# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_ADTA_2-27_THF_oX_100K_2-fold_publ
_database_code_depnum_ccdc_archive 'CCDC 1915299'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;
_audit_creation_date             2019-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H20 O8, 8.75(O)'
_chemical_formula_sum            'C14 H20 O16.75'
_chemical_formula_weight         456.30
_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      cubic
_space_group_IT_number           201
_space_group_name_H-M_alt        'P n -3'
_space_group_name_Hall           '-P 2ab 2bc 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x+1/2, y, -z+1/2'
'x, -y+1/2, -z+1/2'
'z, x, y'
'z, -x+1/2, -y+1/2'
'-z+1/2, -x+1/2, y'
'-z+1/2, x, -y+1/2'
'y, z, x'
'-y+1/2, z, -x+1/2'
'y, -z+1/2, -x+1/2'
'-y+1/2, -z+1/2, x'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x-1/2, -y, z-1/2'
'-x, y-1/2, z-1/2'
'-z, -x, -y'
'-z, x-1/2, y-1/2'
'z-1/2, x-1/2, -y'
'z-1/2, -x, y-1/2'
'-y, -z, -x'
'y-1/2, -z, x-1/2'
'-y, z-1/2, x-1/2'
'y-1/2, z-1/2, -x'

_cell_length_a                   11.4074(5)
_cell_length_b                   11.4074(5)
_cell_length_c                   11.4074(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1484.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6150
_cell_measurement_temperature    200
_cell_measurement_theta_max      29.768
_cell_measurement_theta_min      2.525
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.4751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.021
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.397
_exptl_crystal_size_mid          0.385
_exptl_crystal_size_min          0.379
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15739
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.472
_diffrn_reflns_theta_min         1.785
_diffrn_ambient_temperature      200
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                656
_reflns_number_total             761
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         761
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0859
_refine_ls_restrained_S_all      1.271
_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)+(0.1422P)²+0.1067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2151
_refine_ls_wR_factor_ref         0.2255
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.506(13)
 0.494(13)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
3. Restrained distances
 H1-H2_$1
 2.1 with sigma of 0.04
 H2-H1_$2
 2.1 with sigma of 0.04
4. Restrained planarity
 H2_$1, O2_$1, C3, O1, H1
 with sigma of 0.001
 H2, O2, C3, O1_$2, H1_$2
 with sigma of 0.001
5. Uiso/Uaniso restraints and constraints
Uanis(O5S) \\sim Ueq, Uanis(O4S) \\sim Ueq, Uanis(O2S) \\sim Ueq, Uanis(O3S)
\\sim Ueq, Uanis(O1S) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
6. Others
 Fixed Sof: O1(0.33333) H1(0.33333) O2(0.33333) H2(0.33333) H1A(0.5) H1B(0.5)
 O1S(0.125) O2S(0.125) O3S(0.125) O4S(0.25) O5S(0.04167) O6S(0.0625)
7.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
7.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_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 0.6142(7) 0.5875(7) 0.4913(4) 0.073(2) Uani 0.3333 1 d . . . A 1
H1 H 0.5647 0.5420 0.4612 0.110 Uiso 0.3333 1 calc DGR . . A 1
O2 O 0.5430(8) 0.6449(5) 0.5151(7) 0.101(4) Uani 0.3333 1 d . . . A 2
H2 H 0.5031 0.5952 0.4781 0.151 Uiso 0.3333 1 calc DGR . . A 2
C1 C 0.7500 0.7500 0.59417(12) 0.0307(5) Uani 1 2 d S T P . .
H1A H 0.7997 0.7003 0.5433 0.037 Uiso 0.5 1 calc R . . . .
H1B H 0.7003 0.7997 0.5433 0.037 Uiso 0.5 1 calc R . . . .
C2 C 0.67231(8) 0.67231(8) 0.67231(8) 0.0289(5) Uani 1 3 d S T P . .
C3 C 0.59580(9) 0.59580(9) 0.59580(9) 0.0339(5) Uani 1 3 d S T P . .
O1S O 0.357(4) 0.811(4) 0.460(4) 0.142(13) Uani 0.125 1 d . U . B 5
O2S O 0.420(3) 0.854(2) 0.429(3) 0.093(7) Uani 0.125 1 d . U . C 3
O3S O 0.389(3) 0.868(3) 0.4776(19) 0.078(6) Uani 0.125 1 d . U . D 4
O4S O 0.5146(14) 0.9500(11) 0.4279(11) 0.101(4) Uani 0.25 1 d . U . . 2
O5S O 0.5000 1.0000 0.5000 0.092(6) Uani 0.25 6 d S TU P E 1
O6S O 0.7500 0.881(4) 0.2500 0.26(4) Uani 0.125 2 d S T P F 6


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C3 1.215(5) . ?
O2 H2 0.8400 . ?
O2 C3 1.235(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5380(10) . ?
C1 C2 1.5380(10) 2_665 ?
C2 C1 1.5380(10) 5 ?
C2 C1 1.5380(10) 9 ?
C2 C3 1.512(2) . ?
C3 O1 1.215(5) 5 ?
C3 O1 1.215(5) 9 ?
C3 O2 1.235(5) 5 ?
C3 O2 1.235(5) 9 ?
O4S O4S 1.019(14) 18_665 ?
O4S O4S 1.76(2) 12_665 ?
O4S O4S 1.76(2) 6_566 ?
O4S O4S 1.019(14) 24_566 ?

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 . . ?
C3 O2 H2 109.5 . . ?
H1A C1 H1B 108.3 . . ?
C2 C1 H1A 109.8 2_665 . ?
C2 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 2_665 . ?
C2 C1 H1B 109.8 . . ?
C2 C1 C2 109.16(13) 2_665 . ?
C1 C2 C1 109.63(7) . 9 ?
C1 C2 C1 109.63(7) . 5 ?
C1 C2 C1 109.63(7) 9 5 ?
C3 C2 C1 109.32(7) . 5 ?
C3 C2 C1 109.32(7) . . ?
C3 C2 C1 109.32(7) . 9 ?
O1 C3 O1 96.1(3) 9 . ?
O1 C3 O1 96.1(3) . 5 ?
O1 C3 O1 96.1(3) 9 5 ?
O1 C3 C2 120.8(2) . . ?
O1 C3 C2 120.8(2) 5 . ?
O1 C3 C2 120.8(2) 9 . ?
O2 C3 O2 101.3(3) . 5 ?
O2 C3 O2 101.3(3) 5 9 ?
O2 C3 O2 101.3(3) . 9 ?
O2 C3 C2 116.8(2) . . ?
O2 C3 C2 116.8(2) 9 . ?
O2 C3 C2 116.8(2) 5 . ?
O4S O4S O4S 119.1(5) 18_665 24_566 ?
O4S O4S O4S 30.5(2) 24_566 6_566 ?
O4S O4S O4S 90.002(5) 18_665 6_566 ?
O4S O4S O4S 30.5(2) 18_665 12_665 ?
O4S O4S O4S 60.001(4) 12_665 6_566 ?
O4S O4S O4S 90.002(2) 24_566 12_665 ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.506(13)
2 0.494(13)

####################################################################### 
# 
# 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_ADTA_2-2_THF_4-fold_publ
_database_code_depnum_ccdc_archive 'CCDC 1915301'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;
_audit_creation_date             2018-12-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 O8, 0.25(C4 H8 O)'
_chemical_formula_sum            'C15 H18 O8.25'
_chemical_formula_weight         330.29
_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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   16.4008(15)
_cell_length_b                   16.4008(15)
_cell_length_c                   22.397(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6024.5(13)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.134
_cell_measurement_theta_min      2.484
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.4879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1044 before and 0.0737 after correction.
The Ratio of minimum to maximum transmission is 0.6542.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2784
_exptl_crystal_size_max          0.124
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.106
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            40618
_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         29.134
_diffrn_reflns_theta_min         2.484
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3187
_reflns_number_total             4055
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4055
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.058
_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)+(0.0725P)²+8.5815P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1517
_refine_ls_wR_factor_ref         0.1635
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 O7-H7 = O5-H5 = O2-H2 = O4-H4
 0.82 with sigma of 0.01
 C16-C16_$3
 1.51 with sigma of 0.01
3. Rigid body (RIGU) restrains
 O9, C15, C16
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Fixed Sof: O9(0.25) C15(0.5) H15A(0.5) H15B(0.5) C16(0.5) H16A(0.5) H16B(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B),
 C15(H15A,H15B), C16(H16A,H16B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O8 O 0.60206(8) 0.71971(7) 0.50630(5) 0.0256(3) Uani 1 1 d . . . . .
O7 O 0.64225(8) 0.78721(7) 0.42456(5) 0.0247(3) Uani 1 1 d D . . . .
O3 O 0.77747(7) 0.58178(8) 0.24742(5) 0.0268(3) Uani 1 1 d . . . . .
O5 O 0.59538(9) 0.34945(7) 0.42386(6) 0.0307(3) Uani 1 1 d D . . . .
O6 O 0.62549(9) 0.41762(7) 0.50713(5) 0.0298(3) Uani 1 1 d . . . . .
O4 O 0.84384(7) 0.54642(9) 0.33048(5) 0.0309(3) Uani 1 1 d D . . . .
O1 O 0.47472(7) 0.55365(9) 0.24134(5) 0.0318(3) Uani 1 1 d . . . . .
O2 O 0.40596(7) 0.59421(9) 0.32177(6) 0.0333(3) Uani 1 1 d D . . . .
C8 C 0.61757(8) 0.56819(8) 0.45455(6) 0.0158(3) Uani 1 1 d . . . . .
H8A H 0.6646 0.5654 0.4822 0.019 Uiso 1 1 calc R . . . .
H8B H 0.5670 0.5708 0.4787 0.019 Uiso 1 1 calc R . . . .
C5 C 0.61600(8) 0.49213(8) 0.41473(6) 0.0155(3) Uani 1 1 d . . . . .
C3 C 0.54739(8) 0.57276(8) 0.33399(6) 0.0156(3) Uani 1 1 d . . . . .
C13 C 0.61254(9) 0.41616(9) 0.45368(7) 0.0184(3) Uani 1 1 d . . . . .
C1 C 0.70013(8) 0.56474(9) 0.33761(6) 0.0165(3) Uani 1 1 d . . . . .
C9 C 0.54962(8) 0.64934(8) 0.37357(6) 0.0163(3) Uani 1 1 d . . . . .
H9A H 0.4990 0.6528 0.3976 0.020 Uiso 1 1 calc R . . . .
H9B H 0.5532 0.6987 0.3483 0.020 Uiso 1 1 calc R . . . .
C2 C 0.62546(8) 0.56936(9) 0.29624(6) 0.0170(3) Uani 1 1 d . . . . .
H2A H 0.6291 0.6186 0.2708 0.020 Uiso 1 1 calc R . . . .
H2B H 0.6241 0.5209 0.2699 0.020 Uiso 1 1 calc R . . . .
C14 C 0.62288(9) 0.72062(9) 0.45395(7) 0.0174(3) Uani 1 1 d . . . . .
C10 C 0.62447(8) 0.64466(8) 0.41536(6) 0.0152(3) Uani 1 1 d . . . . .
C4 C 0.54150(9) 0.49564(9) 0.37330(6) 0.0168(3) Uani 1 1 d . . . . .
H4A H 0.4909 0.4973 0.3973 0.020 Uiso 1 1 calc R . . . .
H4B H 0.5399 0.4464 0.3477 0.020 Uiso 1 1 calc R . . . .
C6 C 0.69493(9) 0.48791(9) 0.37693(6) 0.0173(3) Uani 1 1 d . . . . .
H6A H 0.7431 0.4849 0.4035 0.021 Uiso 1 1 calc R . . . .
H6B H 0.6942 0.4386 0.3515 0.021 Uiso 1 1 calc R . . . .
C7 C 0.70301(8) 0.64133(9) 0.37784(6) 0.0169(3) Uani 1 1 d . . . . .
H7A H 0.7512 0.6388 0.4044 0.020 Uiso 1 1 calc R . . . .
H7B H 0.7075 0.6910 0.3529 0.020 Uiso 1 1 calc R . . . .
C12 C 0.77749(9) 0.56451(9) 0.30020(7) 0.0198(3) Uani 1 1 d . . . . .
C11 C 0.47299(9) 0.57386(9) 0.29368(7) 0.0185(3) Uani 1 1 d . . . . .
O9 O 0.5000 0.7500 0.2291(3) 0.0850(19) Uani 0.5 2 d S TU P . .
C15 C 0.5688(5) 0.7532(4) 0.1904(3) 0.0836(18) Uani 0.5 1 d . U . . .
H15A H 0.5969 0.6998 0.1904 0.100 Uiso 0.5 1 calc R . . . .
H15B H 0.6076 0.7950 0.2047 0.100 Uiso 0.5 1 calc R . . . .
C16 C 0.5412(4) 0.7741(6) 0.1270(4) 0.0810(18) Uani 0.5 1 d D U . . .
H16A H 0.5797 0.7533 0.0964 0.097 Uiso 0.5 1 calc R . . . .
H16B H 0.5330 0.8334 0.1214 0.097 Uiso 0.5 1 calc R . . . .
H5 H 0.5935(18) 0.3098(12) 0.4465(11) 0.067(9) Uiso 1 1 d D . . . .
H7 H 0.642(2) 0.8242(14) 0.4497(11) 0.083(10) Uiso 1 1 d D . . . .
H2 H 0.3695(14) 0.5948(19) 0.2960(10) 0.073(9) Uiso 1 1 d D . . . .
H4 H 0.8828(13) 0.545(2) 0.3069(11) 0.078(10) Uiso 1 1 d 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
O8 C14 1.2213(19) . ?
O7 C14 1.3140(18) . ?
O7 H7 0.827(10) . ?
O3 C12 1.2155(19) . ?
O5 C13 1.3123(18) . ?
O5 H5 0.825(10) . ?
O6 C13 1.2162(19) . ?
O4 C12 1.3161(18) . ?
O4 H4 0.830(10) . ?
O1 C11 1.2184(19) . ?
O2 C11 1.3100(18) . ?
O2 H2 0.832(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C5 1.5336(19) . ?
C8 C10 1.5351(19) . ?
C5 C13 1.5220(19) . ?
C5 C4 1.5355(19) . ?
C5 C6 1.5483(19) . ?
C3 C9 1.5378(19) . ?
C3 C2 1.5353(19) . ?
C3 C4 1.5440(19) . ?
C3 C11 1.5180(19) . ?
C1 C2 1.5376(19) . ?
C1 C6 1.5397(19) . ?
C1 C7 1.547(2) . ?
C1 C12 1.520(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5456(19) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C14 C10 1.5165(19) . ?
C10 C7 1.5389(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
O9 C15 1.424(8) . ?
O9 C15 1.424(8) 6_564 ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.529(11) . ?
C16 C16 1.566(8) 6_564 ?
C16 H16A 0.9900 . ?
C16 H16B 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
C14 O7 H7 106(2) . . ?
C13 O5 H5 111(2) . . ?
C12 O4 H4 108(2) . . ?
C11 O2 H2 106(2) . . ?
H8A C8 H8B 108.2 . . ?
C5 C8 H8A 109.8 . . ?
C5 C8 H8B 109.8 . . ?
C5 C8 C10 109.47(11) . . ?
C10 C8 H8A 109.8 . . ?
C10 C8 H8B 109.8 . . ?
C8 C5 C4 109.53(11) . . ?
C8 C5 C6 109.90(11) . . ?
C13 C5 C8 109.47(11) . . ?
C13 C5 C4 110.32(11) . . ?
C13 C5 C6 107.94(11) . . ?
C4 C5 C6 109.66(11) . . ?
C9 C3 C4 109.99(11) . . ?
C2 C3 C9 109.09(11) . . ?
C2 C3 C4 109.66(11) . . ?
C11 C3 C9 110.63(11) . . ?
C11 C3 C2 110.07(11) . . ?
C11 C3 C4 107.37(11) . . ?
O5 C13 C5 113.51(13) . . ?
O6 C13 O5 123.70(14) . . ?
O6 C13 C5 122.78(13) . . ?
C2 C1 C6 109.93(11) . . ?
C2 C1 C7 109.59(11) . . ?
C6 C1 C7 109.46(11) . . ?
C12 C1 C2 109.43(11) . . ?
C12 C1 C6 111.06(11) . . ?
C12 C1 C7 107.32(11) . . ?
C3 C9 H9A 109.9 . . ?
C3 C9 H9B 109.9 . . ?
C3 C9 C10 109.12(11) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
C3 C2 C1 109.53(11) . . ?
C3 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
O8 C14 O7 123.96(13) . . ?
O8 C14 C10 122.82(13) . . ?
O7 C14 C10 113.14(13) . . ?
C8 C10 C9 109.17(11) . . ?
C8 C10 C7 110.18(11) . . ?
C14 C10 C8 110.12(11) . . ?
C14 C10 C9 106.90(11) . . ?
C14 C10 C7 110.78(11) . . ?
C7 C10 C9 109.62(11) . . ?
C5 C4 C3 109.00(11) . . ?
C5 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C5 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
C1 C6 C5 108.82(11) . . ?
C1 C6 H6A 109.9 . . ?
C1 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
C1 C7 H7A 109.9 . . ?
C1 C7 H7B 109.9 . . ?
C10 C7 C1 108.75(11) . . ?
C10 C7 H7A 109.9 . . ?
C10 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
O3 C12 O4 123.63(14) . . ?
O3 C12 C1 122.35(13) . . ?
O4 C12 C1 113.98(13) . . ?
O1 C11 O2 123.43(14) . . ?
O1 C11 C3 123.39(13) . . ?
O2 C11 C3 113.07(13) . . ?
C15 O9 C15 104.9(7) 6_564 . ?
O9 C15 H15A 109.7 . . ?
O9 C15 H15B 109.7 . . ?
O9 C15 C16 109.9(6) . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
C15 C16 C16 98.2(4) . 6_564 ?
C15 C16 H16A 112.1 . . ?
C15 C16 H16B 112.1 . . ?
C16 C16 H16A 112.1 6_564 . ?
C16 C16 H16B 112.1 6_564 . ?
H16A C16 H16B 109.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 O8 0.825(10) 1.822(11) 2.6431(16) 173(3) 14_546
O7 H7 O6 0.827(10) 1.832(12) 2.6440(16) 167(3) 14_556
O2 H2 O3 0.832(10) 1.807(12) 2.6236(16) 167(3) 10_556
O4 H4 O1 0.830(10) 1.860(11) 2.6851(17) 172(3) 10_656

