# Supplementary Information (SI) for CrystEngComm.
# 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_exp_2562
_database_code_depnum_ccdc_archive 'CCDC 2413045'
loop_
_audit_author_name
_audit_author_address
'H. H. Li'
;Fuzhou University
China
;
_audit_update_record             
;
2024-12-26 deposited with the CCDC.	2025-04-16 downloaded from the CCDC.
;
_audit_creation_date             2024-12-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H19 Cl3 O8'
_chemical_formula_sum            'C12 H19 Cl3 O8'
_chemical_formula_weight         397.62
_chemical_absolute_configuration rm
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.3167(6)
_cell_length_b                   12.0459(10)
_cell_length_c                   18.1855(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1602.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3774
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.0380
_cell_measurement_theta_min      3.1040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13282
_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            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1207
_diffrn_reflns_av_unetI/netI     0.0869
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12477
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.346
_diffrn_reflns_theta_min         2.028
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00 -30.00   0.50    8.39    --   -9.80  29.00-180.00   68
  2  ω    -44.00  28.00   0.50    8.39    --   -9.80  55.00 -90.00  144
  3  ω    -99.00  80.00   0.50    8.39    --   -9.80  55.00 -60.00  358
  4  ω    -97.00 -69.00   0.50    8.39    --   -9.80  55.00-150.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0898123000
_diffrn_orient_matrix_UB_12      -0.0063244000
_diffrn_orient_matrix_UB_13      -0.0141123000
_diffrn_orient_matrix_UB_21      -0.0218337000
_diffrn_orient_matrix_UB_22      0.0360055000
_diffrn_orient_matrix_UB_23      -0.0296068000
_diffrn_orient_matrix_UB_31      0.0292089000
_diffrn_orient_matrix_UB_32      0.0461883000
_diffrn_orient_matrix_UB_33      0.0210897000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.657
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.786
_reflns_number_gt                2883
_reflns_number_total             3738
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.570
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.131
_refine_ls_abs_structure_details 
;
 Flack x determined using 907 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3738
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0671
_refine_ls_restrained_S_all      1.120
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1591
_refine_ls_wR_factor_ref         0.1833
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H4), C11(H17), C6(H10), C10(H15), C3(H5), C5(H8), C9(H13), C4(H7)
2.b Secondary CH2 refined with riding coordinates:
 C1(H3,H2), C7(H12,H11), C12(H18,H19)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H6), O8(H14), O7(H16), O1(H1), O4(H9)
;
_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 0.8107(2) 1.03351(11) 0.35621(9) 0.0422(4) Uani 1 1 d . . . . .
Cl2 Cl 0.2273(2) 0.48116(13) 0.36434(10) 0.0451(4) Uani 1 1 d . . . . .
Cl3 Cl 0.6922(3) 0.33031(14) 0.55498(9) 0.0527(5) Uani 1 1 d . . . . .
O5 O 0.7066(5) 0.6405(3) 0.3637(2) 0.0260(7) Uani 1 1 d . . . . .
O2 O 0.5709(5) 0.8163(3) 0.3553(2) 0.0270(8) Uani 1 1 d . . . . .
O6 O 0.6147(5) 0.4903(3) 0.4238(2) 0.0285(8) Uani 1 1 d . . . . .
O3 O 1.1324(5) 0.8703(4) 0.3544(2) 0.0361(9) Uani 1 1 d . . . . .
H6 H 1.198811 0.867324 0.390725 0.054 Uiso 1 1 calc GR . . . .
O8 O 0.7412(7) 0.5283(3) 0.2407(2) 0.0401(10) Uani 1 1 d . . . . .
H14 H 0.784139 0.483584 0.211391 0.060 Uiso 1 1 calc GR . . . .
O7 O 0.6940(6) 0.2700(3) 0.2960(2) 0.0375(9) Uani 1 1 d . . . . .
H16 H 0.791043 0.243899 0.281581 0.056 Uiso 1 1 calc GR . . . .
O1 O 0.3524(5) 0.8694(3) 0.4778(2) 0.0387(10) Uani 1 1 d . . . . .
H1 H 0.275029 0.910581 0.495741 0.058 Uiso 1 1 calc GR . . . .
O4 O 0.9835(6) 0.7033(3) 0.2675(3) 0.0431(11) Uani 1 1 d . . . . .
H9 H 0.921002 0.650366 0.254378 0.065 Uiso 1 1 calc GR . . . .
C2 C 0.6479(8) 0.8561(4) 0.4234(3) 0.0272(11) Uani 1 1 d . . . . .
H4 H 0.663498 0.792802 0.456617 0.033 Uiso 1 1 calc R . . . .
C11 C 0.6467(8) 0.3734(4) 0.4078(3) 0.0278(11) Uani 1 1 d . . . . .
H17 H 0.530929 0.332501 0.408530 0.033 Uiso 1 1 calc R . . . .
C8 C 0.5821(7) 0.5501(4) 0.3579(3) 0.0247(10) Uani 1 1 d . . . . .
C6 C 0.6799(7) 0.7363(4) 0.3189(3) 0.0259(11) Uani 1 1 d . . . . .
