# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_mo_240604tianwf_0m
_database_code_depnum_ccdc_archive 'CCDC 2530950'
loop_
_audit_author_name
_audit_author_address
Yongqin
;Nanchang University
China
;
_audit_update_record             
;
2026-02-13 deposited with the CCDC.	2026-05-22 downloaded from the CCDC.
;
_audit_creation_date             2024-06-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 O6'
_chemical_formula_sum            'C18 H18 O6'
_chemical_formula_weight         330.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.1773(3)
_cell_length_b                   9.3818(3)
_cell_length_c                   10.6454(3)
_cell_angle_alpha                68.4670(10)
_cell_angle_beta                 77.7630(10)
_cell_angle_gamma                79.6440(10)
_cell_volume                     827.96(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7999
_cell_measurement_temperature    303.00
_cell_measurement_theta_max      28.241
_cell_measurement_theta_min      2.349
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0718 before and 0.0550 after correction.
The Ratio of minimum to maximum transmission is 0.9537.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28087
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.309
_diffrn_reflns_theta_min         2.083
_diffrn_ambient_temperature      303.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3232
_reflns_number_total             4098
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4098
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.051
_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)+(0.0613P)²+0.1570P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1330
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4A), C6(H6), C18(H18), C3(H3), C2(H2), C1(H1), C14(H14), C17(H17),
 C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_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
O4 O 0.69414(10) 0.77502(11) 0.54532(8) 0.0456(2) Uani 1 1 d . . . . .
H4 H 0.633424 0.847722 0.511713 0.068 Uiso 1 1 calc R U . . .
O5 O 0.55627(12) 0.66717(12) 0.91628(9) 0.0531(3) Uani 1 1 d . . . . .
H5 H 0.478832 0.638228 0.912092 0.080 Uiso 1 1 calc R U . . .
O1 O 0.44738(12) 0.67061(14) 0.54834(11) 0.0598(3) Uani 1 1 d . . . . .
O3 O 0.48978(13) 0.98146(13) 0.83915(12) 0.0647(3) Uani 1 1 d . . . . .
O2 O 0.44739(15) 0.96134(13) 0.64927(11) 0.0696(3) Uani 1 1 d . . . . .
O6 O 0.37528(11) 0.61482(16) 0.77258(12) 0.0692(3) Uani 1 1 d . . . . .
C5 C 0.72584(13) 0.52934(14) 0.71578(12) 0.0387(3) Uani 1 1 d . . . . .
C7 C 0.62718(13) 0.68343(14) 0.67470(11) 0.0381(3) Uani 1 1 d . . . . .
C9 C 0.51002(14) 0.91413(15) 0.74720(13) 0.0443(3) Uani 1 1 d . . . . .
C11 C 0.46862(14) 0.65394(16) 0.67202(14) 0.0461(3) Uani 1 1 d . . . . .
C8 C 0.61608(14) 0.76343(14) 0.78517(11) 0.0396(3) Uani 1 1 d . . . . .
C4 C 0.66950(17) 0.39521(16) 0.80718(13) 0.0492(3) Uani 1 1 d . . . . .
H4A H 0.567835 0.396763 0.843108 0.059 Uiso 1 1 calc R U . . .
C13 C 0.76971(15) 0.79556(16) 0.79140(14) 0.0460(3) Uani 1 1 d . . . . .
C6 C 0.87728(15) 0.52333(17) 0.66210(15) 0.0515(3) Uani 1 1 d . . . . .
H6 H 0.916970 0.611907 0.599823 0.062 Uiso 1 1 calc R U . . .
C18 C 0.83919(18) 0.9150(2) 0.69034(18) 0.0605(4) Uani 1 1 d . . . . .
H18 H 0.789371 0.980485 0.619157 0.073 Uiso 1 1 calc R U . . .
C3 C 0.7635(2) 0.25896(18) 0.84533(17) 0.0621(4) Uani 1 1 d . . . . .
H3 H 0.724767 0.169637 0.907141 0.074 Uiso 1 1 calc R U . . .
C2 C 0.9133(2) 0.25482(19) 0.79265(19) 0.0659(4) Uani 1 1 d . . . . .