_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_ADTA_2-34_THF-1-2-dimethoxybenzene_publ
_database_code_depnum_ccdc_archive 'CCDC 1915303'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;
_audit_creation_date             2018-12-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C14 H16 O8), 4(C8 H10 O2)'
_chemical_formula_sum            'C60 H72 O24'
_chemical_formula_weight         1177.17
_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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   16.2380(2)
_cell_length_b                   16.2380(2)
_cell_length_c                   22.3825(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5901.65(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.01(10)
_cell_measurement_reflns_used    8969
_cell_measurement_theta_min      2.4890
_cell_measurement_theta_max      30.0790
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_min  0.71430
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.643
_oxdiff_exptl_absorpt_empirical_full_max 1.395
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_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             2496
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            45910
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.360
_diffrn_reflns_theta_min         2.509
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0227345000
_diffrn_orient_matrix_UB_12      -0.0050706000
_diffrn_orient_matrix_UB_13      -0.0267912000
_diffrn_orient_matrix_UB_21      -0.0353263000
_diffrn_orient_matrix_UB_22      -0.0107974000
_diffrn_orient_matrix_UB_23      0.0168476000
_diffrn_orient_matrix_UB_31      -0.0119427000
_diffrn_orient_matrix_UB_32      0.0419919000
_diffrn_orient_matrix_UB_33      0.0011003000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -109.00  16.00   1.00   10.00    --  -20.00 -68.00   0.00  125
  2  ω   -109.00  16.00   1.00   10.00    --  -20.00 -68.00 120.00  125
  3  ω   -109.00  16.00   1.00   10.00    --  -20.00 -68.00 240.00  125
  4  ω   -109.00  16.00   1.00   10.00    --  -20.00 -30.00  90.00  125
  5  ω    -90.00  90.00   1.00    1.00    --    0.00   0.00   0.00  180
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  Rigaku_AFC12K_724P_007HF_Mo
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2383
_reflns_number_total             3006
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
;
_computing_data_collection       
;
'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
;
_computing_data_reduction        
;
'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
;
_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    ?
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3006
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.064
_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)+(0.0692P)²+4.1353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1421
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: H9A(0.5) H9B(0.5) H14A(0.5) H14B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C14(H14A,H14B), C11(H11A,H11B), C16(H16A,H16B)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C3(H3), C4(H4)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C7(H7A,H7B,H7C)
3.d Idealised tetrahedral OH refined as rotating group:
 O4(H4A), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.29084(7) 0.80209(7) 0.19561(5) 0.0294(3) Uani 1 1 d . . . . .
O4 O 0.34305(8) 0.69253(8) 0.24158(6) 0.0346(3) Uani 1 1 d . . . . .
H4A H 0.2987 0.6954 0.2608 0.052 Uiso 1 1 calc GR . . . .
O1 O 0.45331(8) 0.58832(8) 0.50700(6) 0.0345(3) Uani 1 1 d . . . . .
O2 O 0.55998(8) 0.54210(7) 0.55886(6) 0.0351(3) Uani 1 1 d . . . . .
H2 H 0.5526 0.5005 0.5372 0.053 Uiso 1 1 calc GR . . . .
O5 O 0.35617(10) 0.78393(10) 0.40124(7) 0.0516(4) Uani 1 1 d . . . . .
O6 O 0.30306(10) 0.92945(10) 0.42300(9) 0.0617(5) Uani 1 1 d . . . . .
C13 C 0.34585(9) 0.75214(10) 0.20227(6) 0.0194(3) Uani 1 1 d . . . . .
C9 C 0.5000 0.7500 0.54559(9) 0.0185(5) Uani 1 2 d S T P . .
H9A H 0.4507 0.7468 0.5197 0.022 Uiso 0.5 1 calc R . . . .
H9B H 0.5493 0.7532 0.5197 0.022 Uiso 0.5 1 calc R . . . .
C14 C 0.5000 0.7500 0.20463(9) 0.0183(4) Uani 1 2 d S T P . .
H14A H 0.5012 0.7994 0.2305 0.022 Uiso 0.5 1 calc R . . . .
H14B H 0.4988 0.7006 0.2305 0.022 Uiso 0.5 1 calc R . . . .
C15 C 0.42280(9) 0.75183(9) 0.16441(6) 0.0176(3) Uani 1 1 d . . . . .
C11 C 0.42707(9) 0.66840(9) 0.62481(6) 0.0180(3) Uani 1 1 d . . . . .
H11A H 0.3775 0.6655 0.5992 0.022 Uiso 1 1 calc R . . . .
H11B H 0.4288 0.6183 0.6500 0.022 Uiso 1 1 calc R . . . .
C12 C 0.50521(9) 0.59658(9) 0.54674(6) 0.0194(3) Uani 1 1 d . . . . .
C10 C 0.50500(9) 0.67292(9) 0.58553(6) 0.0180(3) Uani 1 1 d . . . . .
C16 C 0.42372(9) 0.82878(9) 0.12489(6) 0.0181(3) Uani 1 1 d . . . . .
H16A H 0.4236 0.8789 0.1501 0.022 Uiso 1 1 calc R . . . .
H16B H 0.3740 0.8298 0.0993 0.022 Uiso 1 1 calc R . . . .
C1 C 0.30447(13) 0.79022(13) 0.44919(9) 0.0406(5) Uani 1 1 d . . . . .
C6 C 0.27880(13) 0.72547(13) 0.48469(9) 0.0422(5) Uani 1 1 d . . . . .
H6 H 0.2969 0.6711 0.4761 0.051 Uiso 1 1 calc R . . . .
C2 C 0.27657(13) 0.87009(13) 0.46177(11) 0.0453(5) Uani 1 1 d . . . . .
C5 C 0.22670(13) 0.73933(15) 0.53280(10) 0.0481(6) Uani 1 1 d . . . . .
H5 H 0.2089 0.6944 0.5567 0.058 Uiso 1 1 calc R . . . .
C3 C 0.22591(13) 0.88302(14) 0.51021(11) 0.0500(6) Uani 1 1 d . . . . .
H3 H 0.2080 0.9373 0.5193 0.060 Uiso 1 1 calc R . . . .
C4 C 0.20066(13) 0.81773(16) 0.54602(11) 0.0515(6) Uani 1 1 d . . . . .
H4 H 0.1657 0.8273 0.5793 0.062 Uiso 1 1 calc R . . . .
C8 C 0.38648(16) 0.70448(15) 0.38680(10) 0.0538(6) Uani 1 1 d . . . . .
H8A H 0.4218 0.7081 0.3514 0.081 Uiso 1 1 calc GR . . . .
H8B H 0.3401 0.6675 0.3786 0.081 Uiso 1 1 calc GR . . . .
H8C H 0.4185 0.6830 0.4205 0.081 Uiso 1 1 calc GR . . . .
C7 C 0.26800(16) 1.00885(15) 0.42766(18) 0.0743(9) Uani 1 1 d . . . . .
H7A H 0.2916 1.0448 0.3969 0.111 Uiso 1 1 calc GR . . . .
H7B H 0.2798 1.0317 0.4673 0.111 Uiso 1 1 calc GR . . . .
H7C H 0.2083 1.0052 0.4220 0.111 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
O3 C13 1.2159(19) . ?
O4 H4A 0.8400 . ?
O4 C13 1.3088(19) . ?
O1 C12 1.2325(19) . ?
O2 H2 0.8400 . ?
O2 C12 1.2834(19) . ?
O5 C1 1.366(3) . ?
O5 C8 1.418(3) . ?
O6 C2 1.366(3) . ?
O6 C7 1.413(3) . ?
C13 C15 1.510(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5402(18) 6_564 ?
C9 C10 1.5402(18) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5435(18) . ?
C14 C15 1.5435(18) 6_564 ?
C15 C16 1.544(2) 12_766 ?
C15 C16 1.531(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.530(2) 15_566 ?
C11 C10 1.543(2) . ?
C12 C10 1.514(2) . ?
C10 C11 1.530(2) 12_767 ?
C16 C15 1.544(2) 15_565 ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C1 C6 1.382(3) . ?
C1 C2 1.402(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.388(3) . ?
C2 C3 1.377(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.374(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(3) . ?
C4 H4 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O4 H4A 109.5 . . ?
C12 O2 H2 109.5 . . ?
C1 O5 C8 117.40(18) . . ?
C2 O6 C7 118.0(2) . . ?
O3 C13 O4 123.39(14) . . ?
O3 C13 C15 122.78(14) . . ?
O4 C13 C15 113.80(13) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.9 . . ?
C10 C9 H9A 109.9 6_564 . ?
C10 C9 H9B 109.9 6_564 . ?
C10 C9 H9B 109.9 . . ?
C10 C9 C10 109.04(16) . 6_564 ?
H14A C14 H14B 108.3 . . ?
C15 C14 H14A 110.0 6_564 . ?
C15 C14 H14A 110.0 . . ?
C15 C14 H14B 110.0 . . ?
C15 C14 H14B 110.0 6_564 . ?
C15 C14 C15 108.66(16) 6_564 . ?
C13 C15 C14 110.18(12) . . ?
C13 C15 C16 107.99(12) . 12_766 ?
C13 C15 C16 109.25(12) . . ?
C14 C15 C16 109.27(11) . 12_766 ?
C16 C15 C14 110.16(11) . . ?
C16 C15 C16 109.96(10) . 12_766 ?
H11A C11 H11B 108.3 . . ?
C10 C11 H11A 109.8 15_566 . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
C10 C11 H11B 109.8 15_566 . ?
C10 C11 C10 109.16(14) 15_566 . ?
O1 C12 O2 123.46(14) . . ?
O1 C12 C10 120.09(13) . . ?
O2 C12 C10 116.42(13) . . ?
C9 C10 C11 109.04(11) . . ?
C11 C10 C9 110.11(11) 12_767 . ?
C11 C10 C11 109.78(10) 12_767 . ?
C12 C10 C9 109.44(12) . . ?
C12 C10 C11 111.54(12) . 12_767 ?
C12 C10 C11 106.85(12) . . ?
C15 C16 C15 108.89(14) . 15_565 ?
C15 C16 H16A 109.9 15_565 . ?
C15 C16 H16A 109.9 . . ?
C15 C16 H16B 109.9 15_565 . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
O5 C1 C6 125.4(2) . . ?
O5 C1 C2 115.17(19) . . ?
C6 C1 C2 119.4(2) . . ?
C1 C6 H6 119.8 . . ?
C1 C6 C5 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
O6 C2 C1 115.0(2) . . ?
O6 C2 C3 125.5(2) . . ?
C3 C2 C1 119.5(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.8 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
O5 C8 H8A 109.5 . . ?
O5 C8 H8B 109.5 . . ?
O5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O6 C7 H7A 109.5 . . ?
O6 C7 H7B 109.5 . . ?
O6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4A O3 0.84 1.75 2.5905(16) 176.5 13_565
O2 H2 O1 0.84 1.75 2.5893(16) 174.8 9_666

_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_ADTA_3-38_ethanol-tetradecane_3-fold_publ
_database_code_depnum_ccdc_archive 'CCDC 1915300'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;
# end Validation Reply Form
_audit_creation_date             2018-12-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 O8, 0.43(C14 H30)'
_chemical_formula_sum            'C20 H28.9 O8'
_chemical_formula_weight         397.29
_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           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+3/4, -y+3/4, z'
'-x+3/4, y, -z+3/4'
'x, -y+3/4, -z+3/4'
'x, y+1/2, z+1/2'
'-x+3/4, -y+5/4, z+1/2'
'-x+3/4, y+1/2, -z+5/4'
'x, -y+5/4, -z+5/4'
'x+1/2, y, z+1/2'
'-x+5/4, -y+3/4, z+1/2'
'-x+5/4, y, -z+5/4'
'x+1/2, -y+3/4, -z+5/4'
'x+1/2, y+1/2, z'
'-x+5/4, -y+5/4, z'
'-x+5/4, y+1/2, -z+3/4'
'x+1/2, -y+5/4, -z+3/4'
'-x, -y, -z'
'x-3/4, y-3/4, -z'
'x-3/4, -y, z-3/4'
'-x, y-3/4, z-3/4'
'-x, -y+1/2, -z+1/2'
'x-3/4, y-1/4, -z+1/2'
'x-3/4, -y+1/2, z-1/4'
'-x, y-1/4, z-1/4'
'-x+1/2, -y, -z+1/2'
'x-1/4, y-3/4, -z+1/2'
'x-1/4, -y, z-1/4'
'-x+1/2, y-3/4, z-1/4'
'-x+1/2, -y+1/2, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y+1/2, z-3/4'
'-x+1/2, y-1/4, z-3/4'

_cell_length_a                   7.3713(11)
_cell_length_b                   22.951(4)
_cell_length_c                   23.585(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3990.0(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1322
_cell_measurement_temperature    200
_cell_measurement_theta_max      25.694
_cell_measurement_theta_min      2.477
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0979 before and 0.0743 after correction. The Ratio of minimum to maximum transmission is 0.6123. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1703
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8009
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.377
_diffrn_reflns_theta_min         2.477
_diffrn_ambient_temperature      200
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                628
_reflns_number_total             1028
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     67
_refine_ls_number_reflns         1028
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0634
_refine_ls_restrained_S_all      1.044
_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)+(0.1230P)²+3.7672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1830
_refine_ls_wR_factor_ref         0.2143
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid body (RIGU) restrains
 C7, C6
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Others
 Fixed Sof: H4A(0.5) H4B(0.5) H3A(0.5) H3B(0.5) H1A(0.5) H1B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3A,H3B), C1(H1A,H1B)
4.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O2 O 0.2324(3) 0.48604(10) 0.48359(9) 0.0519(7) Uani 1 1 d . . . . .
O1 O -0.0263(3) 0.45076(11) 0.44997(9) 0.0514(8) Uani 1 1 d . . . . .
C4 C 0.3750 0.3750 0.45035(13) 0.0267(9) Uani 1 2 d S T P . .
C5 C 0.1395(3) 0.45206(12) 0.45024(10) 0.0302(7) Uani 1 1 d . . . . .
C2 C 0.2539(3) 0.41363(11) 0.41262(9) 0.0272(7) Uani 1 1 d . . . . .
C3 C 0.3750 0.45273(16) 0.3750 0.0293(9) Uani 1 2 d S T P . .
C1 C 0.1335(5) 0.3750 0.3750 0.0272(8) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C5 1.302(3) . ?
O1 C5 1.222(3) . ?
C4 C2 1.541(3) . ?
C4 C2 1.541(3) 2 ?
C5 C2 1.508(3) . ?
C2 C3 1.546(3) . ?
C2 C1 1.536(3) . ?
C3 C2 1.546(3) 3 ?
C1 C2 1.536(3) 4 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C4 C2 109.5(3) 2 . ?
O2 C5 C2 114.3(2) . . ?
O1 C5 O2 122.9(3) . . ?
O1 C5 C2 122.8(2) . . ?
C4 C2 C3 109.30(16) . . ?
C5 C2 C4 108.70(19) . . ?
C5 C2 C3 108.7(2) . . ?
C5 C2 C1 110.8(2) . . ?
C1 C2 C4 109.64(17) . . ?
C1 C2 C3 109.69(16) . . ?
C2 C3 C2 109.0(3) . 3 ?
C2 C1 C2 109.5(3) 4 . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT043_ADTA_3-38_ethanol-tetradecane_3-fold_publ 
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..      12.96 Check 
RESPONSE: Due to disorder, the tetradecane solvent molecule 
was modelled without riding H-atoms. However, H-atoms 
for this molecule were included in the refined formula_sum.
;
_vrf_PLAT260_ADTA_3-38_ethanol-tetradecane_3-fold_publ 
;
PROBLEM: Large Average Ueq of Residue Including        C6      0.168 Check 
RESPONSE: C6 was modelled as a tetradecane solvent molecule that 
was disordered in the 1-D voids in the crystal structure. 
;
####################################################################### 
# 
# 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_TMA_1-12_MeOH-Acetone_P-1_publ
_database_code_depnum_ccdc_archive 'CCDC 1915305'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT043_TMA_1-12_MeOH-Acetone_P-1_publ 
;
PROBLEM: Calculated and Reported Mol. Weight Differ by .. 2.52 Check
RESPONSE: Disordered solvent in large 1-D pores in the structure 
could not be resolved and was tentatively modelled at disordered 
H2O. H atoms for these molecules were only added to the unit 
cell atom count, but not refined as part of the structure. 
;
# end Validation Reply Form

_audit_creation_date             2018-05-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 O6, 2.25(H2 O)'
_chemical_formula_sum            'C9 H10.50 O8.25'
_chemical_formula_weight         250.67
_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                   3.5960(9)
_cell_length_b                   8.934(2)
_cell_length_c                   17.937(4)
_cell_angle_alpha                77.839(7)
_cell_angle_beta                 86.729(7)
_cell_angle_gamma                88.967(7)
_cell_volume                     562.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    903
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.265
_cell_measurement_theta_min      2.326
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0757 before and 0.0545 after correction.
The Ratio of minimum to maximum transmission is 0.6607.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             261
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.1317
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5370
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.659
_diffrn_reflns_theta_min         2.327
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1156
_reflns_number_total             2353
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2353
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1470
_refine_ls_R_factor_gt           0.0676
_refine_ls_restrained_S_all      0.931
_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)+(0.0991P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1598
_refine_ls_wR_factor_ref         0.1898
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O1S) \\sim Ueq, Uanis(O2S) \\sim Ueq, Uanis(O3S) \\sim Ueq, Uanis(O4S)
\\sim Ueq, Uanis(O5S) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
3. Others
 Fixed Sof: O5S(0.25) O3S(0.25) O2S(0.25) O1S(0.25) O4S(0.25)
4.a Free rotating group:
 O7(H7A,H7B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C4(H4A)
4.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O5(H5), O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.3009(8) 0.9394(3) 0.60273(16) 0.0274(7) Uani 1 1 d . . . . .
O1 O 0.7608(8) 0.4231(3) 0.57737(15) 0.0299(7) Uani 1 1 d . . . . .
H1 H 0.7978 0.3485 0.5561 0.045 Uiso 1 1 calc GR . . . .
O2 O 1.0249(8) 0.2674(3) 0.67501(16) 0.0312(7) Uani 1 1 d . . . . .
O5 O 0.3510(8) 1.0012(3) 0.71606(15) 0.0328(8) Uani 1 1 d . . . . .
H5 H 0.2486 1.0826 0.6941 0.049 Uiso 1 1 calc GR . . . .
O7 O 0.9844(9) 0.2043(3) 0.50979(16) 0.0313(8) Uani 1 1 d . . . . .
H7A H 1.0863 0.1357 0.5427 0.047 Uiso 1 1 d G . . . .
H7B H 0.8439 0.1624 0.4837 0.047 Uiso 1 1 d G . . . .
O3 O 1.0305(8) 0.4242(3) 0.92410(15) 0.0313(7) Uani 1 1 d . . . . .
O4 O 0.7563(8) 0.6464(3) 0.93541(15) 0.0327(8) Uani 1 1 d . . . . .
H4 H 0.8417 0.6238 0.9790 0.049 Uiso 1 1 calc GR . . . .
C7 C 0.8637(11) 0.3860(4) 0.6478(2) 0.0226(9) Uani 1 1 d . . . . .
C9 C 0.3882(11) 0.9068(4) 0.6689(2) 0.0204(9) Uani 1 1 d . . . . .
C3 C 0.7682(10) 0.5799(4) 0.8153(2) 0.0198(8) Uani 1 1 d . . . . .
C2 C 0.8412(11) 0.4708(4) 0.7708(2) 0.0223(9) Uani 1 1 d . . . . .
H2 H 0.9405 0.3736 0.7933 0.027 Uiso 1 1 calc R . . . .
C1 C 0.7697(10) 0.5032(4) 0.6939(2) 0.0202(8) Uani 1 1 d . . . . .
C6 C 0.6214(11) 0.6456(4) 0.6606(2) 0.0217(9) Uani 1 1 d . . . . .
H6 H 0.5695 0.6677 0.6081 0.026 Uiso 1 1 calc R . . . .
C5 C 0.5492(10) 0.7560(4) 0.7050(2) 0.0193(8) Uani 1 1 d . . . . .
C8 C 0.8605(11) 0.5439(4) 0.8970(2) 0.0234(9) Uani 1 1 d . . . . .
C4 C 0.6254(10) 0.7225(4) 0.7819(2) 0.0226(9) Uani 1 1 d . . . . .
H4A H 0.5794 0.7975 0.8119 0.027 Uiso 1 1 calc R . . . .
O5S O 1.148(12) 0.017(3) 0.9684(18) 0.111(9) Uani 0.25 1 d . U P A 5
O3S O 1.770(15) 0.038(3) 0.945(2) 0.144(10) Uani 0.25 1 d . U P B 3
O2S O 1.710(9) 0.070(2) 0.8737(14) 0.122(8) Uani 0.25 1 d . U P C 2
O1S O 2.194(11) 0.054(3) 0.8948(16) 0.144(9) Uani 0.25 1 d . U P D 1
O4S O 1.431(16) 0.021(3) 0.965(2) 0.138(12) Uani 0.25 1 d . U P E 4


_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
O6 C9 1.220(4) . ?
O1 H1 0.8400 . ?
O1 C7 1.309(4) . ?
O2 C7 1.220(4) . ?
O5 H5 0.8400 . ?
O5 C9 1.314(4) . ?
O7 H7A 0.8500 . ?
O7 H7B 0.8503 . ?
O3 C8 1.243(4) . ?
O4 H4 0.8400 . ?
O4 C8 1.296(4) . ?
C7 C1 1.488(5) . ?
C9 C5 1.488(4) . ?
C3 C2 1.397(5) . ?
C3 C8 1.487(5) . ?
C3 C4 1.391(5) . ?
C2 H2 0.9500 . ?
C2 C1 1.386(5) . ?
C1 C6 1.397(5) . ?
C6 H6 0.9500 . ?
C6 C5 1.404(5) . ?
C5 C4 1.392(5) . ?
C4 H4A 0.9500 . ?
O5S O5S 1.49(7) 2_757 ?
O4S O4S 1.35(7) 2_857 ?