H10 H 0.620602 0.714582 0.272750 0.031 Uiso 1 1 calc R . . . .
C1 C 0.5089(8) 0.9337(5) 0.4563(4) 0.0360(14) Uani 1 1 d . . . . .
H3 H 0.560313 0.971177 0.498676 0.043 Uiso 1 1 calc R . . . .
H2 H 0.473445 0.989362 0.420446 0.043 Uiso 1 1 calc R . . . .
C10 C 0.7266(7) 0.3738(4) 0.3303(3) 0.0285(11) Uani 1 1 d . . . . .
H15 H 0.858397 0.387740 0.332681 0.034 Uiso 1 1 calc R . . . .
C3 C 0.8341(8) 0.9093(4) 0.4106(3) 0.0288(11) Uani 1 1 d . . . . .
H5 H 0.887626 0.928897 0.458311 0.035 Uiso 1 1 calc R . . . .
C5 C 0.8707(7) 0.7833(4) 0.3023(3) 0.0284(11) Uani 1 1 d . . . . .
H8 H 0.856074 0.846034 0.268511 0.034 Uiso 1 1 calc R . . . .
C9 C 0.6316(7) 0.4712(4) 0.2929(3) 0.0289(11) Uani 1 1 d . . . . .
H13 H 0.519203 0.445302 0.269157 0.035 Uiso 1 1 calc R . . . .
C4 C 0.9592(7) 0.8263(5) 0.3720(3) 0.0294(12) Uani 1 1 d . . . . .
H7 H 0.977575 0.763127 0.405190 0.035 Uiso 1 1 calc R . . . .
C7 C 0.3852(7) 0.5937(4) 0.3577(3) 0.0309(12) Uani 1 1 d . . . . .
H12 H 0.362851 0.634725 0.312646 0.037 Uiso 1 1 calc R . . . .
H11 H 0.367745 0.643863 0.398782 0.037 Uiso 1 1 calc R . . . .
C12 C 0.7771(9) 0.3249(5) 0.4626(3) 0.0364(13) Uani 1 1 d . . . . .
H18 H 0.891869 0.365024 0.460063 0.044 Uiso 1 1 calc R . . . .
H19 H 0.801212 0.248193 0.449582 0.044 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
Cl1 C3 1.802(5) . ?
Cl2 C7 1.785(5) . ?
Cl3 C12 1.793(6) . ?
O5 C8 1.424(6) . ?
O5 C6 1.426(6) . ?
O2 C2 1.442(6) . ?
O2 C6 1.415(6) . ?
O6 C11 1.457(6) . ?
O6 C8 1.419(6) . ?
O3 C4 1.410(6) . ?
O8 C9 1.420(7) . ?
O7 C10 1.417(6) . ?
O1 C1 1.436(7) . ?
O4 C5 1.418(6) . ?
C2 C1 1.505(8) . ?
C2 C3 1.524(8) . ?
C11 C10 1.526(8) . ?
C11 C12 1.498(8) . ?
C8 C9 1.558(7) . ?
C8 C7 1.533(7) . ?
C6 C5 1.536(7) . ?
C10 C9 1.524(8) . ?
C3 C4 1.527(8) . ?
C5 C4 1.515(8) . ?

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
C8 O5 C6 119.3(4) . . ?
C6 O2 C2 114.1(4) . . ?
C8 O6 C11 110.4(4) . . ?
O2 C2 C1 106.5(4) . . ?
O2 C2 C3 111.0(4) . . ?
C1 C2 C3 113.8(4) . . ?
O6 C11 C10 104.1(4) . . ?
O6 C11 C12 110.3(4) . . ?
C12 C11 C10 111.8(5) . . ?
O5 C8 C9 111.9(4) . . ?
O5 C8 C7 109.8(4) . . ?
O6 C8 O5 102.6(4) . . ?
O6 C8 C9 107.0(4) . . ?
O6 C8 C7 109.5(4) . . ?
C7 C8 C9 115.2(4) . . ?
O5 C6 C5 106.6(4) . . ?
O2 C6 O5 111.2(4) . . ?
O2 C6 C5 110.7(4) . . ?
O1 C1 C2 108.2(5) . . ?
O7 C10 C11 109.8(4) . . ?
O7 C10 C9 114.0(4) . . ?
C9 C10 C11 103.8(4) . . ?
C2 C3 Cl1 110.3(4) . . ?
C2 C3 C4 109.3(4) . . ?
C4 C3 Cl1 110.4(4) . . ?
O4 C5 C6 111.5(4) . . ?
O4 C5 C4 110.9(5) . . ?
C4 C5 C6 110.5(4) . . ?
O8 C9 C8 110.1(4) . . ?
O8 C9 C10 114.4(5) . . ?
C10 C9 C8 103.7(4) . . ?
O3 C4 C3 113.4(5) . . ?
O3 C4 C5 108.8(5) . . ?
C5 C4 C3 110.6(4) . . ?
C8 C7 Cl2 110.3(4) . . ?
C11 C12 Cl3 112.9(4) . . ?