H2 H 0.976332 0.163270 0.819153 0.079 Uiso 1 1 calc R U . . .
C1 C 0.96955(18) 0.3861(2) 0.7008(2) 0.0655(4) Uani 1 1 d . . . . .
H1 H 1.070980 0.383044 0.664017 0.079 Uiso 1 1 calc R U . . .
C14 C 0.8444(2) 0.7009(2) 0.89871(19) 0.0656(4) Uani 1 1 d . . . . .
H14 H 0.798033 0.621171 0.968559 0.079 Uiso 1 1 calc R U . . .
C10 C 0.3880(2) 1.1220(2) 0.8181(2) 0.0730(5) Uani 1 1 d . . . . .
H10A H 0.422816 1.197497 0.732235 0.110 Uiso 1 1 calc R U . . .
H10B H 0.383886 1.160587 0.890832 0.110 Uiso 1 1 calc R U . . .
H10C H 0.289645 1.101095 0.817136 0.110 Uiso 1 1 calc R U . . .
C17 C 0.9837(2) 0.9380(3) 0.6944(3) 0.0843(6) Uani 1 1 d . . . . .
H17 H 1.030839 1.017751 0.625406 0.101 Uiso 1 1 calc R U . . .
C15 C 0.9876(3) 0.7253(3) 0.9015(3) 0.0941(8) Uani 1 1 d . . . . .
H15 H 1.037670 0.661174 0.972949 0.113 Uiso 1 1 calc R U . . .
C12 C 0.3006(2) 0.6409(3) 0.5390(2) 0.0821(6) Uani 1 1 d . . . . .
H12A H 0.286881 0.679533 0.444877 0.123 Uiso 1 1 calc R U . . .
H12B H 0.224176 0.691733 0.589917 0.123 Uiso 1 1 calc R U . . .
H12C H 0.293915 0.531914 0.576001 0.123 Uiso 1 1 calc R U . . .
C16 C 1.0559(2) 0.8426(3) 0.8003(4) 0.1023(9) Uani 1 1 d . . . . .
H16 H 1.152314 0.857967 0.803190 0.123 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 H4 0.8200 . ?
O4 C7 1.4054(14) . ?
O5 H5 0.8200 . ?
O5 C8 1.4118(14) . ?
O1 C11 1.3201(16) . ?
O1 C12 1.454(2) . ?
O3 C9 1.3139(16) . ?
O3 C10 1.4455(18) . ?
O2 C9 1.1987(16) . ?
O6 C11 1.2044(17) . ?
C5 C7 1.5278(16) . ?
C5 C4 1.3854(18) . ?
C5 C6 1.3856(18) . ?
C7 C11 1.5372(17) . ?
C7 C8 1.5894(16) . ?
C9 C8 1.5370(17) . ?
C8 C13 1.5133(18) . ?
C4 H4A 0.9300 . ?
C4 C3 1.384(2) . ?
C13 C18 1.379(2) . ?
C13 C14 1.390(2) . ?
C6 H6 0.9300 . ?
C6 C1 1.382(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.393(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.369(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.368(3) . ?
C1 H1 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.382(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C17 H17 0.9300 . ?
C17 C16 1.369(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.362(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C16 H16 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O4 H4 109.5 . . ?
C8 O5 H5 109.5 . . ?
C11 O1 C12 115.65(13) . . ?
C9 O3 C10 117.36(12) . . ?
C4 C5 C7 122.16(11) . . ?
C4 C5 C6 118.63(12) . . ?
C6 C5 C7 119.21(11) . . ?
O4 C7 C5 107.53(9) . . ?
O4 C7 C11 111.62(9) . . ?
O4 C7 C8 110.87(10) . . ?
C5 C7 C11 109.05(10) . . ?
C5 C7 C8 109.27(9) . . ?
C11 C7 C8 108.46(9) . . ?
O3 C9 C8 111.76(11) . . ?
O2 C9 O3 123.74(12) . . ?
O2 C9 C8 124.41(12) . . ?
O1 C11 C7 112.79(11) . . ?
