula_weight           162.14
_chemical_absolute_configuration    'C6 H10 O5'
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'orthorhombic'
_space_group_IT_number             19
_space_group_name_H-M_alt          'P 21 21 21'
_space_group_name_Hall             'P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'

_cell_length_a                     6.676(4)
_cell_length_b                     7.531(4)
_cell_length_c                     13.279(7)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       667.6(6)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      865
_cell_measurement_temperature      296(2)
_cell_measurement_theta_max        22.19
_cell_measurement_theta_min        3.07
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.142
_exptl_absorpt_correction_T_max    0.7456
_exptl_absorpt_correction_T_min    0.6923
_exptl_absorpt_correction_type     'none'
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0573 before and 0.0482 after correction.
The Ratio of minimum to maximum transmission is 0.9285.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              ?
_exptl_crystal_density_diffrn      1.613
_exptl_crystal_density_meas        .
_exptl_crystal_density_method      'not measured'
_exptl_crystal_description          'block'
_exptl_crystal_F_000               344
_exptl_crystal_size_max            ?
_exptl_crystal_size_mid            ?
_exptl_crystal_size_min            ?
_exptl_special_details
;
 ? 
;
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0384
_diffrn_reflns_av_unetI/netI       0.0490
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  0.997
_diffrn_reflns_limit_h_max         8
_diffrn_reflns_limit_h_min         -8
_diffrn_reflns_limit_k_max         9
_diffrn_reflns_limit_k_min         -9
_diffrn_reflns_limit_l_max         17
_diffrn_reflns_limit_l_min         -13
_diffrn_reflns_number              4172
_diffrn_reflns_point_group_measured_fraction_full  0.997
_diffrn_reflns_point_group_measured_fraction_max  0.992
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           27.496
_diffrn_reflns_theta_min           3.068
_diffrn_ambient_temperature        296.15
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  0.997
_diffrn_measurement_device_type    'CCD area detector'
_diffrn_measurement_method         'phi and omega scans'
_diffrn_radiation_monochromator    'graphite'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.667
_reflns_Friedel_fraction_full      0.994
_reflns_Friedel_fraction_max       0.984
_reflns_number_gt                  1209
_reflns_number_total               1522
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.38A (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max           0.190
_refine_diff_density_min           -0.188
_refine_diff_density_rms           0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 387 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -0.1(10)
_refine_ls_extinction_coef         0.042(8)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref     1.048
_refine_ls_hydrogen_treatment      refall
_refine_ls_matrix_type             full
_refine_ls_number_parameters       141
_refine_ls_number_reflns           1522
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0534
_refine_ls_R_factor_gt             0.0384
_refine_ls_restrained_S_all        1.048
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0456P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0872
_refine_ls_wR_factor_ref           0.0947
_refine_special_details            ?
_olex2_refinement_description
;
;
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary       ?
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 C1 C 0.8220(4) 0.1231(4) 0.9461(2) 0.0225(6) Uani 1 1 d . . . . .
 C2 C 1.0052(4) 0.0742(4) 0.8809(2) 0.0230(7) Uani 1 1 d . . . . .
 C3 C 0.6656(5) -0.1488(4) 0.8668(2) 0.0279(7) Uani 1 1 d . . . . .
 C4 C 0.6770(5) -0.0332(4) 0.9604(2) 0.0244(7) Uani 1 1 d . . . . .
 C5 C 0.9490(5) -0.0555(5) 0.7982(2) 0.0291(8) Uani 1 1 d . . . . .
 C6 C 0.6074(6) -0.0463(6) 0.7732(3) 0.0342(8) Uani 1 1 d . . . . .
 O1 O 0.7444(4) -0.1462(3) 1.04034(18) 0.0307(6) Uani 1 1 d . . . . .
 O2 O 1.1640(3) 0.0032(3) 0.94013(17) 0.0303(5) Uani 1 1 d . . . . .
 O3 O 0.7977(3) 0.0170(3) 0.73476(15) 0.0362(6) Uani 1 1 d . . . . .
 O4 O 0.7233(4) 0.2687(3) 0.89911(17) 0.0343(6) Uani 1 1 d . . . . .
 O5 O 0.8650(3) -0.2092(3) 0.84086(15) 0.0298(6) Uani 1 1 d . . . . .
 H3 H 0.583(4) -0.254(3) 0.880(2) 0.014(7) Uiso 1 1 d . . . . .
 H4 H 0.543(5) 0.019(4) 0.9734(19) 0.013(7) Uiso 1 1 d . . . . .
 H2 H 1.060(5) 0.191(4) 0.854(2) 0.026(8) Uiso 1 1 d . . . . .
 H5 H 1.068(5) -0.089(5) 0.759(3) 0.035(10) Uiso 1 1 d . . . . .
 H1 H 0.858(4) 0.158(4) 1.010(2) 0.019(7) Uiso 1 1 d . . . . .
 H6A H 0.549(5) -0.120(5) 0.726(3) 0.035(10) Uiso 1 1 d . . . . .
 H4A H 0.713(6) 0.347(5) 0.940(3) 0.040(11) Uiso 1 1 d . . . . .
 H1A H 0.733(8) -0.099(6) 1.089(4) 0.070(15) Uiso 1 1 d . . . . .
 H2A H 1.149(7) -0.103(6) 0.948(3) 0.075(16) Uiso 1 1 d . . . . .
 H6B H 0.530(6) 0.056(6) 0.789(3) 0.046(12) Uiso 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 C1 C2 1.543(4) . ?
 C1 C4 1.536(4) . ?
 C1 O4 1.424(3) . ?
 C2 C5 1.517(4) . ?
 C2 O2 1.424(4) . ?
 C3 C4 1.519(4) . ?
 C3 C6 1.514(4) . ?
 C3 O5 1.448(4) . ?
 C4 O1 1.433(4) . ?
 C5 O3 1.424(4) . ?
 C5 O5 1.406(4) . ?
 C6 O3 1.449(4) . ?

