# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_w
_database_code_depnum_ccdc_archive 'CCDC 1937066'
_audit_update_record             
;
2019-06-28 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             2019-04-23
_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         'C13 H16 O10'
_chemical_formula_sum            'C13 H16 O10'
_chemical_formula_weight         332.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.095(2)
_cell_length_b                   9.4714(14)
_cell_length_c                   11.1536(18)
_cell_angle_alpha                90
_cell_angle_beta                 102.690(9)
_cell_angle_gamma                90
_cell_volume                     1452.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1827
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.57
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6034
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0833 before and 0.0444 after correction.
The Ratio of minimum to maximum transmission is 0.8094.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             696
_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  0.0435
_diffrn_reflns_av_unetI/netI     0.0690
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7218
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.585
_diffrn_reflns_theta_min         2.611
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2143
_reflns_number_total             3293
_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 V8.32B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.32B (?, 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         0.513
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.020(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1396
_refine_ls_R_factor_gt           0.1080
_refine_ls_restrained_S_all      1.172
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1530P)²+4.2247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3398
_refine_ls_wR_factor_ref         0.3577
_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
2.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C12(H12A,H12B,H12C)
;
_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
O1 O 0.2480(2) 0.5929(3) 0.7488(3) 0.0304(8) Uani 1 1 d . . . . .
O2 O 0.3343(3) 0.3967(4) 0.8305(4) 0.0393(9) Uani 1 1 d . . . . .
O3 O 0.2282(3) 0.4194(4) 0.9487(3) 0.0427(10) Uani 1 1 d . . . . .
O4 O 0.2000(3) 0.7157(5) 0.5150(4) 0.0514(11) Uani 1 1 d . . . . .
O5 O 0.3741(3) 0.8180(6) 0.8752(4) 0.0625(14) Uani 1 1 d . . . . .
O6 O 0.4799(4) 0.9313(5) 0.7937(5) 0.0629(14) Uani 1 1 d . . . . .
O7 O 0.3867(4) 0.4050(6) 1.0360(5) 0.0727(16) Uani 1 1 d . . . . .
O8 O 0.1001(3) 0.8147(6) 0.6160(5) 0.0685(15) Uani 1 1 d . . . . .
C1 C 0.2448(3) 0.4441(5) 0.7496(4) 0.0308(11) Uani 1 1 d . . . . .
C2 C 0.1700(3) 0.4029(5) 0.8232(5) 0.0309(11) Uani 1 1 d . . . . .
C3 C 0.4041(4) 0.7134(6) 0.7974(5) 0.0401(13) Uani 1 1 d . . . . .
H3 H 0.432192 0.632263 0.847330 0.048 Uiso 1 1 calc R . . . .
C4 C 0.3192(3) 0.6644(5) 0.6974(5) 0.0323(11) Uani 1 1 d . . . . .
H4 H 0.343784 0.598457 0.643665 0.039 Uiso 1 1 calc R . . . .
C5 C 0.3224(4) 0.4060(6) 0.9467(5) 0.0412(13) Uani 1 1 d . . . . .
C6 C 0.2645(4) 0.7814(6) 0.6190(5) 0.0394(12) Uani 1 1 d . . . . .
H6 H 0.309904 0.845383 0.591157 0.047 Uiso 1 1 calc R . . . .
O9 O 0.0409(4) 0.6732(8) 0.4568(6) 0.096(2) Uani 1 1 d . . . . .
O10 O 0.4008(6) 1.0472(7) 0.9157(7) 0.101(2) Uani 1 1 d . . . . .
C7 C 0.4840(4) 0.7896(7) 0.7497(6) 0.0476(15) Uani 1 1 d . . . . .
H7A H 0.547060 0.747418 0.782481 0.057 Uiso 1 1 calc R . . . .
H7B H 0.471090 0.787226 0.660682 0.057 Uiso 1 1 calc R . . . .
C8 C 0.2344(5) 0.3785(7) 0.6255(6) 0.0506(15) Uani 1 1 d . . . . .
H8A H 0.170836 0.398421 0.576617 0.076 Uiso 1 1 calc GR . . . .
H8B H 0.243063 0.278208 0.634156 0.076 Uiso 1 1 calc GR . . . .
H8C H 0.282756 0.416805 0.585941 0.076 Uiso 1 1 calc GR . . . .
C9 C 0.0831(4) 0.5007(7) 0.8067(6) 0.0468(15) Uani 1 1 d . . . . .
H9A H 0.045962 0.478936 0.866891 0.070 Uiso 1 1 calc GR . . . .
H9B H 0.043026 0.488470 0.725803 0.070 Uiso 1 1 calc GR . . . .
H9C H 0.105077 0.596806 0.816782 0.070 Uiso 1 1 calc GR . . . .
C10 C 0.1936(5) 0.8645(7) 0.6775(6) 0.0513(15) Uani 1 1 d . . . . .
H10A H 0.205066 0.846002 0.765057 0.062 Uiso 1 1 calc R . . . .
H10B H 0.199684 0.965150 0.664801 0.062 Uiso 1 1 calc R . . . .
C11 C 0.1078(5) 0.7310(8) 0.5248(7) 0.0592(18) Uani 1 1 d . . . . .
C12 C 0.1388(5) 0.2490(6) 0.8083(6) 0.0495(15) Uani 1 1 d . . . . .
H12A H 0.195271 0.189457 0.826939 0.074 Uiso 1 1 calc GR . . . .
H12B H 0.104380 0.232639 0.725195 0.074 Uiso 1 1 calc GR . . . .
H12C H 0.097140 0.227819 0.863395 0.074 Uiso 1 1 calc GR . . . .
C13 C 0.4173(5) 0.9418(8) 0.8657(7) 0.0588(17) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.410(6) . ?
O1 C4 1.432(5) . ?
O2 C1 1.451(6) . ?
O2 C5 1.346(7) . ?
O3 C2 1.467(6) . ?
O3 C5 1.339(7) . ?
O4 C6 1.448(7) . ?
O4 C11 1.337(8) . ?
O5 C3 1.440(8) . ?
O5 C13 1.337(9) . ?
O6 C7 1.435(8) . ?
O6 C13 1.320(9) . ?
O7 C5 1.191(7) . ?
O8 C10 1.426(8) . ?
O8 C11 1.313(9) . ?
C1 C2 1.523(7) . ?
C1 C8 1.495(8) . ?
C2 C9 1.516(7) . ?
C2 C12 1.521(7) . ?
