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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc21923k
_database_code_depnum_ccdc_archive 'CCDC 1885547'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/chem.202003367 2020
loop_
_audit_author_name
_audit_author_address
amala
;university of hyderabad
India
;
_audit_update_record             
;
2018-12-17 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H10 O6'
_chemical_formula_sum            'C11 H10 O6'
_chemical_formula_weight         238.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.1420(14)
_cell_length_b                   6.8138(8)
_cell_length_c                   13.6024(17)
_cell_angle_alpha                90
_cell_angle_beta                 102.714(4)
_cell_angle_gamma                90
_cell_volume                     1007.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    7547
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      26.56

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.130
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9744
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30428
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_av_R_equivalents  0.0888
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.671
_diffrn_reflns_theta_max         27.967
_diffrn_reflns_theta_full        25.242
_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 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2409
_reflns_number_gt                1799
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+0.4676P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2409
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
O3 O 0.42031(11) 0.69088(18) 0.52393(9) 0.0301(3) Uani 1 1 d . . . . .
O5 O 0.16899(12) 0.38052(19) 0.40134(10) 0.0354(3) Uani 1 1 d . . . . .
H5 H 0.1516 0.3257 0.3464 0.053 Uiso 1 1 calc R U . . .
O6 O 0.34613(12) 0.7377(2) 0.29429(9) 0.0358(3) Uani 1 1 d . . . . .
H6 H 0.3865 0.8085 0.3381 0.054 Uiso 1 1 calc R U . . .
O2 O 0.30785(13) 0.86752(19) 0.60689(10) 0.0396(4) Uani 1 1 d . . . . .
O1 O 0.36756(14) 0.4600(2) 0.69009(10) 0.0468(4) Uani 1 1 d . . . . .
O4 O 0.50625(15) 0.9424(2) 0.61866(12) 0.0563(5) Uani 1 1 d . . . . .
C5 C 0.30642(15) 0.5795(2) 0.51352(12) 0.0237(4) Uani 1 1 d . . . . .
C4 C 0.27136(16) 0.5054(2) 0.40503(12) 0.0249(4) Uani 1 1 d . . . . .
H4 H 0.3397 0.4279 0.3909 0.030 Uiso 1 1 calc R U . . .
C3 C 0.23949(16) 0.6682(2) 0.32623(13) 0.0286(4) Uani 1 1 d . . . . .
H3 H 0.1856 0.6091 0.2669 0.034 Uiso 1 1 calc R U . . .
C6A C 0.21872(17) 0.7346(3) 0.54070(13) 0.0294(4) Uani 1 1 d . . . . .
C11B C 0.33176(17) 0.4089(3) 0.58547(13) 0.0322(4) Uani 1 1 d . . . . .
H11B H 0.3739 0.2960 0.5637 0.039 Uiso 1 1 calc R U . . .
C7C C 0.41816(19) 0.8424(3) 0.58646(14) 0.0357(4) Uani 1 1 d . . . . .
C2D C 0.16834(18) 0.8326(3) 0.35921(15) 0.0361(4) Uani 1 1 d . . . . .
H2D H 0.1285 0.9205 0.3106 0.043 Uiso 1 1 calc R U . . .
C1E C 0.15891(18) 0.8601(3) 0.45284(15) 0.0361(4) Uani 1 1 d . . . . .
H1E H 0.1115 0.9655 0.4657 0.043 Uiso 1 1 calc R U . . .
C8F C 0.12805(19) 0.6611(3) 0.59817(15) 0.0409(5) Uani 1 1 d . . . . .
H8F H 0.0598 0.7383 0.6001 0.049 Uiso 1 1 calc R U . . .
C9G C 0.1403(2) 0.4927(3) 0.64603(15) 0.0439(5) Uani 1 1 d . . . . .
H9G H 0.0786 0.4522 0.6776 0.053 Uiso 1 1 calc R U . . .
C10H C 0.2480(2) 0.3663(3) 0.65146(15) 0.0419(5) Uani 1 1 d . . . . .
H10H H 0.2398 0.2286 0.6697 0.050 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C7C 1.341(2) . ?
O3 C5 1.458(2) . ?
O5 C4 1.415(2) . ?
O5 H5 0.8200 . ?
O6 C3 1.432(2) . ?
O6 H6 0.8200 . ?
O2 C7C 1.330(2) . ?
O2 C6A 1.491(2) . ?
O1 C11B 1.434(2) . ?
O1 C10H 1.466(3) . ?
O4 C7C 1.196(2) . ?
C5 C11B 1.506(2) . ?
C5 C4 1.527(2) . ?
C5 C6A 1.539(2) . ?
C4 C3 1.529(2) . ?
C4 H4 0.9800 . ?
C3 C2D 1.497(3) . ?
C3 H3 0.9800 . ?
C6A C8F 1.493(3) . ?
C6A C1E 1.501(3) . ?
C11B C10H 1.459(3) . ?
C11B H11B 0.9800 . ?
C2D C1E 1.314(3) . ?
C2D H2D 0.9300 . ?
C1E H1E 0.9300 . ?
C8F C9G 1.311(3) . ?
C8F H8F 0.9300 . ?
C9G C10H 1.466(3) . ?
C9G H9G 0.9300 . ?
C10H H10H 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7C O3 C5 108.99(14) . . ?
C4 O5 H5 109.5 . . ?
C3 O6 H6 109.5 . . ?
C7C O2 C6A 108.61(13) . . ?
C11B O1 C10H 60.40(12) . . ?
O3 C5 C11B 107.70(14) . . ?
O3 C5 C4 107.33(13) . . ?
C11B C5 C4 110.13(14) . . ?
O3 C5 C6A 101.80(13) . . ?
C11B C5 C6A 114.35(14) . . ?
C4 C5 C6A 114.73(14) . . ?
O5 C4 C5 105.43(13) . . ?
O5 C4 C3 110.51(14) . . ?
C5 C4 C3 114.09(13) . . ?
O5 C4 H4 108.9 . . ?
C5 C4 H4 108.9 . . ?
C3 C4 H4 108.9 . . ?
O6 C3 C2D 111.89(14) . . ?
O6 C3 C4 111.86(14) . . ?
C2D C3 C4 112.92(14) . . ?
O6 C3 H3 106.6 . . ?
C2D C3 H3 106.6 . . ?
C4 C3 H3 106.6 . . ?
O2 C6A C8F 108.96(15) . . ?
O2 C6A C1E 104.76(14) . . ?
C8F C6A C1E 112.02(16) . . ?
O2 C6A C5 100.86(14) . . ?
C8F C6A C5 115.73(16) . . ?
C1E C6A C5 113.21(15) . . ?
O1 C11B C10H 60.90(13) . . ?
O1 C11B C5 115.38(15) . . ?
C10H C11B C5 119.97(16) . . ?
O1 C11B H11B 116.3 . . ?
C10H C11B H11B 116.3 . . ?
C5 C11B H11B 116.3 . . ?
O4 C7C O2 124.90(19) . . ?
O4 C7C O3 122.9(2) . . ?
O2 C7C O3 112.20(15) . . ?
C1E C2D C3 123.89(17) . . ?
C1E C2D H2D 118.1 . . ?
C3 C2D H2D 118.1 . . ?
C2D C1E C6A 125.04(17) . . ?
C2D C1E H1E 117.5 . . ?
C6A C1E H1E 117.5 . . ?
C9G C8F C6A 122.98(19) . . ?
C9G C8F H8F 118.5 . . ?
C6A C8F H8F 118.5 . . ?
C8F C9G C10H 122.30(19) . . ?
C8F C9G H9G 118.8 . . ?
C10H C9G H9G 118.8 . . ?
C11B C10H C9G 118.64(18) . . ?
C11B C10H O1 58.70(12) . . ?
C9G C10H O1 115.52(18) . . ?
C11B C10H H10H 117.0 . . ?
C9G C10H H10H 117.0 . . ?
O1 C10H H10H 117.0 . . ?