O6 C11 O1 123.50(13) . . ?
O6 C11 C7 123.67(12) . . ?
O5 C8 C7 110.60(10) . . ?
O5 C8 C9 108.01(10) . . ?
O5 C8 C13 108.29(10) . . ?
C9 C8 C7 108.93(9) . . ?
C13 C8 C7 110.53(9) . . ?
C13 C8 C9 110.44(10) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 C5 120.42(14) . . ?
C3 C4 H4A 119.8 . . ?
C18 C13 C8 121.17(12) . . ?
C18 C13 C14 119.12(15) . . ?
C14 C13 C8 119.69(14) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 C5 120.22(14) . . ?
C1 C6 H6 119.9 . . ?
C13 C18 H18 119.9 . . ?
C13 C18 C17 120.30(18) . . ?
C17 C18 H18 119.9 . . ?
C4 C3 H3 119.8 . . ?
C2 C3 C4 120.41(15) . . ?
C2 C3 H3 119.8 . . ?
C3 C2 H2 120.2 . . ?
C1 C2 C3 119.61(14) . . ?
C1 C2 H2 120.2 . . ?
C6 C1 H1 119.6 . . ?
C2 C1 C6 120.71(15) . . ?
C2 C1 H1 119.6 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.0 . . ?
O3 C10 H10A 109.5 . . ?
O3 C10 H10B 109.5 . . ?
O3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C18 C17 H17 120.1 . . ?
C16 C17 C18 119.7(2) . . ?
C16 C17 H17 120.1 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.7 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C17 C16 H16 119.8 . . ?
C15 C16 C17 120.44(18) . . ?
C15 C16 H16 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C7 C11 O1 22.31(15) . . . . ?
O4 C7 C11 O6 -160.01(14) . . . . ?
O4 C7 C8 O5 -176.82(9) . . . . ?
O4 C7 C8 C9 64.62(12) . . . . ?
O4 C7 C8 C13 -56.89(13) . . . . ?
O5 C8 C13 C18 -163.62(12) . . . . ?
O5 C8 C13 C14 18.14(16) . . . . ?
O3 C9 C8 O5 56.32(14) . . . . ?
O3 C9 C8 C7 176.51(11) . . . . ?
O3 C9 C8 C13 -61.92(14) . . . . ?
O2 C9 C8 O5 -120.33(15) . . . . ?
O2 C9 C8 C7 -0.15(18) . . . . ?
O2 C9 C8 C13 121.42(15) . . . . ?
C5 C7 C11 O1 -96.35(13) . . . . ?
C5 C7 C11 O6 81.34(16) . . . . ?
C5 C7 C8 O5 -58.47(12) . . . . ?
C5 C7 C8 C9 -177.04(10) . . . . ?
C5 C7 C8 C13 61.45(13) . . . . ?
C5 C4 C3 C2 -0.4(2) . . . . ?
C5 C6 C1 C2 -0.2(2) . . . . ?
C7 C5 C4 C3 -177.82(13) . . . . ?
C7 C5 C6 C1 178.15(13) . . . . ?
C7 C8 C13 C18 75.08(15) . . . . ?
C7 C8 C13 C14 -103.16(14) . . . . ?
C9 C8 C13 C18 -45.54(15) . . . . ?
C9 C8 C13 C14 136.22(13) . . . . ?
C11 C7 C8 O5 60.30(12) . . . . ?
C11 C7 C8 C9 -58.27(12) . . . . ?
C11 C7 C8 C13 -179.78(10) . . . . ?
C8 C7 C11 O1 144.74(11) . . . . ?
C8 C7 C11 O6 -37.57(18) . . . . ?
C8 C13 C18 C17 -176.80(14) . . . . ?
C8 C13 C14 C15 176.96(14) . . . . ?
C4 C5 C7 O4 -155.05(11) . . . . ?
C4 C5 C7 C11 -33.86(15) . . . . ?
C4 C5 C7 C8 84.54(14) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C4 C3 C2 C1 -0.6(3) . . . . ?
C13 C18 C17 C16 -0.9(3) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C6 C5 C7 O4 26.13(15) . . . . ?