C3 C4 1.518(7) . ?
C3 C7 1.527(7) . ?
C4 C6 1.514(7) . ?
C6 C10 1.527(8) . ?
O9 C11 1.204(9) . ?
O10 C13 1.191(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C4 120.1(4) . . ?
C5 O2 C1 107.7(4) . . ?
C5 O3 C2 108.8(4) . . ?
C11 O4 C6 109.8(5) . . ?
C13 O5 C3 110.8(5) . . ?
C13 O6 C7 111.1(5) . . ?
C11 O8 C10 110.4(5) . . ?
O1 C1 O2 106.8(4) . . ?
O1 C1 C2 106.6(4) . . ?
O1 C1 C8 114.0(4) . . ?
O2 C1 C2 101.3(4) . . ?
O2 C1 C8 110.0(4) . . ?
C8 C1 C2 117.0(4) . . ?
O3 C2 C1 100.3(4) . . ?
O3 C2 C9 108.6(4) . . ?
O3 C2 C12 107.1(4) . . ?
C9 C2 C1 114.5(4) . . ?
C9 C2 C12 111.5(4) . . ?
C12 C2 C1 113.9(4) . . ?
O5 C3 C4 111.3(4) . . ?
O5 C3 C7 102.8(5) . . ?
C4 C3 C7 114.3(5) . . ?
O1 C4 C3 111.1(4) . . ?
O1 C4 C6 105.3(4) . . ?
C3 C4 C6 114.8(5) . . ?
O3 C5 O2 110.8(4) . . ?
O7 C5 O2 124.9(6) . . ?
O7 C5 O3 124.2(6) . . ?
O4 C6 C4 107.4(4) . . ?
O4 C6 C10 102.1(4) . . ?
C4 C6 C10 115.4(5) . . ?
O6 C7 C3 103.6(5) . . ?
O8 C10 C6 104.2(5) . . ?
O8 C11 O4 112.1(6) . . ?
O9 C11 O4 122.7(8) . . ?
O9 C11 O8 125.2(7) . . ?
O6 C13 O5 111.1(6) . . ?
O10 C13 O5 124.0(7) . . ?
O10 C13 O6 124.9(8) . . ?

_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_19aug1a_0m
_database_code_depnum_ccdc_archive 'CCDC 1946539'
loop_
_audit_author_name
_audit_author_address
'Hui Zhou'
;dalian university of technology
China
;
_audit_update_record             
;
2019-08-11 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             2019-08-06
_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         'C9 H8 O9'
_chemical_formula_sum            'C9 H8 O9'
_chemical_formula_weight         260.15
_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'
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                   5.709(4)
_cell_length_b                   12.143(8)
_cell_length_c                   14.775(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1024.3(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1113
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.686
_cell_measurement_theta_min      2.757
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0539 before and 0.0456 after correction. The Ratio of minimum to maximum transmission is 0.8812. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_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  0.0375
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6472
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.352
_diffrn_reflns_theta_min         2.171
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1555
_reflns_number_total             2326
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.32B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.32B (?, 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         0.128
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -2(2)
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      0.989
_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)+(0.0397P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0900
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 3(2)
 -2(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B)
;
_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
O1 O 0.2337(3) 0.47827(15) 0.62332(14) 0.0470(5) Uani 1 1 d . . . . .
O2 O 0.4928(4) 0.34669(15) 0.64820(15) 0.0536(6) Uani 1 1 d . . . . .
O3 O 0.7359(4) 0.66329(16) 0.63283(15) 0.0513(5) Uani 1 1 d . . . . .
O4 O 0.4881(5) 0.80122(17) 0.62313(17) 0.0659(7) Uani 1 1 d . . . . .
O5 O 0.8549(5) 0.8225(2) 0.57275(17) 0.0764(8) Uani 1 1 d . . . . .
O6 O 0.4674(4) 0.37260(18) 0.45539(16) 0.0580(6) Uani 1 1 d . . . . .
O7 O 0.7006(4) 0.4690(2) 0.36590(16) 0.0626(6) Uani 1 1 d . . . . .
O8 O 0.3375(4) 0.4245(2) 0.32006(18) 0.0810(9) Uani 1 1 d . . . . .
O9 O 0.1160(4) 0.3175(2) 0.68269(18) 0.0739(8) Uani 1 1 d . . . . .
C1 C 0.2671(6) 0.3756(3) 0.6546(2) 0.0502(8) Uani 1 1 d . . . . .
C2 C 0.6230(5) 0.4294(2) 0.5989(2) 0.0428(7) Uani 1 1 d . . . . .
H2 H 0.769560 0.448855 0.632388 0.051 Uiso 1 1 calc R . . . .
C3 C 0.4544(5) 0.5271(2) 0.59868(18) 0.0363(6) Uani 1 1 d . . . . .
H3 H 0.443694 0.558471 0.536227 0.044 Uiso 1 1 calc R . . . .
C4 C 0.5176(5) 0.6175(2) 0.66512(18) 0.0402(7) Uani 1 1 d . . . . .
H4 H 0.535958 0.587106 0.727631 0.048 Uiso 1 1 calc R . . . .
C5 C 0.7039(7) 0.7678(3) 0.6065(2) 0.0516(8) Uani 1 1 d . . . . .
C6 C 0.3512(5) 0.7160(2) 0.6648(2) 0.0500(8) Uani 1 1 d . . . . .
H6A H 0.208404 0.700034 0.629143 0.060 Uiso 1 1 calc R . . . .
H6B H 0.305283 0.736630 0.727171 0.060 Uiso 1 1 calc R . . . .
C7 C 0.6820(6) 0.3840(3) 0.5070(2) 0.0511(8) Uani 1 1 d . . . . .
H7 H 0.759703 0.310629 0.513447 0.061 Uiso 1 1 calc R . . . .
C8 C 0.4887(6) 0.4225(3) 0.3743(2) 0.0553(8) Uani 1 1 d . . . . .
C9 C 0.8313(5) 0.4592(3) 0.4479(2) 0.0605(9) Uani 1 1 d . . . . .
H9A H 0.852969 0.531995 0.476861 0.073 Uiso 1 1 calc R . . . .
H9B H 0.986946 0.426073 0.436397 0.073 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.343(4) . ?
O1 C3 1.439(3) . ?
O2 C1 1.339(4) . ?
O2 C2 1.446(3) . ?
O3 C4 1.446(3) . ?
O3 C5 1.340(4) . ?