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
O3 H6 O1 0.82 1.94 2.761(6) 176.6 1_655 yes
O8 H14 O3 0.82 1.92 2.733(5) 174.9 3_745 yes
O7 H16 O4 0.82 1.94 2.748(5) 168.9 3_745 yes
O4 H9 O8 0.82 1.99 2.797(6) 168.6 . yes

_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 4.696
_oxdiff_exptl_absorpt_empirical_full_min 0.437
####################################################################### 
# 
# 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_guisuan2
_database_code_depnum_ccdc_archive 'CCDC 2413049'
loop_
_audit_author_name
_audit_author_address
'H. H. Li'
;Fuzhou University
China
;
_audit_update_record             
;
2024-12-26 deposited with the CCDC.	2025-04-16 downloaded from the CCDC.
;
_audit_creation_date             2024-12-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H19 Cl3 O8'
_chemical_formula_sum            'C12 H19 Cl3 O8'
_chemical_formula_weight         397.62
_chemical_absolute_configuration ?
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.2843(6)
_cell_length_b                   12.0048(8)
_cell_length_c                   18.0766(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1580.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5017
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8960
_cell_measurement_theta_min      2.8330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.618
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60800
_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            ?
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9331
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.793
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.484
_diffrn_reflns_theta_min         2.036
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.835
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00   9.00   0.50    3.41    --   -9.60  36.00 -15.00   52
  2  ω    -70.00 -14.00   0.50    3.41    --   -9.60  55.00 -60.00  112
  3  ω    -74.00  80.00   0.50    3.41    --   -9.60  55.00-180.00  308
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0151392000
_diffrn_orient_matrix_UB_12      0.0466994000
_diffrn_orient_matrix_UB_13      -0.0232266000
_diffrn_orient_matrix_UB_21      0.0552680000
_diffrn_orient_matrix_UB_22      0.0248484000
_diffrn_orient_matrix_UB_23      0.0277843000
_diffrn_orient_matrix_UB_31      0.0786697000
_diffrn_orient_matrix_UB_32      -0.0263965000
_diffrn_orient_matrix_UB_33      -0.0150949000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.662
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.738
_reflns_number_gt                3183
_reflns_number_total             3488
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details 
;
 Flack x determined using 1196 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.804
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3488
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      0.804
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.1039
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H17), C2(H4), C3(H5), C10(H15), C6(H10), C4(H7), C9(H13), C5(H8)
2.b Secondary CH2 refined with riding coordinates:
 C1(H3,H2), C12(H18,H19), C7(H12,H11)
2.c Idealised tetrahedral OH refined as rotating group:
 O8(H14), O3(H6), O4(H9), O1(H1), O7(H16)
;
_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 0.81095(12) -0.03484(6) 0.64383(4) 0.02230(19) Uani 1 1 d . . . . .
Cl2 Cl 0.22594(11) 0.51994(7) 0.63613(5) 0.0241(2) Uani 1 1 d . . . . .
Cl3 Cl 0.69080(13) 0.66985(7) 0.44396(4) 0.0275(2) Uani 1 1 d . . . . .
O5 O 0.7059(3) 0.35937(16) 0.63644(11) 0.0130(4) Uani 1 1 d . . . . .
O6 O 0.6141(3) 0.51012(16) 0.57583(10) 0.0143(4) Uani 1 1 d . . . . .
O2 O 0.5703(3) 0.18292(16) 0.64460(11) 0.0135(4) Uani 1 1 d . . . . .
O8 O 0.7414(3) 0.47169(17) 0.75939(12) 0.0211(5) Uani 1 1 d . . . . .
H14 H 0.782680 0.516001 0.789639 0.032 Uiso 1 1 calc GR . . . .
O3 O 1.1333(3) 0.13029(19) 0.64547(12) 0.0188(5) Uani 1 1 d . . . . .
H6 H 1.199903 0.132316 0.608914 0.028 Uiso 1 1 calc GR . . . .
O4 O 0.9834(3) 0.29688(19) 0.73251(13) 0.0233(5) Uani 1 1 d . . . . .
H9 H 0.923586 0.353408 0.740676 0.035 Uiso 1 1 calc GR . . . .
O1 O 0.3499(3) 0.12954(19) 0.52189(12) 0.0202(5) Uani 1 1 d . . . . .
H1 H 0.291617 0.095672 0.490252 0.030 Uiso 1 1 calc GR . . . .
O7 O 0.6935(3) 0.73113(17) 0.70427(12) 0.0192(5) Uani 1 1 d . . . . .
H16 H 0.787485 0.751972 0.725078 0.029 Uiso 1 1 calc GR . . . .
C11 C 0.6453(4) 0.6266(2) 0.59195(16) 0.0143(6) Uani 1 1 d . . . . .
H17 H 0.528628 0.667272 0.591183 0.017 Uiso 1 1 calc R . . . .
C2 C 0.6472(4) 0.1434(2) 0.57639(15) 0.0135(6) Uani 1 1 d . . . . .
H4 H 0.663011 0.207047 0.543036 0.016 Uiso 1 1 calc R . . . .
C8 C 0.5817(4) 0.4495(2) 0.64243(16) 0.0119(5) Uani 1 1 d . . . . .