C6 C5 C7 C11 147.31(12) . . . . ?
C6 C5 C7 C8 -94.29(13) . . . . ?
C6 C5 C4 C3 1.0(2) . . . . ?
C18 C13 C14 C15 -1.3(2) . . . . ?
C18 C17 C16 C15 0.1(3) . . . . ?
C3 C2 C1 C6 0.9(3) . . . . ?
C14 C13 C18 C17 1.5(2) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C10 O3 C9 O2 -1.2(2) . . . . ?
C10 O3 C9 C8 -177.90(13) . . . . ?
C12 O1 C11 O6 1.0(2) . . . . ?
C12 O1 C11 C7 178.66(13) . . . . ?

_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_1
_database_code_depnum_ccdc_archive 'CCDC 2530949'
loop_
_audit_author_name
_audit_author_address
Yongqin
;Nanchang University
China
;
_audit_update_record             
;
2026-04-27 deposited with the CCDC.	2026-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Cl2 O6'
_chemical_formula_weight         399.21

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   I2/a

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   12.471(5)
_cell_length_b                   10.552(2)
_cell_length_c                   14.011(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.55(2)
_cell_angle_gamma                90.00
_cell_volume                     1835.1(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4328
_cell_measurement_theta_min      2.421
_cell_measurement_theta_max      25.508

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.385
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.5389
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12051
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_av_sigmaI/netI    0.0649
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         28.36
_reflns_number_total             2224
_reflns_number_gt                1487
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1034P)²+1.7393P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2224
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.2000
_refine_ls_wR_factor_gt          0.1765
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.01209(8) 0.01413(8) 0.80609(7) 0.0589(3) Uani 1 1 d . . .
O1 O 0.63320(16) 0.42018(19) 0.91416(13) 0.0386(5) Uani 1 1 d . . .
H1 H 0.6152 0.4627 0.8663 0.058 Uiso 1 1 calc R . .
O2 O 0.85487(19) 0.62711(19) 0.94472(15) 0.0470(6) Uani 1 1 d . . .
O3 O 0.7232(2) 0.6053(2) 0.82557(15) 0.0525(6) Uani 1 1 d . . .
C1 C 0.7725(2) 0.5682(3) 0.89819(19) 0.0366(6) Uani 1 1 d . . .
C2 C 0.8120(2) 0.3358(2) 0.90576(17) 0.0312(6) Uani 1 1 d . . .
C3 C 0.7432(2) 0.4411(2) 0.94333(18) 0.0325(6) Uani 1 1 d . . .
C4 C 0.9211(2) 0.3507(3) 0.8965(2) 0.0390(7) Uani 1 1 d . . .
H2 H 0.9538 0.4281 0.9121 0.047 Uiso 1 1 calc R . .
C5 C 0.8252(3) 0.1195(3) 0.8514(2) 0.0446(7) Uani 1 1 d . . .
H3 H 0.7935 0.0413 0.8362 0.053 Uiso 1 1 calc R . .
C6 C 0.9336(3) 0.1384(3) 0.84390(19) 0.0404(7) Uani 1 1 d . . .
C7 C 0.9815(3) 0.2539(3) 0.8648(2) 0.0424(7) Uani 1 1 d . . .
H4 H 1.0541 0.2661 0.8575 0.051 Uiso 1 1 calc R . .
C8 C 0.7650(2) 0.2183(3) 0.8817(2) 0.0392(7) Uani 1 1 d . . .
H5 H 0.6918 0.2067 0.8863 0.047 Uiso 1 1 calc R . .
C9 C 0.8891(4) 0.7441(3) 0.9014(3) 0.0637(10) Uani 1 1 d . . .
H6 H 0.9054 0.7274 0.8370 0.096 Uiso 1 1 calc R . .
H7 H 0.9522 0.7763 0.9382 0.096 Uiso 1 1 calc R . .
H8 H 0.8323 0.8056 0.9004 0.096 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 C6 1.749(3) . ?
O1 C3 1.410(3) . ?
O1 H1 0.8200 . ?
O2 C1 1.318(4) . ?