O4 C5 1.320(4) . ?
O4 C6 1.436(4) . ?
O5 C5 1.197(4) . ?
O6 C7 1.450(4) . ?
O6 C8 1.349(4) . ?
O7 C8 1.341(4) . ?
O7 C9 1.428(4) . ?
O8 C8 1.178(4) . ?
O9 C1 1.189(4) . ?
C2 H2 1.0000 . ?
C2 C3 1.527(4) . ?
C2 C7 1.504(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.516(4) . ?
C4 H4 1.0000 . ?
C4 C6 1.527(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7 1.0000 . ?
C7 C9 1.524(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C3 110.2(2) . . ?
C1 O2 C2 110.4(2) . . ?
C5 O3 C4 110.0(2) . . ?
C5 O4 C6 111.5(2) . . ?
C8 O6 C7 110.4(2) . . ?
C8 O7 C9 111.0(3) . . ?
O2 C1 O1 110.8(3) . . ?
O9 C1 O1 124.6(3) . . ?
O9 C1 O2 124.5(3) . . ?
O2 C2 H2 110.2 . . ?
O2 C2 C3 102.5(2) . . ?
O2 C2 C7 108.3(2) . . ?
C3 C2 H2 110.2 . . ?
C7 C2 H2 110.2 . . ?
C7 C2 C3 115.0(2) . . ?
O1 C3 C2 103.3(2) . . ?
O1 C3 H3 109.7 . . ?
O1 C3 C4 110.0(2) . . ?
C2 C3 H3 109.7 . . ?
C4 C3 C2 114.2(2) . . ?
C4 C3 H3 109.7 . . ?
O3 C4 C3 105.7(2) . . ?
O3 C4 H4 110.9 . . ?
O3 C4 C6 103.5(2) . . ?
C3 C4 H4 110.9 . . ?
C3 C4 C6 114.6(2) . . ?
C6 C4 H4 110.9 . . ?
O4 C5 O3 111.4(3) . . ?
O5 C5 O3 123.2(3) . . ?
O5 C5 O4 125.4(3) . . ?
O4 C6 C4 103.1(2) . . ?
O4 C6 H6A 111.1 . . ?
O4 C6 H6B 111.1 . . ?
C4 C6 H6A 111.1 . . ?
C4 C6 H6B 111.1 . . ?
H6A C6 H6B 109.1 . . ?
O6 C7 C2 108.7(2) . . ?
O6 C7 H7 109.9 . . ?
O6 C7 C9 103.2(2) . . ?
C2 C7 H7 109.9 . . ?
C2 C7 C9 115.0(3) . . ?
C9 C7 H7 109.9 . . ?
O7 C8 O6 110.7(3) . . ?
O8 C8 O6 123.2(3) . . ?
O8 C8 O7 126.1(3) . . ?
O7 C9 C7 104.1(3) . . ?
O7 C9 H9A 110.9 . . ?
O7 C9 H9B 110.9 . . ?
C7 C9 H9A 110.9 . . ?
C7 C9 H9B 110.9 . . ?
H9A C9 H9B 109.0 . . ?

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 C3 C4 O3 -178.09(19) . . . . ?
O1 C3 C4 C6 -64.8(3) . . . . ?
O2 C2 C3 O1 -15.9(3) . . . . ?
O2 C2 C3 C4 103.7(3) . . . . ?
O2 C2 C7 O6 68.0(3) . . . . ?
O2 C2 C7 C9 -176.9(2) . . . . ?
O3 C4 C6 O4 6.2(3) . . . . ?
O6 C7 C9 O7 -7.7(3) . . . . ?
C1 O1 C3 C2 12.7(3) . . . . ?
C1 O1 C3 C4 -109.6(3) . . . . ?
C1 O2 C2 C3 14.6(3) . . . . ?
C1 O2 C2 C7 -107.4(3) . . . . ?
C2 O2 C1 O1 -7.4(3) . . . . ?
C2 O2 C1 O9 171.3(3) . . . . ?
C2 C3 C4 O3 66.2(3) . . . . ?
C2 C3 C4 C6 179.5(2) . . . . ?
C2 C7 C9 O7 -125.9(3) . . . . ?
C3 O1 C1 O2 -4.0(3) . . . . ?
C3 O1 C1 O9 177.3(3) . . . . ?
C3 C2 C7 O6 -46.1(3) . . . . ?
C3 C2 C7 C9 69.1(4) . . . . ?
C3 C4 C6 O4 -108.4(3) . . . . ?
C4 O3 C5 O4 4.3(3) . . . . ?
C4 O3 C5 O5 -176.1(3) . . . . ?
C5 O3 C4 C3 114.3(3) . . . . ?
C5 O3 C4 C6 -6.6(3) . . . . ?
C5 O4 C6 C4 -4.2(3) . . . . ?
C6 O4 C5 O3 0.1(4) . . . . ?
C6 O4 C5 O5 -179.4(3) . . . . ?
C7 O6 C8 O7 -0.8(3) . . . . ?
C7 O6 C8 O8 180.0(3) . . . . ?
C7 C2 C3 O1 101.5(3) . . . . ?
C7 C2 C3 C4 -139.0(3) . . . . ?
C8 O6 C7 C2 128.0(3) . . . . ?
C8 O6 C7 C9 5.4(3) . . . . ?
C8 O7 C9 C7 7.8(4) . . . . ?
C9 O7 C8 O6 -4.7(4) . . . . ?
C9 O7 C8 O8 174.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 3(2)
2 -2(2)

####################################################################### 
# 
# 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_19may23c_0m
_database_code_depnum_ccdc_archive 'CCDC 1937068'
_audit_update_record             
;
2019-06-28 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             2019-05-24
_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         'C13 H16 O10'
_chemical_formula_sum            'C13 H16 O10'
_chemical_formula_weight         332.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   10.764(8)
_cell_length_b                   11.060(8)
_cell_length_c                   25.394(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3023(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1170
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      19.035
_cell_measurement_theta_min      2.481
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1564 before and 0.1049 after correction. The Ratio of minimum to maximum transmission is 0.4509. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_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  0.1509
_diffrn_reflns_av_unetI/netI     0.1359
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14707
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         1.604
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1415
_reflns_number_total             2670
_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 V8.32B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.32B (?, 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         0.436
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       0.035(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2670
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1538
_refine_ls_R_factor_gt           0.0942
_refine_ls_restrained_S_all      1.021
_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)+(0.1123P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1967
_refine_ls_wR_factor_ref         0.2404
_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
2.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C8(H8A,H8B)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_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
O1 O 0.5787(3) 0.4741(2) 0.57011(12) 0.0531(9) Uani 1 1 d . . . . .