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 O1 H1 109.5 . . ?
C9 O5 H5 109.5 . . ?
H7A O7 H7B 109.5 . . ?
C8 O4 H4 109.5 . . ?
O1 C7 C1 114.1(3) . . ?
O2 C7 O1 124.6(3) . . ?
O2 C7 C1 121.3(4) . . ?
O6 C9 O5 123.6(3) . . ?
O6 C9 C5 123.6(3) . . ?
O5 C9 C5 112.8(3) . . ?
C2 C3 C8 119.3(3) . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 C8 121.0(3) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2 119.8 . . ?
C2 C1 C7 118.9(3) . . ?
C2 C1 C6 119.9(3) . . ?
C6 C1 C7 121.2(3) . . ?
C1 C6 H6 120.1 . . ?
C1 C6 C5 119.9(3) . . ?
C5 C6 H6 120.1 . . ?
C6 C5 C9 119.3(3) . . ?
C4 C5 C9 121.0(3) . . ?
C4 C5 C6 119.7(3) . . ?
O3 C8 O4 124.1(4) . . ?
O3 C8 C3 120.8(3) . . ?
O4 C8 C3 115.1(3) . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?

_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_ADTA_7-38_dioxane-tetradecane_3-fold_publ
_database_code_depnum_ccdc_archive 'CCDC 1915302'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT043_ADTA_7-38_dioxane-tetradecane_3-fold_publ 
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..      12.79 Check 
RESPONSE: Due to disorder, the tetradecane solvent molecule 
was modelled without riding H-atoms. However, H-atoms 
for this molecule were included in the refined formula_sum.
;
# end Validation Reply Form

_audit_creation_date             2018-12-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 O8, 0.43(C14 H30)'
_chemical_formula_sum            'C20.02 H28.86 O8'
_chemical_formula_weight         397.50
_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      tetragonal
_space_group_IT_number           141
_space_group_name_H-M_alt        'I 41/a m d'
_space_group_name_Hall           '-I 4bd 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+1/4, x+3/4, z+1/4'
'y+1/4, -x+1/4, z+3/4'
'-x+1/2, y, -z+1/2'
'x, -y, -z'
'y+1/4, x+3/4, -z+1/4'
'-y+1/4, -x+1/4, -z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+3/4, x+5/4, z+3/4'
'y+3/4, -x+3/4, z+5/4'
'-x+1, y+1/2, -z+1'
'x+1/2, -y+1/2, -z+1/2'
'y+3/4, x+5/4, -z+3/4'
'-y+3/4, -x+3/4, -z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-1/4, -x-3/4, -z-1/4'
'-y-1/4, x-1/4, -z-3/4'
'x-1/2, -y, z-1/2'
'-x, y, z'
'-y-1/4, -x-3/4, z-1/4'
'y-1/4, x-1/4, z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y+1/4, -x-1/4, -z+1/4'
'-y+1/4, x+1/4, -z-1/4'
'x, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
'-y+1/4, -x-1/4, z+1/4'
'y+1/4, x+1/4, z-1/4'

_cell_length_a                   16.429(3)
_cell_length_b                   16.429(3)
_cell_length_c                   7.3580(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1986.0(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2537
_cell_measurement_temperature    200
_cell_measurement_theta_max      25.936
_cell_measurement_theta_min      2.478
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4644
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
Reflections not merged
7998 Corrected reflections written to file PC_8_638_200K_0m.hkl
Estimated minimum and maximum transmission:  0.4644  0.7454
The ratio of these values is more reliable than their absolute values!
Additional spherical absorption correction applied with mu*r =  0.2000
Lambda/2 correction factor = 0.00150
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7390
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.377
_diffrn_reflns_theta_min         2.479
_diffrn_ambient_temperature      200
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                407
_reflns_number_total             554
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     47
_refine_ls_number_reflns         554
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0650
_refine_ls_restrained_S_all      1.134
_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)+(0.0935P)²+3.5705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1850
_refine_ls_wR_factor_ref         0.1993
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 O2-H2
 0.82 with sigma of 0.02
3. Others
 Fixed Sof: H3A(0.5) H3B(0.5) H1A(0.25) H1B(0.25)
4.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.65056(17) 0.2500 0.2242(3) 0.0489(10) Uani 1 2 d S T P . .
O2 O 0.71998(17) 0.2500 0.4818(4) 0.0515(10) Uani 1 2 d DS T P . .
C4 C 0.6520(2) 0.2500 0.3892(4) 0.0275(8) Uani 1 2 d S T P . .
C2 C 0.57633(19) 0.2500 0.5038(4) 0.0235(8) Uani 1 2 d S T P . .
C3 C 0.57611(14) 0.32611(14) 0.6250 0.0255(8) Uani 1 2 d S T P . .
H3A H 0.6256 0.3266 0.7018 0.031 Uiso 0.5 1 calc R . . . .
H3B H 0.5766 0.3756 0.5482 0.031 Uiso 0.5 1 calc R . . . .
C1 C 0.5000 0.2500 0.3834(6) 0.0244(11) Uani 1 4 d S T P . .
H1A H 0.5000 0.2988 0.3046 0.029 Uiso 0.5 2 calc RS T P . .
H1B H 0.5000 0.2012 0.3046 0.029 Uiso 0.5 2 calc RS T P . .
C5 C 0.7653(7) 0.0196(7) 0.560(3) 0.195(10) Uani 0.754(18) 1 d . . . . .
H2 H 0.760(3) 0.2500 0.413(8) 0.10(2) Uiso 1 2 d DS T P . .


_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 C4 1.214(4) . ?
O2 C4 1.309(4) . ?
O2 H2 0.84(2) . ?
C4 C2 1.502(4) . ?
C2 C3 1.536(3) 27_566 ?
C2 C3 1.536(3) . ?
C2 C1 1.535(4) . ?
C3 C2 1.536(3) 20_657 ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C1 C2 1.535(4) 10_554 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C5 C5 1.09(3) 6_556 ?
C5 C5 1.928(6) 12_554 ?
C5 C5 1.928(6) 11_534 ?
C5 C5 1.25(4) 16 ?

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
C4 O2 H2 111(5) . . ?
O1 C4 O2 122.5(3) . . ?
O1 C4 C2 123.1(3) . . ?
O2 C4 C2 114.4(3) . . ?
C4 C2 C3 109.15(18) . 27_566 ?
C4 C2 C3 109.15(18) . . ?
C4 C2 C1 110.6(3) . . ?
C3 C2 C3 109.0(2) . 27_566 ?
C1 C2 C3 109.45(16) . 27_566 ?
C1 C2 C3 109.45(16) . . ?
C2 C3 C2 109.9(3) 20_657 . ?
C2 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 20_657 . ?
C2 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 20_657 . ?
H3A C3 H3B 108.2 . . ?
C2 C1 C2 109.5(4) 10_554 . ?
C2 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 10_554 . ?
C2 C1 H1B 109.8 10_554 . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
C5 C5 C5 110.3(17) 6_556 16 ?
C5 C5 C5 125.2(17) 16 11_534 ?
C5 C5 C5 37.6(15) 6_556 11_534 ?
C5 C5 C5 127(2) 6_556 12_554 ?
C5 C5 C5 155.5(7) 12_554 11_534 ?
C5 C5 C5 32.1(12) 16 12_554 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.84(2) 1.78(2) 2.612(4) 177(8) 5_655

_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_TMA_3-31_EtOH-cyclohexanone_publ
_database_code_depnum_ccdc_archive 'CCDC 1915304'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT922_TMA_3-31_EtOH-cyclohexanone_publ 
;
PROBLEM: wR2 in the CIF and FCF Differ by ...............     0.0064 Check 
RESPONSE: The following WGHT scheme was used during refinement:
 'w=1/[\s^2^(Fo^2^)+(0.1529P)^2^+3.7273P] where P=(Fo^2^+2Fc^2^)/3'
;
# end Validation Reply Form

_audit_creation_date             2018-05-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 O6, C6 H10 O'
_chemical_formula_sum            'C15 H16 O7'
_chemical_formula_weight         308.28
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   27.254(3)
_cell_length_b                   16.7260(16)
_cell_length_c                   6.7365(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.207(3)
_cell_angle_gamma                90
_cell_volume                     3022.3(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4792
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.390
_cell_measurement_theta_min      2.436
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0862 before and 0.0623 after correction. The Ratio of minimum to maximum transmission is 0.6902. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.085
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.047
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            16923
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.450
_diffrn_reflns_theta_min         1.435
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2261
_reflns_number_total             3117
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3117
_refine_ls_number_restraints     116
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0731
_refine_ls_restrained_S_all      1.121
_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)+(0.1529P)²+3.7273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2250
_refine_ls_wR_factor_ref         0.2492
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C13-C14 = C15-C14 = C10-C15 = C11-C10 = C12-C11 = C16-C11 = C13-C12 = C17-C16
 = C17-C18 = C19-C18 = C19-C10
 1.52 with sigma of 0.02
 O9-C19
 1.23 with sigma of 0.02
 C10-C18
 2.56 with sigma of 0.04
 C17-C11
 2.56 with sigma of 0.04
 C15-C13
 2.56 with sigma of 0.04
 C12-C10
 2.56 with sigma of 0.04
 C19-C17
 2.56 with sigma of 0.04
 C10-O9 \\sim O9-C18
 with sigma of 0.02
3. Restrained planarity
 H5, O5, C8, O6, H6
 with sigma of 0.01
4. Rigid body (RIGU) restrains
 C13, O8, C14, C15, C10, C12, O7, C11, C19, C16, C18, C17, O9
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: H5(0.5) H6(0.5) O8(0.6) O7(0.25) C14(0.75) C15(0.75) H15A(0.75)
 H15B(0.75) H10A(0.75) H10B(0.75) H11A(0.75) H11B(0.75) H11C(0.25) H11D(0.25)
 C12(0.75) H12A(0.75) H12B(0.75) C13(0.75) H13A(0.75) H13B(0.75) C18(0.25)
 H18A(0.25) H18B(0.25) C19(0.25) C17(0.25) H17A(0.25) H17B(0.25) C16(0.25)
 H16A(0.25) H16B(0.25) O9(0.15)
6.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C10(H10A,H10B), C11(H11A,H11B), C11(H11C,H11D), C12(H12A,
 H12B), C13(H13A,H13B), C18(H18A,H18B), C17(H17A,H17B), C16(H16A,H16B)
6.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3A), C5(H5A)
6.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3), O5(H5), O6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.30334(6) 0.32744(10) 0.3622(3) 0.0284(5) Uani 1 1 d . . . . .
O2 O 0.23521(6) 0.39558(10) 0.2201(3) 0.0301(5) Uani 1 1 d . . . . .
H2 H 0.2227 0.3496 0.2059 0.045 Uiso 1 1 calc GR . . . .
O3 O 0.23591(6) 0.68559(10) 0.2090(3) 0.0299(5) Uani 1 1 d . . . . .
H3 H 0.2230 0.7313 0.1981 0.045 Uiso 1 1 calc GR . . . .
O4 O 0.30315(7) 0.75388(10) 0.3594(3) 0.0335(5) Uani 1 1 d . . . . .
O5 O 0.45521(7) 0.60751(10) 0.6428(3) 0.0347(5) Uani 1 1 d . . . . .
H5 H 0.4846 0.6004 0.7032 0.052 Uiso 0.5 1 calc GR . P . .
O6 O 0.45582(7) 0.47351(10) 0.6382(3) 0.0295(5) Uani 1 1 d . . . . .
H6 H 0.4852 0.4807 0.6986 0.044 Uiso 0.5 1 calc GR . P . .
C1 C 0.28170(9) 0.54060(13) 0.3100(3) 0.0216(5) Uani 1 1 d . . . . .
H1 H 0.2475 0.5405 0.2490 0.026 Uiso 1 1 calc R . . . .
C2 C 0.30713(9) 0.61243(13) 0.3534(3) 0.0221(5) Uani 1 1 d . . . . .
C3 C 0.35739(9) 0.61288(14) 0.4433(3) 0.0226(5) Uani 1 1 d . . . . .
H3A H 0.3746 0.6621 0.4722 0.027 Uiso 1 1 calc R . . . .
C4 C 0.38213(9) 0.54080(13) 0.4904(4) 0.0219(5) Uani 1 1 d . . . . .
C5 C 0.35720(9) 0.46847(13) 0.4467(3) 0.0213(5) Uani 1 1 d . . . . .
H5A H 0.3743 0.4193 0.4779 0.026 Uiso 1 1 calc R . . . .
C6 C 0.30701(9) 0.46885(13) 0.3571(3) 0.0214(5) Uani 1 1 d . . . . .
C7 C 0.28155(9) 0.69073(14) 0.3059(4) 0.0238(5) Uani 1 1 d . . . . .
C8 C 0.43476(9) 0.54069(13) 0.5974(4) 0.0232(5) Uani 1 1 d . . . . .
C9 C 0.28115(9) 0.39055(13) 0.3132(4) 0.0223(5) Uani 1 1 d . . . . .
O8 O 0.3407(5) 0.0427(6) 0.466(2) 0.192(5) Uani 0.6 1 d . U P A 1
O7 O 0.4349(9) 0.2514(14) 0.800(3) 0.148(7) Uani 0.25 1 d . U P B 2
C14 C 0.3785(4) 0.0880(5) 0.4798(13) 0.113(2) Uani 0.75 1 d D U P A 1
C15 C 0.3999(4) 0.1277(5) 0.6726(13) 0.110(3) Uani 0.75 1 d D U P A 1
H15A H 0.3738 0.1318 0.7575 0.132 Uiso 0.75 1 calc R . P A 1
H15B H 0.4273 0.0943 0.7457 0.132 Uiso 0.75 1 calc R . P A 1
C10 C 0.4184(3) 0.2045(4) 0.6443(11) 0.131(2) Uani 1 1 d D U . . .
H10A H 0.4441 0.2157 0.7646 0.157 Uiso 0.75 1 calc R . P B 1
H10B H 0.3906 0.2421 0.6501 0.157 Uiso 0.75 1 calc R . P B 1
C11 C 0.4398(3) 0.2281(5) 0.4715(11) 0.133(2) Uani 1 1 d D U . . .
H11A H 0.4408 0.2872 0.4623 0.160 Uiso 0.75 1 calc R . P C 1
H11B H 0.4744 0.2078 0.4857 0.160 Uiso 0.75 1 calc R . P C 1
H11C H 0.4189 0.2727 0.4077 0.160 Uiso 0.25 1 calc R . P D 2
H11D H 0.4727 0.2518 0.5274 0.160 Uiso 0.25 1 calc R . P D 2
C12 C 0.4104(3) 0.1964(5) 0.2964(13) 0.105(2) Uani 0.75 1 d D U P A 1
H12A H 0.4285 0.2057 0.1834 0.126 Uiso 0.75 1 calc R . P A 1
H12B H 0.3794 0.2283 0.2679 0.126 Uiso 0.75 1 calc R . P A 1
C13 C 0.3957(4) 0.1106(5) 0.2901(13) 0.125(3) Uani 0.75 1 d D U P A 1
H13A H 0.3686 0.1012 0.1738 0.149 Uiso 0.75 1 calc R . P A 1
H13B H 0.4245 0.0769 0.2725 0.149 Uiso 0.75 1 calc R . P A 1
C18 C 0.4391(16) 0.0650(14) 0.481(3) 0.145(10) Uani 0.25 1 d D U P B 2
H18A H 0.4622 0.0211 0.5323 0.174 Uiso 0.25 1 calc R . P B 2
H18B H 0.4063 0.0394 0.4338 0.174 Uiso 0.25 1 calc R . P B 2
C19 C 0.4326(13) 0.1119(11) 0.664(3) 0.125(7) Uani 0.25 1 d D U P B 2
C17 C 0.456(2) 0.0924(14) 0.294(5) 0.195(18) Uani 0.25 1 d D U P B 2
H17A H 0.4910 0.0791 0.2953 0.233 Uiso 0.25 1 calc R . P B 2
H17B H 0.4348 0.0696 0.1723 0.233 Uiso 0.25 1 calc R . P B 2
C16 C 0.4483(11) 0.1775(14) 0.309(3) 0.113(6) Uani 0.25 1 d D U P B 2
H16A H 0.4778 0.2012 0.2641 0.135 Uiso 0.25 1 calc R . P B 2
H16B H 0.4198 0.1891 0.1991 0.135 Uiso 0.25 1 calc R . P B 2
O9 O 0.4587(13) 0.0919(17) 0.831(4) 0.157(10) Uani 0.15 1 d D U P B 2


_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 C9 1.232(3) . ?
O2 H2 0.8400 . ?
O2 C9 1.300(3) . ?
O3 H3 0.8400 . ?
O3 C7 1.301(3) . ?
O4 C7 1.232(3) . ?
O5 H5 0.8400 . ?
O5 C8 1.262(3) . ?
O6 H6 0.8400 . ?
O6 C8 1.270(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.392(3) . ?
C1 C6 1.393(3) . ?
C2 C3 1.396(3) . ?
C2 C7 1.492(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.390(3) . ?
C4 C5 1.393(3) . ?
C4 C8 1.487(3) . ?
C5 H5A 0.9500 . ?
C5 C6 1.394(3) . ?
C6 C9 1.492(3) . ?
O8 C14 1.269(14) . ?
O7 C10 1.32(2) . ?
C14 C15 1.483(11) . ?
C14 C13 1.485(11) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C10 1.406(9) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.447(8) . ?
C10 C19 1.597(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 H11C 0.9900 . ?
C11 H11D 0.9900 . ?
C11 C12 1.408(10) . ?
C11 C16 1.436(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.489(11) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.500(17) . ?
C18 C17 1.479(18) . ?
C19 O9 1.264(19) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C16 1.443(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 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
C9 O2 H2 109.5 . . ?
C7 O3 H3 109.5 . . ?
C8 O5 H5 109.5 . . ?
C8 O6 H6 109.5 . . ?
C2 C1 H1 120.4 . . ?
C2 C1 C6 119.2(2) . . ?
C6 C1 H1 120.4 . . ?
C1 C2 C3 120.6(2) . . ?
C1 C2 C7 121.1(2) . . ?
C3 C2 C7 118.3(2) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3A 120.2 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 C8 119.9(2) . . ?
C5 C4 C8 119.6(2) . . ?
C4 C5 H5A 120.3 . . ?
C4 C5 C6 119.5(2) . . ?
C6 C5 H5A 120.3 . . ?
C1 C6 C5 120.7(2) . . ?
C1 C6 C9 120.9(2) . . ?
C5 C6 C9 118.3(2) . . ?
O3 C7 C2 114.7(2) . . ?
O4 C7 O3 124.6(2) . . ?
O4 C7 C2 120.6(2) . . ?
O5 C8 O6 124.6(2) . . ?
O5 C8 C4 117.6(2) . . ?
O6 C8 C4 117.8(2) . . ?
O1 C9 O2 124.7(2) . . ?
O1 C9 C6 120.5(2) . . ?
O2 C9 C6 114.8(2) . . ?
O8 C14 C15 121.2(11) . . ?
O8 C14 C13 117.7(11) . . ?
C15 C14 C13 120.3(8) . . ?
C14 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C10 C15 C14 112.7(7) . . ?
C10 C15 H15A 109.1 . . ?
C10 C15 H15B 109.1 . . ?
O7 C10 C11 110.3(11) . . ?
O7 C10 C19 117.7(16) . . ?
C15 C10 H10A 106.2 . . ?
C15 C10 H10B 106.2 . . ?
C15 C10 C11 124.4(7) . . ?
H10A C10 H10B 106.4 . . ?
C11 C10 H10A 106.2 . . ?
C11 C10 H10B 106.2 . . ?
C11 C10 C19 101.8(10) . . ?
C10 C11 H11A 110.0 . . ?
C10 C11 H11B 110.0 . . ?
C10 C11 H11C 105.7 . . ?
C10 C11 H11D 105.7 . . ?
H11A C11 H11B 108.3 . . ?
H11C C11 H11D 106.1 . . ?
C12 C11 C10 108.7(7) . . ?
C12 C11 H11A 110.0 . . ?
C12 C11 H11B 110.0 . . ?
C16 C11 C10 126.6(12) . . ?
C16 C11 H11C 105.7 . . ?
C16 C11 H11D 105.7 . . ?
C11 C12 H12A 107.3 . . ?
C11 C12 H12B 107.3 . . ?
C11 C12 C13 119.9(7) . . ?
H12A C12 H12B 106.9 . . ?
C13 C12 H12A 107.3 . . ?
C13 C12 H12B 107.3 . . ?
C14 C13 C12 110.2(7) . . ?
C14 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
H18A C18 H18B 105.8 . . ?
C19 C18 H18A 105.0 . . ?
C19 C18 H18B 105.0 . . ?
C17 C18 H18A 105.0 . . ?
C17 C18 H18B 105.0 . . ?
C17 C18 C19 129(2) . . ?
C18 C19 C10 120.1(17) . . ?
O9 C19 C10 114.9(17) . . ?
O9 C19 C18 118(2) . . ?
C18 C17 H17A 111.7 . . ?
C18 C17 H17B 111.7 . . ?
H17A C17 H17B 109.4 . . ?
C16 C17 C18 101(2) . . ?
C16 C17 H17A 111.7 . . ?
C16 C17 H17B 111.7 . . ?
C11 C16 C17 132(2) . . ?
C11 C16 H16A 104.1 . . ?
C11 C16 H16B 104.1 . . ?
C17 C16 H16A 104.1 . . ?
C17 C16 H16B 104.1 . . ?
H16A C16 H16B 105.5 . . ?

