# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_20200911_tof-112
_database_code_depnum_ccdc_archive 'CCDC 2494192'
loop_
_audit_author_name
_audit_author_address
'Hanli Ruan'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2025-10-09 deposited with the CCDC.	2025-11-11 downloaded from the CCDC.
;
_audit_creation_date             2020-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 Cl2 O5'
_chemical_formula_sum            'C13 H12 Cl2 O5'
_chemical_formula_weight         319.13
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   9.4456(5)
_cell_length_b                   6.6650(3)
_cell_length_c                   10.5231(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.933(5)
_cell_angle_gamma                90
_cell_volume                     652.55(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3860
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.6160
_cell_measurement_theta_min      4.7340
_shelx_estimated_absorpt_T_max   0.801
_shelx_estimated_absorpt_T_min   0.336
_exptl_absorpt_coefficient_mu    4.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (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    1.624
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6109
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        65.933
_diffrn_reflns_theta_max         65.933
_diffrn_reflns_theta_min         4.265
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     41.00 104.00   0.50    0.50    --   95.20 -23.00 114.00  126
  2  ω    106.00 132.00   0.50    0.50    --   95.20  23.00 -80.00   52
  3  ω    135.00 162.00   0.50    0.50    --   95.20  23.00 -80.00   54
  4  ω     12.00  37.00   0.50    0.50    --   95.20 -23.00 114.00   50
  5  ω    -43.00  20.00   0.50    0.50    --    0.00 -57.00 -60.00  126
  6  ω    -28.00  31.00   0.50    0.50    --    0.00 -82.00   0.00  118
  7  ω    -19.00   6.00   0.50    0.50    --    0.00 -82.00-120.00   50
  8  ω      1.00  29.00   0.50    0.50    --    0.00 -82.00  60.00   56
  9  ω     12.00  37.00   0.50    0.50    --    0.00  23.00 -80.00   50
 10  ω    -59.00 -34.00   0.50    0.50    --    0.00 -23.00 114.00   50
 11  ω    -16.00  10.00   0.50    0.50    --    0.00  57.00-150.00   52
 12  ω    -89.00 -61.00   0.50    0.50    --    0.00 -57.00 -60.00   56
 13  ω    123.00 185.00   0.50    0.50    --   95.20  61.00  30.00  124
 14  ω    120.00 184.00   0.50    0.50    --   95.20  61.00  90.00  128
 15  ω     72.00  98.00   0.50    0.50    --   95.20  61.00  30.00   52
 16  ω     73.00  99.00   0.50    0.50    --   95.20  61.00   8.31   52
 17  ω     74.00 101.00   0.50    0.50    --   95.20  57.00 -27.96   54
 18  ω     36.00  91.00   0.50    0.50    --   95.20 -77.00  30.00  110
 19  ω      8.00 117.00   0.50    0.50    --   95.20 -61.00 -30.00  218
 20  ω     75.00 108.00   0.50    0.50    --   95.20  61.00  90.00   66
 21  ω     73.00  98.00   0.50    0.50    --   95.20  61.00   0.00   50
 22  ω     80.00 105.00   0.50    0.50    --   95.20  45.00   0.00   50
 23  ω    158.00 185.00   0.50    0.50    --   95.20  61.00  60.00   54
 24  ω     81.00 144.00   0.50    0.50    --   95.20  45.00  60.00  126
 25  ω    147.00 180.00   0.50    0.50    --   95.20  45.00  60.00   66
 26  ω    111.00 136.00   0.50    0.50    --   95.20  74.00  63.20   50
 27  ω     80.00 107.00   0.50    0.50    --   95.20  45.00 -30.00   54
 28  ω    124.00 159.00   0.50    0.50    --   95.20  45.00 -30.00   70
 29  ω     83.00 118.00   0.50    0.50    --   95.20  45.00  30.00   70
 30  ω     77.00 104.00   0.50    0.50    --   95.20  53.00   2.45   54
 31  ω     74.00 100.00   0.50    0.50    --   95.20  61.00 -60.00   52
 32  ω    119.00 144.00   0.50    0.50    --   95.20  61.00 -60.00   50
 33  ω     75.00 118.00   0.50    0.50    --   95.20 -82.00-120.00   86
 34  ω     67.00  93.00   0.50    0.50    --   95.20  74.00  63.20   52
 35  ω     73.00  98.00   0.50    0.50    --   95.20  61.00 -30.00   50
 36  ω     79.00 175.00   0.50    0.50    --   95.20  30.00   0.00  192
 37  ω     80.00 105.00   0.50    0.50    --   95.20  30.00 -30.00   50
 38  ω     33.00 107.00   0.50    0.50    --   95.20 -30.00 -60.00  148
 39  ω     72.00 103.00   0.50    0.50    --   95.20  61.00  60.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1551486000
_diffrn_orient_matrix_UB_12      0.0663748000
_diffrn_orient_matrix_UB_13      -0.0528369000
_diffrn_orient_matrix_UB_21      -0.0295198000
_diffrn_orient_matrix_UB_22      0.0203190000
_diffrn_orient_matrix_UB_23      0.1389163000
_diffrn_orient_matrix_UB_31      0.0495470000
_diffrn_orient_matrix_UB_32      0.2205146000
_diffrn_orient_matrix_UB_33      0.0030197000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1201
_reflns_number_total             1238
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1238
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0981
_refine_ls_restrained_S_all      1.206
_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)+(0.0260P)²+6.9787P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2145
_refine_ls_wR_factor_ref         0.2149
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H9A,H9B} of C9
 At 1.5 times of:
  All O(H) groups, {H12A,H12B} of C12
2. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3. Others
 Fixed Sof: H9A(0.5) H9B(0.5) H10(0.5) H12A(0.5) H4A(0.5) O5(0.5) H5A(0.5)
4.a Riding coordinates:
 C12(H12A,H12B)
4.b Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
4.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
4.d Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7)
4.e Idealised tetrahedral OH refined as rotating group:
 O4(H4A), O5(H5A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 -0.0516(9) 0.7500 1.0656(8) 0.0229(19) Uani 1 2 d S T P . .