O2 O 0.4439(3) 0.6011(2) 0.59905(13) 0.0571(9) Uani 1 1 d . . . . .
O3 O 0.3321(3) 0.8320(3) 0.59351(13) 0.0601(10) Uani 1 1 d . . . . .
O4 O 0.4995(3) 0.8952(3) 0.63552(14) 0.0687(11) Uani 1 1 d . . . . .
O5 O 0.3437(3) 0.9527(2) 0.72009(13) 0.0591(9) Uani 1 1 d . . . . .
O6 O 0.5117(3) 1.0362(3) 0.75547(15) 0.0724(11) Uani 1 1 d . . . . .
O7 O 0.3435(4) 1.1500(3) 0.73970(16) 0.0843(12) Uani 1 1 d . . . . .
O8 O 0.4398(3) 0.9877(3) 0.56124(16) 0.0834(12) Uani 1 1 d . . . . .
O9 O 0.4250(3) 0.4050(2) 0.62277(14) 0.0607(10) Uani 1 1 d . . . . .
O10 O 0.6837(3) 0.3827(3) 0.65662(16) 0.0745(11) Uani 1 1 d . . . . .
C1 C 0.4779(4) 0.4829(4) 0.59947(18) 0.0479(11) Uani 1 1 d . . . . .
C2 C 0.3311(4) 0.6280(4) 0.6275(2) 0.0559(13) Uani 1 1 d . . . . .
H2A H 0.326810 0.579946 0.659449 0.067 Uiso 1 1 calc R . . . .
H2B H 0.259136 0.609484 0.606005 0.067 Uiso 1 1 calc R . . . .
C3 C 0.3335(4) 0.7604(4) 0.64087(18) 0.0501(12) Uani 1 1 d . . . . .
H3 H 0.260648 0.780364 0.662296 0.060 Uiso 1 1 calc R . . . .
C4 C 0.4245(5) 0.9114(4) 0.5937(2) 0.0617(13) Uani 1 1 d . . . . .
C5 C 0.4514(4) 0.8028(4) 0.66936(18) 0.0498(12) Uani 1 1 d . . . . .
H5 H 0.510801 0.735822 0.671084 0.060 Uiso 1 1 calc R . . . .
C6 C 0.4320(4) 0.8530(4) 0.72358(19) 0.0522(12) Uani 1 1 d . . . . .
H6 H 0.399495 0.790010 0.746936 0.063 Uiso 1 1 calc R . . . .
C7 C 0.3958(5) 1.0545(4) 0.7388(2) 0.0628(14) Uani 1 1 d . . . . .
C8 C 0.5467(5) 0.9110(4) 0.7481(2) 0.0659(15) Uani 1 1 d . . . . .
H8A H 0.566871 0.873257 0.781491 0.079 Uiso 1 1 calc R . . . .
H8B H 0.617737 0.904372 0.724771 0.079 Uiso 1 1 calc R . . . .
C9 C 0.6342(4) 0.3525(3) 0.5659(2) 0.0542(12) Uani 1 1 d . . . . .
C10 C 0.6697(4) 0.3119(4) 0.6210(2) 0.0600(13) Uani 1 1 d . . . . .
C11 C 0.6922(7) 0.1783(5) 0.6295(3) 0.103(2) Uani 1 1 d . . . . .
H11A H 0.725705 0.165558 0.664089 0.154 Uiso 1 1 calc GR . . . .
H11B H 0.749936 0.149231 0.603633 0.154 Uiso 1 1 calc GR . . . .
H11C H 0.615091 0.135304 0.626154 0.154 Uiso 1 1 calc GR . . . .
C12 C 0.5469(5) 0.2692(4) 0.5359(2) 0.0702(15) Uani 1 1 d . . . . .
H12A H 0.473422 0.255296 0.556470 0.105 Uiso 1 1 calc GR . . . .
H12B H 0.587684 0.193531 0.529237 0.105 Uiso 1 1 calc GR . . . .
H12C H 0.524374 0.306123 0.503041 0.105 Uiso 1 1 calc GR . . . .
C13 C 0.7538(5) 0.3763(5) 0.5350(3) 0.0854(19) Uani 1 1 d . . . . .
H13A H 0.733943 0.415435 0.502288 0.128 Uiso 1 1 calc GR . . . .
H13B H 0.794886 0.300942 0.527924 0.128 Uiso 1 1 calc GR . . . .
H13C H 0.807678 0.427409 0.555269 0.128 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
O1 C1 1.321(5) . ?
O1 C9 1.476(5) . ?
O2 C1 1.357(5) . ?
O2 C2 1.444(5) . ?
O3 C3 1.440(5) . ?
O3 C4 1.327(6) . ?
O4 C4 1.347(6) . ?
O4 C5 1.432(5) . ?
O5 C6 1.458(5) . ?
O5 C7 1.344(5) . ?
O6 C7 1.333(6) . ?
O6 C8 1.447(5) . ?
O7 C7 1.197(6) . ?
O8 C4 1.191(6) . ?
O9 C1 1.190(5) . ?
O10 C10 1.205(6) . ?
C2 C3 1.503(6) . ?
C3 C5 1.534(6) . ?
C5 C6 1.499(6) . ?
C6 C8 1.524(6) . ?
C9 C10 1.520(7) . ?
C9 C12 1.521(6) . ?
C9 C13 1.531(7) . ?
C10 C11 1.513(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C9 116.1(3) . . ?
C1 O2 C2 114.9(3) . . ?
C4 O3 C3 110.7(4) . . ?
C4 O4 C5 110.6(4) . . ?
C7 O5 C6 109.9(3) . . ?
C7 O6 C8 110.4(3) . . ?
O1 C1 O2 106.7(3) . . ?
O9 C1 O1 128.4(4) . . ?
O9 C1 O2 124.9(4) . . ?
O2 C2 C3 107.4(3) . . ?
O3 C3 C2 110.3(4) . . ?
O3 C3 C5 103.6(3) . . ?
C2 C3 C5 114.8(3) . . ?
O3 C4 O4 111.3(4) . . ?
O8 C4 O3 124.8(5) . . ?
O8 C4 O4 123.9(5) . . ?
O4 C5 C3 103.6(4) . . ?