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
 C4 C1 C2 112.7(2) . . ?
 O4 C1 C2 107.8(2) . . ?
 O4 C1 C4 110.6(2) . . ?
 C5 C2 C1 111.3(3) . . ?
 O2 C2 C1 111.7(2) . . ?
 O2 C2 C5 110.0(2) . . ?
 C6 C3 C4 113.1(3) . . ?
 O5 C3 C4 109.2(2) . . ?
 O5 C3 C6 101.6(3) . . ?
 C3 C4 C1 111.7(2) . . ?
 O1 C4 C1 110.4(2) . . ?
 O1 C4 C3 106.3(2) . . ?
 O3 C5 C2 110.9(3) . . ?
 O5 C5 C2 109.7(2) . . ?
 O5 C5 O3 105.7(3) . . ?
 O3 C6 C3 103.4(3) . . ?
 C5 O3 C6 106.7(2) . . ?
 C5 O5 C3 101.8(2) . . ?

_olex2_submission_special_instructions  'No special instructions were received'


data_248K
_audit_creation_date               2020-09-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic
;
 ? 
;
_chemical_formula_moiety           'C6 H10 O5'
_chemical_formula_sum              'C6 H10 O5'
_chemical_formula_weight           162.14
_chemical_absolute_configuration   'C6 H10 O5'
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'orthorhombic'
_space_group_IT_number             19
_space_group_name_H-M_alt          'P 21 21 21'
_space_group_name_Hall             'P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'