C3 C 0.2062(9) 0.7500 1.0966(8) 0.0232(19) Uani 1 2 d S T P . .
C4 C 0.2074(9) 0.7500 0.9682(8) 0.0214(19) Uani 1 2 d S T P . .
H4 H 0.2966 0.7500 0.9379 0.026 Uiso 1 2 calc RS T P . .
C4A C 0.0746(9) 0.7500 0.8767(8) 0.0206(18) Uani 1 2 d S T P . .
C5 C 0.0733(10) 0.7500 0.7445(8) 0.0221(19) Uani 1 2 d S T P . .
H5 H 0.1603 0.7500 0.7106 0.027 Uiso 1 2 calc RS T P . .
C6 C -0.0607(9) 0.7500 0.6627(7) 0.0198(18) Uani 1 2 d S T P . .
C7 C -0.1891(9) 0.7500 0.7101(8) 0.0217(18) Uani 1 2 d S T P . .
H7 H -0.2782 0.7500 0.6522 0.026 Uiso 1 2 calc RS T P . .
C8 C -0.1870(9) 0.7500 0.8412(8) 0.0229(19) Uani 1 2 d S T P . .
C8A C -0.0530(10) 0.7500 0.9267(8) 0.0225(19) Uani 1 2 d S T P . .
C9 C 0.3312(9) 0.7500 1.2044(7) 0.0214(18) Uani 1 2 d S T P B .
H9A H 0.3238 0.6303 1.2586 0.026 Uiso 0.5 1 calc R . . . .
H9B H 0.3238 0.8697 1.2586 0.026 Uiso 0.5 1 calc R . . . .
C10 C 0.4782(10) 0.7500 1.1665(9) 0.032(2) Uani 1 2 d S T P . .
H10 H 0.4873 0.8729 1.1140 0.038 Uiso 0.5 1 calc R . . B .
C11 C 0.6006(10) 0.7500 1.2830(8) 0.033(2) Uani 1 2 d S T P B .
H11 H 0.6939 0.7500 1.2503 0.040 Uiso 1 2 calc RS T P . .
C12 C 0.0520(10) 0.7500 0.4747(8) 0.026(2) Uani 1 2 d S TU P . .
H12A H 0.0261 0.7354 0.3809 0.039 Uiso 0.5 1 d R . . A -1
H12B H 0.1138 0.6379 0.5099 0.039 Uiso 1 1 d R . . A -1
Cl1 Cl 0.5946(2) 0.5326(4) 1.3782(2) 0.0600(8) Uani 1 1 d . . . . .
O1 O -0.1567(6) 0.7500 1.1170(5) 0.0269(15) Uani 1 2 d S T P . .
O2 O 0.0796(6) 0.7500 1.1431(5) 0.0233(13) Uani 1 2 d S T P . .
O3 O -0.0767(6) 0.7500 0.5314(5) 0.0230(14) Uani 1 2 d S T P . .
O4 O -0.3151(6) 0.7500 0.8848(6) 0.0307(16) Uani 1 2 d S T P . .
H4A H -0.3026 0.7932 0.9609 0.046 Uiso 0.5 1 calc GR . . . .
O5 O 0.5030(9) 0.5778(18) 1.0920(8) 0.038(3) Uani 0.5 1 d . . . B -1
H5A H 0.4430 0.4880 1.1008 0.057 Uiso 0.5 1 calc GR . . B -1


_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 C8A 1.460(11) . ?
C1 O1 1.209(10) . ?
C1 O2 1.361(10) . ?
C3 C4 1.354(11) . ?
C3 C9 1.490(12) . ?
C3 O2 1.367(10) . ?
C4 H4 0.9500 . ?
C4 C4A 1.444(12) . ?
C4A C5 1.389(11) . ?
C4A C8A 1.396(12) . ?
C5 H5 0.9500 . ?
C5 C6 1.403(12) . ?
C6 C7 1.389(12) . ?
C6 O3 1.363(9) . ?
C7 H7 0.9500 . ?
C7 C8 1.376(11) . ?