O4 C5 C6 109.7(3) . . ?
C6 C5 C3 115.6(4) . . ?
O5 C6 C5 108.3(3) . . ?
O5 C6 C8 103.6(3) . . ?
C5 C6 C8 114.8(4) . . ?
O6 C7 O5 112.0(4) . . ?
O7 C7 O5 123.4(5) . . ?
O7 C7 O6 124.6(5) . . ?
O6 C8 C6 104.1(4) . . ?
O1 C9 C10 107.7(4) . . ?
O1 C9 C12 109.8(4) . . ?
O1 C9 C13 102.8(3) . . ?
C10 C9 C12 116.0(4) . . ?
C10 C9 C13 108.2(4) . . ?
C12 C9 C13 111.5(5) . . ?
O10 C10 C9 122.1(4) . . ?
O10 C10 C11 120.5(5) . . ?
C11 C10 C9 117.4(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
O1 C9 C10 O10 -20.2(6) . . . . ?
O1 C9 C10 C11 162.1(4) . . . . ?
O2 C2 C3 O3 63.5(4) . . . . ?
O2 C2 C3 C5 -53.0(5) . . . . ?
O3 C3 C5 O4 1.7(4) . . . . ?
O3 C3 C5 C6 121.7(4) . . . . ?
O4 C5 C6 O5 60.1(4) . . . . ?
O4 C5 C6 C8 -55.1(5) . . . . ?
O5 C6 C8 O6 -0.3(5) . . . . ?
C1 O1 C9 C10 -60.1(5) . . . . ?
C1 O1 C9 C12 67.0(5) . . . . ?
C1 O1 C9 C13 -174.2(4) . . . . ?
C1 O2 C2 C3 158.6(4) . . . . ?
C2 O2 C1 O1 177.5(4) . . . . ?
C2 O2 C1 O9 -3.2(7) . . . . ?
C2 C3 C5 O4 122.0(4) . . . . ?
C2 C3 C5 C6 -118.0(4) . . . . ?
C3 O3 C4 O4 5.6(5) . . . . ?
C3 O3 C4 O8 -174.3(5) . . . . ?
C3 C5 C6 O5 -56.5(5) . . . . ?
C3 C5 C6 C8 -171.7(4) . . . . ?
C4 O3 C3 C2 -127.7(4) . . . . ?
C4 O3 C3 C5 -4.4(4) . . . . ?
C4 O4 C5 C3 1.5(5) . . . . ?
C4 O4 C5 C6 -122.5(4) . . . . ?
C5 O4 C4 O3 -4.4(5) . . . . ?
C5 O4 C4 O8 175.5(5) . . . . ?
C5 C6 C8 O6 117.5(4) . . . . ?
C6 O5 C7 O6 -0.5(6) . . . . ?
C6 O5 C7 O7 179.0(5) . . . . ?
C7 O5 C6 C5 -121.7(4) . . . . ?
C7 O5 C6 C8 0.5(5) . . . . ?
C7 O6 C8 C6 0.1(5) . . . . ?
C8 O6 C7 O5 0.3(6) . . . . ?
C8 O6 C7 O7 -179.2(5) . . . . ?
C9 O1 C1 O2 178.7(3) . . . . ?
C9 O1 C1 O9 -0.6(7) . . . . ?
C12 C9 C10 O10 -143.7(5) . . . . ?
C12 C9 C10 C11 38.6(6) . . . . ?
C13 C9 C10 O10 90.2(5) . . . . ?
C13 C9 C10 C11 -87.5(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_work1
_database_code_depnum_ccdc_archive 'CCDC 1940555'
_audit_update_record             
;
2019-07-14 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H6 O6'
_chemical_formula_weight         174.11

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

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

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

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

_cell_length_a                   11.6926(10)
_cell_length_b                   5.2936(5)
_cell_length_c                   12.0745(11)
_cell_angle_alpha                90
_cell_angle_beta                 118.2550(10)
_cell_angle_gamma                90
_cell_volume                     658.31(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3361
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.163
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3725
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.342
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             1147
_reflns_number_gt                1054
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1147
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1448
_refine_ls_wR_factor_gt          0.1399
_refine_ls_goodness_of_fit_ref   1.298
_refine_ls_restrained_S_all      1.298
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.12454(11) 0.7536(3) 0.32962(11) 0.0354(4) Uani 1 1 d . . . . .
O2 O 0.07958(11) 1.0223(2) 0.17145(10) 0.0230(4) Uani 1 1 d . . . . .
O3 O 0.13717(11) 0.6300(2) 0.15842(12) 0.0285(4) Uani 1 1 d . . . . .
O4 O 0.32788(10) 0.8073(2) 0.62467(11) 0.0326(4) Uani 1 1 d . . . . .
O5 O 0.17779(11) 0.50700(19) 0.58240(11) 0.0222(4) Uani 1 1 d . . . . .
O6 O 0.14592(11) 0.8900(2) 0.63559(11) 0.0269(4) Uani 1 1 d . . . . .
C1 C 0.11433(14) 0.7975(3) 0.22862(15) 0.0233(5) Uani 1 1 d . . . . .
C2 C 0.07171(17) 1.0059(3) 0.04822(15) 0.0207(4) Uani 1 1 d . . . . .
H2 H 0.114794 1.154337 0.032276 0.025 Uiso 1 1 calc R U . . .
C3 C 0.14528(16) 0.7649(3) 0.05776(16) 0.0279(5) Uani 1 1 d . . . . .
H3A H 0.103724 0.668142 -0.021855 0.033 Uiso 1 1 calc R U . . .
H3B H 0.236624 0.800594 0.079482 0.033 Uiso 1 1 calc R U . . .
C4 C 0.22629(15) 0.7418(3) 0.61506(14) 0.0226(4) Uani 1 1 d . . . . .
C5 C 0.04864(16) 0.4993(3) 0.57027(15) 0.0189(4) Uani 1 1 d . . . . .
H5 H 0.037095 0.345317 0.611930 0.023 Uiso 1 1 calc R U . . .
C6 C 0.04523(16) 0.7369(3) 0.63910(15) 0.0248(5) Uani 1 1 d . . . . .
H6A H -0.040398 0.821199 0.595275 0.030 Uiso 1 1 calc R U . . .
H6B H 0.065048 0.698909 0.726664 0.030 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
O1 C1 1.1907(18) . ?
O2 C1 1.339(2) . ?
O2 C2 1.4494(18) . ?