_cell_length_a                     6.6601(17)
_cell_length_b                     7.5006(19)
_cell_length_c                     13.260(3)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       662.4(3)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      1456
_cell_measurement_temperature      246(2)
_cell_measurement_theta_max        24.39
_cell_measurement_theta_min        3.07
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.144
_exptl_absorpt_correction_T_max    0.7456
_exptl_absorpt_correction_T_min    0.6898
_exptl_absorpt_correction_type     'none'
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0556 before and 0.0457 after correction.
The Ratio of minimum to maximum transmission is 0.9252.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              ?
_exptl_crystal_density_diffrn      1.626
_exptl_crystal_density_meas        .
_exptl_crystal_density_method      'not measured'
_exptl_crystal_description         'block'
_exptl_crystal_F_000               344
_exptl_crystal_size_max            ?
_exptl_crystal_size_mid            ?
_exptl_crystal_size_min            ?
_exptl_special_details
;
 ? 
;
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0306
_diffrn_reflns_av_unetI/netI       0.0383
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  1.000
_diffrn_reflns_limit_h_max         8
_diffrn_reflns_limit_h_min         -7
_diffrn_reflns_limit_k_max         9
_diffrn_reflns_limit_k_min         -9
_diffrn_reflns_limit_l_max         9
_diffrn_reflns_limit_l_min         -17
_diffrn_reflns_number              4080
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  0.997
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           27.318
_diffrn_reflns_theta_min           3.072
_diffrn_ambient_temperature        246.15
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  1.000
_diffrn_measurement_device_type    'CCD area detector'
_diffrn_measurement_method         'phi and omega scans'
_diffrn_radiation_monochromator    'graphite'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.668
_reflns_Friedel_fraction_full      1.000
_reflns_Friedel_fraction_max       0.992
_reflns_number_gt                  1323
_reflns_number_total               1498
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max           0.166
_refine_diff_density_min           -0.146
_refine_diff_density_rms           0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 481 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -0.1(8)
_refine_ls_extinction_coef         0.085(8)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref     1.039
_refine_ls_hydrogen_treatment      refall
_refine_ls_matrix_type             full
_refine_ls_number_parameters       141
_refine_ls_number_reflns           1498
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0365
_refine_ls_R_factor_gt             0.0308
_refine_ls_restrained_S_all        1.039
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0294P)²+0.0643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0655
_refine_ls_wR_factor_ref           0.0683
_refine_special_details            ?
_olex2_refinement_description
;
;
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary       ?
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 C1 C -0.8236(3) -0.1245(3) -0.94621(16) 0.0183(4) Uani 1 1 d . . . . .
 C2 C -1.0061(3) -0.0750(3) -0.88108(16) 0.0197(5) Uani 1 1 d . . . . .
 C3 C -0.6661(3) 0.1487(3) -0.86725(17) 0.0224(5) Uani 1 1 d . . . . .
 C4 C -0.6773(3) 0.0331(3) -0.96043(16) 0.0198(5) Uani 1 1 d . . . . .
 C5 C -0.9505(4) 0.0556(3) -0.79837(17) 0.0239(5) Uani 1 1 d . . . . .
 C6 C -0.6076(4) 0.0450(4) -0.77337(19) 0.0286(6) Uani 1 1 d . . . . .
 O1 O -0.7449(3) 0.1455(2) -1.04075(12) 0.0243(4) Uani 1 1 d . . . . .
 O2 O -1.1656(2) -0.0029(2) -0.94007(13) 0.0246(4) Uani 1 1 d . . . . .
 O3 O -0.7980(2) -0.0177(2) -0.73485(11) 0.0299(4) Uani 1 1 d . . . . .
 O4 O -0.7238(3) -0.2705(2) -0.89885(13) 0.0276(4) Uani 1 1 d . . . . .
 O5 O -0.8652(2) 0.20953(19) -0.84095(12) 0.0245(4) Uani 1 1 d . . . . .
 H3 H -0.587(3) 0.255(3) -0.8789(17) 0.014(5) Uiso 1 1 d . . . . .
 H4 H -0.541(3) -0.016(3) -0.9731(16) 0.015(5) Uiso 1 1 d . . . . .
 H2 H -1.058(4) -0.191(3) -0.8509(19) 0.028(6) Uiso 1 1 d . . . . .
 H5 H -1.069(3) 0.089(3) -0.759(2) 0.027(7) Uiso 1 1 d . . . . .
 H1 H -0.869(3) -0.161(3) -1.0137(17) 0.016(6) Uiso 1 1 d . . . . .
 H6A H -0.544(4) 0.119(4) -0.724(2) 0.035(8) Uiso 1 1 d . . . . .
 H4A H -0.705(4) -0.352(4) -0.942(2) 0.036(7) Uiso 1 1 d . . . . .
 H1A H -0.707(5) 0.095(4) -1.094(3) 0.058(10) Uiso 1 1 d . . . . .
 H2A H -1.159(4) 0.103(4) -0.947(2) 0.043(9) Uiso 1 1 d . . . . .
 H6B H -0.518(4) -0.057(4) -0.7901(18) 0.029(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
 C1 C2 1.537(3) . ?
 C1 C4 1.543(3) . ?
 C1 O4 1.427(2) . ?
 C2 C5 1.517(3) . ?
 C2 O2 1.425(3) . ?
 C3 C4 1.511(3) . ?
 C3 C6 1.519(3) . ?
 C3 O5 1.445(3) . ?
 C4 O1 1.431(3) . ?
 C5 O3 1.430(3) . ?
 C5 O5 1.405(3) . ?
 C6 O3 1.445(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
 C2 C1 C4 112.51(17) . . ?
 O4 C1 C2 107.86(17) . . ?
 O4 C1 C4 110.35(16) . . ?
 C5 C2 C1 111.66(18) . . ?
 O2 C2 C1 111.88(17) . . ?
 O2 C2 C5 109.52(18) . . ?
 C4 C3 C6 112.91(19) . . ?
 O5 C3 C4 109.45(17) . . ?
 O5 C3 C6 101.48(18) . . ?
 C3 C4 C1 111.76(17) . . ?
 O1 C4 C1 110.11(17) . . ?
 O1 C4 C3 106.64(16) . . ?
 O3 C5 C2 110.6(2) . . ?
 O5 C5 C2 109.80(18) . . ?
 O5 C5 O3 105.40(17) . . ?
 O3 C6 C3 103.40(18) . . ?
 C5 O3 C6 106.84(16) . . ?
 C5 O5 C3 102.05(16) . . ?