C8 C8A 1.421(12) . ?
C8 O4 1.365(10) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.509(12) . ?
C10 H10 1.0000 . ?
C10 C11 1.534(11) . ?
C10 O5 1.432(11) . ?
C11 H11 1.0000 . ?
C11 Cl1 1.768(5) 4_575 ?
C11 Cl1 1.768(5) . ?
C12 H12A 0.9801 . ?
C12 H12B 0.9800 . ?
C12 O3 1.444(10) . ?
O4 H4A 0.8400 . ?
O5 H5A 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C8A 125.5(8) . . ?
O1 C1 O2 117.8(8) . . ?
O2 C1 C8A 116.7(7) . . ?
C4 C3 C9 128.2(8) . . ?
C4 C3 O2 121.0(8) . . ?
O2 C3 C9 110.8(7) . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C4A 120.6(8) . . ?
C4A C4 H4 119.7 . . ?
C5 C4A C4 121.6(8) . . ?
C5 C4A C8A 121.2(8) . . ?
C8A C4A C4 117.1(7) . . ?
C4A C5 H5 121.1 . . ?
C4A C5 C6 117.8(8) . . ?
C6 C5 H5 121.1 . . ?
C7 C6 C5 122.1(7) . . ?
O3 C6 C5 123.5(8) . . ?
O3 C6 C7 114.4(7) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.9(8) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C8A 119.4(8) . . ?
O4 C8 C7 118.4(8) . . ?
O4 C8 C8A 122.1(8) . . ?
C4A C8A C1 121.2(8) . . ?
C4A C8A C8 119.6(8) . . ?
C8 C8A C1 119.1(8) . . ?
C3 C9 H9A 108.2 . . ?
C3 C9 H9B 108.2 . . ?
C3 C9 C10 116.3(7) . . ?
H9A C9 H9B 107.4 . . ?
C10 C9 H9A 108.2 . . ?
C10 C9 H9B 108.2 . . ?
C9 C10 H10 108.5 . . ?
C9 C10 C11 112.9(7) . . ?
C11 C10 H10 108.5 . . ?
O5 C10 C9 113.0(6) . . ?
O5 C10 H10 108.5 . . ?
O5 C10 C11 105.4(6) . . ?
C10 C11 H11 108.2 . . ?
C10 C11 Cl1 111.1(4) . . ?
C10 C11 Cl1 111.1(4) . 4_575 ?
Cl1 C11 H11 108.2 . . ?
Cl1 C11 H11 108.2 4_575 . ?
Cl1 C11 Cl1 110.1(5) 4_575 . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12A 109.6 . . ?
O3 C12 H12B 109.4 . . ?
C1 O2 C3 123.3(7) . . ?
C6 O3 C12 117.7(6) . . ?
C8 O4 H4A 109.5 . . ?
C10 O5 H5A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C4 C4A C5 180.000(4) . . . . ?
C3 C4 C4A C8A 0.000(4) . . . . ?
C3 C9 C10 C11 180.000(4) . . . . ?
C3 C9 C10 O5 -60.5(6) . . . . ?
C4 C3 C9 C10 0.000(5) . . . . ?
C4 C3 O2 C1 0.000(5) . . . . ?
C4 C4A C5 C6 180.000(3) . . . . ?
C4 C4A C8A C1 0.000(4) . . . . ?
C4 C4A C8A C8 180.000(3) . . . . ?
C4A C5 C6 C7 0.000(3) . . . . ?
C4A C5 C6 O3 180.000(2) . . . . ?
C5 C4A C8A C1 180.000(3) . . . . ?
C5 C4A C8A C8 0.000(4) . . . . ?
C5 C6 C7 C8 0.000(3) . . . . ?
C5 C6 O3 C12 0.000(3) . . . . ?
C6 C7 C8 C8A 0.000(3) . . . . ?
C6 C7 C8 O4 180.000(2) . . . . ?
C7 C6 O3 C12 180.000(2) . . . . ?
C7 C8 C8A C1 180.000(3) . . . . ?
C7 C8 C8A C4A 0.000(4) . . . . ?
C8A C1 O2 C3 0.000(5) . . . . ?
C8A C4A C5 C6 0.000(4) . . . . ?
C9 C3 C4 C4A 180.000(4) . . . . ?
C9 C3 O2 C1 180.000(4) . . . . ?
C9 C10 C11 Cl1 61.4(4) . . . . ?
C9 C10 C11 Cl1 -61.4(4) . . . 4_575 ?
O1 C1 C8A C4A 180.000(4) . . . . ?
O1 C1 C8A C8 0.000(4) . . . . ?
O1 C1 O2 C3 180.000(4) . . . . ?
O2 C1 C8A C4A 0.000(4) . . . . ?
O2 C1 C8A C8 180.000(4) . . . . ?
O2 C3 C4 C4A 0.000(5) . . . . ?
O2 C3 C9 C10 180.000(4) . . . . ?
O3 C6 C7 C8 180.000(3) . . . . ?
O4 C8 C8A C1 0.000(4) . . . . ?
O4 C8 C8A C4A 180.000(3) . . . . ?