_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_TMA_2-33_Pentane_Activated_C2c_200K_publ
_database_code_depnum_ccdc_archive 'CCDC 1915307'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT602_TMA_2-33_Pentane_Activated_C2c_200K_publ 
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure        ! Info 
RESPONSE: There are large 1-D voids in the crystal structure which contain 
no ordered electron density. 
;
_vrf_PLAT049_TMA_2-33_Pentane_Activated_C2c_200K_publ 
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.8872 Check 
RESPONSE: There are large 1-D voids in the crystal structure which contain 
no ordered electron density, accounting a crystal density < 1 g/cm3.
;
# end Validation Reply Form

_audit_creation_date             2018-05-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 O6'
_chemical_formula_sum            'C9 H6 O6'
_chemical_formula_weight         210.14
_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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   26.075(2)
_cell_length_b                   16.4837(12)
_cell_length_c                   3.6749(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.076(2)
_cell_angle_gamma                90
_cell_volume                     1573.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3425
_cell_measurement_temperature    200
_cell_measurement_theta_max      26.318
_cell_measurement_theta_min      2.471
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0920 before and 0.0644 after correction. The Ratio of minimum to maximum transmission is 0.6036. 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    0.887
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            8938
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.686
_diffrn_reflns_theta_min         2.471
_diffrn_ambient_temperature      200
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1324
_reflns_number_total             1723
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         1723
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.042
_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)+(0.0633P)²+0.2903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1206
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: H1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
3.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_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 0.45408(4) 0.56771(6) 0.8196(3) 0.0555(3) Uani 1 1 d . . . . .
H1 H 0.4848 0.5606 0.9035 0.083 Uiso 0.5 1 calc GR . . . .
O2 O 0.30489(4) 0.28432(5) 0.2673(3) 0.0534(3) Uani 1 1 d . . . . .
H2 H 0.2882 0.2439 0.1835 0.080 Uiso 1 1 calc GR . . . .
O3 O 0.24020(3) 0.35097(6) -0.0406(3) 0.0502(3) Uani 1 1 d . . . . .
C1 C 0.43358(6) 0.5000 0.7390(5) 0.0355(4) Uani 1 2 d S T P . .
C2 C 0.38121(6) 0.5000 0.5399(4) 0.0337(4) Uani 1 2 d S T P . .
C3 C 0.35689(5) 0.42658(7) 0.4486(3) 0.0346(3) Uani 1 1 d . . . . .
H3 H 0.3736 0.3767 0.5117 0.042 Uiso 1 1 calc R . . . .
C4 C 0.30786(4) 0.42702(7) 0.2640(3) 0.0341(3) Uani 1 1 d . . . . .
C5 C 0.28330(6) 0.5000 0.1725(4) 0.0342(4) Uani 1 2 d S T P . .
H5 H 0.2498 0.5000 0.0476 0.041 Uiso 1 2 calc RS T P . .
C6 C 0.28199(5) 0.34918(7) 0.1551(3) 0.0373(3) 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 H1 0.8400 . ?
O1 C1 1.2615(12) . ?
O2 H2 0.8400 . ?
O2 C6 1.2753(14) . ?
O3 C6 1.2516(15) . ?
C1 O1 1.2615(12) 6_565 ?
C1 C2 1.491(2) . ?
C2 C3 1.3934(14) . ?
C2 C3 1.3934(14) 6_565 ?
C3 H3 0.9500 . ?
C3 C4 1.3933(16) . ?
C4 C5 1.3901(14) . ?
C4 C6 1.4878(16) . ?
C5 C4 1.3902(14) 6_565 ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C6 O2 H2 109.5 . . ?
O1 C1 O1 124.45(15) . 6_565 ?
O1 C1 C2 117.77(8) . . ?
O1 C1 C2 117.77(8) 6_565 . ?
C3 C2 C1 119.72(7) 6_565 . ?
C3 C2 C1 119.71(7) . . ?
C3 C2 C3 120.57(15) 6_565 . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.42(11) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C6 120.08(10) . . ?
C5 C4 C3 120.36(11) . . ?
C5 C4 C6 119.54(11) . . ?
C4 C5 C4 119.86(15) . 6_565 ?
C4 C5 H5 120.1 6_565 . ?
C4 C5 H5 120.1 . . ?
O2 C6 C4 116.60(10) . . ?
O3 C6 O2 124.37(11) . . ?
O3 C6 C4 119.02(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O1 0.84 1.82 2.6325(17) 163.1 2_657
O2 H2 O3 0.84 1.79 2.6222(13) 171.5 7

_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_TMA_2-33_Pentane_Activated_C2c_350K_publ
_database_code_depnum_ccdc_archive 'CCDC 1915306'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT602_TMA_2-33_Pentane_Activated_C2c_350K_publ 
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure        ! Info 
RESPONSE: There are large 1-D voids in the crystal structure which contain 
no ordered electron density. 
;
_vrf_PLAT049_TMA_2-33_Pentane_Activated_C2c_350K_publ 
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.8645 Check 
RESPONSE: There are large 1-D voids in the crystal structure which contain 
no ordered electron density, accounting a crystal density < 1 g/cm3.
;
# end Validation Reply Form

_audit_creation_date             2018-05-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 O6'
_chemical_formula_sum            'C9 H6 O6'
_chemical_formula_weight         210.14
_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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   26.240(5)
_cell_length_b                   16.529(3)
_cell_length_c                   3.7452(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.283(6)
_cell_angle_gamma                90
_cell_volume                     1614.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3253
_cell_measurement_temperature    350
_cell_measurement_theta_max      25.796
_cell_measurement_theta_min      2.465
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0824 before and 0.0597 after correction. The Ratio of minimum to maximum transmission is 0.6181. 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    0.864
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            9783
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.472
_diffrn_reflns_theta_min         2.464
_diffrn_ambient_temperature      350
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1183
_reflns_number_total             1731
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.026
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         1731
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.020
_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)+(0.0654P)²+0.2603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1342
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: H1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
3.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.45376(4) 0.56714(6) 0.8205(4) 0.0937(5) Uani 1 1 d . . . . .
H1 H 0.4837 0.5600 0.9032 0.141 Uiso 0.5 1 calc GR . . . .
O2 O 0.30475(4) 0.28517(6) 0.2582(4) 0.0960(4) Uani 1 1 d . . . . .
H2 H 0.2893 0.2462 0.1635 0.144 Uiso 1 1 calc GR . . . .
O3 O 0.23986(4) 0.35158(7) -0.0385(3) 0.0904(4) Uani 1 1 d . . . . .
C1 C 0.43317(7) 0.5000 0.7387(5) 0.0624(5) Uani 1 2 d S T P . .
C2 C 0.38097(7) 0.5000 0.5387(5) 0.0574(5) Uani 1 2 d S T P . .
C3 C 0.35674(5) 0.42702(8) 0.4468(4) 0.0602(4) Uani 1 1 d . . . . .
H3 H 0.3731 0.3783 0.5091 0.072 Uiso 1 1 calc R . . . .
C4 C 0.30778(5) 0.42719(8) 0.2608(4) 0.0590(4) Uani 1 1 d . . . . .
C5 C 0.28344(7) 0.5000 0.1686(5) 0.0597(5) Uani 1 2 d S T P . .
H5 H 0.2507 0.5000 0.0448 0.072 Uiso 1 2 calc RS T P . .
C6 C 0.28211(5) 0.34957(8) 0.1527(4) 0.0662(4) 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 H1 0.8200 . ?
O1 C1 1.2574(13) . ?
O2 H2 0.8200 . ?
O2 C6 1.2613(16) . ?
O3 C6 1.2528(16) . ?
C1 O1 1.2574(13) 6_565 ?
C1 C2 1.487(2) . ?
C2 C3 1.3892(16) . ?
C2 C3 1.3892(16) 6_565 ?
C3 H3 0.9300 . ?
C3 C4 1.3929(18) . ?
C4 C5 1.3882(15) . ?
C4 C6 1.4845(18) . ?
C5 C4 1.3882(16) 6_565 ?
C5 H5 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C6 O2 H2 109.5 . . ?
O1 C1 O1 123.91(17) . 6_565 ?
O1 C1 C2 118.04(9) 6_565 . ?
O1 C1 C2 118.04(9) . . ?
C3 C2 C1 119.74(8) . . ?
C3 C2 C1 119.74(8) 6_565 . ?
C3 C2 C3 120.52(16) 6_565 . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.63(13) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C6 120.06(12) . . ?
C5 C4 C3 120.00(13) . . ?
C5 C4 C6 119.92(12) . . ?
C4 C5 C4 120.22(16) . 6_565 ?
C4 C5 H5 119.9 . . ?
C4 C5 H5 119.9 6_565 . ?
O2 C6 C4 117.38(12) . . ?
O3 C6 O2 123.95(13) . . ?
O3 C6 C4 118.66(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O1 0.82 1.85 2.642(2) 163.4 2_657
O2 H2 O3 0.82 1.83 2.6354(15) 168.0 7

_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_TMA_7-35_Dioxane-1-3-dimethoxybenzene_C2m_100K_publ
_database_code_depnum_ccdc_archive 'CCDC 1915308'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;
_audit_creation_date             2019-02-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 O0, 7.5(O)'
_chemical_formula_sum            'C9 H6 O13.50'
_chemical_formula_weight         330.14
_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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   25.869(4)
_cell_length_b                   16.419(3)
_cell_length_c                   3.6060(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.617(4)
_cell_angle_gamma                90
_cell_volume                     1528.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5675
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.495
_cell_measurement_theta_min      2.481
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.745552
_exptl_absorpt_correction_T_min  0.461222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
Final HKLF 4 output contains 16286 reflections, Rint = 0.0561
 (11151 with I > 3sig(I), Rint = 0.0547)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1664
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.481
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1533
_reflns_number_total             1664
_reflns_special_details          
;
 _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 v8.34A (Bruker, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1664
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0688
_refine_ls_restrained_S_all      1.069
_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)+(0.1231P)²+2.1499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1992
_refine_ls_wR_factor_ref         0.2049
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.930(4)
 0.070(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 O2-H2
 0.83 with sigma of 0.01
4. Others
 Fixed Sof: O1S(0.25) O9S(0.5) O2S(0.25) O8S(0.5) O3S(0.25) O6S(0.25)
 O15S(0.25) O10S(0.25) O7S(0.25) O5S(0.25) H3(0.5) O4S(0.25) O13S(0.125)
 O14S(0.125) O11S(0.125) O12S(0.125)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3A), C1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.75944(6) 0.65018(9) 1.0312(4) 0.0304(5) Uani 1 1 d . . . . .
O2 O 0.69473(6) 0.71677(9) 0.7191(4) 0.0323(5) Uani 1 1 d D . . . .
O3 O 0.54555(7) 0.43169(10) 0.1814(5) 0.0364(5) Uani 1 1 d . . . . .
C6 C 0.71836(8) 0.65127(11) 0.8362(5) 0.0229(5) Uani 1 1 d . . . . .
C2 C 0.69222(8) 0.57340(11) 0.7248(5) 0.0217(5) Uani 1 1 d . . . . .
C3 C 0.64285(8) 0.57376(11) 0.5452(5) 0.0221(5) Uani 1 1 d . . . . .
H3A H 0.6260 0.6238 0.4845 0.027 Uiso 1 1 calc R . . . .
C1 C 0.71705(10) 0.5000 0.8140(7) 0.0213(6) Uani 1 2 d S T P . .
H1 H 0.7507 0.5000 0.9351 0.026 Uiso 1 2 calc RS T P . .
C4 C 0.61844(10) 0.5000 0.4556(7) 0.0220(6) Uani 1 2 d S T P . .
C5 C 0.56603(11) 0.5000 0.2605(7) 0.0221(6) Uani 1 2 d S T P . .
O1S O 0.8486(9) 0.5000 0.524(6) 0.183(7) Uiso 0.5 2 d S T P A 1
O9S O 0.5669(6) 0.7705(10) 0.551(6) 0.196(6) Uiso 0.5 1 d . . . B 10
O2S O 0.8523(9) 0.5000 0.948(6) 0.184(7) Uiso 0.5 2 d S T P C 2
O8S O 0.5789(10) 0.7824(16) 0.196(9) 0.247(8) Uiso 0.5 1 d . . . D 13
O3S O 0.6319(19) 0.088(3) 0.416(13) 0.237(16) Uiso 0.25 1 d . . . E 4
O6S O 0.4090(17) 0.189(3) 0.147(15) 0.235(15) Uiso 0.25 1 d . . . F 6
O15S O 0.5030(15) 1.0000 0.722(9) 0.290(16) Uiso 0.5 2 d S T P G 15
O10S O 0.5604(11) 0.7649(17) 0.927(10) 0.159(8) Uiso 0.25 1 d . . . H 8
O7S O 0.6034(15) 0.863(2) 0.531(13) 0.202(12) Uiso 0.25 1 d . . . I 12
H2 H 0.7086(13) 0.7597(14) 0.801(10) 0.067(11) Uiso 1 1 d D . . . .
O5S O 0.3936(15) 0.857(3) 0.778(13) 0.208(13) Uiso 0.25 1 d . . . J 5
H3 H 0.517(2) 0.430(3) 0.082(17) 0.038(16) Uiso 0.5 1 d . . . . .
O4S O 0.3790(14) 0.910(2) 0.104(11) 0.210(12) Uiso 0.25 1 d . . . K 3
O13S O 0.556(3) 0.956(4) 0.08(2) 0.23(3) Uiso 0.125 1 d . . . L 16
O14S O 0.477(4) 0.907(7) 0.57(4) 0.31(5) Uiso 0.125 1 d . . . M 14
O11S O 0.5139(18) 0.768(3) 0.646(11) 0.143(13) Uiso 0.125 1 d . . . N 9
O12S O 0.5000 0.760(4) 1.0000 0.24(2) Uiso 0.25 2 d S T P O 7


_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 C6 1.237(3) . ?
O2 C6 1.295(2) . ?
O2 H2 0.836(10) . ?
O3 C5 1.265(2) . ?
O3 H3 0.80(6) . ?
C6 C2 1.490(3) . ?
C2 C3 1.395(3) . ?
C2 C1 1.394(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.394(2) . ?
C1 C2 1.394(2) 6_565 ?
C1 H1 0.9500 . ?
C4 C3 1.394(2) 6_565 ?
C4 C5 1.488(4) . ?
C5 O3 1.265(2) 6_565 ?
O15S O15S 1.60(6) 5_676 ?
O13S O13S 1.44(14) 6_575 ?
O14S O14S 1.3(2) 2_656 ?
O11S O11S 1.24(8) 2_656 ?