_olex2_submission_special_instructions  'No special instructions were received'



data_198K
_audit_creation_date               2020-09-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic
;
 ? 
;
_chemical_formula_moiety           'C6 H10 O5'
_chemical_formula_sum              'C6 H10 O5'
_chemical_formula_weight           162.14
_chemical_absolute_configuration   'C6 H10 O5'
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'orthorhombic'
_space_group_IT_number             19
_space_group_name_H-M_alt          'P 21 21 21'
_space_group_name_Hall             'P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'

_cell_length_a                     6.6457(18)
_cell_length_b                     7.476(2)
_cell_length_c                     13.260(4)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       658.9(3)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      1460
_cell_measurement_temperature      198(2)
_cell_measurement_theta_max        24.40
_cell_measurement_theta_min        3.07
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.144
_exptl_absorpt_correction_T_max    0.7456
_exptl_absorpt_correction_T_min    0.6749
_exptl_absorpt_correction_type     'none'
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0602 before and 0.0473 after correction.
The Ratio of minimum to maximum transmission is 0.9052.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              ?
_exptl_crystal_density_diffrn      1.635
_exptl_crystal_density_meas        .
_exptl_crystal_density_method      'not measured'
_exptl_crystal_description         'block'
_exptl_crystal_F_000               344
_exptl_crystal_size_max            ?
_exptl_crystal_size_mid            ?
_exptl_crystal_size_min            ?
_exptl_special_details
;
 ? 
;
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0349
_diffrn_reflns_av_unetI/netI       0.0403
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.997
_diffrn_reflns_limit_h_max         8
_diffrn_reflns_limit_h_min         -7
_diffrn_reflns_limit_k_max         9
_diffrn_reflns_limit_k_min         -9
_diffrn_reflns_limit_l_max         9
_diffrn_reflns_limit_l_min         -17
_diffrn_reflns_number              3988
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.996
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           27.194
_diffrn_reflns_theta_min           3.072
_diffrn_ambient_temperature        197.65
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.997
_diffrn_measurement_device_type    'CCD area detector'
_diffrn_measurement_method         'phi and omega scans'
_diffrn_radiation_monochromator    'graphite'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.669
_reflns_Friedel_fraction_full      1.000
_reflns_Friedel_fraction_max       0.995
_reflns_number_gt                  1303
_reflns_number_total               1462
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max           0.253
_refine_diff_density_min           -0.186
_refine_diff_density_rms           0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 486 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -0.2(8)