O5 C10 C11 Cl1 -62.3(9) . . . . ?
O5 C10 C11 Cl1 174.8(6) . . . 4_575 ?

_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 2.123
_oxdiff_exptl_absorpt_empirical_full_min 0.536
####################################################################### 
# 
# 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_20201127_tof-112-1
_database_code_depnum_ccdc_archive 'CCDC 2494193'
loop_
_audit_author_name
_audit_author_address
'Hanli Ruan'
;Huazhong University of Science and Technology
China
;
_audit_update_record             
;
2025-10-09 deposited with the CCDC.	2025-11-11 downloaded from the CCDC.
;
_audit_creation_date             2020-12-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 Cl2 O5'
_chemical_formula_sum            'C13 H12 Cl2 O5'
_chemical_formula_weight         319.13
_chemical_absolute_configuration ad
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.36335(3)
_cell_length_b                   25.31599(12)
_cell_length_c                   11.98481(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.0783(5)
_cell_angle_gamma                90
_cell_volume                     1323.002(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22005
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.6280
_cell_measurement_theta_min      3.4970
_shelx_estimated_absorpt_T_max   0.657
_shelx_estimated_absorpt_T_min   0.393
_exptl_absorpt_coefficient_mu    4.589
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.28b (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    1.602
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26037
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.030
_diffrn_reflns_theta_min         3.492
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  36.00   0.50    0.50    --   16.00  70.00  -9.29   90
  2  ω     45.00 101.00   0.50    0.50    --   16.00  70.00  -9.29  112
  3  ω      6.00  37.00   0.50    0.50    --   32.00  71.00-132.25   62
  4  ω    -46.00   2.00   0.50    0.50    --   40.00 -41.00-111.99   96
  5  ω      7.00  58.00   0.50    0.50    --   40.00 -41.00-111.99  102
  6  ω     28.00  58.00   0.50    0.50    --   44.00  73.00  -5.80   60
  7  ω     96.00 123.00   0.50    0.50    --   44.00  73.00  -5.80   54
  8  ω     31.00  58.00   0.50    0.50    --   52.00  74.00  60.96   54
  9  ω     36.00  62.00   0.50    0.50    --   56.00  74.00-141.55   52
 10  ω     31.00  71.00   0.50    0.50    --   56.00  74.00  11.74   80
 11  ω    123.00 149.00   0.50    0.50    --   60.00  75.00 -60.40   52
 12  ω     34.00  77.00   0.50    0.50    --   60.00  70.00 166.92   86
 13  ω     32.00  75.00   0.50    0.50    --   60.00  75.00 -60.40   86
 14  ω     40.00 102.00   0.50    0.50    --   64.00  72.00-177.39  124
 15  ω     39.00  64.00   0.50    0.50    --   64.00  75.00  82.39   50
 16  ω    117.00 153.00   0.50    0.50    --   68.00  74.00 -97.80   72
 17  ω     40.00  82.00   0.50    0.50    --   68.00  74.00 -97.80   84
 18  ω     45.00  77.00   0.50    0.50    --   72.00  75.00  98.22   64
 19  ω     48.00  78.00   0.50    0.50    --   76.00  75.00-120.84   60
 20  ω     48.00 109.00   0.50    0.50    --   76.00  74.00  83.65  122
 21  ω     70.00 130.00   0.50    0.50    --   94.60  65.00 113.74  120
 22  ω    115.00 184.00   0.50    0.50    --   94.60  75.00  -5.26  138
 23  ω    136.00 182.00   0.50    0.50    --   94.60  71.00 160.76   92
 24  ω     91.00 126.00   0.50    0.50    --   94.60 -82.00 -30.00   70
 25  ω     66.00 106.00   0.50    0.50    --   94.60  75.00  -5.26   80
 26  ω      5.00  88.00   0.50    0.50    --   94.60 -82.00 -30.00  166
 27  ω     26.00 126.00   0.50    0.50    --   94.60 -82.00 120.00  200
 28  ω     74.00 142.00   0.50    0.50    --   94.60  61.00  52.26  136
 29  ω    148.00 176.00   0.50    0.50    --   94.60  61.00  52.26   56
 30  ω    140.00 183.00   0.50    0.50    --   94.60  60.00 -94.93   86
 31  ω     67.00 128.00   0.50    0.50    --   94.60  71.00 160.76  122
 32  ω     80.00 126.00   0.50    0.50    --   94.60 -82.00-150.00   92
 33  ω     46.00  72.00   0.50    0.50    --   94.60 -82.00-150.00   52
 34  ω     71.00 136.00   0.50    0.50    --   94.60  60.00 -94.93  130