_refine_diff_density_max         0.273
_refine_diff_density_min         -0.231
_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_13
_database_code_depnum_ccdc_archive 'CCDC 2164510'
loop_
_audit_author_name
_audit_author_address
'Ahmad Husain'
;DAV University Jalandhar
India
;
_audit_update_record             
;
2024-01-30 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;
_audit_creation_date             2024-01-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H12 O7'
_chemical_formula_sum            'C11 H12 O7'
_chemical_formula_weight         256.21
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   12.0789(3)
_cell_length_b                   10.0528(2)
_cell_length_c                   8.6569(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1051.17(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1693
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.7920
_cell_measurement_theta_min      3.9300
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94012
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2391
_diffrn_reflns_point_group_measured_fraction_full 0.716
_diffrn_reflns_point_group_measured_fraction_max 0.716
_diffrn_reflns_theta_full        25.022
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_min         3.373
_diffrn_ambient_temperature      298.00
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     39.00  76.00   1.00   15.25    --   19.64 178.00 -60.00   37
  2  ω    -36.00  -3.00   1.00   15.25    --   19.64 -57.00-120.00   33
  3  ω    -31.00  42.00   1.00   15.25    --   19.64 -77.00 -30.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0085464000
_diffrn_orient_matrix_UB_12      -0.0607702000
_diffrn_orient_matrix_UB_13      -0.0398686000
_diffrn_orient_matrix_UB_21      -0.0572542000
_diffrn_orient_matrix_UB_22      0.0146979000
_diffrn_orient_matrix_UB_23      -0.0062286000
_diffrn_orient_matrix_UB_31      0.0098519000
_diffrn_orient_matrix_UB_32      0.0327120000
_diffrn_orient_matrix_UB_33      -0.0713047000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.334
_reflns_Friedel_fraction_full    0.388
_reflns_Friedel_fraction_max     0.388
_reflns_number_gt                1261
_reflns_number_total             1329
_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       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43d (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 298 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1329
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.092
_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)+(0.0356P)²+0.2503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0723
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C7(H7), C8(H8), C2(H2A)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4A), C3(H3A), C6(H6), C5(H5)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1), O4(H4), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_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
O2 O 0.29122(15) 0.9462(2) 0.8608(3) 0.0331(5) Uani 1 1 d . . . . .
H2 H 0.302374 0.977942 0.946662 0.050 Uiso 1 1 calc R U . . .
O1 O 0.42912(15) 1.03424(18) 0.6108(3) 0.0280(5) Uani 1 1 d . . . . .
H1 H 0.489302 1.056518 0.646159 0.042 Uiso 1 1 calc R U . . .
O4 O 0.64568(15) 0.95988(18) 0.6479(3) 0.0278(5) Uani 1 1 d . . . . .
H4 H 0.688885 0.978698 0.717572 0.042 Uiso 1 1 calc R U . . .
O6 O 0.39918(17) 0.64971(19) 0.4489(3) 0.0304(5) Uani 1 1 d . . . . .
C11 C 0.4393(2) 0.7405(3) 0.3492(4) 0.0277(7) Uani 1 1 d . . . . .
C1 C 0.4095(2) 0.8982(3) 0.6448(4) 0.0232(6) Uani 1 1 d . . . . .
H1A H 0.342306 0.873289 0.588423 0.028 Uiso 1 1 calc R U . . .
O5 O 0.50958(15) 0.82617(19) 0.4199(2) 0.0255(5) Uani 1 1 d . . . . .
O7 O 0.41665(19) 0.7477(2) 0.2154(3) 0.0394(6) Uani 1 1 d . . . . .
C7 C 0.7020(2) 0.7333(3) 0.5874(4) 0.0278(7) Uani 1 1 d . . . . .
H7 H 0.719341 0.764542 0.482896 0.033 Uiso 1 1 calc R U . . .
C8 C 0.6145(2) 0.8236(3) 0.6605(4) 0.0234(6) Uani 1 1 d . . . . .
H8 H 0.608226 0.801078 0.770333 0.028 Uiso 1 1 calc R U . . .
C10 C 0.4625(2) 0.6599(3) 0.5959(4) 0.0256(6) Uani 1 1 d . . . . .
O3 O 0.79994(16) 0.7340(2) 0.6799(3) 0.0400(6) Uani 1 1 d . . . . .
H3 H 0.835384 0.801964 0.662573 0.060 Uiso 1 1 calc R U . . .
C4 C 0.3905(2) 0.6320(3) 0.7320(4) 0.0296(7) Uani 1 1 d . . . . .
H4A H 0.364892 0.545697 0.746559 0.036 Uiso 1 1 calc R U . . .
C2 C 0.3864(2) 0.8701(3) 0.8135(3) 0.0264(7) Uani 1 1 d . . . . .
H2A H 0.450746 0.894699 0.876230 0.032 Uiso 1 1 calc R U . . .
C3 C 0.3615(2) 0.7246(3) 0.8331(4) 0.0319(7) Uani 1 1 d . . . . .
H3A H 0.323467 0.698048 0.921242 0.038 Uiso 1 1 calc R U . . .
C9 C 0.5018(2) 0.8058(3) 0.5857(4) 0.0229(6) Uani 1 1 d . . . . .
C6 C 0.6604(2) 0.5939(3) 0.5811(5) 0.0348(7) Uani 1 1 d . . . . .
H6 H 0.712167 0.525686 0.574415 0.042 Uiso 1 1 calc R U . . .
C5 C 0.5550(2) 0.5612(3) 0.5845(4) 0.0310(7) Uani 1 1 d . . . . .
H5 H 0.536809 0.471389 0.579481 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 H2 0.8200 . ?
O2 C2 1.440(3) . ?
O1 H1 0.8200 . ?
O1 C1 1.419(3) . ?
O4 H4 0.8200 . ?
O4 C8 1.425(3) . ?
O6 C11 1.347(4) . ?
O6 C10 1.488(4) . ?
C11 O5 1.356(4) . ?
C11 O7 1.192(4) . ?
C1 H1A 0.9800 . ?
C1 C2 1.513(4) . ?
C1 C9 1.539(4) . ?
O5 C9 1.453(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.531(4) . ?
C7 O3 1.429(3) . ?
C7 C6 1.491(4) . ?
C8 H8 0.9800 . ?
C8 C9 1.518(4) . ?
C10 C4 1.490(5) . ?
C10 C9 1.544(4) . ?
C10 C5 1.498(4) . ?
O3 H3 0.8200 . ?
C4 H4A 0.9300 . ?
C4 C3 1.325(5) . ?
C2 H2A 0.9800 . ?
C2 C3 1.503(4) . ?
C3 H3A 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.315(4) . ?
C5 H5 0.9300 . ?

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 O2 H2 109.5 . . ?
C1 O1 H1 109.5 . . ?
C8 O4 H4 109.5 . . ?
C11 O6 C10 108.5(2) . . ?
O6 C11 O5 111.5(3) . . ?
O7 C11 O6 125.6(3) . . ?
O7 C11 O5 122.9(3) . . ?
O1 C1 H1A 106.3 . . ?
O1 C1 C2 114.3(2) . . ?
O1 C1 C9 113.1(2) . . ?
C2 C1 H1A 106.3 . . ?
C2 C1 C9 110.0(2) . . ?
C9 C1 H1A 106.3 . . ?
C11 O5 C9 108.4(2) . . ?
C8 C7 H7 109.8 . . ?
O3 C7 H7 109.8 . . ?
O3 C7 C8 109.7(3) . . ?
O3 C7 C6 107.7(2) . . ?
C6 C7 H7 109.8 . . ?
C6 C7 C8 109.8(2) . . ?
O4 C8 C7 110.8(2) . . ?
O4 C8 H8 108.5 . . ?
O4 C8 C9 108.5(2) . . ?
C7 C8 H8 108.5 . . ?
C9 C8 C7 111.9(2) . . ?
C9 C8 H8 108.5 . . ?
O6 C10 C4 111.3(2) . . ?
O6 C10 C9 100.1(2) . . ?
O6 C10 C5 106.3(2) . . ?
C4 C10 C9 113.8(2) . . ?
C4 C10 C5 111.2(3) . . ?
C5 C10 C9 113.3(2) . . ?
C7 O3 H3 109.5 . . ?
C10 C4 H4A 118.5 . . ?