C3 C 0.8334(4) 0.0900(2) 0.58902(16) 0.0149(6) Uani 1 1 d . . . . .
H5 H 0.886666 0.070346 0.540976 0.018 Uiso 1 1 calc R . . . .
C10 C 0.7256(4) 0.6272(2) 0.66992(15) 0.0151(6) Uani 1 1 d . . . . .
H15 H 0.857972 0.613343 0.667390 0.018 Uiso 1 1 calc R . . . .
C6 C 0.6793(4) 0.2626(2) 0.68161(15) 0.0127(6) Uani 1 1 d . . . . .
H10 H 0.619364 0.284094 0.727997 0.015 Uiso 1 1 calc R . . . .
C1 C 0.5079(4) 0.0654(3) 0.54294(18) 0.0179(7) Uani 1 1 d . . . . .
H3 H 0.559577 0.028560 0.499944 0.021 Uiso 1 1 calc R . . . .
H2 H 0.473235 0.008827 0.578652 0.021 Uiso 1 1 calc R . . . .
C4 C 0.9601(4) 0.1743(3) 0.62750(16) 0.0142(6) Uani 1 1 d . . . . .
H7 H 0.978014 0.237836 0.594223 0.017 Uiso 1 1 calc R . . . .
C9 C 0.6313(4) 0.5293(2) 0.70747(16) 0.0156(6) Uani 1 1 d . . . . .
H13 H 0.518427 0.554911 0.731584 0.019 Uiso 1 1 calc R . . . .
C5 C 0.8698(4) 0.2163(2) 0.69814(16) 0.0146(6) Uani 1 1 d . . . . .
H8 H 0.856212 0.153158 0.732068 0.017 Uiso 1 1 calc R . . . .
C12 C 0.7762(5) 0.6762(3) 0.53662(17) 0.0199(7) Uani 1 1 d . . . . .
H18 H 0.892142 0.636638 0.539174 0.024 Uiso 1 1 calc R . . . .
H19 H 0.799126 0.753356 0.549572 0.024 Uiso 1 1 calc R . . . .
C7 C 0.3838(4) 0.4060(2) 0.64258(17) 0.0160(6) Uani 1 1 d . . . . .
H12 H 0.361063 0.364701 0.687769 0.019 Uiso 1 1 calc R . . . .
H11 H 0.365848 0.356010 0.601073 0.019 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
Cl1 C3 1.804(3) . ?
Cl2 C7 1.790(3) . ?
Cl3 C12 1.788(3) . ?
O5 C8 1.415(3) . ?
O5 C6 1.434(3) . ?
O6 C11 1.446(3) . ?
O6 C8 1.426(3) . ?
O2 C2 1.435(3) . ?
O2 C6 1.411(3) . ?
O8 C9 1.415(4) . ?
O3 C4 1.406(3) . ?
O4 C5 1.417(4) . ?
O1 C1 1.437(4) . ?
O7 C10 1.412(3) . ?
C11 C10 1.526(4) . ?
C11 C12 1.505(4) . ?
C2 C3 1.517(4) . ?
C2 C1 1.508(4) . ?
C8 C9 1.558(4) . ?
C8 C7 1.533(4) . ?
C3 C4 1.536(4) . ?
C10 C9 1.522(4) . ?
C6 C5 1.524(4) . ?
C4 C5 1.522(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O5 C6 119.3(2) . . ?
C8 O6 C11 110.4(2) . . ?
C6 O2 C2 114.3(2) . . ?
O6 C11 C10 104.6(2) . . ?
O6 C11 C12 110.4(2) . . ?
C12 C11 C10 111.6(3) . . ?
O2 C2 C3 111.0(2) . . ?
O2 C2 C1 106.7(2) . . ?
C1 C2 C3 113.5(2) . . ?
O5 C8 O6 102.7(2) . . ?
O5 C8 C9 112.3(2) . . ?
O5 C8 C7 109.9(2) . . ?
O6 C8 C9 106.6(2) . . ?
O6 C8 C7 109.3(2) . . ?
C7 C8 C9 115.2(2) . . ?
C2 C3 Cl1 110.6(2) . . ?
C2 C3 C4 109.1(2) . . ?
C4 C3 Cl1 110.7(2) . . ?
O7 C10 C11 110.3(2) . . ?
O7 C10 C9 114.3(2) . . ?
C9 C10 C11 103.6(2) . . ?
O5 C6 C5 106.5(2) . . ?
O2 C6 O5 110.8(2) . . ?
O2 C6 C5 111.0(2) . . ?
O1 C1 C2 108.2(2) . . ?
O3 C4 C3 113.3(3) . . ?
O3 C4 C5 108.6(2) . . ?
C5 C4 C3 109.8(2) . . ?
O8 C9 C8 109.4(2) . . ?
O8 C9 C10 114.7(3) . . ?
C10 C9 C8 104.1(2) . . ?
O4 C5 C6 111.7(2) . . ?
O4 C5 C4 110.0(3) . . ?
C4 C5 C6 110.5(2) . . ?
C11 C12 Cl3 112.7(2) . . ?