 35  ω     52.00 118.00   0.50    0.50    --   94.60 -82.00  60.00  132
 36  ω    150.00 184.00   0.50    0.50    --   94.60  55.00 -58.54   68
 37  ω     21.00  47.00   0.50    0.50    --   94.60 -82.00  60.00   52
 38  ω     67.00 125.00   0.50    0.50    --   94.60  71.00 -21.51  116
 39  ω     74.00 134.00   0.50    0.50    --   94.60  55.00 -58.54  120
 40  ω     84.00 109.00   0.50    0.50    --   94.60 -82.00 -90.00   50
 41  ω      5.00  74.00   0.50    0.50    --   94.60 -82.00 -90.00  138
 42  ω    129.00 155.00   0.50    0.50    --   94.60  56.00-132.32   52
 43  ω     71.00 182.00   0.50    0.50    --   94.60  61.00-150.00  222
 44  ω     75.00 101.00   0.50    0.50    --   94.60  61.00 -30.00   52
 45  ω    112.00 183.00   0.50    0.50    --   94.60  61.00 -30.00  142
 46  ω     78.00 152.00   0.50    0.50    --   94.60  61.00  60.00  148
 47  ω     67.00 113.00   0.50    0.50    --   94.60  72.00  21.45   92
 48  ω     71.00 175.00   0.50    0.50    --   94.60  61.00 150.00  208
 49  ω    135.00 168.00   0.50    0.50    --   94.60  65.00 113.74   66
 50  ω     76.00 122.00   0.50    0.50    --   94.60  56.00-132.32   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1120766000
_diffrn_orient_matrix_UB_12      0.0512140000
_diffrn_orient_matrix_UB_13      -0.0547434000
_diffrn_orient_matrix_UB_21      -0.0575472000
_diffrn_orient_matrix_UB_22      0.0305843000
_diffrn_orient_matrix_UB_23      0.1083641000
_diffrn_orient_matrix_UB_31      0.3300680000
_diffrn_orient_matrix_UB_32      -0.0120519000
_diffrn_orient_matrix_UB_33      0.0424769000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                5223
_reflns_number_total             5243
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 2470 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5243
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0192
_refine_ls_R_factor_gt           0.0191
_refine_ls_restrained_S_all      1.044
_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)+(0.0344P)²+0.2183P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0523
_refine_ls_wR_factor_ref         0.0523
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C10B(H10B), C11B(H11B)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C9B(H9BA,H9BB)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4A), C5(H5A), C7(H7), C4B(H4BA), C5B(H5BA), C7B(H7B)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C12B(H12D,H12E,H12F)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5), O4B(H4B), O5B(H5B)
;
_atom_sites_solution_hydrogens   geom
_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
Cl1 Cl 0.53960(14) 0.91651(2) 0.79130(4) 0.03122(14) Uani 1 1 d . . . . .
Cl2 Cl 0.59460(12) 0.94666(2) 0.55969(4) 0.02332(11) Uani 1 1 d . . . . .
O1 O -0.3606(4) 0.74651(6) 0.26669(12) 0.0213(3) Uani 1 1 d . . . . .
O2 O -0.0420(3) 0.78536(5) 0.38755(11) 0.0175(3) Uani 1 1 d . . . . .
O3 O 0.0766(3) 0.54814(6) 0.55560(12) 0.0202(3) Uani 1 1 d . . . . .
O4 O -0.4425(4) 0.64261(6) 0.27368(12) 0.0234(3) Uani 1 1 d . . . . .
H4 H -0.4769 0.6729 0.2523 0.035 Uiso 1 1 calc GR . . . .
O5 O 0.7017(3) 0.82776(6) 0.63401(12) 0.0203(3) Uani 1 1 d . . . . .
H5 H 0.7132 0.8065 0.6857 0.030 Uiso 1 1 calc GR . . . .
C1 C -0.1807(5) 0.74073(8) 0.34831(16) 0.0172(4) Uani 1 1 d . . . . .
C3 C 0.1614(4) 0.78461(8) 0.47971(16) 0.0167(4) Uani 1 1 d . . . . .
C4 C 0.2320(5) 0.73960(8) 0.53214(16) 0.0167(4) Uani 1 1 d . . . . .
H4A H 0.3709 0.7400 0.5929 0.020 Uiso 1 1 calc R . . . .
C4A C 0.0967(4) 0.69024(8) 0.49639(16) 0.0161(4) Uani 1 1 d . . . . .
C5 C 0.1634(5) 0.64272(8) 0.55015(16) 0.0171(4) Uani 1 1 d . . . . .
H5A H 0.2977 0.6419 0.6122 0.021 Uiso 1 1 calc R . . . .
C6 C 0.0269(5) 0.59629(8) 0.51015(16) 0.0171(4) Uani 1 1 d . . . . .
C7 C -0.1777(5) 0.59677(8) 0.41718(17) 0.0191(4) Uani 1 1 d . . . . .
H7 H -0.2672 0.5655 0.3918 0.023 Uiso 1 1 calc R . . . .
C8 C -0.2461(5) 0.64368(8) 0.36353(16) 0.0182(4) Uani 1 1 d . . . . .
C8A C -0.1096(4) 0.69150(8) 0.40231(16) 0.0161(4) Uani 1 1 d . . . . .
C9 C 0.2710(4) 0.83964(7) 0.50404(16) 0.0166(4) Uani 1 1 d . . . . .
H9A H 0.1015 0.8639 0.4909 0.020 Uiso 1 1 calc R . . . .