O2 C9 1.458(4) . ?
O3 C1 1.202(3) . ?
C1 C3 1.542(4) . ?
C2 C4 1.388(4) . ?
C2 C8 1.398(4) . ?
C2 C3 1.529(4) . ?
C3 C3 1.581(5) 2_657 ?
C4 C7 1.368(4) . ?
C4 H2 0.9300 . ?
C5 C8 1.376(4) . ?
C5 C6 1.380(5) . ?
C5 H3 0.9300 . ?
C6 C7 1.376(4) . ?
C7 H4 0.9300 . ?
C8 H5 0.9300 . ?
C9 H6 0.9600 . ?
C9 H7 0.9600 . ?
C9 H8 0.9600 . ?

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
C3 O1 H1 109.5 . . ?
C1 O2 C9 116.0(3) . . ?
O3 C1 O2 125.1(3) . . ?
O3 C1 C3 120.5(3) . . ?
O2 C1 C3 114.3(2) . . ?
C4 C2 C8 118.0(3) . . ?
C4 C2 C3 122.6(2) . . ?
C8 C2 C3 119.4(2) . . ?
O1 C3 C2 110.4(2) . . ?
O1 C3 C1 106.3(2) . . ?
C2 C3 C1 109.1(2) . . ?
O1 C3 C3 107.4(3) . 2_657 ?
C2 C3 C3 109.7(2) . 2_657 ?
C1 C3 C3 113.91(16) . 2_657 ?
C7 C4 C2 121.5(3) . . ?
C7 C4 H2 119.3 . . ?
C2 C4 H2 119.3 . . ?
C8 C5 C6 118.8(3) . . ?
C8 C5 H3 120.6 . . ?
C6 C5 H3 120.6 . . ?
C7 C6 C5 121.3(3) . . ?
C7 C6 Cl1 119.0(2) . . ?
C5 C6 Cl1 119.7(2) . . ?
C4 C7 C6 119.2(3) . . ?
C4 C7 H4 120.4 . . ?
C6 C7 H4 120.4 . . ?
C5 C8 C2 121.2(3) . . ?
C5 C8 H5 119.4 . . ?
C2 C8 H5 119.4 . . ?
O2 C9 H6 109.5 . . ?
O2 C9 H7 109.5 . . ?
H6 C9 H7 109.5 . . ?
O2 C9 H8 109.5 . . ?
H6 C9 H8 109.5 . . ?
H7 C9 H8 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
C9 O2 C1 O3 -2.1(5) . . . . ?
C9 O2 C1 C3 176.6(3) . . . . ?
C4 C2 C3 O1 159.0(2) . . . . ?
C8 C2 C3 O1 -22.6(3) . . . . ?
C4 C2 C3 C1 42.5(3) . . . . ?
C8 C2 C3 C1 -139.1(3) . . . . ?
C4 C2 C3 C3 -82.9(3) . . . 2_657 ?
C8 C2 C3 C3 95.5(3) . . . 2_657 ?
O3 C1 C3 O1 -26.5(3) . . . . ?
O2 C1 C3 O1 154.8(2) . . . . ?
O3 C1 C3 C2 92.6(3) . . . . ?
O2 C1 C3 C2 -86.1(3) . . . . ?
O3 C1 C3 C3 -144.5(3) . . . 2_657 ?
O2 C1 C3 C3 36.8(4) . . . 2_657 ?
C8 C2 C4 C7 0.0(4) . . . . ?
C3 C2 C4 C7 178.4(3) . . . . ?
C8 C5 C6 C7 -0.9(5) . . . . ?
C8 C5 C6 Cl1 179.7(2) . . . . ?
C2 C4 C7 C6 -1.6(4) . . . . ?
C5 C6 C7 C4 2.0(5) . . . . ?
Cl1 C6 C7 C4 -178.5(2) . . . . ?
C6 C5 C8 C2 -0.7(4) . . . . ?
C4 C2 C8 C5 1.1(4) . . . . ?
C3 C2 C8 C5 -177.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_theta_full        28.36
_diffrn_measured_fraction_theta_full 0.968
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.090