C3 C4 C10 123.0(3) . . ?
C3 C4 H4A 118.5 . . ?
O2 C2 C1 108.9(2) . . ?
O2 C2 H2A 110.0 . . ?
O2 C2 C3 109.0(2) . . ?
C1 C2 H2A 110.0 . . ?
C3 C2 C1 109.1(2) . . ?
C3 C2 H2A 110.0 . . ?
C4 C3 C2 123.8(3) . . ?
C4 C3 H3A 118.1 . . ?
C2 C3 H3A 118.1 . . ?
C1 C9 C10 109.3(2) . . ?
O5 C9 C1 106.9(2) . . ?
O5 C9 C8 110.3(2) . . ?
O5 C9 C10 102.2(2) . . ?
C8 C9 C1 115.9(2) . . ?
C8 C9 C10 111.4(2) . . ?
C7 C6 H6 117.9 . . ?
C5 C6 C7 124.1(3) . . ?
C5 C6 H6 117.9 . . ?
C10 C5 H5 118.0 . . ?
C6 C5 C10 123.9(3) . . ?
C6 C5 H5 118.0 . . ?

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 O4 0.82 1.95 2.765(3) 170.1 2_675 yes
O1 H1 O4 0.82 2.12 2.739(3) 131.8 . yes
O4 H4 O2 0.82 1.91 2.717(3) 169.3 4_575 yes
O3 H3 O1 0.82 2.05 2.867(3) 176.8 4_575 yes

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
O2 C2 C3 C4 138.8(3) . . . . ?
O1 C1 C2 O2 58.4(3) . . . . ?
O1 C1 C2 C3 177.2(2) . . . . ?
O1 C1 C9 O5 -58.0(3) . . . . ?
O1 C1 C9 C8 65.3(3) . . . . ?
O1 C1 C9 C10 -167.9(2) . . . . ?
O4 C8 C9 C1 -54.0(3) . . . . ?
O4 C8 C9 O5 67.6(3) . . . . ?
O4 C8 C9 C10 -179.7(2) . . . . ?
O6 C11 O5 C9 -10.4(3) . . . . ?
O6 C10 C4 C3 -111.0(3) . . . . ?
O6 C10 C9 C1 83.6(3) . . . . ?
O6 C10 C9 O5 -29.4(2) . . . . ?
O6 C10 C9 C8 -147.1(2) . . . . ?
O6 C10 C5 C6 115.2(4) . . . . ?
C11 O6 C10 C4 145.6(2) . . . . ?
C11 O6 C10 C9 25.0(3) . . . . ?
C11 O6 C10 C5 -93.1(3) . . . . ?
C11 O5 C9 C1 -89.3(2) . . . . ?
C11 O5 C9 C8 144.0(2) . . . . ?
C11 O5 C9 C10 25.5(3) . . . . ?
C1 C2 C3 C4 20.1(4) . . . . ?
O7 C11 O5 C9 169.0(3) . . . . ?
C7 C8 C9 C1 -176.6(2) . . . . ?
C7 C8 C9 O5 -55.0(3) . . . . ?
C7 C8 C9 C10 57.7(3) . . . . ?
C7 C6 C5 C10 -0.3(6) . . . . ?
C8 C7 C6 C5 22.3(5) . . . . ?
C10 O6 C11 O5 -10.4(3) . . . . ?
C10 O6 C11 O7 170.1(3) . . . . ?
C10 C4 C3 C2 7.1(5) . . . . ?
O3 C7 C8 O4 70.1(3) . . . . ?
O3 C7 C8 C9 -168.7(2) . . . . ?
O3 C7 C6 C5 141.8(4) . . . . ?
C4 C10 C9 C1 -35.2(3) . . . . ?
C4 C10 C9 O5 -148.2(2) . . . . ?
C4 C10 C9 C8 94.1(3) . . . . ?
C4 C10 C5 C6 -123.5(4) . . . . ?
C2 C1 C9 O5 172.9(2) . . . . ?
C2 C1 C9 C8 -63.8(3) . . . . ?
C2 C1 C9 C10 63.0(3) . . . . ?
C9 C1 C2 O2 -173.2(2) . . . . ?
C9 C1 C2 C3 -54.4(3) . . . . ?
C9 C10 C4 C3 1.2(4) . . . . ?
C9 C10 C5 C6 6.2(5) . . . . ?
C6 C7 C8 O4 -171.7(3) . . . . ?
C6 C7 C8 C9 -50.4(4) . . . . ?
C5 C10 C4 C3 130.7(3) . . . . ?
C5 C10 C9 C1 -163.6(3) . . . . ?
C5 C10 C9 O5 83.4(3) . . . . ?
C5 C10 C9 C8 -34.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.166
_oxdiff_exptl_absorpt_empirical_full_min 0.895
####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 2164511'
loop_
_audit_author_name
_audit_author_address
'Ahmad Husain'
;DAV University Jalandhar
India
;
_audit_update_record             
;
2024-01-30 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;
_audit_creation_date             2024-01-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 O6, H2 O'
_chemical_formula_sum            'C11 H12 O7'
_chemical_formula_weight         256.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.5680(2)
_cell_length_b                   27.9778(8)
_cell_length_c                   12.4818(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.584(3)
_cell_angle_gamma                90
_cell_volume                     2291.30(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9649
_cell_measurement_temperature    295.5(2)
_cell_measurement_theta_max      26.7560
_cell_measurement_theta_min      2.1780
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20101
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.281
_diffrn_reflns_theta_min         2.188
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.5(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00  17.00   0.50   24.66    --  -15.60 -86.00  56.00  120
  2  ω     14.00  49.00   0.50   24.66    --   16.22 -86.00  56.00   70
  3  ω    -38.00   2.00   0.50   24.66    --   16.22 -86.00  56.00   80
  4  ω    -17.00  20.00   0.50   24.66    --  -15.60 -94.00 -30.00   74
  5  ω    -37.00  15.00   0.50   24.66    --  -15.60 -94.00 -60.00  104
  6  ω     28.00  53.00   0.50   24.66    --   16.22 -94.00 -90.00   50
  7  ω    -19.00   8.00   0.50   24.66    --  -15.60 -30.00 -60.00   54
  8  ω    -33.00  19.00   0.50   24.66    --   16.22 -94.00 -90.00  104
  9  ω    -36.00   9.00   0.50   24.66    --  -15.60 -94.00-150.00   90
 10  ω    -67.00 -33.00   0.50   24.66    --  -15.60 -30.00 -60.00   68
 11  ω    -85.00  -2.00   0.50   24.66    --  -15.60 -45.00 -60.00  166
 12  ω      3.00  89.00   0.50   24.66    --   16.22  30.00-150.00  172
 13  ω    -47.00   9.00   0.50   24.66    --  -15.60  86.00 174.00  112
 14  ω    -10.00  15.00   0.50   24.66    --   16.22  86.00 174.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0426118000
_diffrn_orient_matrix_UB_12      0.0095972000
_diffrn_orient_matrix_UB_13      -0.0465741000
_diffrn_orient_matrix_UB_21      -0.0364432000
_diffrn_orient_matrix_UB_22      -0.0199789000
_diffrn_orient_matrix_UB_23      -0.0301363000
_diffrn_orient_matrix_UB_31      -0.0924285000
_diffrn_orient_matrix_UB_32      0.0122994000
_diffrn_orient_matrix_UB_33      -0.0126270000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3398
_reflns_number_total             4879
_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       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         4879
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0668P)²+0.0191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1414
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O14(H14A,H14B), O13(H13A,H13B)
2.b Ternary CH refined with riding coordinates:
 C1(H1A), C19(H19), C12(H12), C8(H8), C2(H2A), C7(H7), C18(H18), C13(H13)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C15(H15), C6(H6), C3(H3), C14(H14), C16(H16), C17(H17)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O7(H7A), O2(H2), O8(H8A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
O4 O 0.68390(19) 0.64110(4) 0.22518(10) 0.0366(3) Uani 1 1 d . . . . .
O5 O 0.42929(18) 0.62160(4) 0.10881(10) 0.0389(3) Uani 1 1 d . . . . .