H9B H 0.4288 0.8486 0.4523 0.020 Uiso 1 1 calc R . . . .
C10 C 0.3997(4) 0.84746(8) 0.62306(16) 0.0162(4) Uani 1 1 d . . . . .
H10 H 0.2708 0.8279 0.6742 0.019 Uiso 1 1 calc R . . . .
C11 C 0.3890(5) 0.90615(8) 0.65336(17) 0.0197(4) Uani 1 1 d . . . . .
H11 H 0.1741 0.9174 0.6504 0.024 Uiso 1 1 calc R . . . .
C12 C 0.2742(5) 0.54518(8) 0.65383(18) 0.0219(4) Uani 1 1 d . . . . .
H12A H 0.4748 0.5577 0.6368 0.033 Uiso 1 1 calc GR . . . .
H12B H 0.2879 0.5092 0.6787 0.033 Uiso 1 1 calc GR . . . .
H12C H 0.1921 0.5666 0.7116 0.033 Uiso 1 1 calc GR . . . .
Cl1B Cl 0.18949(13) 0.92861(2) 0.28941(4) 0.02458(12) Uani 1 1 d . . . . .
Cl2B Cl 0.32809(11) 0.95336(2) 0.06095(4) 0.02070(11) Uani 1 1 d . . . . .
O1B O 0.6912(3) 0.74038(6) -0.22320(11) 0.0185(3) Uani 1 1 d . . . . .
O2B O 0.3953(3) 0.78183(5) -0.10675(11) 0.0161(3) Uani 1 1 d . . . . .
O3B O 0.2267(3) 0.54560(5) 0.05731(12) 0.0204(3) Uani 1 1 d . . . . .
O4B O 0.7488(3) 0.63660(6) -0.21540(12) 0.0200(3) Uani 1 1 d . . . . .
H4B H 0.7886 0.6666 -0.2361 0.030 Uiso 1 1 calc GR . . . .
O5B O 0.5056(3) 0.84360(5) 0.15227(12) 0.0180(3) Uani 1 1 d . . . . .
H5B H 0.5263 0.8171 0.1911 0.027 Uiso 1 1 calc GR . . . .
C1B C 0.5166(4) 0.73607(8) -0.14481(16) 0.0154(4) Uani 1 1 d . . . . .
C3B C 0.1964(4) 0.78262(8) -0.01906(16) 0.0155(4) Uani 1 1 d . . . . .
C4B C 0.1154(4) 0.73820(8) 0.03215(16) 0.0157(4) Uani 1 1 d . . . . .
H4BA H -0.0193 0.7398 0.0904 0.019 Uiso 1 1 calc R . . . .
C4C C 0.2344(4) 0.68775(8) -0.00184(16) 0.0147(4) Uani 1 1 d . . . . .
C5B C 0.1583(4) 0.64074(8) 0.05034(15) 0.0157(4) Uani 1 1 d . . . . .
H5BA H 0.0270 0.6408 0.1098 0.019 Uiso 1 1 calc R . . . .
C6B C 0.2818(5) 0.59354(8) 0.01213(16) 0.0167(4) Uani 1 1 d . . . . .
C7B C 0.4798(5) 0.59257(8) -0.07703(16) 0.0179(4) Uani 1 1 d . . . . .
H7B H 0.5595 0.5606 -0.1010 0.022 Uiso 1 1 calc R . . . .
C8B C 0.5569(4) 0.63898(8) -0.12934(16) 0.0163(4) Uani 1 1 d . . . . .
C8C C 0.4355(4) 0.68761(8) -0.09226(16) 0.0147(4) Uani 1 1 d . . . . .
C9B C 0.1027(4) 0.83804(7) 0.00723(16) 0.0161(4) Uani 1 1 d . . . . .
H9BA H -0.1173 0.8416 -0.0050 0.019 Uiso 1 1 calc R . . . .
H9BB H 0.2017 0.8623 -0.0428 0.019 Uiso 1 1 calc R . . . .
C10B C 0.1904(4) 0.85267(7) 0.12858(16) 0.0142(4) Uani 1 1 d . . . . .
H10B H 0.0704 0.8309 0.1786 0.017 Uiso 1 1 calc R . . . .
C11B C 0.1136(4) 0.91075(7) 0.14781(16) 0.0163(4) Uani 1 1 d . . . . .
H11B H -0.1052 0.9161 0.1302 0.020 Uiso 1 1 calc R . . . .
C12B C 0.0396(5) 0.54376(8) 0.15358(18) 0.0219(4) Uani 1 1 d . . . . .
H12D H -0.1609 0.5573 0.1342 0.033 Uiso 1 1 calc GR . . . .
H12E H 0.1321 0.5649 0.2122 0.033 Uiso 1 1 calc GR . . . .
H12F H 0.0227 0.5079 0.1786 0.033 Uiso 1 1 calc GR . . . .


_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
Cl1 C11 1.776(2) . ?
Cl2 C11 1.786(2) . ?
O1 C1 1.240(2) . ?
O2 C1 1.358(2) . ?