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
C6 O2 H2 114(3) . . ?
C5 O3 H3 120(4) . . ?
O1 C6 O2 124.65(18) . . ?
O1 C6 C2 120.01(17) . . ?
O2 C6 C2 115.33(17) . . ?
C3 C2 C6 120.56(17) . . ?
C1 C2 C6 119.01(18) . . ?
C1 C2 C3 120.39(18) . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 C2 119.47(18) . . ?
C4 C3 H3A 120.3 . . ?
C2 C1 C2 119.7(2) 6_565 . ?
C2 C1 H1 120.2 6_565 . ?
C2 C1 H1 120.2 . . ?
C3 C4 C3 120.6(2) . 6_565 ?
C3 C4 C5 119.71(12) 6_565 . ?
C3 C4 C5 119.70(12) . . ?
O3 C5 O3 124.9(3) . 6_565 ?
O3 C5 C4 117.57(13) 6_565 . ?
O3 C5 C4 117.57(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.836(10) 1.782(11) 2.618(2) 178(4) 7_667
O3 H3 O3 0.80(6) 1.83(6) 2.622(3) 175(6) 2_655

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.930(4)
2 0.070(4)

####################################################################### 
# 
# 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_tma_6-18
_database_code_depnum_ccdc_archive 'CCDC 1915310'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;
_audit_creation_date             2019-02-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 O6, C3 H8 O'
_chemical_formula_sum            'C12 H14 O7'
_chemical_formula_weight         270.23
_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                   9.1671(17)
_cell_length_b                   9.4589(18)
_cell_length_c                   9.6179(17)
_cell_angle_alpha                93.220(5)
_cell_angle_beta                 116.280(5)
_cell_angle_gamma                118.728(5)
_cell_volume                     616.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2579
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      31.078
_cell_measurement_theta_min      2.514
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.4729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0821 before and 0.0498 after correction. The Ratio of minimum to maximum transmission is 0.6337. 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    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.315
_exptl_crystal_size_min          0.079
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_av_unetI/netI     0.0798
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8579
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.139
_diffrn_reflns_theta_min         2.513
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2510
_reflns_number_total             3929
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3929
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      0.914
_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)+(0.0559P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1203
_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. Restrained distances
 O3-H3 = O1-H1 = O6-H6
 0.83 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6A)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.24490(14) 0.24062(13) 0.71886(12) 0.0244(2) Uani 1 1 d D . . . .
H1 H 0.301(2) 0.262(2) 0.8234(12) 0.049(6) Uiso 1 1 d D . . . .
O2 O 0.54398(13) 0.34081(13) 0.76165(11) 0.0255(2) Uani 1 1 d . . . . .
O3 O 0.59758(14) 0.35982(13) 0.26695(12) 0.0261(2) Uani 1 1 d D . . . .
H3 H 0.655(3) 0.374(3) 0.214(2) 0.073(8) Uiso 1 1 d D . . . .
O4 O 0.33042(14) 0.27029(13) 0.01930(11) 0.0253(2) Uani 1 1 d . . . . .
O5 O -0.32876(14) 0.04364(13) 0.18307(11) 0.0247(2) Uani 1 1 d . . . . .
O6 O -0.29773(14) 0.06839(13) -0.03488(11) 0.0235(2) Uani 1 1 d D . . . .
H6 H -0.4167(15) 0.034(2) -0.080(2) 0.057(6) Uiso 1 1 d D . . . .
C1 C 0.36937(19) 0.28164(17) 0.66983(16) 0.0196(3) Uani 1 1 d . . . . .
C2 C 0.38515(18) 0.28727(16) 0.41815(15) 0.0189(3) Uani 1 1 d . . . . .
H2 H 0.521698 0.333085 0.484952 0.023 Uiso 1 1 calc R . . . .
C3 C 0.27292(18) 0.24904(16) 0.48894(15) 0.0182(3) Uani 1 1 d . . . . .
C4 C 0.07292(18) 0.18181(16) 0.39097(16) 0.0190(3) Uani 1 1 d . . . . .
H4 H -0.003870 0.154872 0.438988 0.023 Uiso 1 1 calc R . . . .
C5 C -0.01457(18) 0.15405(17) 0.22225(16) 0.0190(3) Uani 1 1 d . . . . .
C6 C 0.09619(18) 0.19124(16) 0.15145(15) 0.0190(3) Uani 1 1 d . . . . .
H6A H 0.035756 0.171220 0.036240 0.023 Uiso 1 1 calc R . . . .
C7 C 0.29670(18) 0.25817(16) 0.24927(15) 0.0185(3) Uani 1 1 d . . . . .
C8 C 0.40951(19) 0.29612(17) 0.16745(15) 0.0193(3) Uani 1 1 d . . . . .
C9 C -0.22916(19) 0.08376(17) 0.12112(16) 0.0199(3) Uani 1 1 d . . . . .
O7 O -0.22770(14) 0.41116(14) 0.10713(12) 0.0260(2) Uani 1 1 d . . . . .
H7 H -0.304(3) 0.385(2) 0.005(2) 0.041(5) Uiso 1 1 d . . . . .
C10 C 0.2554(2) 0.81948(19) 0.42380(19) 0.0317(4) Uani 1 1 d . . . . .
H10A H 0.329965 0.831078 0.372124 0.048 Uiso 1 1 calc GR . . . .
H10B H 0.340794 0.852270 0.543348 0.048 Uiso 1 1 calc GR . . . .
H10C H 0.208782 0.894445 0.400714 0.048 Uiso 1 1 calc GR . . . .
C11 C 0.0788(2) 0.63314(18) 0.35389(17) 0.0243(3) Uani 1 1 d . . . . .
H11A H 0.125633 0.557767 0.382306 0.029 Uiso 1 1 calc R . . . .
H11B H 0.000848 0.621716 0.403328 0.029 Uiso 1 1 calc R . . . .
C12 C -0.04883(19) 0.57898(18) 0.16944(17) 0.0248(3) Uani 1 1 d . . . . .
H12A H -0.081703 0.662935 0.140333 0.030 Uiso 1 1 calc R . . . .
H12B H 0.023182 0.575548 0.118634 0.030 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 1.3214(16) . ?
O2 C1 1.2194(16) . ?
O3 C8 1.3141(16) . ?
O4 C8 1.2212(15) . ?
O5 C9 1.2274(15) . ?
O6 C9 1.3115(16) . ?
C1 C3 1.4897(18) . ?
C2 C3 1.3940(18) . ?
C2 C7 1.3930(17) . ?
C3 C4 1.3913(18) . ?
C4 C5 1.3937(18) . ?
C5 C6 1.3836(18) . ?
C5 C9 1.4945(18) . ?
C6 C7 1.3956(18) . ?
C7 C8 1.4876(18) . ?
O7 C12 1.4451(17) . ?
C10 C11 1.530(2) . ?
C11 C12 1.5041(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C3 112.40(11) . . ?
O2 C1 O1 124.18(12) . . ?
O2 C1 C3 123.42(12) . . ?
C7 C2 C3 119.87(12) . . ?
C2 C3 C1 119.39(11) . . ?
C4 C3 C1 120.59(12) . . ?
C4 C3 C2 120.02(12) . . ?
C3 C4 C5 119.89(12) . . ?
C4 C5 C9 118.45(12) . . ?
C6 C5 C4 120.26(12) . . ?
C6 C5 C9 121.29(12) . . ?
C5 C6 C7 120.00(12) . . ?
C2 C7 C6 119.97(12) . . ?
C2 C7 C8 122.04(12) . . ?
C6 C7 C8 117.99(11) . . ?
O3 C8 C7 114.77(11) . . ?
O4 C8 O3 123.78(12) . . ?
O4 C8 C7 121.46(12) . . ?
O5 C9 O6 124.47(12) . . ?
O5 C9 C5 121.03(12) . . ?
O6 C9 C5 114.50(11) . . ?
C12 C11 C10 109.95(13) . . ?
O7 C12 C11 109.47(12) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O4 0.858(9) 1.773(11) 2.5951(14) 159.8(18) 1_556 yes
O3 H3 O7 0.857(10) 1.729(10) 2.5847(14) 178(2) 1_655 yes
O6 H6 O5 0.841(9) 1.786(9) 2.6266(15) 178(2) 2_455 yes
O7 H7 O2 0.85(2) 2.01(2) 2.8493(15) 173.0(17) 1_454 yes

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

data_TMA_3-36_EtOH_Ph2O_publ
_database_code_depnum_ccdc_archive 'CCDC 1915309'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;
_audit_creation_date             2018-05-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C9 H6 O6), 2(C12 H10 O)'
_chemical_formula_sum            'C51 H38 O20'
_chemical_formula_weight         970.81
_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 0.0028 0.0015 '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 0.0101 0.0057 '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                   10.50240(6)
_cell_length_b                   15.88590(7)
_cell_length_c                   16.60930(7)
_cell_angle_alpha                113.7260(4)
_cell_angle_beta                 98.4480(4)
_cell_angle_gamma                106.8020(4)
_cell_volume                     2316.46(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    21452
_cell_measurement_temperature    200
_cell_measurement_theta_max      35.6992161017
_cell_measurement_theta_min      1.35437565248
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.995896160689
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.052: AIMLESS, version 0.6.2 : 15/01/18
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.078
_exptl_crystal_size_mid          0.028
_exptl_crystal_size_min          0.024
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            36998
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         28.152
_diffrn_reflns_theta_min         1.361
_diffrn_ambient_temperature      200
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_area_resol_mean PILATUS_2M_S_N_24_0107_Diamond
_diffrn_detector_type            PILATUS_2M_S_N_24_0107_Diamond
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.6889
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8999
_reflns_number_total             12320
_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       
'DIALS 2theta refinement, DIALS 1.9.3-gb491019a-release'
_computing_data_collection       'Diamond I19 GDA, (Diamond, RAL, Didcot, UK)'
_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.9.3-gb491019a-release (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 0.5.546-gdf2e0b53-dials-1.9 (Winter, G., 2010)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2014)'
_computing_structure_solution    'XT (Sheldrick, 2014)'
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     700
_refine_ls_number_reflns         12320
_refine_ls_number_restraints     196
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.113
_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)+(0.0900P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1429
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O17-H17 = O14-H14 = O1-H1 = O16-H16 = O8-H8 = O9-H9 = O3-H3 = O12-H12 = O6-H6
 0.82 with sigma of 0.02
 C16-H8
 1.79 with sigma of 0.04
3. Rigid body (RIGU) restrains
 O20, C40, C46, C41, C45, C47, C51, C42, C44, C48, C50, C43, C49
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O19, C28, C34, C29, C33, C35, C39, C30, C32, C36, C38, C31, C37
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C29(H29), C30(H30), C31(H31), C32(H32), C33(H33), C35(H35), C36(H36),
 C37(H37), C38(H38), C39(H39), C45(H45), C44(H44), C43(H43), C42(H42), C41(H41),
  C47(H47), C48(H48), C49(H49), C50(H50), C51(H51)
4.b Fitted hexagon refined as free rotating group:
 C40(C45,C44,C43,C42,C41)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.25801(8) 0.57341(5) 0.54135(5) 0.04235(18) Uani 1 1 d D . . . .
O2 O 0.10812(8) 0.44126(6) 0.54189(5) 0.0470(2) Uani 1 1 d . . . . .
O3 O 0.10033(8) 0.43518(5) 0.83190(5) 0.04244(18) Uani 1 1 d D . . . .
O4 O 0.25003(8) 0.56189(5) 0.96519(5) 0.04090(18) Uani 1 1 d . . . . .
O5 O 0.53110(8) 0.87065(5) 0.96739(5) 0.04156(18) Uani 1 1 d . . . . .
O6 O 0.54199(8) 0.87047(5) 0.83362(5) 0.03993(17) Uani 1 1 d D . . . .
C1 C 0.25567(9) 0.57752(7) 0.68467(6) 0.02832(18) Uani 1 1 d . . . . .
C2 C 0.20907(9) 0.52540(7) 0.73197(6) 0.02850(18) Uani 1 1 d . . . . .
C3 C 0.25462(9) 0.57341(6) 0.82783(6) 0.02687(17) Uani 1 1 d . . . . .
C4 C 0.34808(9) 0.67258(6) 0.87663(6) 0.02744(18) Uani 1 1 d . . . . .
C5 C 0.39438(9) 0.72371(6) 0.82848(6) 0.02682(17) Uani 1 1 d . . . . .
C6 C 0.34838(9) 0.67695(7) 0.73288(6) 0.02839(18) Uani 1 1 d . . . . .
C7 C 0.20324(10) 0.52678(7) 0.58217(6) 0.03074(19) Uani 1 1 d . . . . .
C8 C 0.20104(9) 0.52140(6) 0.88053(6) 0.02857(18) Uani 1 1 d . . . . .
C9 C 0.49595(9) 0.82943(6) 0.88263(6) 0.02862(18) Uani 1 1 d . . . . .
O7 O 0.62380(8) 0.60519(5) 0.58729(5) 0.04253(18) Uani 1 1 d . . . . .
O8 O 0.47613(8) 0.47564(5) 0.59321(5) 0.04299(19) Uani 1 1 d D . . . .
O9 O 0.48372(8) 0.47075(5) 0.88187(5) 0.04130(18) Uani 1 1 d D . . . .
O10 O 0.61357(8) 0.60638(5) 1.01624(4) 0.04148(18) Uani 1 1 d . . . . .
O11 O 0.89943(8) 0.91133(5) 1.01300(5) 0.04050(18) Uani 1 1 d . . . . .
O12 O 0.91164(8) 0.90681(5) 0.87789(5) 0.03699(16) Uani 1 1 d D . . . .
C10 C 0.62547(9) 0.61354(6) 0.73299(6) 0.02575(17) Uani 1 1 d . . . . .
C11 C 0.57933(9) 0.56276(6) 0.78152(6) 0.02654(17) Uani 1 1 d . . . . .
C12 C 0.62454(9) 0.61288(6) 0.87737(6) 0.02586(17) Uani 1 1 d . . . . .
C13 C 0.71615(9) 0.71260(6) 0.92497(6) 0.02592(17) Uani 1 1 d . . . . .
C14 C 0.76342(9) 0.76194(6) 0.87585(6) 0.02492(17) Uani 1 1 d . . . . .
C15 C 0.71815(9) 0.71299(6) 0.77980(6) 0.02637(17) Uani 1 1 d . . . . .
C16 C 0.57421(9) 0.56301(6) 0.63053(6) 0.02870(18) Uani 1 1 d D . . . .
C17 C 0.57290(9) 0.56191(6) 0.93128(6) 0.02850(18) Uani 1 1 d . . . . .
C18 C 0.86452(9) 0.86752(6) 0.92867(6) 0.02687(17) Uani 1 1 d . . . . .
O13 O 0.00803(8) 0.35640(5) -0.06402(5) 0.04282(18) Uani 1 1 d . . . . .
O14 O 0.15207(8) 0.48760(5) 0.06888(5) 0.04148(18) Uani 1 1 d D . . . .
O15 O 0.15080(8) 0.48565(5) 0.36168(5) 0.04171(18) Uani 1 1 d . . . . .
O16 O 0.01252(9) 0.34936(6) 0.36295(5) 0.04576(19) Uani 1 1 d D . . . .
O17 O -0.28777(8) 0.05573(5) 0.07374(5) 0.04145(18) Uani 1 1 d D . . . .
O18 O -0.26623(8) 0.04966(5) -0.06065(5) 0.04480(19) Uani 1 1 d . . . . .
C19 C 0.00457(9) 0.34806(6) 0.07480(6) 0.02694(17) Uani 1 1 d . . . . .
C20 C -0.09069(9) 0.24953(6) 0.02752(6) 0.02841(18) Uani 1 1 d . . . . .
C21 C -0.13669(9) 0.19972(6) 0.07653(6) 0.02754(18) Uani 1 1 d . . . . .
C22 C -0.08882(9) 0.24749(6) 0.17221(6) 0.02828(18) Uani 1 1 d . . . . .
C23 C 0.00654(9) 0.34641(6) 0.21927(6) 0.02734(17) Uani 1 1 d . . . . .
C24 C 0.05309(9) 0.39681(6) 0.17050(6) 0.02749(18) Uani 1 1 d . . . . .
C25 C 0.05554(9) 0.39872(6) 0.02063(6) 0.02874(18) Uani 1 1 d . . . . .
C26 C -0.23778(10) 0.09394(6) 0.02355(6) 0.03033(19) Uani 1 1 d . . . . .
C27 C 0.06058(10) 0.39771(7) 0.32142(6) 0.02985(18) Uani 1 1 d . . . . .
O19 O 0.35697(17) 0.90722(9) 0.67133(8) 0.1064(5) Uani 1 1 d . U . . .
C28 C 0.29553(16) 0.87566(10) 0.57951(9) 0.0616(3) Uani 1 1 d . U . . .
C29 C 0.30960(17) 0.93773(10) 0.53983(9) 0.0629(4) Uani 1 1 d . U . . .
H29 H 0.3657 1.0068 0.5755 0.075 Uiso 1 1 calc R . . . .
C30 C 0.24087(17) 0.89807(12) 0.44737(10) 0.0694(4) Uani 1 1 d . U . . .
H30 H 0.2483 0.9404 0.4196 0.083 Uiso 1 1 calc R . . . .
C31 C 0.16127(16) 0.79720(13) 0.39500(11) 0.0743(4) Uani 1 1 d . U . . .
H31 H 0.1142 0.7702 0.3314 0.089 Uiso 1 1 calc R . . . .
C32 C 0.15093(15) 0.73697(11) 0.43539(12) 0.0732(4) Uani 1 1 d . U . . .
H32 H 0.0982 0.6674 0.3992 0.088 Uiso 1 1 calc R . . . .
C33 C 0.21543(15) 0.77528(10) 0.52742(11) 0.0681(4) Uani 1 1 d . U . . .
H33 H 0.2050 0.7329 0.5552 0.082 Uiso 1 1 calc R . . . .
C34 C 0.44349(19) 1.00698(11) 0.72701(9) 0.0728(4) Uani 1 1 d . U . . .
C35 C 0.5784(2) 1.04051(13) 0.72622(11) 0.0792(4) Uani 1 1 d . U . . .
H35 H 0.6128 0.9962 0.6866 0.095 Uiso 1 1 calc R . . . .
C36 C 0.66357(19) 1.13793(13) 0.78262(11) 0.0807(4) Uani 1 1 d . U . . .
H36 H 0.7571 1.1617 0.7818 0.097 Uiso 1 1 calc R . . . .
C37 C 0.6147(2) 1.20129(13) 0.84024(10) 0.0805(5) Uani 1 1 d . U . . .
H37 H 0.6746 1.2690 0.8795 0.097 Uiso 1 1 calc R . . . .
C38 C 0.4792(2) 1.16792(15) 0.84207(11) 0.0848(5) Uani 1 1 d . U . . .
H38 H 0.4463 1.2126 0.8825 0.102 Uiso 1 1 calc R . . . .
C39 C 0.39026(19) 1.06868(15) 0.78473(11) 0.0808(5) Uani 1 1 d . U . . .
H39 H 0.2966 1.0444 0.7853 0.097 Uiso 1 1 calc R . . . .
O20 O 0.75604(13) 0.74226(8) 0.28618(8) 0.0871(4) Uani 1 1 d . U . . .
C40 C 0.70607(10) 0.75272(7) 0.35964(6) 0.0642(4) Uani 1 1 d . U . . .
C45 C 0.58124(10) 0.76650(8) 0.35952(7) 0.0811(4) Uani 1 1 d G U . . .
H45 H 0.5316 0.7696 0.3088 0.097 Uiso 1 1 calc R . . . .
C44 C 0.52912(10) 0.77573(9) 0.43355(9) 0.0927(6) Uani 1 1 d G U . . .
H44 H 0.4438 0.7852 0.4335 0.111 Uiso 1 1 calc R . . . .
C43 C 0.60182(13) 0.77119(8) 0.50770(7) 0.0859(5) Uani 1 1 d G U . . .
H43 H 0.5662 0.7775 0.5583 0.103 Uiso 1 1 calc R . . . .
C42 C 0.72665(11) 0.75741(7) 0.50782(6) 0.0805(5) Uani 1 1 d G U . . .
H42 H 0.7763 0.7543 0.5585 0.097 Uiso 1 1 calc R . . . .
C41 C 0.77877(8) 0.74817(7) 0.43379(8) 0.0698(4) Uani 1 1 d G U . . .
H41 H 0.8641 0.7388 0.4339 0.084 Uiso 1 1 calc R . . . .
C46 C 0.84611(14) 0.82709(10) 0.28982(9) 0.0574(3) Uani 1 1 d . U . . .
C47 C 0.89302(14) 0.92053(9) 0.36457(8) 0.0577(3) Uani 1 1 d . U . . .
H47 H 0.8637 0.9296 0.4179 0.069 Uiso 1 1 calc R . . . .
C48 C 0.98282(18) 1.00046(11) 0.36088(10) 0.0724(4) Uani 1 1 d . U . . .
H48 H 1.0145 1.0652 0.4117 0.087 Uiso 1 1 calc R . . . .
C49 C 1.02746(19) 0.98765(15) 0.28409(12) 0.0814(5) Uani 1 1 d . U . . .
H49 H 1.0908 1.0430 0.2825 0.098 Uiso 1 1 calc R . . . .
C50 C 0.97931(18) 0.89401(15) 0.21009(11) 0.0770(5) Uani 1 1 d . U . . .
H50 H 1.0090 0.8849 0.1569 0.092 Uiso 1 1 calc R . . . .
C51 C 0.88900(16) 0.81361(12) 0.21221(9) 0.0676(4) Uani 1 1 d . U . . .
H51 H 0.8561 0.7491 0.1608 0.081 Uiso 1 1 calc R . . . .
H15 H 0.7477(12) 0.7484(9) 0.7432(8) 0.036(3) Uiso 1 1 d . . . . .
H6A H 0.3790(12) 0.7127(8) 0.6992(8) 0.035(3) Uiso 1 1 d . . . . .
H13 H 0.7461(11) 0.7466(8) 0.9925(8) 0.037(3) Uiso 1 1 d . . . . .
H24 H 0.1156(13) 0.4635(10) 0.2013(8) 0.043(3) Uiso 1 1 d . . . . .
H11 H 0.5158(13) 0.4945(9) 0.7504(8) 0.039(3) Uiso 1 1 d . . . . .
H2 H 0.1482(12) 0.4561(9) 0.6969(8) 0.037(3) Uiso 1 1 d . . . . .
H4 H 0.3792(12) 0.7063(9) 0.9441(8) 0.037(3) Uiso 1 1 d . . . . .
H20 H -0.1240(12) 0.2161(9) -0.0408(9) 0.042(3) Uiso 1 1 d . . . . .
H22 H -0.1153(13) 0.2148(9) 0.2077(9) 0.046(3) Uiso 1 1 d . . . . .
H12 H 0.9759(15) 0.9723(10) 0.9126(10) 0.064(4) Uiso 1 1 d D . . . .
H9 H 0.4566(15) 0.4454(11) 0.9187(9) 0.058(4) Uiso 1 1 d D . . . .
H6 H 0.6025(17) 0.9345(11) 0.8741(11) 0.081(5) Uiso 1 1 d D . . . .
H17 H -0.3486(16) -0.0102(11) 0.0358(11) 0.085(5) Uiso 1 1 d D . . . .
H3 H 0.0737(18) 0.4118(13) 0.8677(11) 0.085(5) Uiso 1 1 d D . . . .
H14 H 0.1819(15) 0.5123(10) 0.0323(9) 0.073(5) Uiso 1 1 d D . . . .
H8 H 0.464(6) 0.448(3) 0.5341(14) 0.41(3) Uiso 1 1 d D . . . .
H1 H 0.216(3) 0.5414(19) 0.4788(12) 0.163(10) Uiso 1 1 d D . . . .
H16 H 0.048(3) 0.380(2) 0.4184(12) 0.178(12) Uiso 1 1 d 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 C7 1.2695(11) . ?
O1 H1 0.917(17) . ?
O2 C7 1.2566(11) . ?
O3 C8 1.2917(11) . ?
O3 H3 0.859(14) . ?
O4 C8 1.2345(11) . ?
O5 C9 1.2299(11) . ?
O6 C9 1.2969(11) . ?
O6 H6 0.917(14) . ?
C1 C2 1.3945(12) . ?
C1 C6 1.3957(12) . ?
C1 C7 1.4882(12) . ?
C2 C3 1.3905(12) . ?
C2 H2 0.963(12) . ?
C3 C4 1.3953(12) . ?
C3 C8 1.4912(11) . ?
C4 C5 1.3944(11) . ?
C4 H4 0.979(12) . ?
C5 C6 1.3873(12) . ?
C5 C9 1.4947(11) . ?
C6 H6A 0.971(12) . ?
O7 C16 1.2375(11) . ?
O8 C16 1.2904(11) . ?
O8 H8 0.870(19) . ?
O9 C17 1.2967(11) . ?
O9 H9 0.894(12) . ?
O10 C17 1.2325(11) . ?
O11 C18 1.2239(11) . ?
O12 C18 1.3090(10) . ?
O12 H12 0.932(13) . ?
C10 C11 1.3955(11) . ?
C10 C15 1.3957(11) . ?
C10 C16 1.4872(12) . ?
C11 C12 1.3903(12) . ?
C11 H11 0.958(13) . ?
C12 C13 1.3956(11) . ?
C12 C17 1.4912(11) . ?
C13 C14 1.3911(11) . ?
C13 H13 0.979(12) . ?
C14 C15 1.3931(12) . ?
C14 C18 1.4909(11) . ?
C15 H15 1.006(12) . ?
O13 C25 1.2318(11) . ?
O14 C25 1.2988(11) . ?
O14 H14 0.893(13) . ?
O15 C27 1.2623(11) . ?
O16 C27 1.2748(11) . ?
O16 H16 0.812(17) . ?
O17 C26 1.3002(11) . ?
O17 H17 0.931(13) . ?
O18 C26 1.2265(11) . ?
C19 C20 1.3936(12) . ?
C19 C24 1.3890(12) . ?
C19 C25 1.4894(11) . ?
C20 C21 1.3912(12) . ?
C20 H20 0.991(13) . ?
C21 C22 1.3886(12) . ?
C21 C26 1.4932(12) . ?
C22 C23 1.3982(12) . ?
C22 H22 0.951(13) . ?
C23 C24 1.3957(11) . ?
C23 C27 1.4839(12) . ?
C24 H24 0.937(13) . ?
O19 C28 1.3792(17) . ?
O19 C34 1.3906(18) . ?
C28 C29 1.3769(18) . ?
C28 C33 1.3782(19) . ?
C29 H29 0.9500 . ?
C29 C30 1.382(2) . ?
C30 H30 0.9500 . ?
C30 C31 1.383(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.362(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.369(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.366(2) . ?
C34 C39 1.382(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.363(2) . ?
C36 H36 0.9500 . ?
C36 C37 1.364(2) . ?
C37 H37 0.9500 . ?
C37 C38 1.377(3) . ?
C38 H38 0.9500 . ?
C38 C39 1.394(3) . ?
C39 H39 0.9500 . ?
O20 C40 1.3665(13) . ?
O20 C46 1.3765(17) . ?
C40 C45 1.3900 . ?
C40 C41 1.3900 . ?
C45 H45 0.9500 . ?
C45 C44 1.3900 . ?
C44 H44 0.9500 . ?
C44 C43 1.3900 . ?
C43 H43 0.9500 . ?
C43 C42 1.3900 . ?
C42 H42 0.9500 . ?
C42 C41 1.3900 . ?
C41 H41 0.9500 . ?
C46 C47 1.3792(18) . ?
C46 C51 1.3836(19) . ?
C47 H47 0.9500 . ?
C47 C48 1.376(2) . ?
C48 H48 0.9500 . ?
C48 C49 1.382(2) . ?
C49 H49 0.9500 . ?
C49 C50 1.375(2) . ?
C50 H50 0.9500 . ?
C50 C51 1.370(2) . ?
C51 H51 0.9500 . ?