O11 O 0.1099(2) 0.65802(5) 0.72589(11) 0.0451(4) Uani 1 1 d . . . . .
O10 O 0.3649(2) 0.60659(4) 0.70522(11) 0.0439(4) Uani 1 1 d . . . . .
O1 O 0.8179(2) 0.65799(5) 0.00682(11) 0.0448(4) Uani 1 1 d . . . . .
H1 H 0.902967 0.677839 -0.009491 0.067 Uiso 1 1 calc R U . . .
O3 O 0.9935(2) 0.54574(5) 0.12394(11) 0.0465(4) Uani 1 1 d . . . . .
O9 O 0.6865(2) 0.70250(5) 0.61712(11) 0.0455(4) Uani 1 1 d . . . . .
O7 O 0.4826(2) 0.67508(6) 0.87541(10) 0.0497(4) Uani 1 1 d . . . . .
H7A H 0.558041 0.666858 0.926219 0.075 Uiso 1 1 calc R U . . .
O6 O 0.3975(2) 0.68483(5) 0.21653(12) 0.0527(4) Uani 1 1 d . . . . .
O2 O 0.8192(2) 0.54504(5) 0.39385(11) 0.0524(4) Uani 1 1 d . . . . .
H2 H 0.734997 0.566066 0.403417 0.079 Uiso 1 1 calc R U . . .
O8 O 0.5132(2) 0.60485(5) 0.44487(13) 0.0608(4) Uani 1 1 d . . . . .
H8A H 0.414991 0.590115 0.466182 0.091 Uiso 1 1 calc R U . . .
O14 O 0.1151(2) 0.71854(6) 0.96158(13) 0.0616(5) Uani 1 1 d G . . . .
H14A H 0.149291 0.738562 1.010535 0.092 Uiso 1 1 d G U . . .
H14B H 0.220658 0.709344 0.930489 0.092 Uiso 1 1 d G U . . .
O12 O 0.0727(3) 0.58151(6) 0.77234(16) 0.0812(6) Uani 1 1 d . . . . .
C9 C 0.7655(3) 0.60474(6) 0.15862(14) 0.0313(4) Uani 1 1 d . . . . .
C20 C 0.4502(3) 0.65266(6) 0.68663(14) 0.0345(4) Uani 1 1 d . . . . .
C11 C 0.4944(3) 0.65219(7) 0.18633(15) 0.0377(4) Uani 1 1 d . . . . .
C10 C 0.5737(3) 0.58154(6) 0.10689(15) 0.0335(4) Uani 1 1 d . . . . .
C21 C 0.2612(3) 0.68424(7) 0.66601(15) 0.0369(4) Uani 1 1 d . . . . .
C1 C 0.9096(3) 0.62412(6) 0.07744(15) 0.0379(4) Uani 1 1 d . . . . .
H1A H 1.030302 0.638019 0.114515 0.045 Uiso 1 1 calc R U . . .
O13 O 1.2106(3) 0.54514(8) 0.4894(2) 0.0988(7) Uani 1 1 d G . . . .
H13A H 1.088212 0.546450 0.464518 0.148 Uiso 1 1 d G U . . .
H13B H 1.222998 0.517171 0.515314 0.148 Uiso 1 1 d G U . . .
C19 C 0.5970(3) 0.65587(7) 0.59695(15) 0.0397(5) Uani 1 1 d . . . . .
H19 H 0.702492 0.631330 0.607554 0.048 Uiso 1 1 calc R U . . .
C12 C 0.5860(3) 0.67054(7) 0.77968(15) 0.0405(5) Uani 1 1 d . . . . .
H12 H 0.704326 0.649472 0.790758 0.049 Uiso 1 1 calc R U . . .
C4 C 0.5994(3) 0.56443(7) -0.00491(15) 0.0402(5) Uani 1 1 d . . . . .
H4 H 0.485870 0.557420 -0.049341 0.048 Uiso 1 1 calc R U . . .
C8 C 0.9047(3) 0.56838(7) 0.21430(15) 0.0386(5) Uani 1 1 d . . . . .
H8 H 1.011517 0.585134 0.256862 0.046 Uiso 1 1 calc R U . . .
C5 C 0.4886(3) 0.54231(7) 0.17324(15) 0.0393(5) Uani 1 1 d . . . . .
H5 H 0.353211 0.533593 0.159967 0.047 Uiso 1 1 calc R U . . .
C2 C 0.9634(3) 0.57612(7) 0.02853(16) 0.0426(5) Uani 1 1 d . . . . .
H2A H 1.087255 0.578164 -0.012156 0.051 Uiso 1 1 calc R U . . .
C15 C 0.2880(3) 0.73403(7) 0.70670(16) 0.0434(5) Uani 1 1 d . . . . .
H15 H 0.174755 0.753272 0.716149 0.052 Uiso 1 1 calc R U . . .
C22 C 0.1731(3) 0.61265(8) 0.73766(17) 0.0496(5) Uani 1 1 d . . . . .
C7 C 0.8084(3) 0.53092(7) 0.28335(15) 0.0428(5) Uani 1 1 d . . . . .
H7 H 0.888228 0.501517 0.277474 0.051 Uiso 1 1 calc R U . . .
C6 C 0.5946(3) 0.51947(7) 0.24927(16) 0.0458(5) Uani 1 1 d . . . . .
H6 H 0.531199 0.494489 0.283913 0.055 Uiso 1 1 calc R U . . .
C3 C 0.7844(3) 0.55932(7) -0.04026(16) 0.0441(5) Uani 1 1 d . . . . .
H3 H 0.803545 0.545509 -0.106831 0.053 Uiso 1 1 calc R U . . .
C18 C 0.5075(3) 0.65284(7) 0.48275(16) 0.0461(5) Uani 1 1 d . . . . .
H18 H 0.593946 0.672058 0.437438 0.055 Uiso 1 1 calc R U . . .
C13 C 0.6494(3) 0.71711(7) 0.72770(16) 0.0452(5) Uani 1 1 d . . . . .
H13 H 0.771549 0.730787 0.763748 0.054 Uiso 1 1 calc R U . . .
C14 C 0.4717(3) 0.75062(7) 0.72914(18) 0.0484(5) Uani 1 1 d . . . . .
H14 H 0.491361 0.782746 0.745719 0.058 Uiso 1 1 calc R U . . .
C16 C 0.1862(3) 0.68505(8) 0.55100(16) 0.0500(5) Uani 1 1 d . . . . .
H16 H 0.053283 0.695209 0.535629 0.060 Uiso 1 1 calc R U . . .
C17 C 0.2958(3) 0.67238(9) 0.47060(17) 0.0558(6) Uani 1 1 d . . . . .
H17 H 0.238302 0.675751 0.401558 0.067 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C9 1.4324(19) . ?
O4 C11 1.351(2) . ?
O5 C11 1.347(2) . ?
O5 C10 1.469(2) . ?
O11 C21 1.467(2) . ?
O11 C22 1.342(2) . ?
O10 C20 1.429(2) . ?
O10 C22 1.352(2) . ?
O1 H1 0.8200 . ?
O1 C1 1.411(2) . ?
O3 C8 1.440(2) . ?
O3 C2 1.469(2) . ?
O9 C19 1.448(2) . ?
O9 C13 1.470(2) . ?
O7 H7A 0.8200 . ?
O7 C12 1.407(2) . ?
O6 C11 1.184(2) . ?
O2 H2 0.8200 . ?
O2 C7 1.433(2) . ?
O8 H8A 0.8200 . ?
O8 C18 1.424(2) . ?
O14 H14A 0.8515 . ?
O14 H14B 0.8496 . ?
O12 C22 1.186(2) . ?
C9 C10 1.533(2) . ?
C9 C1 1.518(2) . ?
C9 C8 1.516(2) . ?
C20 C21 1.536(2) . ?
C20 C19 1.513(2) . ?
C20 C12 1.517(3) . ?
C10 C4 1.492(2) . ?
C10 C5 1.498(2) . ?
C21 C15 1.490(3) . ?
C21 C16 1.497(3) . ?
C1 H1A 0.9800 . ?
C1 C2 1.523(3) . ?