O3 C1 1.338(2) . ?
O3 C3 1.4509(19) . ?
O4 C4 1.1892(19) . ?
O5 C4 1.345(2) . ?
O5 C5 1.4470(19) . ?
O6 C4 1.3346(19) . ?
O6 C6 1.4465(19) . ?
C2 C3 1.512(2) . ?
C2 C2 1.524(3) 3_575 ?
C2 H2 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C6 1.518(2) . ?
C5 C5 1.532(3) 3_566 ?
C5 H5 1.0000 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

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 C2 109.40(11) . . ?
C1 O3 C3 108.44(13) . . ?
C4 O5 C5 109.31(11) . . ?
C4 O6 C6 109.28(12) . . ?
O1 C1 O3 124.48(16) . . ?
O1 C1 O2 124.08(16) . . ?
O3 C1 O2 111.43(13) . . ?
O2 C2 C3 102.42(12) . . ?
O2 C2 C2 107.39(15) . 3_575 ?
C3 C2 C2 113.83(16) . 3_575 ?
O2 C2 H2 110.9 . . ?
C3 C2 H2 110.9 . . ?
C2 C2 H2 110.9 3_575 . ?
O3 C3 C2 102.63(11) . . ?
O3 C3 H3A 111.2 . . ?
C2 C3 H3A 111.2 . . ?
O3 C3 H3B 111.2 . . ?
C2 C3 H3B 111.2 . . ?
H3A C3 H3B 109.2 . . ?
O4 C4 O6 124.68(16) . . ?
O4 C4 O5 124.12(15) . . ?
O6 C4 O5 111.20(13) . . ?
O5 C5 C6 102.58(12) . . ?
O5 C5 C5 107.71(15) . 3_566 ?
C6 C5 C5 113.84(16) . 3_566 ?
O5 C5 H5 110.8 . . ?
C6 C5 H5 110.8 . . ?
C5 C5 H5 110.8 3_566 . ?
O6 C6 C5 102.45(11) . . ?
O6 C6 H6A 111.3 . . ?
C5 C6 H6A 111.3 . . ?
O6 C6 H6B 111.3 . . ?
C5 C6 H6B 111.3 . . ?
H6A C6 H6B 109.2 . . ?

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 O3 C1 O1 -166.49(15) . . . . ?
C3 O3 C1 O2 12.93(18) . . . . ?
C2 O2 C1 O1 -177.66(14) . . . . ?
C2 O2 C1 O3 2.92(18) . . . . ?
C1 O2 C2 C3 -16.43(16) . . . . ?
C1 O2 C2 C2 103.74(16) . . . 3_575 ?
C1 O3 C3 C2 -22.24(17) . . . . ?
O2 C2 C3 O3 22.58(16) . . . . ?
C2 C2 C3 O3 -93.01(18) 3_575 . . . ?
C6 O6 C4 O4 -168.99(15) . . . . ?
C6 O6 C4 O5 10.76(17) . . . . ?
C5 O5 C4 O4 -175.53(14) . . . . ?
C5 O5 C4 O6 4.71(17) . . . . ?
C4 O5 C5 C6 -16.98(16) . . . . ?
C4 O5 C5 C5 103.41(16) . . . 3_566 ?
C4 O6 C6 C5 -20.52(16) . . . . ?
O5 C5 C6 O6 21.85(15) . . . . ?
C5 C5 C6 O6 -94.21(18) 3_566 . . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.043



####################################################################### 
# 
# 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_19june12a_0m
_database_code_depnum_ccdc_archive 'CCDC 1937067'
_audit_update_record             
;
2019-06-28 deposited with the CCDC.	2019-10-28 downloaded from the CCDC.
;
_audit_creation_date             2019-06-19
_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         'C15 H17 Cl3 O10'
_chemical_formula_sum            'C15 H17 Cl3 O10'
_chemical_formula_weight         463.64
_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                   8.238(7)
_cell_length_b                   13.923(12)
_cell_length_c                   17.649(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2024(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1372
_cell_measurement_temperature    293
_cell_measurement_theta_max      18.218
_cell_measurement_theta_min      2.728
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.502
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0844 before and 0.0542 after correction. The Ratio of minimum to maximum transmission is 0.6206. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_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  0.0618
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10369
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.023
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_min         1.863
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2013
_reflns_number_total             3582
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.32B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.32B (?, 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         0.380
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1207
_refine_ls_R_factor_gt           0.0658
_refine_ls_restrained_S_all      1.031
_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)+(0.0976P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1611
_refine_ls_wR_factor_ref         0.1913
_refine_special_details          ?
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.1(2)
 -0.1(2)
2. 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
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C12(H12), C13(H13)
3.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_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 -0.0518(3) 0.6832(2) 0.93929(16) 0.1154(11) Uani 1 1 d . . . . .
Cl2 Cl -0.0561(4) 0.6433(3) 0.77874(18) 0.1278(13) Uani 1 1 d . . . . .
Cl3 Cl -0.1894(3) 0.8213(3) 0.8377(2) 0.1418(15) Uani 1 1 d . . . . .
O1 O 0.2515(7) 0.7154(4) 0.8469(3) 0.0794(16) Uani 1 1 d . . . . .
O2 O 0.4248(7) 0.6736(4) 0.7495(3) 0.0734(15) Uani 1 1 d . . . . .
O3 O 0.4804(5) 0.8409(3) 0.6450(3) 0.0622(13) Uani 1 1 d . . . . .
O4 O 0.4014(7) 0.8720(5) 0.5244(3) 0.0780(17) Uani 1 1 d . . . . .
O5 O 0.6659(7) 0.8667(4) 0.5103(3) 0.0746(16) Uani 1 1 d . . . . .
O6 O 0.5121(8) 0.7816(6) 0.4324(4) 0.097(2) Uani 1 1 d . . . . .
O7 O 0.1413(7) 0.8285(5) 0.7713(3) 0.0859(18) Uani 1 1 d . . . . .
O8 O 0.4289(8) 0.5456(4) 0.6123(4) 0.0908(19) Uani 1 1 d . . . . .
O9 O 0.6924(10) 0.5592(6) 0.6123(5) 0.103(2) Uani 1 1 d . . . . .
O10 O 0.5828(12) 0.4156(5) 0.5927(4) 0.120(3) Uani 1 1 d . . . . .
C1 C -0.0335(11) 0.7333(8) 0.8486(6) 0.094(3) Uani 1 1 d . . . . .