O2 C3 1.392(2) . ?
O3 C6 1.349(2) . ?
O3 C12 1.436(2) . ?
O4 C8 1.352(3) . ?
O5 C10 1.411(2) . ?
C1 C8A 1.433(3) . ?
C3 C4 1.332(3) . ?
C3 C9 1.498(3) . ?
C4 C4A 1.440(3) . ?
C4A C5 1.390(3) . ?
C4A C8A 1.418(3) . ?
C5 C6 1.395(3) . ?
C6 C7 1.402(3) . ?
C7 C8 1.378(3) . ?
C8 C8A 1.420(3) . ?
C9 C10 1.527(3) . ?
C10 C11 1.531(3) . ?
Cl1B C11B 1.776(2) . ?
Cl2B C11B 1.787(2) . ?
O1B C1B 1.236(2) . ?
O2B C1B 1.359(2) . ?
O2B C3B 1.387(2) . ?
O3B C6B 1.354(2) . ?
O3B C12B 1.438(3) . ?
O4B C8B 1.353(2) . ?
O5B C10B 1.413(2) . ?
C1B C8C 1.429(3) . ?
C3B C4B 1.335(3) . ?
C3B C9B 1.498(2) . ?
C4B C4C 1.443(3) . ?
C4C C5B 1.390(3) . ?
C4C C8C 1.419(3) . ?
C5B C6B 1.395(3) . ?
C6B C7B 1.398(3) . ?
C7B C8B 1.379(3) . ?
C8B C8C 1.418(3) . ?
C9B C10B 1.536(3) . ?
C10B C11B 1.527(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C3 121.81(15) . . ?
C6 O3 C12 117.46(15) . . ?
O1 C1 O2 115.88(18) . . ?
O1 C1 C8A 125.39(19) . . ?
O2 C1 C8A 118.73(17) . . ?
O2 C3 C9 109.37(16) . . ?
C4 C3 O2 121.06(18) . . ?
C4 C3 C9 129.57(18) . . ?
C3 C4 C4A 121.11(19) . . ?
C5 C4A C4 122.42(18) . . ?
C5 C4A C8A 120.29(18) . . ?
C8A C4A C4 117.29(18) . . ?
C4A C5 C6 119.35(18) . . ?
O3 C6 C5 124.21(18) . . ?
O3 C6 C7 114.63(17) . . ?
C5 C6 C7 121.16(18) . . ?
C8 C7 C6 119.93(18) . . ?
O4 C8 C7 118.33(18) . . ?
O4 C8 C8A 121.60(18) . . ?
C7 C8 C8A 120.06(18) . . ?
C4A C8A C1 119.98(18) . . ?
C4A C8A C8 119.20(18) . . ?
C8 C8A C1 120.81(18) . . ?
C3 C9 C10 113.98(16) . . ?
O5 C10 C9 110.59(16) . . ?
O5 C10 C11 110.94(16) . . ?
C9 C10 C11 109.53(15) . . ?
Cl1 C11 Cl2 108.85(11) . . ?
C10 C11 Cl1 110.53(14) . . ?
C10 C11 Cl2 112.83(14) . . ?
C1B O2B C3B 121.89(15) . . ?
C6B O3B C12B 117.66(16) . . ?
O1B C1B O2B 115.99(18) . . ?
O1B C1B C8C 125.45(18) . . ?
O2B C1B C8C 118.56(17) . . ?
O2B C3B C9B 110.84(16) . . ?
C4B C3B O2B 121.31(17) . . ?
C4B C3B C9B 127.84(18) . . ?
C3B C4B C4C 120.79(17) . . ?
C5B C4C C4B 122.44(17) . . ?
C5B C4C C8C 120.40(18) . . ?
C8C C4C C4B 117.16(17) . . ?
C4C C5B C6B 118.95(18) . . ?
O3B C6B C5B 124.06(18) . . ?
O3B C6B C7B 114.43(17) . . ?
C5B C6B C7B 121.50(18) . . ?
C8B C7B C6B 120.00(18) . . ?
O4B C8B C7B 118.44(18) . . ?
O4B C8B C8C 121.74(17) . . ?
C7B C8B C8C 119.82(18) . . ?
C4C C8C C1B 120.28(17) . . ?
C8B C8C C1B 120.39(18) . . ?
C8B C8C C4C 119.33(18) . . ?
C3B C9B C10B 111.38(16) . . ?
O5B C10B C9B 111.00(15) . . ?
O5B C10B C11B 110.08(15) . . ?
C11B C10B C9B 109.06(15) . . ?
Cl1B C11B Cl2B 108.64(10) . . ?
C10B C11B Cl1B 110.79(13) . . ?
C10B C11B Cl2B 111.77(13) . . ?

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
O4 H4 O1 0.82 1.94 2.656(2) 145.8 .
O5 H5 O1B 0.82 2.00 2.798(2) 163.1 1_556
O4B H4B O1B 0.82 1.92 2.641(2) 145.7 .