O13 H13A 0.8495 . ?
O13 H13B 0.8491 . ?
C19 H19 0.9800 . ?
C19 C18 1.520(3) . ?
C12 H12 0.9800 . ?
C12 C13 1.522(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.319(3) . ?
C8 H8 0.9800 . ?
C8 C7 1.513(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.317(3) . ?
C2 H2A 0.9800 . ?
C2 C3 1.500(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.311(3) . ?
C7 H7 0.9800 . ?
C7 C6 1.484(3) . ?
C6 H6 0.9300 . ?
C3 H3 0.9300 . ?
C18 H18 0.9800 . ?
C18 C17 1.495(3) . ?
C13 H13 0.9800 . ?
C13 C14 1.498(3) . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.310(3) . ?
C17 H17 0.9300 . ?

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
C11 O4 C9 108.51(14) . . ?
C11 O5 C10 108.18(14) . . ?
C22 O11 C21 108.40(14) . . ?
C22 O10 C20 108.26(14) . . ?
C1 O1 H1 109.5 . . ?
C8 O3 C2 109.64(14) . . ?
C19 O9 C13 109.29(13) . . ?
C12 O7 H7A 109.5 . . ?
C7 O2 H2 109.5 . . ?
C18 O8 H8A 109.5 . . ?
H14A O14 H14B 109.4 . . ?
O4 C9 C10 102.90(13) . . ?
O4 C9 C1 113.23(14) . . ?
O4 C9 C8 116.39(14) . . ?
C1 C9 C10 113.29(15) . . ?
C8 C9 C10 112.10(14) . . ?
C8 C9 C1 99.44(14) . . ?
O10 C20 C21 103.08(15) . . ?
O10 C20 C19 116.20(15) . . ?
O10 C20 C12 113.23(14) . . ?
C19 C20 C21 112.29(15) . . ?
C19 C20 C12 100.06(15) . . ?
C12 C20 C21 112.43(16) . . ?
O5 C11 O4 111.68(15) . . ?
O6 C11 O4 124.22(18) . . ?
O6 C11 O5 124.11(18) . . ?
O5 C10 C9 100.88(13) . . ?
O5 C10 C4 111.12(15) . . ?
O5 C10 C5 107.03(14) . . ?
C4 C10 C9 113.83(15) . . ?
C4 C10 C5 110.05(15) . . ?
C5 C10 C9 113.39(15) . . ?
O11 C21 C20 100.84(14) . . ?
O11 C21 C15 111.47(15) . . ?
O11 C21 C16 107.16(16) . . ?
C15 C21 C20 113.48(16) . . ?
C15 C21 C16 109.96(16) . . ?
C16 C21 C20 113.45(16) . . ?
O1 C1 C9 113.28(15) . . ?
O1 C1 H1A 110.0 . . ?
O1 C1 C2 116.23(16) . . ?
C9 C1 H1A 110.0 . . ?
C9 C1 C2 96.63(14) . . ?
C2 C1 H1A 110.0 . . ?
H13A O13 H13B 104.6 . . ?
O9 C19 C20 101.07(14) . . ?
O9 C19 H19 109.2 . . ?
O9 C19 C18 110.49(15) . . ?
C20 C19 H19 109.2 . . ?
C20 C19 C18 117.28(17) . . ?
C18 C19 H19 109.2 . . ?
O7 C12 C20 112.98(16) . . ?
O7 C12 H12 110.2 . . ?
O7 C12 C13 115.87(16) . . ?
C20 C12 H12 110.2 . . ?
C20 C12 C13 96.80(15) . . ?
C13 C12 H12 110.2 . . ?
C10 C4 H4 120.2 . . ?
C3 C4 C10 119.51(18) . . ?
C3 C4 H4 120.2 . . ?
O3 C8 C9 101.15(14) . . ?
O3 C8 H8 109.3 . . ?
O3 C8 C7 109.63(15) . . ?
C9 C8 H8 109.3 . . ?
C7 C8 C9 117.83(15) . . ?
C7 C8 H8 109.3 . . ?
C10 C5 H5 118.1 . . ?
C6 C5 C10 123.78(18) . . ?
C6 C5 H5 118.1 . . ?
O3 C2 C1 102.14(15) . . ?
O3 C2 H2A 111.7 . . ?
O3 C2 C3 110.86(16) . . ?
C1 C2 H2A 111.7 . . ?
C3 C2 C1 108.42(16) . . ?
C3 C2 H2A 111.7 . . ?
C21 C15 H15 120.1 . . ?
C14 C15 C21 119.81(18) . . ?
C14 C15 H15 120.1 . . ?
O11 C22 O10 111.95(17) . . ?
O12 C22 O11 124.1(2) . . ?
O12 C22 O10 123.9(2) . . ?
O2 C7 C8 110.69(16) . . ?
O2 C7 H7 107.4 . . ?
O2 C7 C6 109.92(16) . . ?
C8 C7 H7 107.4 . . ?
C6 C7 C8 113.63(16) . . ?
C6 C7 H7 107.4 . . ?
C5 C6 C7 124.36(19) . . ?
C5 C6 H6 117.8 . . ?
C7 C6 H6 117.8 . . ?
C4 C3 C2 118.98(18) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
O8 C18 C19 110.43(17) . . ?
O8 C18 H18 107.5 . . ?
O8 C18 C17 110.44(19) . . ?
C19 C18 H18 107.5 . . ?
C17 C18 C19 113.17(17) . . ?
C17 C18 H18 107.5 . . ?
O9 C13 C12 102.84(15) . . ?
O9 C13 H13 111.9 . . ?
O9 C13 C14 110.34(17) . . ?
C12 C13 H13 111.9 . . ?
C14 C13 C12 107.62(16) . . ?
C14 C13 H13 111.9 . . ?
C15 C14 C13 119.06(18) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C21 C16 H16 117.9 . . ?
C17 C16 C21 124.21(19) . . ?
C17 C16 H16 117.9 . . ?
C18 C17 H17 117.9 . . ?
C16 C17 C18 124.2(2) . . ?
C16 C17 H17 117.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O14 0.82 1.85 2.6644(19) 173.9 1_654 yes
O7 H7A O5 0.82 2.77 3.3076(18) 124.6 1_556 yes
O7 H7A O1 0.82 1.96 2.728(2) 156.3 1_556 yes
O2 H2 O4 0.82 3.07 3.5038(18) 116.0 . yes
O2 H2 O8 0.82 1.91 2.713(2) 167.6 . yes
O8 H8A O10 0.82 3.05 3.4345(19) 111.2 . yes
O8 H8A O13 0.82 1.87 2.674(2) 165.6 1_455 yes
C1 H1A O5 0.98 2.66 3.419(2) 134.0 1_655 yes
C1 H1A O6 0.98 2.98 3.958(2) 176.4 1_655 yes
O13 H13A O2 0.85 1.94 2.785(2) 173.4 . yes
C19 H19 O11 0.98 3.09 3.668(3) 119.1 1_655 yes
C12 H12 O11 0.98 2.83 3.552(2) 131.3 1_655 yes
C12 H12 O12 0.98 3.09 4.057(3) 167.6 1_655 yes
C5 H5 O3 0.93 2.41 3.284(2) 156.7 1_455 yes
C2 H2A O5 0.98 2.91 3.422(2) 113.2 1_655 yes
C2 H2A O12 0.98 2.69 3.312(3) 121.8 1_654 yes
C15 H15 O4 0.93 2.96 3.569(2) 124.6 4_576 yes
C15 H15 O6 0.93 2.51 3.431(2) 169.4 4_576 yes
C7 H7 O12 0.98 2.42 3.322(3) 152.6 3_666 yes
C6 H6 O10 0.93 2.91 3.580(2) 130.0 3_666 yes
C3 H3 O3 0.93 2.89 3.464(2) 120.9 3_765 yes
C3 H3 O12 0.93 2.58 3.137(3) 118.9 1_654 yes
C18 H18 O4 0.98 2.87 3.482(2) 121.0 . yes
C18 H18 O6 0.98 3.01 3.485(3) 111.0 . yes
C18 H18 O14 0.98 3.08 3.679(3) 120.9 4_675 yes
C13 H13 O6 0.98 2.58 3.198(2) 121.1 4_676 yes
C14 H14 O4 0.93 2.94 3.570(2) 126.4 4_576 yes
C14 H14 O6 0.93 2.86 3.339(3) 113.6 4_676 yes
C16 H16 O9 0.93 2.66 3.455(2) 143.2 1_455 yes
C17 H17 O6 0.93 2.59 3.289(3) 132.3 . yes

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
O4 C9 C10 O5 27.13(16) . . . . ?