C8 C7 Cl2 110.1(2) . . ?

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
O8 H14 O3 0.82 1.91 2.723(3) 174.3 3_756 yes
O3 H6 O1 0.82 1.92 2.735(3) 176.9 1_655 yes
O4 H9 O8 0.82 1.97 2.784(3) 169.8 . yes
O7 H16 O4 0.82 1.91 2.732(3) 175.8 3_756 yes

_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 1.322
_oxdiff_exptl_absorpt_empirical_full_min 0.768
####################################################################### 
# 
# 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_xinsuan
_database_code_depnum_ccdc_archive 'CCDC 2413047'
loop_
_audit_author_name
_audit_author_address
'H. H. Li'
;Fuzhou University
China
;
_audit_update_record             
;
2024-12-26 deposited with the CCDC.	2025-04-16 downloaded from the CCDC.
;
_audit_creation_date             2024-12-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H19 Cl3 O8'
_chemical_formula_sum            'C12 H19 Cl3 O8'
_chemical_formula_weight         397.62
_chemical_absolute_configuration ?
_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'
Cl Cl 0.1484 0.1585 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.041(4)
_cell_length_b                   7.3141(12)
_cell_length_c                   18.158(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1599.2(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    679
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      17.99
_cell_measurement_theta_min      2.24
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6238
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0893 before and 0.0778 after correction.
The Ratio of minimum to maximum transmission is 0.8371.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1569
_diffrn_reflns_av_unetI/netI     0.1516
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9243
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.044
_diffrn_reflns_theta_max         25.044
_diffrn_reflns_theta_min         2.243
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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         0.707
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                1553
_reflns_number_total             2750
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 
;
 Flack x determined using 452 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.857
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2750
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1385
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      0.857
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1737
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H17), C10(H15), C5(H8), C6(H10), C2(H4), C3(H5), C4(H7), C9(H13)
2.b Secondary CH2 refined with riding coordinates:
 C1(H3,H2), C7(H12,H11), C12(H18,H19)
2.c Idealised tetrahedral OH refined as rotating group:
 O7(H16), O8(H14), O1(H1), O4(H9), O3(H6)
;
_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 0.7835(2) 0.4394(4) 0.60612(17) 0.0424(8) Uani 1 1 d . . . . .
Cl2 Cl 0.2312(2) 1.0230(3) 0.61443(17) 0.0458(8) Uani 1 1 d . . . . .
Cl3 Cl 0.0803(3) 0.5576(4) 0.80476(16) 0.0536(9) Uani 1 1 d . . . . .
O5 O 0.3903(5) 0.5438(7) 0.6135(3) 0.0227(14) Uani 1 1 d . . . . .
O2 O 0.5659(5) 0.6787(7) 0.6056(4) 0.0251(15) Uani 1 1 d . . . . .
O6 O 0.2397(5) 0.6352(8) 0.6736(4) 0.0294(17) Uani 1 1 d . . . . .
O7 O 0.0206(5) 0.5572(9) 0.5459(4) 0.0355(17) Uani 1 1 d . . . . .
H16 H 0.000913 0.465276 0.523623 0.053 Uiso 1 1 calc GR . . . .
O8 O 0.2783(5) 0.5096(10) 0.4911(4) 0.0393(19) Uani 1 1 d . . . . .
H14 H 0.233546 0.462340 0.462919 0.059 Uiso 1 1 calc GR . . . .
O1 O 0.6193(6) 0.8970(8) 0.7284(4) 0.0365(18) Uani 1 1 d . . . . .
H1 H 0.658775 0.967487 0.751812 0.055 Uiso 1 1 calc GR . . . .
O4 O 0.4530(6) 0.2660(9) 0.5178(5) 0.043(2) Uani 1 1 d . . . . .
H9 H 0.394778 0.322686 0.512721 0.064 Uiso 1 1 calc GR . . . .
O3 O 0.6200(6) 0.1167(8) 0.6043(4) 0.0355(17) Uani 1 1 d . . . . .
H6 H 0.616925 0.049727 0.640426 0.053 Uiso 1 1 calc GR . . . .
C11 C 0.1237(7) 0.6013(13) 0.6576(5) 0.025(2) Uani 1 1 d . . . . .
H17 H 0.082984 0.717231 0.658162 0.030 Uiso 1 1 calc R . . . .
C10 C 0.1244(8) 0.5245(12) 0.5800(5) 0.025(2) Uani 1 1 d . . . . .
H15 H 0.138324 0.392601 0.581895 0.030 Uiso 1 1 calc R . . . .
C8 C 0.3006(7) 0.6669(11) 0.6071(6) 0.024(2) Uani 1 1 d . . . . .
C5 C 0.5322(8) 0.3785(12) 0.5532(5) 0.026(2) Uani 1 1 d . . . . .
H8 H 0.595194 0.392486 0.519427 0.031 Uiso 1 1 calc R . . . .
C6 C 0.4866(7) 0.5704(13) 0.5690(5) 0.027(2) Uani 1 1 d . . . . .
H10 H 0.465417 0.629361 0.522583 0.032 Uiso 1 1 calc R . . . .