C2 C 0.1273(10) 0.7831(7) 0.8420(5) 0.078(2) Uani 1 1 d . . . . .
H2 H 0.138834 0.830485 0.882646 0.093 Uiso 1 1 calc R . . . .
C3 C 0.3801(10) 0.7453(6) 0.7985(5) 0.069(2) Uani 1 1 d . . . . .
H3 H 0.473534 0.766859 0.828397 0.083 Uiso 1 1 calc R . . . .
C4 C 0.3548(9) 0.6902(6) 0.6766(5) 0.066(2) Uani 1 1 d . . . . .
H4 H 0.247347 0.660054 0.675568 0.079 Uiso 1 1 calc R . . . .
C5 C 0.3320(9) 0.7990(6) 0.6718(4) 0.0608(19) Uani 1 1 d . . . . .
H5 H 0.238430 0.817036 0.640570 0.073 Uiso 1 1 calc R . . . .
C6 C 0.4627(11) 0.9151(6) 0.5920(5) 0.066(2) Uani 1 1 d . . . . .
C7 C 0.5264(10) 0.8348(8) 0.4835(6) 0.077(2) Uani 1 1 d . . . . .
C8 C 0.6378(11) 0.9438(6) 0.5648(5) 0.077(2) Uani 1 1 d . . . . .
C9 C 0.7641(12) 0.9351(9) 0.6266(6) 0.108(4) Uani 1 1 d . . . . .
H9A H 0.753140 0.873959 0.651283 0.162 Uiso 1 1 calc GR . . . .
H9B H 0.748910 0.985546 0.662981 0.162 Uiso 1 1 calc GR . . . .
H9C H 0.870543 0.940154 0.604807 0.162 Uiso 1 1 calc GR . . . .
C10 C 0.6430(17) 1.0354(7) 0.5229(6) 0.112(4) Uani 1 1 d . . . . .
H10A H 0.745382 1.041146 0.497284 0.167 Uiso 1 1 calc GR . . . .
H10B H 0.630404 1.087876 0.557704 0.167 Uiso 1 1 calc GR . . . .
H10C H 0.556660 1.036883 0.486382 0.167 Uiso 1 1 calc GR . . . .
C11 C 0.3553(14) 0.9926(7) 0.6157(6) 0.104(4) Uani 1 1 d . . . . .
H11A H 0.249278 0.967070 0.626068 0.156 Uiso 1 1 calc GR . . . .
H11B H 0.347893 1.039579 0.576077 0.156 Uiso 1 1 calc GR . . . .
H11C H 0.397761 1.022147 0.660688 0.156 Uiso 1 1 calc GR . . . .
C12 C 0.3109(9) 0.8270(7) 0.7534(4) 0.068(2) Uani 1 1 d . . . . .
H12 H 0.364043 0.888163 0.765120 0.081 Uiso 1 1 calc R . . . .
C13 C 0.4537(10) 0.6489(6) 0.6136(5) 0.067(2) Uani 1 1 d . . . . .
H13 H 0.421055 0.677207 0.565120 0.081 Uiso 1 1 calc R . . . .
C14 C 0.5703(15) 0.5005(9) 0.6039(6) 0.091(3) Uani 1 1 d . . . . .
C15 C 0.6376(10) 0.6559(6) 0.6235(5) 0.077(2) Uani 1 1 d . . . . .
H15A H 0.684680 0.698778 0.586165 0.093 Uiso 1 1 calc R . . . .
H15B H 0.665337 0.678621 0.673770 0.093 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 C1 1.752(11) . ?
Cl2 C1 1.768(11) . ?
Cl3 C1 1.786(11) . ?
O1 C2 1.393(11) . ?
O1 C3 1.423(9) . ?
O2 C3 1.371(9) . ?
O2 C4 1.428(9) . ?
O3 C5 1.434(9) . ?
O3 C6 1.402(9) . ?
O4 C6 1.429(10) . ?
O4 C7 1.360(10) . ?
O5 C7 1.319(11) . ?
O5 C8 1.461(11) . ?
O6 C7 1.174(11) . ?
O7 C2 1.403(10) . ?
O7 C12 1.433(10) . ?
O8 C13 1.453(10) . ?
O8 C14 1.331(13) . ?
O9 C14 1.304(13) . ?
O9 C15 1.434(11) . ?
O10 C14 1.203(12) . ?
C1 C2 1.500(13) . ?
C2 H2 0.9800 . ?
C3 H3 0.9800 . ?
C3 C12 1.502(12) . ?
C4 H4 0.9800 . ?
C4 C5 1.529(11) . ?
C4 C13 1.494(11) . ?
C5 H5 0.9800 . ?
C5 C12 1.502(11) . ?
C6 C8 1.572(13) . ?
C6 C11 1.457(12) . ?
C8 C9 1.512(14) . ?
C8 C10 1.476(13) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12 0.9800 . ?
C13 H13 0.9800 . ?
C13 C15 1.528(12) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C3 108.2(6) . . ?
C3 O2 C4 110.0(6) . . ?
C6 O3 C5 115.5(6) . . ?
C7 O4 C6 109.6(7) . . ?
C7 O5 C8 110.2(7) . . ?
C2 O7 C12 105.6(6) . . ?
C14 O8 C13 110.2(8) . . ?
C14 O9 C15 111.1(8) . . ?
Cl1 C1 Cl2 110.3(6) . . ?
Cl1 C1 Cl3 108.1(6) . . ?
Cl2 C1 Cl3 109.6(5) . . ?
C2 C1 Cl1 109.3(7) . . ?
C2 C1 Cl2 111.5(7) . . ?
C2 C1 Cl3 108.1(8) . . ?
O1 C2 O7 107.5(7) . . ?
O1 C2 C1 109.4(8) . . ?
O1 C2 H2 109.8 . . ?
O7 C2 C1 110.5(7) . . ?
O7 C2 H2 109.8 . . ?
C1 C2 H2 109.8 . . ?
O1 C3 H3 110.6 . . ?
O1 C3 C12 104.9(7) . . ?
O2 C3 O1 111.5(7) . . ?
O2 C3 H3 110.6 . . ?
O2 C3 C12 108.6(7) . . ?
C12 C3 H3 110.6 . . ?
O2 C4 H4 108.2 . . ?
O2 C4 C5 105.1(6) . . ?
O2 C4 C13 112.8(6) . . ?
C5 C4 H4 108.2 . . ?