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 O1 H1 113.7(18) . . ?
C8 O3 H3 109.3(12) . . ?
C9 O6 H6 106.9(11) . . ?
C2 C1 C6 120.44(8) . . ?
C2 C1 C7 119.37(8) . . ?
C6 C1 C7 120.18(8) . . ?
C1 C2 H2 118.7(7) . . ?
C3 C2 C1 119.55(8) . . ?
C3 C2 H2 121.7(7) . . ?
C2 C3 C4 120.44(8) . . ?
C2 C3 C8 120.85(8) . . ?
C4 C3 C8 118.67(7) . . ?
C3 C4 H4 120.2(7) . . ?
C5 C4 C3 119.43(8) . . ?
C5 C4 H4 120.4(7) . . ?
C4 C5 C9 118.19(8) . . ?
C6 C5 C4 120.64(8) . . ?
C6 C5 C9 121.16(8) . . ?
C1 C6 H6A 119.6(7) . . ?
C5 C6 C1 119.49(8) . . ?
C5 C6 H6A 120.9(7) . . ?
O1 C7 C1 117.38(8) . . ?
O2 C7 O1 124.42(8) . . ?
O2 C7 C1 118.19(8) . . ?
O3 C8 C3 115.45(7) . . ?
O4 C8 O3 124.24(8) . . ?
O4 C8 C3 120.29(8) . . ?
O5 C9 O6 124.89(8) . . ?
O5 C9 C5 120.06(8) . . ?
O6 C9 C5 115.05(7) . . ?
C16 O8 H8 108(3) . . ?
C17 O9 H9 109.8(9) . . ?
C18 O12 H12 113.0(9) . . ?
C11 C10 C16 120.42(7) . . ?
C15 C10 C11 120.58(8) . . ?
C15 C10 C16 118.99(7) . . ?
C10 C11 H11 121.6(7) . . ?
C12 C11 C10 119.28(8) . . ?
C12 C11 H11 119.1(7) . . ?
C11 C12 C13 120.67(8) . . ?
C11 C12 C17 120.60(7) . . ?
C13 C12 C17 118.71(7) . . ?
C12 C13 H13 119.3(7) . . ?
C14 C13 C12 119.54(8) . . ?
C14 C13 H13 121.2(7) . . ?
C13 C14 C15 120.47(7) . . ?
C13 C14 C18 118.26(7) . . ?
C15 C14 C18 121.27(7) . . ?
C10 C15 H15 119.0(7) . . ?
C14 C15 C10 119.45(8) . . ?
C14 C15 H15 121.5(7) . . ?
O7 C16 O8 124.65(8) . . ?
O7 C16 C10 120.33(8) . . ?
O8 C16 C10 115.01(7) . . ?
O9 C17 C12 114.82(7) . . ?
O10 C17 O9 124.70(8) . . ?
O10 C17 C12 120.47(8) . . ?
O11 C18 O12 124.31(8) . . ?
O11 C18 C14 120.92(8) . . ?
O12 C18 C14 114.77(7) . . ?
C25 O14 H14 110.9(9) . . ?
C27 O16 H16 113(2) . . ?
C26 O17 H17 109.4(11) . . ?
C20 C19 C25 118.69(7) . . ?
C24 C19 C20 120.33(8) . . ?
C24 C19 C25 120.97(8) . . ?
C19 C20 H20 119.1(7) . . ?
C21 C20 C19 119.74(8) . . ?
C21 C20 H20 121.2(7) . . ?
C20 C21 C26 118.27(8) . . ?
C22 C21 C20 120.53(8) . . ?
C22 C21 C26 121.20(8) . . ?
C21 C22 C23 119.46(8) . . ?
C21 C22 H22 122.7(8) . . ?
C23 C22 H22 117.8(8) . . ?
C22 C23 C27 120.00(8) . . ?
C24 C23 C22 120.29(8) . . ?
C24 C23 C27 119.70(8) . . ?
C19 C24 C23 119.65(8) . . ?
C19 C24 H24 119.3(7) . . ?
C23 C24 H24 121.0(7) . . ?
O13 C25 O14 124.12(8) . . ?
O13 C25 C19 120.59(8) . . ?
O14 C25 C19 115.28(7) . . ?
O17 C26 C21 114.77(8) . . ?
O18 C26 O17 125.16(8) . . ?
O18 C26 C21 120.06(8) . . ?
O15 C27 O16 124.15(8) . . ?
O15 C27 C23 118.49(8) . . ?
O16 C27 C23 117.36(8) . . ?
C28 O19 C34 118.44(11) . . ?
C29 C28 O19 124.06(12) . . ?
C29 C28 C33 120.42(13) . . ?
C33 C28 O19 115.52(12) . . ?
C28 C29 H29 120.5 . . ?
C28 C29 C30 119.01(13) . . ?
C30 C29 H29 120.5 . . ?
C29 C30 H30 119.7 . . ?
C29 C30 C31 120.53(14) . . ?
C31 C30 H30 119.7 . . ?
C30 C31 H31 120.3 . . ?
C32 C31 C30 119.40(14) . . ?
C32 C31 H31 120.3 . . ?
C31 C32 H32 119.5 . . ?
C31 C32 C33 120.91(14) . . ?
C33 C32 H32 119.5 . . ?
C28 C33 H33 120.1 . . ?
C32 C33 C28 119.70(14) . . ?
C32 C33 H33 120.1 . . ?
C35 C34 O19 120.00(16) . . ?
C35 C34 C39 121.94(16) . . ?
C39 C34 O19 118.01(17) . . ?
C34 C35 H35 120.2 . . ?
C36 C35 C34 119.64(16) . . ?
C36 C35 H35 120.2 . . ?
C35 C36 H36 119.9 . . ?
C35 C36 C37 120.16(18) . . ?
C37 C36 H36 119.9 . . ?
C36 C37 H37 119.7 . . ?
C36 C37 C38 120.57(17) . . ?
C38 C37 H37 119.7 . . ?
C37 C38 H38 119.9 . . ?
C37 C38 C39 120.21(17) . . ?
C39 C38 H38 119.9 . . ?
C34 C39 C38 117.46(17) . . ?
C34 C39 H39 121.3 . . ?
C38 C39 H39 121.3 . . ?
C40 O20 C46 117.56(9) . . ?
O20 C40 C45 119.86(9) . . ?
O20 C40 C41 120.14(9) . . ?
C45 C40 C41 120.0 . . ?
C40 C45 H45 120.0 . . ?
C40 C45 C44 120.0 . . ?
C44 C45 H45 120.0 . . ?
C45 C44 H44 120.0 . . ?
C45 C44 C43 120.0 . . ?
C43 C44 H44 120.0 . . ?
C44 C43 H43 120.0 . . ?
C44 C43 C42 120.0 . . ?
C42 C43 H43 120.0 . . ?
C43 C42 H42 120.0 . . ?
C41 C42 C43 120.0 . . ?
C41 C42 H42 120.0 . . ?
C40 C41 H41 120.0 . . ?
C42 C41 C40 120.0 . . ?
C42 C41 H41 120.0 . . ?
O20 C46 C47 123.84(12) . . ?
O20 C46 C51 115.57(12) . . ?
C47 C46 C51 120.59(14) . . ?
C46 C47 H47 120.5 . . ?
C48 C47 C46 119.09(13) . . ?
C48 C47 H47 120.5 . . ?
C47 C48 H48 119.6 . . ?
C47 C48 C49 120.77(15) . . ?
C49 C48 H48 119.6 . . ?
C48 C49 H49 120.3 . . ?
C50 C49 C48 119.34(15) . . ?
C50 C49 H49 120.3 . . ?
C49 C50 H50 119.6 . . ?
C51 C50 C49 120.72(14) . . ?
C51 C50 H50 119.6 . . ?
C46 C51 H51 120.3 . . ?
C50 C51 C46 119.48(14) . . ?
C50 C51 H51 120.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O12 H12 O11 0.932(13) 1.716(13) 2.6426(9) 172.7(15) 2_777
O9 H9 O10 0.894(12) 1.729(12) 2.6196(9) 174.0(14) 2_667
O6 H6 O18 0.917(14) 1.712(14) 2.6205(10) 170.6(17) 1_666
O17 H17 O5 0.931(13) 1.713(14) 2.6426(9) 176.4(16) 1_444
O3 H3 O13 0.859(14) 1.793(14) 2.6506(9) 176.1(18) 1_556
O14 H14 O4 0.893(13) 1.729(13) 2.6213(9) 176.4(14) 1_554
O8 H8 O7 0.870(19) 1.81(3) 2.6338(10) 158(6) 2_666
O1 H1 O15 0.917(17) 1.706(17) 2.6218(10) 176(3) .
O16 H16 O2 0.812(17) 1.791(17) 2.5993(10) 173(3) .

_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_TMA_8-35_butanol-1-3-dimethoxybenzene_publ
_database_code_depnum_ccdc_archive 'CCDC 1915314'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;
_audit_creation_date             2018-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 O6, 5.38(H2 O)'
_chemical_formula_sum            'C9 H16.75 O11.38'
_chemical_formula_weight         306.97
_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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   25.768(4)
_cell_length_b                   16.425(2)
_cell_length_c                   3.6006(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.333(4)
_cell_angle_gamma                90
_cell_volume                     1521.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3371
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.450
_cell_measurement_theta_min      2.480
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1020 before and 0.0711 after correction. The Ratio of minimum to maximum transmission is 0.6013. 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    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             647
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            8267
_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         26.371
_diffrn_reflns_theta_min         2.480
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1293
_reflns_number_total             1618
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.785
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1618
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0887
_refine_ls_restrained_S_all      1.785
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2374
_refine_ls_wR_factor_ref         0.2458
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: H1(0.5) O1W(0.25) O2W(0.25) O3W(0.25) O4W(0.25) O5W(0.5) O6W(0.25)
 O7W(0.5) O8W(0.25) O9W(0.125) O10W(0.0625)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6)
3.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_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 0.45458(7) 0.56825(12) 0.8180(6) 0.0373(6) Uani 1 1 d . . . . .
H1 H 0.4855 0.5613 0.8999 0.056 Uiso 0.5 1 calc GR . . . .
O2 O 0.30514(7) 0.71676(11) 0.2787(5) 0.0335(6) Uani 1 1 d . . . . .
H2 H 0.2902 0.7575 0.1808 0.050 Uiso 1 1 calc GR . . . .
O3 O 0.23999(6) 0.65025(11) -0.0300(5) 0.0311(6) Uani 1 1 d . . . . .
C1 C 0.43416(12) 0.5000 0.7382(9) 0.0236(8) Uani 1 2 d S T P . .
C2 C 0.38133(12) 0.5000 0.5434(9) 0.0238(8) Uani 1 2 d S T P . .
C3 C 0.35683(10) 0.57359(15) 0.4546(7) 0.0246(6) Uani 1 1 d . . . . .
H3 H 0.3737 0.6237 0.5155 0.030 Uiso 1 1 calc R . . . .
C4 C 0.30752(9) 0.57324(14) 0.2761(7) 0.0227(6) Uani 1 1 d . . . . .
C5 C 0.28131(9) 0.65110(15) 0.1646(7) 0.0244(6) Uani 1 1 d . . . . .
C6 C 0.28262(13) 0.5000 0.1860(9) 0.0227(7) Uani 1 2 d S T P . .
H6 H 0.2489 0.5000 0.0639 0.027 Uiso 1 2 calc RS T P . .
O1W O 0.1500(12) 0.5000 0.498(9) 0.289(19) Uani 0.5 2 d S T P A 1
O2W O 0.1465(6) 0.5000 0.056(10) 0.225(11) Uani 0.5 2 d S T P B 2
O3W O 0.1182(19) 0.581(3) -0.014(12) 0.233(15) Uiso 0.25 1 d . . . C 3
O4W O 0.489(2) 0.763(4) 1.249(13) 0.30(2) Uiso 0.25 1 d . . . D 4
O5W O 0.4202(13) 0.783(2) 0.809(13) 0.307(15) Uiso 0.5 1 d . . . E 5
O6W O 0.4270(12) 0.774(2) 1.059(14) 0.171(10) Uiso 0.25 1 d . . . F 6
O7W O 0.4300(7) 0.7760(12) 0.419(8) 0.212(6) Uiso 0.5 1 d . . . G 7
O8W O 0.3949(16) 0.877(2) 0.581(11) 0.217(13) Uiso 0.25 1 d . . . H 8
O9W O 0.4963(17) 1.0000 0.345(9) 0.178(15) Uiso 0.25 2 d S T P I 9
O10W O 0.5000 1.0000 0.0000 0.22(3) Uiso 0.25 4 d S T P J 10


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C1 1.264(2) . ?
O2 H2 0.8400 . ?
O2 C5 1.296(3) . ?
O3 C5 1.240(3) . ?
C1 O1 1.264(2) 6_565 ?
C1 C2 1.495(4) . ?
C2 C3 1.392(3) 6_565 ?
C2 C3 1.392(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(4) . ?
C4 C5 1.490(3) . ?
C4 C6 1.393(3) . ?
C6 C4 1.393(3) 6_565 ?
C6 H6 0.9500 . ?
O9W O9W 1.12(7) 5_676 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C5 O2 H2 109.5 . . ?
O1 C1 O1 124.9(3) . 6_565 ?
O1 C1 C2 117.53(16) . . ?
O1 C1 C2 117.54(16) 6_565 . ?
C3 C2 C1 119.75(15) . . ?
C3 C2 C1 119.76(15) 6_565 . ?
C3 C2 C3 120.5(3) . 6_565 ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 C6 120.5(2) . . ?
C6 C4 C5 118.9(2) . . ?
O2 C5 C4 115.5(2) . . ?
O3 C5 O2 124.3(2) . . ?
O3 C5 C4 120.2(2) . . ?
C4 C6 C4 119.5(3) . 6_565 ?
C4 C6 H6 120.3 6_565 . ?
C4 C6 H6 120.3 . . ?