C2 C 0.6068(7) 0.6018(12) 0.6737(5) 0.026(2) Uani 1 1 d . . . . .
H4 H 0.543541 0.584357 0.706852 0.031 Uiso 1 1 calc R . . . .
C3 C 0.6583(8) 0.4181(13) 0.6592(6) 0.027(2) Uani 1 1 d . . . . .
H5 H 0.678129 0.364469 0.706840 0.033 Uiso 1 1 calc R . . . .
C4 C 0.5755(8) 0.2909(11) 0.6224(6) 0.027(2) Uani 1 1 d . . . . .
H7 H 0.512929 0.272783 0.656106 0.032 Uiso 1 1 calc R . . . .
C1 C 0.6825(8) 0.7407(12) 0.7073(6) 0.031(3) Uani 1 1 d . . . . .
H3 H 0.719105 0.688995 0.750080 0.037 Uiso 1 1 calc R . . . .
H2 H 0.739083 0.775994 0.672024 0.037 Uiso 1 1 calc R . . . .
C9 C 0.2212(8) 0.6192(12) 0.5427(5) 0.028(2) Uani 1 1 d . . . . .
H13 H 0.195543 0.731754 0.518845 0.033 Uiso 1 1 calc R . . . .
C7 C 0.3438(8) 0.8651(11) 0.6088(6) 0.033(3) Uani 1 1 d . . . . .
H12 H 0.386667 0.889208 0.564669 0.039 Uiso 1 1 calc R . . . .
H11 H 0.392265 0.881156 0.651000 0.039 Uiso 1 1 calc R . . . .
C12 C 0.0745(8) 0.4747(15) 0.7125(5) 0.036(3) Uani 1 1 d . . . . .
H18 H 0.113383 0.358712 0.710084 0.043 Uiso 1 1 calc R . . . .
H19 H -0.002436 0.452589 0.699556 0.043 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
Cl1 C3 1.796(10) . ?
Cl2 C7 1.783(9) . ?
Cl3 C12 1.782(11) . ?
O5 C8 1.411(10) . ?
O5 C6 1.427(11) . ?
O2 C6 1.408(11) . ?
O2 C2 1.444(11) . ?
O6 C11 1.448(11) . ?
O6 C8 1.432(12) . ?
O7 C10 1.414(10) . ?
O8 C9 1.411(11) . ?
O1 C1 1.426(11) . ?
O4 C5 1.414(11) . ?
O3 C4 1.421(10) . ?
C11 C10 1.516(13) . ?
C11 C12 1.484(14) . ?
C10 C9 1.517(13) . ?
C8 C9 1.550(14) . ?
C8 C7 1.540(12) . ?
C5 C6 1.534(13) . ?
C5 C4 1.504(13) . ?
C2 C3 1.503(13) . ?
C2 C1 1.495(13) . ?
C3 C4 1.518(13) . ?

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
C8 O5 C6 119.2(7) . . ?
C6 O2 C2 114.6(7) . . ?
C8 O6 C11 110.7(7) . . ?
O6 C11 C10 104.2(7) . . ?
O6 C11 C12 110.9(8) . . ?
C12 C11 C10 113.3(8) . . ?
O7 C10 C11 109.9(8) . . ?
O7 C10 C9 114.0(7) . . ?
C11 C10 C9 104.5(7) . . ?
O5 C8 O6 102.6(7) . . ?
O5 C8 C9 113.0(8) . . ?
O5 C8 C7 109.9(7) . . ?
O6 C8 C9 106.5(7) . . ?
O6 C8 C7 107.9(8) . . ?
C7 C8 C9 115.8(8) . . ?
O4 C5 C6 112.1(7) . . ?
O4 C5 C4 111.4(8) . . ?
C4 C5 C6 110.9(8) . . ?
O5 C6 C5 105.8(7) . . ?
O2 C6 O5 111.1(7) . . ?
O2 C6 C5 111.1(7) . . ?
O2 C2 C3 109.8(8) . . ?
O2 C2 C1 107.0(8) . . ?
C1 C2 C3 115.3(8) . . ?
C2 C3 Cl1 111.2(7) . . ?
C2 C3 C4 110.8(8) . . ?
C4 C3 Cl1 111.6(7) . . ?
O3 C4 C5 108.6(8) . . ?
O3 C4 C3 113.8(8) . . ?
C5 C4 C3 109.5(8) . . ?
O1 C1 C2 109.2(8) . . ?
O8 C9 C10 114.3(8) . . ?
O8 C9 C8 109.1(8) . . ?
C10 C9 C8 103.9(7) . . ?
C8 C7 Cl2 110.7(7) . . ?
C11 C12 Cl3 113.8(8) . . ?

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
O7 H16 O4 0.82 1.94 2.755(9) 173.2 4_456 yes
O8 H14 O3 0.82 1.92 2.737(9) 172.4 4_456 yes
O4 H9 O8 0.82 2.00 2.799(10) 165.7 . yes
O3 H6 O1 0.82 1.95 2.769(10) 176.2 1_545 yes

_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_jisuan
_database_code_depnum_ccdc_archive 'CCDC 2413046'
loop_
_audit_author_name
_audit_author_address
'H. H. Li'
;Fuzhou University
China
;
_audit_update_record             
;
2024-12-26 deposited with the CCDC.	2025-04-16 downloaded from the CCDC.