C13 C4 H4 108.2 . . ?
C13 C4 C5 114.0(7) . . ?
O3 C5 C4 108.4(6) . . ?
O3 C5 H5 112.4 . . ?
O3 C5 C12 108.0(6) . . ?
C4 C5 H5 112.4 . . ?
C12 C5 C4 102.6(7) . . ?
C12 C5 H5 112.4 . . ?
O3 C6 O4 106.5(6) . . ?
O3 C6 C8 107.2(7) . . ?
O3 C6 C11 114.6(7) . . ?
O4 C6 C8 100.2(6) . . ?
O4 C6 C11 109.7(8) . . ?
C11 C6 C8 117.2(8) . . ?
O5 C7 O4 110.0(9) . . ?
O6 C7 O4 124.9(9) . . ?
O6 C7 O5 125.1(8) . . ?
O5 C8 C6 99.2(6) . . ?
O5 C8 C9 107.9(8) . . ?
O5 C8 C10 107.5(8) . . ?
C9 C8 C6 113.0(8) . . ?
C10 C8 C6 113.5(9) . . ?
C10 C8 C9 114.3(9) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O7 C12 C3 105.3(7) . . ?
O7 C12 C5 109.2(6) . . ?
O7 C12 H12 112.1 . . ?
C3 C12 C5 105.6(7) . . ?
C3 C12 H12 112.1 . . ?
C5 C12 H12 112.1 . . ?
O8 C13 C4 108.5(7) . . ?
O8 C13 H13 110.2 . . ?
O8 C13 C15 101.8(7) . . ?
C4 C13 H13 110.2 . . ?
C4 C13 C15 115.6(7) . . ?
C15 C13 H13 110.2 . . ?
O9 C14 O8 111.6(10) . . ?
O10 C14 O8 123.8(12) . . ?
O10 C14 O9 124.6(11) . . ?
O9 C15 C13 103.7(7) . . ?
O9 C15 H15A 111.0 . . ?
O9 C15 H15B 111.0 . . ?
C13 C15 H15A 111.0 . . ?
C13 C15 H15B 111.0 . . ?
H15A C15 H15B 109.0 . . ?

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
Cl1 C1 C2 O1 65.3(9) . . . . ?
Cl1 C1 C2 O7 -176.6(6) . . . . ?
Cl2 C1 C2 O1 -56.9(9) . . . . ?
Cl2 C1 C2 O7 61.2(10) . . . . ?
Cl3 C1 C2 O1 -177.3(6) . . . . ?
Cl3 C1 C2 O7 -59.2(9) . . . . ?
O1 C3 C12 O7 -8.2(9) . . . . ?
O1 C3 C12 C5 -123.7(7) . . . . ?
O2 C3 C12 O7 111.0(7) . . . . ?
O2 C3 C12 C5 -4.5(8) . . . . ?
O2 C4 C5 O3 86.0(7) . . . . ?
O2 C4 C5 C12 -28.1(7) . . . . ?
O2 C4 C13 O8 76.0(8) . . . . ?
O2 C4 C13 C15 -37.5(10) . . . . ?
O3 C5 C12 O7 152.5(7) . . . . ?
O3 C5 C12 C3 -94.7(7) . . . . ?
O3 C6 C8 O5 79.9(7) . . . . ?
O3 C6 C8 C9 -34.1(10) . . . . ?
O3 C6 C8 C10 -166.4(8) . . . . ?
O4 C6 C8 O5 -31.1(8) . . . . ?
O4 C6 C8 C9 -145.1(8) . . . . ?
O4 C6 C8 C10 82.6(9) . . . . ?
O8 C13 C15 O9 10.2(9) . . . . ?
C2 O1 C3 O2 -127.3(7) . . . . ?
C2 O1 C3 C12 -10.0(9) . . . . ?
C2 O7 C12 C3 23.2(9) . . . . ?
C2 O7 C12 C5 136.2(7) . . . . ?
C3 O1 C2 O7 25.3(9) . . . . ?
C3 O1 C2 C1 145.3(7) . . . . ?
C3 O2 C4 C5 27.1(8) . . . . ?
C3 O2 C4 C13 151.9(6) . . . . ?
C4 O2 C3 O1 100.6(7) . . . . ?
C4 O2 C3 C12 -14.4(8) . . . . ?
C4 C5 C12 O7 -93.2(8) . . . . ?
C4 C5 C12 C3 19.7(7) . . . . ?
C4 C13 C15 O9 127.6(8) . . . . ?
C5 O3 C6 O4 -68.3(7) . . . . ?
C5 O3 C6 C8 -174.8(7) . . . . ?
C5 O3 C6 C11 53.2(10) . . . . ?
C5 C4 C13 O8 -164.2(6) . . . . ?
C5 C4 C13 C15 82.3(9) . . . . ?
C6 O3 C5 C4 138.8(6) . . . . ?
C6 O3 C5 C12 -110.7(7) . . . . ?
C6 O4 C7 O5 -12.8(9) . . . . ?
C6 O4 C7 O6 166.6(9) . . . . ?
C7 O4 C6 O3 -83.6(7) . . . . ?
C7 O4 C6 C8 27.9(8) . . . . ?
C7 O4 C6 C11 151.8(8) . . . . ?
C7 O5 C8 C6 26.3(9) . . . . ?
C7 O5 C8 C9 144.2(8) . . . . ?
C7 O5 C8 C10 -92.1(10) . . . . ?
C8 O5 C7 O4 -10.4(10) . . . . ?
C8 O5 C7 O6 170.2(9) . . . . ?
C11 C6 C8 O5 -149.6(8) . . . . ?
C11 C6 C8 C9 96.4(10) . . . . ?
C11 C6 C8 C10 -35.8(12) . . . . ?
C12 O7 C2 O1 -30.3(9) . . . . ?
C12 O7 C2 C1 -149.6(8) . . . . ?
C13 O8 C14 O9 11.0(10) . . . . ?
C13 O8 C14 O10 -171.6(9) . . . . ?
C13 C4 C5 O3 -38.1(9) . . . . ?
C13 C4 C5 C12 -152.2(7) . . . . ?
C14 O8 C13 C4 -135.2(8) . . . . ?
C14 O8 C13 C15 -12.9(9) . . . . ?
C14 O9 C15 C13 -4.8(11) . . . . ?
C15 O9 C14 O8 -3.5(12) . . . . ?
C15 O9 C14 O10 179.0(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.1(2)
2 -0.1(2)