O4 C9 C10 C4 146.22(15) . . . . ?
O4 C9 C10 C5 -86.96(16) . . . . ?
O4 C9 C1 O1 -59.3(2) . . . . ?
O4 C9 C1 C2 178.39(14) . . . . ?
O4 C9 C8 O3 -166.91(14) . . . . ?
O4 C9 C8 C7 73.7(2) . . . . ?
O5 C10 C4 C3 129.44(19) . . . . ?
O5 C10 C5 C6 -130.52(19) . . . . ?
O11 C21 C15 C14 130.50(19) . . . . ?
O11 C21 C16 C17 -129.0(2) . . . . ?
O10 C20 C21 O11 26.49(17) . . . . ?
O10 C20 C21 C15 145.80(14) . . . . ?
O10 C20 C21 C16 -87.75(18) . . . . ?
O10 C20 C19 O9 -167.24(14) . . . . ?
O10 C20 C19 C18 72.6(2) . . . . ?
O10 C20 C12 O7 -60.4(2) . . . . ?
O10 C20 C12 C13 177.77(15) . . . . ?
O1 C1 C2 O3 -163.35(14) . . . . ?
O1 C1 C2 C3 -46.2(2) . . . . ?
O3 C8 C7 O2 148.61(15) . . . . ?
O3 C8 C7 C6 -87.16(19) . . . . ?
O3 C2 C3 C4 69.3(2) . . . . ?
O9 C19 C18 O8 151.04(15) . . . . ?
O9 C19 C18 C17 -84.6(2) . . . . ?
O9 C13 C14 C15 70.2(2) . . . . ?
O7 C12 C13 O9 -161.61(15) . . . . ?
O7 C12 C13 C14 -45.1(2) . . . . ?
O2 C7 C6 C5 118.4(2) . . . . ?
O8 C18 C17 C16 115.8(3) . . . . ?
C9 O4 C11 O5 9.1(2) . . . . ?
C9 O4 C11 O6 -170.76(18) . . . . ?
C9 C10 C4 C3 16.4(3) . . . . ?
C9 C10 C5 C6 -20.2(3) . . . . ?
C9 C1 C2 O3 -43.29(17) . . . . ?
C9 C1 C2 C3 73.81(17) . . . . ?
C9 C8 C7 O2 -96.5(2) . . . . ?
C9 C8 C7 C6 27.7(2) . . . . ?
C20 O10 C22 O11 10.1(2) . . . . ?
C20 O10 C22 O12 -169.9(2) . . . . ?
C20 C21 C15 C14 17.5(3) . . . . ?
C20 C21 C16 C17 -18.6(3) . . . . ?
C20 C19 C18 O8 -93.9(2) . . . . ?
C20 C19 C18 C17 30.5(2) . . . . ?
C20 C12 C13 O9 -41.95(17) . . . . ?
C20 C12 C13 C14 74.57(18) . . . . ?
C11 O4 C9 C10 -23.06(17) . . . . ?
C11 O4 C9 C1 99.61(17) . . . . ?
C11 O4 C9 C8 -146.04(15) . . . . ?
C11 O5 C10 C9 -23.04(17) . . . . ?
C11 O5 C10 C4 -144.06(15) . . . . ?
C11 O5 C10 C5 95.76(16) . . . . ?
C10 O5 C11 O4 10.0(2) . . . . ?
C10 O5 C11 O6 -170.12(18) . . . . ?
C10 C9 C1 O1 57.4(2) . . . . ?
C10 C9 C1 C2 -64.91(17) . . . . ?
C10 C9 C8 O3 75.03(17) . . . . ?
C10 C9 C8 C7 -44.4(2) . . . . ?
C10 C4 C3 C2 -6.9(3) . . . . ?
C10 C5 C6 C7 3.2(3) . . . . ?
C21 O11 C22 O10 8.6(2) . . . . ?
C21 O11 C22 O12 -171.4(2) . . . . ?
C21 C20 C19 O9 74.45(18) . . . . ?
C21 C20 C19 C18 -45.7(2) . . . . ?
C21 C20 C12 O7 56.0(2) . . . . ?
C21 C20 C12 C13 -65.91(18) . . . . ?
C21 C15 C14 C13 -8.3(3) . . . . ?
C21 C16 C17 C18 3.4(4) . . . . ?
C1 C9 C10 O5 -95.49(16) . . . . ?
C1 C9 C10 C4 23.6(2) . . . . ?
C1 C9 C10 C5 150.42(15) . . . . ?
C1 C9 C8 O3 -44.98(16) . . . . ?
C1 C9 C8 C7 -164.41(16) . . . . ?
C1 C2 C3 C4 -42.0(2) . . . . ?
C19 O9 C13 C12 15.40(19) . . . . ?
C19 O9 C13 C14 -99.16(18) . . . . ?
C19 C20 C21 O11 152.29(15) . . . . ?
C19 C20 C21 C15 -88.4(2) . . . . ?
C19 C20 C21 C16 38.1(2) . . . . ?
C19 C20 C12 O7 175.30(15) . . . . ?
C19 C20 C12 C13 53.43(16) . . . . ?
C19 C18 C17 C16 -8.6(3) . . . . ?
C12 C20 C21 O11 -95.78(17) . . . . ?
C12 C20 C21 C15 23.5(2) . . . . ?
C12 C20 C21 C16 149.98(17) . . . . ?
C12 C20 C19 O9 -44.98(17) . . . . ?
C12 C20 C19 C18 -165.13(16) . . . . ?
C12 C13 C14 C15 -41.3(3) . . . . ?
C4 C10 C5 C6 108.6(2) . . . . ?
C8 O3 C2 C1 16.70(19) . . . . ?
C8 O3 C2 C3 -98.63(18) . . . . ?
C8 C9 C10 O5 152.94(14) . . . . ?
C8 C9 C10 C4 -87.97(19) . . . . ?
C8 C9 C10 C5 38.8(2) . . . . ?
C8 C9 C1 O1 176.52(15) . . . . ?
C8 C9 C1 C2 54.22(16) . . . . ?
C8 C7 C6 C5 -6.3(3) . . . . ?
C5 C10 C4 C3 -112.2(2) . . . . ?
C2 O3 C8 C9 17.48(18) . . . . ?
C2 O3 C8 C7 142.61(16) . . . . ?
C15 C21 C16 C17 109.7(2) . . . . ?
C22 O11 C21 C20 -21.73(19) . . . . ?
C22 O11 C21 C15 -142.48(17) . . . . ?
C22 O11 C21 C16 97.16(18) . . . . ?
C22 O10 C20 C21 -23.19(19) . . . . ?
C22 O10 C20 C19 -146.43(17) . . . . ?
C22 O10 C20 C12 98.54(19) . . . . ?
C13 O9 C19 C20 18.22(19) . . . . ?
C13 O9 C19 C18 143.08(16) . . . . ?
C16 C21 C15 C14 -110.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.990
_oxdiff_exptl_absorpt_empirical_full_min 0.350
####################################################################### 
# 
# 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_gm103_a
_audit_block_doi                 10.5517/ccdc.csd.cc2191fv
_database_code_depnum_ccdc_archive 'CCDC 1885526'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/chem.202003367 2020
loop_
_audit_author_name
_audit_author_address
'AMALESWARI RASAMSETTY'
;IIT Bombay
India
;
_audit_update_record             
;
2020-05-31 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;
_audit_creation_date             2020-05-12
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H12 O5'
_chemical_formula_sum            'C10 H12 O5'
_chemical_formula_weight         212.20
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.7437(12)
_cell_length_b                   6.9554(7)
_cell_length_c                   12.3782(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.629(4)
_cell_angle_gamma                90
_cell_volume                     924.01(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6824
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1306 before and 0.0424 after correction. The Ratio of minimum to maximum transmission is 0.9152. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15915
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.022
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_min         2.569
_diffrn_ambient_temperature      298.03
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1522
_reflns_number_total             1606
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1606
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.097
_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)+(0.0369P)²+0.4632P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0878
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C7(H7), C1(H1A), C2(H2A)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5A), C6(H6), C4(H4A), C3(H3)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O5(H5), O4(H4), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.59560(10) 0.04161(16) 0.38084(8) 0.0332(3) Uani 1 1 d . . . . .