;
_audit_creation_date             2024-12-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H19 Cl3 O8'
_chemical_formula_sum            'C12 H19 Cl3 O8'
_chemical_formula_weight         397.62
_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 0.0033 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.2691(14)
_cell_length_b                   11.947(2)
_cell_length_c                   17.987(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1562.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2038
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9430
_cell_measurement_theta_min      3.3190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36641
_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            ?
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8712
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.813
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.484
_diffrn_reflns_theta_min         2.046
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     20.00  79.00   0.50    3.50    --   -9.80  22.00  51.00  118
  2  ω    -22.00  79.00   0.50    3.50    --   -9.80  55.00-150.00  202
  3  ω    -10.00  15.00   0.50    3.50    --   -9.80  55.00-180.00   50
  4  ω    -99.00 -52.00   0.50    3.50    --   -9.80  55.00-150.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0293768000
_diffrn_orient_matrix_UB_12      0.0460121000
_diffrn_orient_matrix_UB_13      0.0219976000
_diffrn_orient_matrix_UB_21      0.0229283000
_diffrn_orient_matrix_UB_22      -0.0301208000
_diffrn_orient_matrix_UB_23      0.0326664000
_diffrn_orient_matrix_UB_31      0.0901987000
_diffrn_orient_matrix_UB_32      0.0224947000
_diffrn_orient_matrix_UB_33      -0.0011439000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.644
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.744
_reflns_number_gt                2919
_reflns_number_total             3530
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details 
;
 Flack x determined using 1032 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.868
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3530
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      0.868
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1258
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H4), C6(H10), C11(H17), C4(H7), C3(H5), C10(H15), C5(H8), C9(H13)
2.b Secondary CH2 refined with riding coordinates:
 C1(H3,H2), C7(H12,H11), C12(H18,H19)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H6), O4(H9), O8(H14), O1(H1), O7(H16)
;
_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 0.81094(16) -0.03474(8) 0.64376(6) 0.0262(3) Uani 1 1 d . . . . .
Cl2 Cl 0.22584(15) 0.51987(9) 0.63608(6) 0.0280(3) Uani 1 1 d . . . . .
Cl3 Cl 0.69088(18) 0.66979(9) 0.44397(6) 0.0318(3) Uani 1 1 d . . . . .
O5 O 0.7061(4) 0.3595(2) 0.63617(15) 0.0165(6) Uani 1 1 d . . . . .
O6 O 0.6140(4) 0.5100(2) 0.57574(14) 0.0180(6) Uani 1 1 d . . . . .
O2 O 0.5695(4) 0.1826(2) 0.64480(15) 0.0172(6) Uani 1 1 d . . . . .
O3 O 1.1336(4) 0.1298(3) 0.64521(16) 0.0215(6) Uani 1 1 d . . . . .
H6 H 1.203578 0.138369 0.609901 0.032 Uiso 1 1 calc GR . . . .
O4 O 0.9837(5) 0.2971(2) 0.73248(18) 0.0272(7) Uani 1 1 d . . . . .
H9 H 0.923684 0.353745 0.741137 0.041 Uiso 1 1 calc GR . . . .
O8 O 0.7416(5) 0.4716(2) 0.75931(15) 0.0250(7) Uani 1 1 d . . . . .
H14 H 0.781222 0.516077 0.790124 0.037 Uiso 1 1 calc GR . . . .
O1 O 0.3502(4) 0.1295(2) 0.52167(15) 0.0237(7) Uani 1 1 d . . . . .
H1 H 0.285449 0.092575 0.493540 0.035 Uiso 1 1 calc GR . . . .
O7 O 0.6940(4) 0.7308(2) 0.70417(16) 0.0227(6) Uani 1 1 d . . . . .
H16 H 0.790430 0.753885 0.722207 0.034 Uiso 1 1 calc GR . . . .
C8 C 0.5817(6) 0.4497(3) 0.6426(2) 0.0155(8) Uani 1 1 d . . . . .
C2 C 0.6470(6) 0.1429(3) 0.5764(2) 0.0178(8) Uani 1 1 d . . . . .
H4 H 0.662598 0.206944 0.542900 0.021 Uiso 1 1 calc R . . . .
C6 C 0.6796(6) 0.2625(3) 0.6818(2) 0.0171(8) Uani 1 1 d . . . . .
H10 H 0.620045 0.284484 0.728411 0.020 Uiso 1 1 calc R . . . .
C11 C 0.6454(6) 0.6264(3) 0.5918(2) 0.0189(8) Uani 1 1 d . . . . .
H17 H 0.528683 0.667468 0.590945 0.023 Uiso 1 1 calc R . . . .
C4 C 0.9597(6) 0.1744(3) 0.6274(2) 0.0175(8) Uani 1 1 d . . . . .
H7 H 0.977613 0.238233 0.594038 0.021 Uiso 1 1 calc R . . . .