_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_tma_8-32_butanol_mesitylene_100k
_database_code_depnum_ccdc_archive 'CCDC 1915313'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;
_audit_creation_date             2019-02-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C9 H6 O6), 8(O)'
_chemical_formula_sum            'C18 H12 O20'
_chemical_formula_weight         548.28
_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      trigonal
_space_group_IT_number           154
_space_group_name_H-M_alt        'P 32 2 1'
_space_group_name_Hall           'P 32 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'x-y, -y, -z+1/3'
'-x, -x+y, -z+2/3'
'y, x, -z'

_cell_length_a                   16.5230(16)
_cell_length_b                   16.5230(16)
_cell_length_c                   19.400(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4586.9(10)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    7663
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.13
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS 
Estimated minimum and maximum transmission:  0.4679  0.7454
The ratio of these values is more reliable than their absolute values!
Additional spherical absorption correction applied with mu*r =  0.2000
Lambda/2 correction factor = 0.00150
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.134
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.039
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0919
_diffrn_reflns_av_unetI/netI     0.0909
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25344
_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         26.373
_diffrn_reflns_theta_min         1.050
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3656
_reflns_number_total             6239
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 1100 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         6239
_refine_ls_number_restraints     230
_refine_ls_R_factor_all          0.1344
_refine_ls_R_factor_gt           0.0777
_refine_ls_restrained_S_all      0.977
_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)+(0.1325P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1893
_refine_ls_wR_factor_ref         0.2266
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.541(4)
 0.459(4)
2. 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
3. Restrained distances
 O10-H10
 0.83 with sigma of 0.01
 O4-H4 = O1-H1
 0.83 with sigma of 0.01
 O6-H6
 0.83 with sigma of 0.01
 H11-O12
 2.25 with sigma of 0.02
 C17-H10
 1.84 with sigma of 0.02
 H12-C18
 1.84 with sigma of 0.02
 C16-H7
 1.84 with sigma of 0.02
4. Restrained planarity
 O9, O10, C17, H10
 with sigma of 0.001
 O11, O12, C18, H11, H12
 with sigma of 0.001
 O7, O8, C16, H7
 with sigma of 0.001
 O3, O4, C8, H4, H3
 with sigma of 0.001
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
6. Others
 Fixed Sof: H3(0.5) H4(0.5) O1S(0.5) O2S(0.5) O3S(0.5) O4S(0.5) O5S(0.5)
 O6S(0.25) O7S(0.5) H11(0.5) H12(0.5) O8S(0.5) O9S(0.5) O10S(0.5) O11S(0.5)
 O12S(0.25) O13S(0.25) O14S(0.5) O15S(0.5) O16S(0.5) O17S(0.25) O18S(0.25)
 O19S(0.25)
7.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4A), C6(H6A), C11(H11A), C13(H13), C15(H15)
7.b Idealised tetrahedral OH refined as rotating group:
 O3(H3), O7(H7), O11(H11), O12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0224(4) 0.4998(5) 0.5061(4) 0.0291(16) Uani 1 1 d D U . . .
O2 O -0.0254(4) 0.3635(5) 0.5022(5) 0.046(2) Uani 1 1 d . U . . .
O3 O 0.2727(5) 0.3637(5) 0.5046(4) 0.0351(16) Uani 1 1 d . U . . .
H3 H 0.3098 0.3430 0.5014 0.053 Uiso 0.5 1 calc GR . . . .
O4 O 0.4073(5) 0.4996(5) 0.5049(4) 0.0357(19) Uani 1 1 d D U . . .
O5 O 0.4072(4) 0.7957(4) 0.4994(4) 0.0238(13) Uani 1 1 d . U . . .
O6 O 0.2718(5) 0.7927(5) 0.5008(5) 0.0390(19) Uani 1 1 d D U . . .
C1 C 0.1212(5) 0.5025(7) 0.5063(5) 0.0232(16) Uani 1 1 d . U . . .
C2 C 0.1687(7) 0.4533(6) 0.5073(4) 0.0236(16) Uani 1 1 d . U . . .
H2 H 0.1356 0.3869 0.5088 0.028 Uiso 1 1 calc R . . . .
C3 C 0.2666(7) 0.5034(6) 0.5062(4) 0.0210(16) Uani 1 1 d . U . . .
C4 C 0.3157(6) 0.5972(7) 0.5049(4) 0.0218(16) Uani 1 1 d . U . . .
H4A H 0.3821 0.6293 0.5052 0.026 Uiso 1 1 calc R . . . .
C5 C 0.2669(6) 0.6478(6) 0.5029(4) 0.0203(16) Uani 1 1 d . U . . .
C6 C 0.1700(7) 0.6010(7) 0.5019(5) 0.0256(19) Uani 1 1 d . U . . .
H6A H 0.1372 0.6344 0.4984 0.031 Uiso 1 1 calc R . . . .
C7 C 0.0165(6) 0.4512(8) 0.5051(4) 0.0234(16) Uani 1 1 d . U . . .
C8 C 0.3178(8) 0.4505(7) 0.5070(4) 0.0274(19) Uani 1 1 d . U . . .
C9 C 0.3184(7) 0.7525(5) 0.4999(4) 0.0186(14) Uani 1 1 d . U . . .
H1 H -0.079(2) 0.479(6) 0.497(5) 0.028 Uiso 1 1 d DR . . . .
H4 H 0.440(9) 0.475(10) 0.5017(9) 0.028 Uiso 0.5 1 d DR . . . .
H6 H 0.310(5) 0.8489(19) 0.493(5) 0.028 Uiso 1 1 d DR . . . .
O1S O 0.7593(19) 0.5898(19) 0.4658(14) 0.126(9) Uiso 0.5 1 d . U . A 1
O2S O 0.749(3) 0.623(3) 0.511(2) 0.177(12) Uiso 0.5 1 d . U . B 2
O3S O 0.777(2) 0.673(2) 0.5845(14) 0.151(9) Uiso 0.5 1 d . U . C 3
O4S O 0.811(3) 0.764(3) 0.706(2) 0.222(17) Uiso 0.5 1 d . U . D 4
O5S O 0.7661(18) 0.7225(19) 0.6400(15) 0.130(9) Uiso 0.5 1 d . U . E 5
O6S O 0.6762(14) 0.6762(14) 0.5000 0.068(6) Uiso 0.5 2 d S TU P F 6
O7S O 0.708(3) 0.649(3) 0.457(2) 0.181(13) Uiso 0.5 1 d . U . G 7
O7 O 0.4217(4) 0.3890(5) 0.6560(4) 0.0347(17) Uani 1 1 d . U . . .
H7 H 0.4004 0.4256 0.6589 0.052 Uiso 1 1 calc DGR . . . .
O8 O 0.5572(5) 0.5222(5) 0.6659(4) 0.0399(19) Uani 1 1 d . U . . .
O9 O 0.8533(4) 0.5223(5) 0.6671(3) 0.0275(14) Uani 1 1 d . U . . .
O10 O 0.8503(5) 0.3851(5) 0.6599(4) 0.0400(18) Uani 1 1 d D U . . .
O11 O 0.5577(5) 0.0914(4) 0.6677(4) 0.0351(17) Uani 1 1 d . U . . .
H11 H 0.5211 0.0334 0.6658 0.053 Uiso 0.5 1 calc DGR . . . .
O12 O 0.4213(5) 0.0917(5) 0.6665(5) 0.051(2) Uani 1 1 d D U . . .
H12 H 0.4002 0.0338 0.6648 0.076 Uiso 0.5 1 calc DGR . . . .
C10 C 0.5602(7) 0.3823(7) 0.6597(5) 0.0275(18) Uani 1 1 d . U . . .
C11 C 0.6586(7) 0.4313(6) 0.6585(4) 0.0231(15) Uani 1 1 d . U . . .
H11A H 0.6922 0.4976 0.6565 0.028 Uiso 1 1 calc R . . . .
C12 C 0.7067(6) 0.3811(7) 0.6603(4) 0.0203(15) Uani 1 1 d . U . . .
C13 C 0.6587(7) 0.2860(7) 0.6623(4) 0.0224(17) Uani 1 1 d . U . . .
H13 H 0.6923 0.2532 0.6610 0.027 Uiso 1 1 calc R . . . .
C14 C 0.5614(7) 0.2358(6) 0.6660(4) 0.0235(15) Uani 1 1 d . U . . .
C15 C 0.5123(6) 0.2840(6) 0.6622(4) 0.0193(16) Uani 1 1 d . U . . .
H15 H 0.4459 0.2502 0.6612 0.023 Uiso 1 1 calc R . . . .
C16 C 0.5117(7) 0.4361(7) 0.6594(4) 0.0228(17) Uani 1 1 d D U . . .
C17 C 0.8106(6) 0.4326(7) 0.6629(4) 0.0223(17) Uani 1 1 d D U . . .
C18 C 0.5102(7) 0.1340(6) 0.6684(4) 0.0260(17) Uani 1 1 d D U . . .
H10 H 0.9084(12) 0.409(3) 0.6605(9) 0.03(3) Uiso 1 1 d D . . . .
O8S O 0.931(3) 0.893(3) 0.514(3) 0.27(2) Uiso 0.5 1 d . U . H 8
O9S O 0.234(3) 0.121(3) 0.616(2) 0.226(18) Uiso 0.5 1 d . U . I 9
O10S O 0.731(4) 0.793(4) 0.700(2) 0.238(17) Uiso 0.5 1 d . U . J 10
O11S O 0.024(4) 0.726(4) 0.385(3) 0.29(2) Uiso 0.5 1 d . U . K 11
O12S O 0.012(7) 0.179(6) 0.381(4) 0.20(3) Uiso 0.25 1 d . U . L 12
O13S O 0.134(3) 0.165(3) 0.383(2) 0.087(11) Uiso 0.25 1 d . U . M 13
O14S O 0.152(3) 0.237(3) 0.314(2) 0.193(14) Uiso 0.5 1 d . U . N 14
O15S O 0.285(2) 0.225(2) 0.7875(17) 0.141(9) Uiso 0.5 1 d . U . O 15
O16S O 0.286(3) 0.231(3) 0.871(2) 0.195(14) Uiso 0.5 1 d . U . P 16
O17S O 0.142(3) 0.924(3) 0.580(2) 0.101(13) Uiso 0.25 1 d . U . Q 17
O18S O 0.111(5) 0.889(5) 0.498(4) 0.19(3) Uiso 0.25 1 d . U . R 18
O19S O 0.835(5) 0.826(5) 0.345(4) 0.19(3) Uiso 0.25 1 d . U . S 19


_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 C7 1.254(12) . ?
O1 H1 0.833(14) . ?
O2 C7 1.257(13) . ?
O3 H3 0.8400 . ?
O3 C8 1.244(12) . ?
O4 C8 1.284(13) . ?
O4 H4 0.832(14) . ?
O5 C9 1.271(11) . ?
O6 C9 1.244(12) . ?
O6 H6 0.834(14) . ?
C1 C2 1.384(14) . ?
C1 C6 1.412(14) . ?
C1 C7 1.499(11) . ?
C2 H2 0.9500 . ?
C2 C3 1.401(13) . ?
C3 C4 1.343(13) . ?
C3 C8 1.489(12) . ?
C4 H4A 0.9500 . ?
C4 C5 1.424(13) . ?
C5 C6 1.387(12) . ?
C5 C9 1.500(10) . ?
C6 H6A 0.9500 . ?
O7 H7 0.8400 . ?
O7 C16 1.290(11) . ?
O8 C16 1.239(12) . ?
O9 C17 1.286(11) . ?
O10 C17 1.252(12) . ?
O10 H10 0.836(14) . ?
O11 H11 0.8400 . ?
O11 C18 1.290(13) . ?
O12 H12 0.8400 . ?
O12 C18 1.274(12) . ?
C10 C11 1.407(13) . ?
C10 C15 1.408(13) . ?
C10 C16 1.465(11) . ?
C11 H11A 0.9500 . ?
C11 C12 1.407(12) . ?
C12 C13 1.362(12) . ?
C12 C17 1.487(11) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(13) . ?
C14 C15 1.394(13) . ?
C14 C18 1.458(11) . ?
C15 H15 0.9500 . ?
O8S O8S 1.24(9) 6_556 ?

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 O1 H1 124(7) . . ?
C8 O3 H3 109.5 . . ?
C8 O4 H4 121(10) . . ?
C9 O6 H6 106(6) . . ?
C2 C1 C6 121.0(8) . . ?
C2 C1 C7 120.1(10) . . ?
C6 C1 C7 118.9(10) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.6(8) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 C8 118.7(9) . . ?
C4 C3 C2 122.3(8) . . ?
C4 C3 C8 119.0(9) . . ?
C3 C4 H4A 120.5 . . ?
C3 C4 C5 119.1(8) . . ?
C5 C4 H4A 120.5 . . ?
C4 C5 C9 121.1(9) . . ?
C6 C5 C4 120.5(8) . . ?
C6 C5 C9 118.3(8) . . ?
C1 C6 H6A 120.8 . . ?
C5 C6 C1 118.4(9) . . ?
C5 C6 H6A 120.8 . . ?
O1 C7 O2 125.1(7) . . ?
O1 C7 C1 117.0(10) . . ?
O2 C7 C1 117.9(10) . . ?
O3 C8 O4 124.3(8) . . ?
O3 C8 C3 119.2(10) . . ?
O4 C8 C3 116.3(9) . . ?
O5 C9 C5 118.6(9) . . ?
O6 C9 O5 123.4(7) . . ?
O6 C9 C5 118.0(9) . . ?
C16 O7 H7 109.5 . . ?
C17 O10 H10 123(3) . . ?
C18 O11 H11 109.5 . . ?
C18 O12 H12 109.5 . . ?
C11 C10 C15 119.0(8) . . ?
C11 C10 C16 118.4(9) . . ?
C15 C10 C16 122.5(9) . . ?
C10 C11 H11A 120.3 . . ?
C12 C11 C10 119.4(7) . . ?
C12 C11 H11A 120.3 . . ?
C11 C12 C17 119.6(9) . . ?
C13 C12 C11 120.4(9) . . ?
C13 C12 C17 119.9(8) . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.3(9) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C18 121.3(10) . . ?
C15 C14 C13 119.0(8) . . ?
C15 C14 C18 119.6(10) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.6(8) . . ?
C14 C15 H15 119.7 . . ?
O7 C16 C10 116.7(9) . . ?
O8 C16 O7 123.6(8) . . ?
O8 C16 C10 119.6(9) . . ?
O9 C17 C12 118.3(9) . . ?
O10 C17 O9 124.6(7) . . ?
O10 C17 C12 117.2(8) . . ?
O11 C18 C14 118.0(10) . . ?
O12 C18 O11 123.4(7) . . ?
O12 C18 C14 118.4(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.541(4)
2 0.459(4)

####################################################################### 
# 
# 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_ADTA_2-35_THF-1-3-dimethoxybenzene_publ
_database_code_depnum_ccdc_archive 'CCDC 1915312'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;
_audit_creation_date             2019-01-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '(C14 H20 O8), 17.5(O)'
_chemical_formula_sum            'C14 H20 O25.50'
_chemical_formula_weight         596.30
_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      tetragonal
_space_group_IT_number           134
_space_group_name_H-M_alt        'P 42/n n m'
_space_group_name_Hall           '-P 4ac 2bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y+1/2, x, z+1/2'
'y, -x+1/2, z+1/2'
'-x+1/2, y, -z+1/2'
'x, -y+1/2, -z+1/2'
'y, x, -z'
'-y+1/2, -x+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y-1/2, -x, -z-1/2'
'-y, x-1/2, -z-1/2'
'x-1/2, -y, z-1/2'
'-x, y-1/2, z-1/2'
'-y, -x, z'
'y-1/2, x-1/2, z'

_cell_length_a                   11.4331(8)
_cell_length_b                   11.4331(8)
_cell_length_c                   11.4312(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1494.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5245
_cell_measurement_temperature    200
_cell_measurement_theta_max      26.358
_cell_measurement_theta_min      2.519
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. 
Estimated minimum and maximum transmission:  0.4951  0.7454
Additional spherical absorption correction applied with mu*r =  0.2000
Lambda/2 correction factor = 0.00150
;
_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       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.135
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            17215
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.360
_diffrn_reflns_theta_min         1.781
_diffrn_ambient_temperature      200
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                682
_reflns_number_total             829
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     98
_refine_ls_number_reflns         829
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0760
_refine_ls_restrained_S_all      1.148
_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)+(0.1228P)²+0.2939P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1852
_refine_ls_wR_factor_ref         0.2009
_refine_special_details          
;
Refined as a 2-component twin with the TWINLAW
TWIN -1 0 0 0 0 1 0 1 0 2
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.532(12)
 0.468(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: O1(0.16667) H1(0.16667) O2(0.33333) H2(0.33333) O3(0.33333)
 H3(0.33333) O4(0.16667) H4(0.16667) H1A(0.5) H1B(0.5) H3B(0.25) H3A(0.25)
 O1S(0.125) O3S(0.125) O4S(0.25) O6S(0.125) O7S(0.0625) O5S(0.125) O9S(0.25)
 O10S(0.25) O11S(0.25) O12S(0.125) O13S(0.25) O8S(0.125) O2S(0.125)
 Fixed X: H1(0.443999) H2(0.402549) H3(0.44502) H4(0.516469)
 Fixed Y: H1(0.556009) H2(0.497789) H3(0.45899) H4(0.499439)
 Fixed Z: H1(0.45728) H2(0.486819) H3(0.55843) H4(0.60143)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3B,H3A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3989(7) 0.6011(7) 0.4880(6) 0.066(4) Uani 0.3333 2 d S TU P A 1
H1 H 0.4440 0.5560 0.4573 0.099 Uiso 0.3333 2 d RS T P B 1
O2 O 0.3518(8) 0.5322(14) 0.5257(13) 0.088(3) Uani 0.3333 1 d . . . A 3
H2 H 0.4025 0.4978 0.4868 0.132 Uiso 0.3333 1 d R . . C 3
O3 O 0.3992(12) 0.4883(7) 0.6025(10) 0.073(3) Uani 0.3333 1 d . . . A 2
H3 H 0.4450 0.4590 0.5584 0.109 Uiso 0.3333 1 d R . . D 2
O4 O 0.4691(6) 0.5309(6) 0.6451(8) 0.079(6) Uani 0.3333 2 d S T P A 1
H4 H 0.5165 0.4994 0.6014 0.118 Uiso 0.1667 1 d R . . E 1
C1 C 0.4062(3) 0.7500 0.7500 0.0308(9) Uani 1 2 d S T P . .
H1A H 0.4568 0.7003 0.7996 0.037 Uiso 0.5 1 calc R . . . .
H1B H 0.4568 0.7996 0.7004 0.037 Uiso 0.5 1 calc R . . . .
C2 C 0.3275(2) 0.6725(2) 0.6725(2) 0.0298(8) Uani 1 2 d S T P A .
C3 C 0.2500 0.7500 0.5951(3) 0.0323(13) Uani 1 4 d S T P . .
H3B H 0.2004 0.7004 0.5444 0.039 Uiso 0.5 2 calc RS T P . .
H3A H 0.2996 0.7996 0.5444 0.039 Uiso 0.5 2 calc RS T P . .
C4 C 0.4047(2) 0.5953(2) 0.5966(3) 0.0354(9) Uani 1 2 d S T P . .
O1S O 0.647(5) 0.787(5) 0.422(4) 0.139(14) Uiso 0.125 1 d . . . F 1
O3S O 0.517(7) 0.806(5) 0.329(5) 0.166(15) Uiso 0.125 1 d . . . G 3
O4S O 0.463(2) 0.887(2) 0.3526(18) 0.132(5) Uiso 0.25 1 d . . . H 4
O6S O 0.630(3) 0.370(3) 0.787(3) 0.173(13) Uiso 0.25 2 d S T P I 6
O7S O 0.319(7) 0.681(7) 0.263(12) 0.23(4) Uiso 0.125 2 d S T P J 7
O5S O 0.5373(13) 0.4627(13) 0.9147(16) 0.086(5) Uiso 0.25 2 d S T P K 5
O9S O 0.5170(13) 0.9573(13) 0.4718(11) 0.096(4) Uiso 0.25 1 d . . . L 9
O10S O 0.5216(14) 0.8957(13) 0.4242(12) 0.089(4) Uiso 0.25 1 d . . . M 10
O11S O 0.580(4) 0.834(4) 0.414(3) 0.191(11) Uiso 0.25 1 d . . . N 11
O12S O 0.708(4) 0.792(4) 0.5000 0.26(3) Uiso 0.25 2 d S T P O 12
O13S O 0.6051(16) 0.8949(16) 0.5000 0.188(7) Uiso 0.5 2 d S T P P 13
O8S O 0.422(6) 0.774(10) 0.272(9) 0.22(3) Uiso 0.125 1 d . . . Q 8
O2S O 0.759(10) 0.613(6) 0.692(5) 0.23(3) Uiso 0.125 1 d . . . R 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.809(10) . ?
O1 C4 1.245(8) . ?
O2 H2 0.830(8) . ?
O2 C4 1.242(7) . ?
O3 H3 0.800(6) . ?
O3 C4 1.228(8) . ?
O4 H4 0.821(9) . ?
O4 C4 1.180(12) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.542(2) . ?
C1 C2 1.542(2) 12_667 ?
C2 C1 1.542(2) 11_567 ?
C2 C3 1.533(5) . ?
C2 C4 1.520(3) . ?
C3 C2 1.533(5) 2_565 ?
C3 H3B 0.9900 . ?
C3 H3A 0.9900 . ?
C4 O2 1.242(7) 15_665 ?
C4 O3 1.228(8) 15_665 ?
O4S O4S 1.22(4) 16_565 ?
O7S O7S 1.60(14) 11_566 ?
O7S O7S 1.60(14) 12_666 ?
O9S O9S 0.77(3) 8_666 ?
O9S O9S 1.233(18) 9_676 ?
O9S O9S 0.97(3) 16_565 ?
O12S O12S 1.35(12) 2_665 ?
O8S O8S 0.74(19) 6_565 ?
O2S O2S 1.35(13) 5_656 ?