H1 H 0.527224 -0.010485 0.382269 0.050 Uiso 1 1 calc GR . . . .
O5 O 0.80768(10) -0.05461(14) 0.50027(9) 0.0347(3) Uani 1 1 d . . . . .
H5 H 0.751530 -0.088387 0.457310 0.052 Uiso 1 1 calc GR . . . .
O4 O 0.63195(10) 0.12912(17) 0.62123(8) 0.0336(3) Uani 1 1 d . . . . .
H4 H 0.667162 0.163289 0.678198 0.050 Uiso 1 1 calc GR . . . .
O3 O 0.64742(10) 0.53900(15) 0.45228(9) 0.0358(3) Uani 1 1 d . . . . .
O2 O 0.80596(13) 0.68352(16) 0.66642(9) 0.0413(3) Uani 1 1 d . . . . .
H2 H 0.796096 0.785437 0.633852 0.062 Uiso 1 1 calc GR . . . .
C9 C 0.68145(12) 0.2321(2) 0.53408(10) 0.0222(3) Uani 1 1 d . . . . .
C10 C 0.81020(13) 0.15067(19) 0.50665(11) 0.0241(3) Uani 1 1 d . . . . .
C8 C 0.68998(13) 0.4506(2) 0.55297(11) 0.0265(3) Uani 1 1 d . . . . .
H8 H 0.630804 0.484361 0.607844 0.032 Uiso 1 1 calc R . . . .
C5 C 0.90241(13) 0.2046(2) 0.59650(12) 0.0302(3) Uani 1 1 d . . . . .
H5A H 0.959140 0.113633 0.623512 0.036 Uiso 1 1 calc R . . . .
C7 C 0.81857(14) 0.5306(2) 0.59041(11) 0.0271(3) Uani 1 1 d . . . . .
H7 H 0.857361 0.583889 0.526842 0.033 Uiso 1 1 calc R . . . .
C1 C 0.59183(12) 0.2210(2) 0.43513(11) 0.0267(3) Uani 1 1 d . . . . .
H1A H 0.506677 0.249248 0.455512 0.032 Uiso 1 1 calc R . . . .
C6 C 0.90368(14) 0.3797(2) 0.63745(12) 0.0305(3) Uani 1 1 d . . . . .
H6 H 0.957829 0.409290 0.695856 0.037 Uiso 1 1 calc R . . . .
C4 C 0.84749(13) 0.2345(2) 0.39992(12) 0.0298(3) Uani 1 1 d . . . . .
H4A H 0.927145 0.209385 0.377092 0.036 Uiso 1 1 calc R . . . .
C3 C 0.77226(15) 0.3415(2) 0.33781(12) 0.0336(4) Uani 1 1 d . . . . .
H3 H 0.799297 0.388498 0.272568 0.040 Uiso 1 1 calc R . . . .
C2 C 0.64328(14) 0.3879(2) 0.37181(12) 0.0322(4) Uani 1 1 d . . . . .
H2A H 0.587882 0.421536 0.309573 0.039 Uiso 1 1 calc R . . . .


_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 H1 0.8200 . ?
O1 C1 1.4186(18) . ?
O5 H5 0.8200 . ?
O5 C10 1.4302(17) . ?
O4 H4 0.8200 . ?
O4 C9 1.4186(16) . ?
O3 C8 1.4452(17) . ?
O3 C2 1.4473(19) . ?
O2 H2 0.8200 . ?
O2 C7 1.4305(17) . ?
C9 C10 1.5469(19) . ?
C9 C8 1.539(2) . ?
C9 C1 1.5248(18) . ?
C10 C5 1.503(2) . ?
C10 C4 1.515(2) . ?
C8 H8 0.9800 . ?
C8 C7 1.541(2) . ?
C5 H5A 0.9300 . ?
C5 C6 1.319(2) . ?
C7 H7 0.9800 . ?
C7 C6 1.493(2) . ?
C1 H1A 0.9800 . ?
C1 C2 1.519(2) . ?
C6 H6 0.9300 . ?
C4 H4A 0.9300 . ?
C4 C3 1.320(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.502(2) . ?
C2 H2A 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C10 O5 H5 109.5 . . ?
C9 O4 H4 109.5 . . ?
C8 O3 C2 106.44(10) . . ?
C7 O2 H2 109.5 . . ?
O4 C9 C10 110.62(11) . . ?
O4 C9 C8 113.87(11) . . ?
O4 C9 C1 109.89(11) . . ?
C8 C9 C10 110.32(11) . . ?
C1 C9 C10 110.07(11) . . ?
C1 C9 C8 101.72(11) . . ?
O5 C10 C9 111.28(11) . . ?
O5 C10 C5 107.47(11) . . ?
O5 C10 C4 109.95(12) . . ?
C5 C10 C9 108.17(11) . . ?
C5 C10 C4 110.96(12) . . ?
C4 C10 C9 108.99(11) . . ?
O3 C8 C9 105.95(11) . . ?
O3 C8 H8 107.8 . . ?
O3 C8 C7 110.45(12) . . ?
C9 C8 H8 107.8 . . ?
C9 C8 C7 116.65(11) . . ?
C7 C8 H8 107.8 . . ?
C10 C5 H5A 119.7 . . ?
C6 C5 C10 120.65(13) . . ?
C6 C5 H5A 119.7 . . ?
O2 C7 C8 110.84(12) . . ?
O2 C7 H7 107.7 . . ?
O2 C7 C6 109.94(12) . . ?
C8 C7 H7 107.7 . . ?
C6 C7 C8 112.83(12) . . ?
C6 C7 H7 107.7 . . ?
O1 C1 C9 113.24(12) . . ?
O1 C1 H1A 110.2 . . ?
O1 C1 C2 114.12(11) . . ?
C9 C1 H1A 110.2 . . ?
C2 C1 C9 98.30(11) . . ?
C2 C1 H1A 110.2 . . ?
C5 C6 C7 120.27(13) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C10 C4 H4A 118.5 . . ?
C3 C4 C10 123.08(13) . . ?
C3 C4 H4A 118.5 . . ?
C4 C3 H3 119.8 . . ?
C4 C3 C2 120.42(13) . . ?
C2 C3 H3 119.8 . . ?
O3 C2 C1 101.56(11) . . ?
O3 C2 C3 110.44(12) . . ?
O3 C2 H2A 111.5 . . ?
C1 C2 H2A 111.5 . . ?
C3 C2 C1 110.05(12) . . ?
C3 C2 H2A 111.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_shelx_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc21b19r
_database_code_depnum_ccdc_archive 'CCDC 1886483'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/chem.202003367 2020
loop_
_audit_author_name
_audit_author_address
'AMALA RASAMSETTY'
;universty of hyderabad
India
;
_audit_update_record             
;
2018-12-20 deposited with the CCDC.	2024-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 O8'
_chemical_formula_sum            'C11 H12 O8'
_chemical_formula_weight         272.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1276(8)
_cell_length_b                   7.5031(8)
_cell_length_c                   11.3065(13)
_cell_angle_alpha                98.614(6)
_cell_angle_beta                 105.390(7)
_cell_angle_gamma                105.364(7)
_cell_volume                     546.16(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4418
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      25.87

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.9787
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16328
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.075
_diffrn_reflns_theta_max         25.678
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.947
_reflns_number_total             1964
_reflns_number_gt                1451
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+1.2614P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1964
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0797
_refine_ls_wR_factor_ref         0.2305
_refine_ls_wR_factor_gt          0.2047
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_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
O001 O 0.4298(5) 0.4266(4) 0.1497(3) 0.0353(8) Uani 1 1 d . . . . .