C3 C 0.8329(6) 0.0906(3) 0.5891(2) 0.0188(8) Uani 1 1 d . . . . .
H5 H 0.886169 0.070830 0.540822 0.023 Uiso 1 1 calc R . . . .
C1 C 0.5067(6) 0.0652(4) 0.5429(2) 0.0228(10) Uani 1 1 d . . . . .
H3 H 0.558124 0.027799 0.499794 0.027 Uiso 1 1 calc R . . . .
H2 H 0.471221 0.008725 0.578890 0.027 Uiso 1 1 calc R . . . .
C10 C 0.7252(6) 0.6270(3) 0.6698(2) 0.0187(8) Uani 1 1 d . . . . .
H15 H 0.857823 0.612676 0.667312 0.022 Uiso 1 1 calc R . . . .
C5 C 0.8695(6) 0.2163(3) 0.6981(2) 0.0184(8) Uani 1 1 d . . . . .
H8 H 0.856038 0.152850 0.732231 0.022 Uiso 1 1 calc R . . . .
C9 C 0.6305(6) 0.5292(3) 0.7071(2) 0.0186(8) Uani 1 1 d . . . . .
H13 H 0.517500 0.554996 0.731365 0.022 Uiso 1 1 calc R . . . .
C7 C 0.3843(6) 0.4059(3) 0.6424(2) 0.0198(8) Uani 1 1 d . . . . .
H12 H 0.361470 0.363985 0.687663 0.024 Uiso 1 1 calc R . . . .
H11 H 0.366843 0.355817 0.600518 0.024 Uiso 1 1 calc R . . . .
C12 C 0.7773(7) 0.6762(3) 0.5363(2) 0.0230(9) Uani 1 1 d . . . . .
H18 H 0.893220 0.636160 0.538810 0.028 Uiso 1 1 calc R . . . .
H19 H 0.800659 0.753674 0.549366 0.028 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
Cl1 C3 1.798(4) . ?
Cl2 C7 1.787(4) . ?
Cl3 C12 1.778(4) . ?
O5 C8 1.412(5) . ?
O5 C6 1.432(4) . ?
O6 C8 1.421(5) . ?
O6 C11 1.439(5) . ?
O2 C2 1.435(5) . ?
O2 C6 1.413(5) . ?
O3 C4 1.409(5) . ?
O4 C5 1.416(5) . ?
O8 C9 1.417(5) . ?
O1 C1 1.425(5) . ?
O7 C10 1.404(5) . ?
C8 C9 1.541(5) . ?
C8 C7 1.527(6) . ?
C2 C3 1.506(6) . ?
C2 C1 1.505(6) . ?
C6 C5 1.516(6) . ?
C11 C10 1.518(5) . ?
C11 C12 1.506(6) . ?
C4 C3 1.526(6) . ?
C4 C5 1.516(5) . ?
C10 C9 1.513(6) . ?

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
C8 O5 C6 119.0(3) . . ?
C8 O6 C11 110.3(3) . . ?
C6 O2 C2 113.9(3) . . ?
O5 C8 O6 102.2(3) . . ?
O5 C8 C9 112.6(3) . . ?
O5 C8 C7 109.9(3) . . ?
O6 C8 C9 106.7(3) . . ?
O6 C8 C7 109.1(3) . . ?
C7 C8 C9 115.4(3) . . ?
O2 C2 C3 111.0(3) . . ?
O2 C2 C1 106.3(3) . . ?
C1 C2 C3 114.4(3) . . ?
O5 C6 C5 106.5(3) . . ?
O2 C6 O5 110.7(3) . . ?
O2 C6 C5 111.2(3) . . ?
O6 C11 C10 104.5(3) . . ?
O6 C11 C12 110.5(3) . . ?
C12 C11 C10 111.5(4) . . ?
O3 C4 C3 113.4(3) . . ?
O3 C4 C5 108.8(3) . . ?
C5 C4 C3 109.5(3) . . ?
C2 C3 Cl1 110.5(3) . . ?
C2 C3 C4 109.8(3) . . ?
C4 C3 Cl1 110.7(3) . . ?
O1 C1 C2 108.4(3) . . ?
O7 C10 C11 110.4(3) . . ?
O7 C10 C9 114.4(3) . . ?
C9 C10 C11 103.5(3) . . ?
O4 C5 C6 111.7(3) . . ?
O4 C5 C4 109.7(4) . . ?
C4 C5 C6 110.6(3) . . ?
O8 C9 C8 109.3(3) . . ?
O8 C9 C10 114.2(4) . . ?
C10 C9 C8 104.3(3) . . ?
C8 C7 Cl2 110.1(3) . . ?
C11 C12 Cl3 112.2(3) . . ?

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
O3 H6 O1 0.82 1.91 2.723(4) 168.6 1_655 yes
O4 H9 O8 0.82 1.96 2.770(4) 169.7 . yes
O8 H14 O3 0.82 1.89 2.710(4) 174.5 3_756 yes
O7 H16 O4 0.82 1.90 2.723(4) 175.8 3_756 yes

_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 2.270
_oxdiff_exptl_absorpt_empirical_full_min 0.668