O5B H5B O1 0.82 2.06 2.8645(19) 169.0 1_655
C9B H9BA O5B 0.97 2.55 3.187(2) 123.6 1_455
C11B H11B O5B 0.98 2.52 3.153(2) 122.1 1_455

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C8A C4A -178.97(18) . . . . ?
O1 C1 C8A C8 0.4(3) . . . . ?
O2 C1 C8A C4A 1.4(3) . . . . ?
O2 C1 C8A C8 -179.25(17) . . . . ?
O2 C3 C4 C4A -1.0(3) . . . . ?
O2 C3 C9 C10 159.47(15) . . . . ?
O3 C6 C7 C8 -179.89(18) . . . . ?
O4 C8 C8A C1 1.2(3) . . . . ?
O4 C8 C8A C4A -179.46(17) . . . . ?
O5 C10 C11 Cl1 -57.30(18) . . . . ?
O5 C10 C11 Cl2 64.84(19) . . . . ?
C1 O2 C3 C4 1.1(3) . . . . ?
C1 O2 C3 C9 -178.86(16) . . . . ?
C3 O2 C1 O1 179.01(17) . . . . ?
C3 O2 C1 C8A -1.3(3) . . . . ?
C3 C4 C4A C5 -179.30(18) . . . . ?
C3 C4 C4A C8A 1.0(3) . . . . ?
C3 C9 C10 O5 79.0(2) . . . . ?
C3 C9 C10 C11 -158.42(16) . . . . ?
C4 C3 C9 C10 -20.5(3) . . . . ?
C4 C4A C5 C6 -179.21(18) . . . . ?
C4 C4A C8A C1 -1.2(3) . . . . ?
C4 C4A C8A C8 179.42(17) . . . . ?
C4A C5 C6 O3 179.69(18) . . . . ?
C4A C5 C6 C7 -0.4(3) . . . . ?
C5 C4A C8A C1 179.08(18) . . . . ?
C5 C4A C8A C8 -0.2(3) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 O4 179.50(18) . . . . ?
C6 C7 C8 C8A 0.0(3) . . . . ?
C7 C8 C8A C1 -179.30(19) . . . . ?
C7 C8 C8A C4A 0.0(3) . . . . ?
C8A C4A C5 C6 0.4(3) . . . . ?
C9 C3 C4 C4A 179.04(18) . . . . ?
C9 C10 C11 Cl1 -179.66(13) . . . . ?
C9 C10 C11 Cl2 -57.52(19) . . . . ?
C12 O3 C6 C5 2.4(3) . . . . ?
C12 O3 C6 C7 -177.54(17) . . . . ?
O1B C1B C8C C4C 179.32(18) . . . . ?
O1B C1B C8C C8B -0.2(3) . . . . ?
O2B C1B C8C C4C -0.5(3) . . . . ?
O2B C1B C8C C8B -179.97(17) . . . . ?
O2B C3B C4B C4C 0.4(3) . . . . ?
O2B C3B C9B C10B -121.13(17) . . . . ?
O3B C6B C7B C8B -179.24(17) . . . . ?
O4B C8B C8C C1B -0.7(3) . . . . ?
O4B C8B C8C C4C 179.80(17) . . . . ?
O5B C10B C11B Cl1B -61.51(18) . . . . ?
O5B C10B C11B Cl2B 59.81(18) . . . . ?
C1B O2B C3B C4B 0.1(3) . . . . ?
C1B O2B C3B C9B 178.88(16) . . . . ?
C3B O2B C1B O1B -179.88(16) . . . . ?
C3B O2B C1B C8C -0.1(3) . . . . ?
C3B C4B C4C C5B 179.21(18) . . . . ?
C3B C4B C4C C8C -0.9(3) . . . . ?
C3B C9B C10B O5B 54.0(2) . . . . ?
C3B C9B C10B C11B 175.40(15) . . . . ?
C4B C3B C9B C10B 57.5(3) . . . . ?
C4B C4C C5B C6B 179.69(18) . . . . ?
C4B C4C C8C C1B 0.9(3) . . . . ?
C4B C4C C8C C8B -179.57(17) . . . . ?
C4C C5B C6B O3B 179.18(18) . . . . ?
C4C C5B C6B C7B 0.1(3) . . . . ?
C5B C4C C8C C1B -179.17(17) . . . . ?
C5B C4C C8C C8B 0.3(3) . . . . ?
C5B C6B C7B C8B 0.0(3) . . . . ?
C6B C7B C8B O4B -179.94(17) . . . . ?
C6B C7B C8B C8C 0.2(3) . . . . ?
C7B C8B C8C C1B 179.19(18) . . . . ?
C7B C8B C8C C4C -0.3(3) . . . . ?
C8C C4C C5B C6B -0.2(3) . . . . ?
C9B C3B C4B C4C -178.15(18) . . . . ?
C9B C10B C11B Cl1B 176.49(13) . . . . ?
C9B C10B C11B Cl2B -62.20(18) . . . . ?
C12B O3B C6B C5B -2.8(3) . . . . ?
C12B O3B C6B C7B 176.43(17) . . . . ?

_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 1.796
_oxdiff_exptl_absorpt_empirical_full_min 0.711