O002 O 0.2984(5) 0.6403(4) 0.2208(3) 0.0354(8) Uani 1 1 d . . . . .
O003 O 0.7396(5) 0.3553(4) 0.3415(3) 0.0405(9) Uani 1 1 d . . . . .
H003 H 0.6498 0.2623 0.2910 0.061 Uiso 1 1 calc R U . . .
O004 O 0.4567(6) 1.0123(4) 0.1795(3) 0.0421(9) Uani 1 1 d . . . . .
H004 H 0.3838 1.0184 0.1116 0.063 Uiso 1 1 calc R U . . .
O005 O 0.7696(6) 1.0305(6) 0.0654(3) 0.0545(11) Uani 1 1 d . . . . .
H005 H 0.8783 1.1172 0.0845 0.082 Uiso 1 1 calc R U . . .
O006 O 0.0889(6) 0.3503(5) 0.1135(4) 0.0577(11) Uani 1 1 d . . . . .
O007 O 0.5108(6) 0.7699(5) 0.4775(3) 0.0514(10) Uani 1 1 d . . . . .
O008 O 1.0027(6) 0.7291(6) 0.4614(4) 0.0570(11) Uani 1 1 d . . . . .
H008 H 1.110(11) 0.703(11) 0.534(7) 0.085 Uiso 1 1 d . U . . .
C009 C 0.5168(6) 0.7429(6) 0.2559(4) 0.0247(9) Uani 1 1 d . . . . .
C00A C 0.6089(6) 0.5802(6) 0.2404(4) 0.0264(9) Uani 1 1 d . . . . .
C00B C 0.5427(7) 0.8630(6) 0.1595(4) 0.0291(10) Uani 1 1 d . . . . .
H00B H 0.4658 0.7818 0.0746 0.035 Uiso 1 1 calc R U . . .
C00C C 0.5865(7) 0.8640(6) 0.3885(4) 0.0330(10) Uani 1 1 d . . . . .
H00C H 0.5917 0.9972 0.3961 0.040 Uiso 1 1 calc R U . . .
C00D C 0.6577(7) 0.5060(6) 0.3608(4) 0.0307(10) Uani 1 1 d . . . . .
H00D H 0.5292 0.4563 0.3788 0.037 Uiso 1 1 calc R U . . .
C00E C 0.7665(7) 0.9414(7) 0.1681(4) 0.0360(11) Uani 1 1 d . . . . .
H00E H 0.8427 1.0360 0.2482 0.043 Uiso 1 1 calc R U . . .
C00F C 0.2595(8) 0.4640(7) 0.1580(5) 0.0372(11) Uani 1 1 d . . . . .
C00G C 0.7825(7) 0.6209(7) 0.1888(4) 0.0346(11) Uani 1 1 d . . . . .
H00G H 0.8427 0.5270 0.1757 0.041 Uiso 1 1 calc R U . . .
C00H C 0.8074(7) 0.6623(7) 0.4748(4) 0.0367(11) Uani 1 1 d . . . . .
H00H H 0.8212 0.6105 0.5501 0.044 Uiso 1 1 calc R U . . .
C00I C 0.8555(7) 0.7845(7) 0.1606(4) 0.0397(12) Uani 1 1 d . . . . .
H00I H 0.9708 0.8023 0.1343 0.048 Uiso 1 1 calc R U . . .
C00J C 0.7266(8) 0.8238(7) 0.4929(4) 0.0394(11) Uani 1 1 d . . . . .
H00J H 0.8150 0.9335 0.5623 0.047 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00F 1.340(6) . ?
O001 C00A 1.477(5) . ?
O002 C00F 1.323(6) . ?
O002 C009 1.456(5) . ?
O003 C00D 1.418(5) . ?
O003 H003 0.8200 . ?
O004 C00B 1.429(5) . ?
O004 H004 0.8200 . ?
O005 C00E 1.426(5) . ?
O005 H005 0.8200 . ?
O006 C00F 1.207(6) . ?
O007 C00J 1.437(6) . ?
O007 C00C 1.450(5) . ?
O008 C00H 1.407(6) . ?
O008 H008 1.05(8) . ?
C009 C00C 1.509(6) . ?
C009 C00B 1.532(5) . ?
C009 C00A 1.540(5) . ?
C00A C00G 1.484(6) . ?
C00A C00D 1.536(6) . ?
C00B C00E 1.517(6) . ?
C00B H00B 0.9800 . ?
C00C C00J 1.457(6) . ?
C00C H00C 0.9800 . ?
C00D C00H 1.527(7) . ?
C00D H00D 0.9800 . ?
C00E C00I 1.481(7) . ?
C00E H00E 0.9800 . ?
C00G C00I 1.321(7) . ?
C00G H00G 0.9300 . ?
C00H C00J 1.483(6) . ?
C00H H00H 0.9800 . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00F O001 C00A 108.1(3) . . ?
C00F O002 C009 109.6(3) . . ?
C00D O003 H003 109.5 . . ?
C00B O004 H004 109.5 . . ?
C00E O005 H005 109.5 . . ?
C00J O007 C00C 60.6(3) . . ?
C00H O008 H008 109(4) . . ?
O002 C009 C00C 108.3(3) . . ?
O002 C009 C00B 106.7(3) . . ?
C00C C009 C00B 112.1(3) . . ?
O002 C009 C00A 102.3(3) . . ?
C00C C009 C00A 115.0(3) . . ?
C00B C009 C00A 111.5(3) . . ?
O001 C00A C00G 110.5(3) . . ?
O001 C00A C00D 104.7(3) . . ?
C00G C00A C00D 112.8(3) . . ?
O001 C00A C009 101.1(3) . . ?
C00G C00A C009 114.5(3) . . ?
C00D C00A C009 112.1(3) . . ?
O004 C00B C00E 111.4(4) . . ?
O004 C00B C009 108.8(3) . . ?
C00E C00B C009 111.4(3) . . ?
O004 C00B H00B 108.4 . . ?
C00E C00B H00B 108.4 . . ?
C009 C00B H00B 108.4 . . ?
O007 C00C C00J 59.3(3) . . ?
O007 C00C C009 115.1(4) . . ?
C00J C00C C009 121.4(4) . . ?
O007 C00C H00C 116.2 . . ?
C00J C00C H00C 116.2 . . ?
C009 C00C H00C 116.2 . . ?
O003 C00D C00H 109.6(3) . . ?
O003 C00D C00A 110.1(3) . . ?
C00H C00D C00A 112.2(3) . . ?
O003 C00D H00D 108.3 . . ?
C00H C00D H00D 108.3 . . ?
C00A C00D H00D 108.3 . . ?
O005 C00E C00I 111.7(4) . . ?
O005 C00E C00B 106.5(3) . . ?
C00I C00E C00B 109.6(4) . . ?
O005 C00E H00E 109.7 . . ?
C00I C00E H00E 109.7 . . ?
C00B C00E H00E 109.7 . . ?
O006 C00F O002 123.4(4) . . ?
O006 C00F O001 124.1(4) . . ?
O002 C00F O001 112.6(4) . . ?
C00I C00G C00A 123.0(4) . . ?
C00I C00G H00G 118.5 . . ?
C00A C00G H00G 118.5 . . ?
O008 C00H C00J 109.1(4) . . ?
O008 C00H C00D 111.8(4) . . ?
C00J C00H C00D 110.0(4) . . ?
O008 C00H H00H 108.6 . . ?
C00J C00H H00H 108.6 . . ?
C00D C00H H00H 108.6 . . ?
C00G C00I C00E 124.5(4) . . ?
C00G C00I H00I 117.8 . . ?
C00E C00I H00I 117.8 . . ?
O007 C00J C00C 60.1(3) . . ?
O007 C00J C00H 114.8(4) . . ?
C00C C00J C00H 122.0(4) . . ?
O007 C00J H00J 116.0 . . ?
C00C C00J H00J 116.0 . . ?
C00H C00J H00J 116.0 . . ?

_refine_diff_density_max         0.953
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.091