_refine_ls_extinction_coef         0.149(13)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref     1.103
_refine_ls_hydrogen_treatment      refall
_refine_ls_matrix_type             full
_refine_ls_number_parameters       141
_refine_ls_number_reflns           1462
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0369
_refine_ls_R_factor_gt             0.0315
_refine_ls_restrained_S_all        1.103
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0374P)²+0.0030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0722
_refine_ls_wR_factor_ref           0.0751
_refine_special_details            ?
_olex2_refinement_description
;
;
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary       ?
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 C1 C 0.8239(3) 1.1255(3) 0.94603(17) 0.0151(5) Uani 1 1 d . . . . .
 C2 C 1.0075(3) 1.0752(3) 0.88107(17) 0.0155(5) Uani 1 1 d . . . . .
 C3 C 0.6662(3) 0.8514(3) 0.86716(18) 0.0181(5) Uani 1 1 d . . . . .
 C4 C 0.6778(3) 0.9678(3) 0.96059(17) 0.0158(5) Uani 1 1 d . . . . .
 C5 C 0.9504(4) 0.9444(3) 0.79833(18) 0.0193(5) Uani 1 1 d . . . . .
 C6 C 0.6071(4) 0.9559(4) 0.77347(19) 0.0229(6) Uani 1 1 d . . . . .
 O1 O 0.7455(3) 0.8550(2) 1.04093(13) 0.0196(4) Uani 1 1 d . . . . .
 O2 O 1.1669(2) 1.0026(2) 0.94016(13) 0.0195(4) Uani 1 1 d . . . . .
 O3 O 0.7984(2) 1.0181(2) 0.73489(12) 0.0235(4) Uani 1 1 d . . . . .
 O4 O 0.7246(3) 1.2721(2) 0.89861(13) 0.0214(4) Uani 1 1 d . . . . .
 O5 O 0.8652(2) 0.7903(2) 0.84094(12) 0.0192(4) Uani 1 1 d . . . . .
 H3 H 0.584(3) 0.746(3) 0.8775(18) 0.009(6) Uiso 1 1 d . . . . .
 H4 H 0.543(4) 1.020(3) 0.9745(17) 0.010(6) Uiso 1 1 d . . . . .
 H2 H 1.061(4) 1.190(3) 0.8504(18) 0.014(6) Uiso 1 1 d . . . . .
 H5 H 1.068(3) 0.910(3) 0.761(2) 0.018(7) Uiso 1 1 d . . . . .
 H1 H 0.870(4) 1.159(3) 1.0129(19) 0.014(6) Uiso 1 1 d . . . . .
 H6A H 0.543(4) 0.876(4) 0.728(2) 0.027(8) Uiso 1 1 d . . . . .
 H4A H 0.709(4) 1.356(4) 0.942(2) 0.021(7) Uiso 1 1 d . . . . .
 H1A H 0.711(5) 0.901(4) 1.090(3) 0.047(10) Uiso 1 1 d . . . . .
 H2A H 1.159(5) 0.890(5) 0.946(3) 0.052(10) Uiso 1 1 d . . . . .
 H6B H 0.523(4) 1.057(4) 0.7925(19) 0.025(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
 C1 C2 1.541(3) . ?
 C1 C4 1.539(3) . ?
 C1 O4 1.426(3) . ?
 C2 C5 1.518(3) . ?
 C2 O2 1.425(3) . ?
 C3 C4 1.516(3) . ?
 C3 C6 1.519(3) . ?
 C3 O5 1.441(3) . ?
 C4 O1 1.431(3) . ?
 C5 O3 1.426(3) . ?
 C5 O5 1.403(3) . ?
 C6 O3 1.447(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
 C4 C1 C2 112.51(18) . . ?
 O4 C1 C2 107.92(18) . . ?
 O4 C1 C4 110.63(17) . . ?
 C5 C2 C1 111.30(19) . . ?
 O2 C2 C1 111.99(18) . . ?
 O2 C2 C5 109.74(18) . . ?
 C4 C3 C6 112.70(19) . . ?
 O5 C3 C4 109.43(18) . . ?
 O5 C3 C6 101.71(19) . . ?
 C3 C4 C1 111.67(18) . . ?
 O1 C4 C1 110.28(17) . . ?
 O1 C4 C3 106.61(17) . . ?
 O3 C5 C2 110.8(2) . . ?
 O5 C5 C2 109.82(19) . . ?
 O5 C5 O3 105.59(18) . . ?
 O3 C6 C3 103.13(19) . . ?
 C5 O3 C6 106.85(17) . . ?
 C5 O5 C3 101.97(16) . . ?

_olex2_submission_special_instructions  'No special instructions were received'