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
C4 O1 H1 111.5(10) . . ?
C4 O2 H2 106.6(8) . . ?
C4 O3 H3 110.5(7) . . ?
C4 O4 H4 113.6(9) . . ?
H1A C1 H1B 108.3 . . ?
C2 C1 H1A 110.0 12_667 . ?
C2 C1 H1A 110.0 . . ?
C2 C1 H1B 110.0 12_667 . ?
C2 C1 H1B 110.0 . . ?
C2 C1 C2 108.6(3) 12_667 . ?
C1 C2 C1 109.9(2) . 11_567 ?
C3 C2 C1 109.66(17) . 11_567 ?
C3 C2 C1 109.66(17) . . ?
C4 C2 C1 108.83(19) . . ?
C4 C2 C1 108.83(19) . 11_567 ?
C4 C2 C3 110.0(3) . . ?
C2 C3 C2 109.6(3) . 2_565 ?
C2 C3 H3B 109.8 2_565 . ?
C2 C3 H3B 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3A 109.8 2_565 . ?
H3B C3 H3A 108.2 . . ?
O1 C4 C2 120.5(6) . . ?
O2 C4 O2 98.0(17) 15_665 . ?
O2 C4 C2 115.3(5) . . ?
O2 C4 C2 115.3(5) 15_665 . ?
O3 C4 O3 95.7(13) 15_665 . ?
O3 C4 C2 121.2(3) . . ?
O3 C4 C2 121.2(3) 15_665 . ?
O4 C4 O1 122.3(7) . . ?
O4 C4 C2 117.2(5) . . ?
O7S O7S O7S 88(4) 11_566 12_666 ?
O9S O9S O9S 89.997(3) 8_666 16_565 ?
O9S O9S O9S 38.4(15) 16_565 9_676 ?
O9S O9S O9S 51.6(15) 8_666 9_676 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O4 0.809(10) 1.830(9) 2.622(13) 165.9(7) 7_556
O2 H2 O2 0.830(8) 2.237(12) 2.98(2) 148.3(12) 7_556
O3 H3 O3 0.800(6) 2.024(7) 2.750(14) 150.8(10) 7_556
O4 H4 O1 0.821(9) 1.817(9) 2.622(13) 166.4(2) 7_556

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.532(12)
2 0.468(12)

####################################################################### 
# 
# 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_TMA_2-33_THF-butylbenzene_publ
_database_code_depnum_ccdc_archive 'CCDC 1915315'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT043_TMA_2-33_THF-bultybenzene_publ 
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..       4.03 Check 
RESPONSE: Disordered electron density was tentatively modelled as disordered
H2O, these were refined without H-atoms, however, H-atoms for these were 
still included in the unit cell atom count.
;
_vrf_PLAT601_TMA_2-33_THF-bultybenzene_publ 
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        150 Ang**3
RESPONSE: These are likely to contain disordered solvent molecules which
could not be resolved during refinement. 
;
# end Validation Reply Form

_audit_creation_date             2018-05-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 O6, 2(H2 O)'
_chemical_formula_sum            'C9 H10 O8'
_chemical_formula_weight         246.17
_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      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'
'y, x, -z'

_cell_length_a                   16.5141(6)
_cell_length_b                   16.5141(6)
_cell_length_c                   9.7096(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2293.20(19)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.105
_cell_measurement_theta_min      2.535
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.4428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0968 before and 0.0703 after correction. The Ratio of minimum to maximum transmission is 0.5937. 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    1.070
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.134
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.039
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            24980
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.535
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  Rigaku_AFC12K_724P_007HF_Mo
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                2533
_reflns_number_total             3095
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
 Flack x determined using 1021 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.0(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3095
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0638
_refine_ls_restrained_S_all      1.061
_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)+(0.1641P)²+0.3647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2062
_refine_ls_wR_factor_ref         0.2217
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained planarity
 H5, C9, O6, O5, H6
 with sigma of 0.001
 H4, O4, C8, O3, H3
 with sigma of 0.1
 O1, C7, O2, H2, H1
 with sigma of 0.001
3. Others
 Fixed Sof: H5(0.5) H1(0.5) H4(0.5) H3(0.5) H2(0.5) H6(0.5) O1W(0.125)
 O7W(0.25) O2W(0.25) O6W(0.25) O5W(0.125) O3W(0.25) O4W(0.25) O8W(0.25)
 O9W(0.25)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4A), C2(H2A), C6(H6A)
4.b Idealised tetrahedral OH refined as rotating group:
 O5(H5), O1(H1), O4(H4), O3(H3), O2(H2), O6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.85082(19) 0.4629(2) 0.4973(2) 0.0299(8) Uani 1 1 d . . . . .
H5 H 0.9088 0.4842 0.4945 0.045 Uiso 0.5 1 calc GR . . A 1
O1 O 0.5555(2) 0.0327(2) 0.5151(3) 0.0352(8) Uani 1 1 d . . . . .
H1 H 0.5200 -0.0255 0.5140 0.053 Uiso 0.5 1 calc GR . . B 2
O4 O 0.5553(2) 0.4641(2) 0.5092(3) 0.0301(8) Uani 1 1 d . . . . .
H4 H 0.5193 0.4862 0.5142 0.045 Uiso 0.5 1 calc GR . . C 1
O3 O 0.4193(2) 0.3287(2) 0.5068(3) 0.0382(8) Uani 1 1 d . . . . .
H3 H 0.3976 0.3651 0.5081 0.057 Uiso 0.5 1 calc GR . . D 2
O2 O 0.4195(2) 0.0320(2) 0.5054(3) 0.0396(9) Uani 1 1 d . . . . .
H2 H 0.3980 -0.0261 0.5053 0.059 Uiso 0.5 1 calc GR . . E 2
O6 O 0.8492(2) 0.3263(2) 0.5041(3) 0.0347(8) Uani 1 1 d . . . . .
H6 H 0.9074 0.3617 0.5006 0.052 Uiso 0.5 1 calc GR . . F 2
C3 C 0.5599(3) 0.3235(3) 0.5124(3) 0.0242(7) Uani 1 1 d . . . . .
C7 C 0.5065(3) 0.0729(2) 0.5106(3) 0.0244(6) Uani 1 1 d . . . . .
C4 C 0.6569(3) 0.37205(19) 0.5099(3) 0.0214(7) Uani 1 1 d . . . . .
H4A H 0.6905 0.4385 0.5102 0.026 Uiso 1 1 calc R . . . .
C5 C 0.70469(19) 0.3225(3) 0.5071(3) 0.0218(6) Uani 1 1 d . . . . .
C2 C 0.5101(2) 0.2260(3) 0.5127(3) 0.0245(7) Uani 1 1 d . . . . .
H2A H 0.4436 0.1931 0.5137 0.029 Uiso 1 1 calc R . . . .
C9 C 0.8093(2) 0.3750(3) 0.5029(3) 0.0233(6) Uani 1 1 d . . . . .
C8 C 0.5076(3) 0.3757(3) 0.5097(3) 0.0243(7) Uani 1 1 d . . . . .
C6 C 0.6569(3) 0.2253(3) 0.5082(3) 0.0244(8) Uani 1 1 d . . . . .
H6A H 0.6900 0.1920 0.5066 0.029 Uiso 1 1 calc R . . . .
C1 C 0.5590(3) 0.17750(19) 0.5115(3) 0.0229(6) Uani 1 1 d . . . . .
O1W O 0.218(2) 0.0000 0.3333 0.117(10) Uiso 0.25 2 d S T P G 1
O7W O 0.7470(16) 0.0411(15) 0.268(2) 0.098(6) Uiso 0.25 1 d . . . H 7
O2W O 0.232(2) 0.058(2) 0.347(2) 0.117(7) Uiso 0.25 1 d . . . I 2
O6W O 0.076(3) 0.023(3) 0.414(5) 0.218(18) Uiso 0.25 1 d . . . J 6
O5W O 0.278(3) 0.0000 0.8333 0.128(12) Uiso 0.25 2 d S T P K 5
O3W O 0.335(2) 0.133(2) 0.882(3) 0.126(8) Uiso 0.25 1 d . . . L 3
O4W O 0.320(2) 0.127(2) 0.800(4) 0.145(10) Uiso 0.25 1 d . . . M 4
O8W O 0.771(2) 0.036(2) 0.140(3) 0.147(10) Uiso 0.25 1 d . . . N 8
O9W O 0.791(2) 0.105(2) 0.343(3) 0.141(9) Uiso 0.25 1 d . . . O 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 H5 0.8400 . ?
O5 C9 1.259(6) . ?
O1 H1 0.8400 . ?
O1 C7 1.278(6) . ?
O4 H4 0.8400 . ?
O4 C8 1.266(6) . ?
O3 H3 0.8400 . ?
O3 C8 1.265(6) . ?
O2 H2 0.8400 . ?
O2 C7 1.246(6) . ?
O6 H6 0.8400 . ?
O6 C9 1.271(6) . ?
C3 C4 1.388(6) . ?
C3 C2 1.395(7) . ?
C3 C8 1.494(4) . ?
C7 C1 1.496(4) . ?
C4 H4A 0.9500 . ?
C4 C5 1.392(6) . ?
C5 C9 1.497(4) . ?
C5 C6 1.390(6) . ?
C2 H2A 0.9500 . ?
C2 C1 1.394(6) . ?
C6 H6A 0.9500 . ?
C6 C1 1.401(7) . ?
O7W O7W 1.73(4) 4 ?
O2W O2W 1.67(6) 4 ?
O6W O6W 1.70(9) 4 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O5 H5 109.5 . . ?
C7 O1 H1 109.5 . . ?
C8 O4 H4 109.5 . . ?
C8 O3 H3 109.5 . . ?
C7 O2 H2 109.5 . . ?
C9 O6 H6 109.5 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 C8 120.0(4) . . ?
C2 C3 C8 119.2(4) . . ?
O1 C7 C1 116.5(4) . . ?
O2 C7 O1 125.3(3) . . ?
O2 C7 C1 118.2(4) . . ?
C3 C4 H4A 120.3 . . ?
C3 C4 C5 119.4(3) . . ?
C5 C4 H4A 120.3 . . ?
C4 C5 C9 119.2(3) . . ?
C6 C5 C4 121.1(2) . . ?
C6 C5 C9 119.6(3) . . ?
C3 C2 H2A 120.4 . . ?
C1 C2 C3 119.1(3) . . ?
C1 C2 H2A 120.4 . . ?
O5 C9 O6 125.1(3) . . ?
O5 C9 C5 118.4(4) . . ?
O6 C9 C5 116.5(4) . . ?
O4 C8 C3 117.4(4) . . ?
O3 C8 O4 124.7(3) . . ?
O3 C8 C3 117.9(4) . . ?
C5 C6 H6A 120.7 . . ?
C5 C6 C1 118.7(3) . . ?
C1 C6 H6A 120.7 . . ?
C2 C1 C7 119.7(4) . . ?
C2 C1 C6 120.9(2) . . ?
C6 C1 C7 119.3(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 O1 0.84 1.78 2.605(4) 166.2 6_656
O4 H4 O4 0.84 1.79 2.613(5) 164.3 6_556
O2 H2 O6 0.84 1.79 2.615(5) 166.2 6_546

_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_pc_ht_1_i418_100k
_database_code_depnum_ccdc_archive 'CCDC 1915311'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;Chemistry Department, University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;
_audit_creation_date             2018-05-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C9 H6 O6), 2(C3 H8 O)'
_chemical_formula_sum            'C24 H28 O14'
_chemical_formula_weight         540.46
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.0126(17)
_cell_length_b                   9.6004(8)
_cell_length_c                   27.383(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.563(2)
_cell_angle_gamma                90
_cell_volume                     4998.0(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7992
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.369
_cell_measurement_theta_min      2.487
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0956 before and 0.0675 after correction.
The Ratio of minimum to maximum transmission is 0.6355.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2272
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.079
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            23878
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.446
_diffrn_reflns_theta_min         1.487
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4122
_reflns_number_total             5145
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.651
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         5145
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      1.039
_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)+(0.0939P)²+4.7971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1624
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All H(H) groups, All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-H1 = O11-H11
 0.82 with sigma of 0.02
 H11-C17
 1.85 with sigma of 0.02
3. Others
 Fixed Sof: H5(0.5) H6(0.5) H7(0.5) H8(0.5)
4.a Ternary CH refined with riding coordinates:
 C20(H20), C23(H23)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6A), C11(H11A), C13(H13), C15(H15)
4.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C)
4.d Idealised tetrahedral OH refined as rotating group:
 O5(H5), O6(H6), O7(H7), O8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.69648(8) 0.36151(14) 0.55617(5) 0.0267(3) Uani 1 1 d D . . . .
O2 O 0.71555(8) 0.44888(14) 0.63107(5) 0.0262(3) Uani 1 1 d . . . . .
O3 O 0.71761(7) 0.96892(14) 0.64556(5) 0.0231(3) Uani 1 1 d . . . . .
O4 O 0.69764(8) 1.09830(14) 0.57887(5) 0.0267(3) Uani 1 1 d . . . . .
O5 O 0.63354(7) 0.87680(14) 0.42412(4) 0.0230(3) Uani 1 1 d . . . . .
H5 H 0.6264 0.8704 0.3939 0.034 Uiso 0.5 1 calc GR . P A 1
O6 O 0.63714(7) 0.64380(14) 0.41790(5) 0.0249(3) Uani 1 1 d . . . . .
H6 H 0.6269 0.6627 0.3887 0.037 Uiso 0.5 1 calc GR . P B 2
C1 C 0.68848(9) 0.60339(19) 0.56528(6) 0.0174(4) Uani 1 1 d . . . . .
C2 C 0.66979(9) 0.61385(19) 0.51612(6) 0.0177(4) Uani 1 1 d . . . . .
H2 H 0.6643 0.5321 0.4969 0.021 Uiso 1 1 calc R . . . .
C3 C 0.65911(9) 0.74486(19) 0.49505(6) 0.0171(4) Uani 1 1 d . . . . .
C4 C 0.66828(9) 0.86457(19) 0.52286(6) 0.0173(4) Uani 1 1 d . . . . .
H4 H 0.6613 0.9537 0.5085 0.021 Uiso 1 1 calc R . . . .
C5 C 0.68773(9) 0.85356(19) 0.57194(6) 0.0174(4) Uani 1 1 d . . . . .
C6 C 0.69699(9) 0.72309(19) 0.59357(6) 0.0178(4) Uani 1 1 d . . . . .
H6A H 0.7090 0.7159 0.6272 0.021 Uiso 1 1 calc R . . . .
C7 C 0.70166(9) 0.46362(19) 0.58799(6) 0.0177(4) Uani 1 1 d . . . . .
C8 C 0.64173(9) 0.75493(19) 0.44223(6) 0.0166(4) Uani 1 1 d . . . . .
C9 C 0.70145(9) 0.9855(2) 0.59939(6) 0.0189(4) Uani 1 1 d . . . . .
O7 O 0.61573(7) 1.34422(14) 0.82386(5) 0.0239(3) Uani 1 1 d . . . . .
H7 H 0.6200 1.3376 0.8543 0.036 Uiso 0.5 1 calc GR . P C 2
O8 O 0.61683(7) 1.11103(14) 0.82912(4) 0.0218(3) Uani 1 1 d . . . . .
H8 H 0.6246 1.1295 0.8587 0.033 Uiso 0.5 1 calc GR . P D 1
O9 O 0.55576(8) 0.83243(14) 0.68981(5) 0.0284(3) Uani 1 1 d . . . . .
O10 O 0.53336(7) 0.92163(14) 0.61570(5) 0.0248(3) Uani 1 1 d . . . . .
O11 O 0.53088(8) 1.44126(14) 0.60270(5) 0.0252(3) Uani 1 1 d D . . . .
O12 O 0.54648(8) 1.56819(14) 0.67016(5) 0.0264(3) Uani 1 1 d . . . . .
C10 C 0.59063(9) 1.21422(19) 0.75269(6) 0.0162(4) Uani 1 1 d . . . . .
C11 C 0.57868(9) 1.33437(18) 0.72549(6) 0.0165(4) Uani 1 1 d . . . . .
H11A H 0.5836 1.4232 0.7404 0.020 Uiso 1 1 calc R . . . .
C12 C 0.55949(9) 1.32448(19) 0.67633(6) 0.0172(4) Uani 1 1 d . . . . .
C13 C 0.55156(9) 1.19518(19) 0.65422(6) 0.0169(4) Uani 1 1 d . . . . .
H13 H 0.5393 1.1889 0.6206 0.020 Uiso 1 1 calc R . . . .
C14 C 0.56178(9) 1.07457(19) 0.68186(6) 0.0170(4) Uani 1 1 d . . . . .
C15 C 0.58206(9) 1.08374(18) 0.73074(6) 0.0157(4) Uani 1 1 d . . . . .
H15 H 0.5901 1.0013 0.7492 0.019 Uiso 1 1 calc R . . . .
C16 C 0.60917(9) 1.22306(18) 0.80543(6) 0.0160(4) Uani 1 1 d . . . . .
C17 C 0.54518(9) 1.45685(18) 0.64924(6) 0.0184(4) Uani 1 1 d D . . . .
C18 C 0.54894(9) 0.93554(19) 0.65871(6) 0.0185(4) Uani 1 1 d . . . . .
O13 O 0.75891(7) 0.70756(14) 0.81418(5) 0.0236(3) Uani 1 1 d . . . . .
C19 C 0.63194(11) 0.7285(2) 0.80337(7) 0.0286(5) Uani 1 1 d . . . . .
H19A H 0.6247 0.6397 0.8203 0.043 Uiso 1 1 calc GR . . . .
H19B H 0.5947 0.7417 0.7788 0.043 Uiso 1 1 calc GR . . . .
H19C H 0.6306 0.8049 0.8271 0.043 Uiso 1 1 calc GR . . . .
C20 C 0.70270(10) 0.7270(2) 0.77855(6) 0.0222(4) Uani 1 1 d . . . . .
H20 H 0.7097 0.8183 0.7617 0.027 Uiso 1 1 calc R . . . .
C21 C 0.70957(11) 0.6120(2) 0.74193(7) 0.0289(5) Uani 1 1 d . . . . .
H21A H 0.7562 0.6159 0.7271 0.043 Uiso 1 1 calc GR . . . .
H21B H 0.6734 0.6227 0.7165 0.043 Uiso 1 1 calc GR . . . .
H21C H 0.7035 0.5220 0.7583 0.043 Uiso 1 1 calc GR . . . .
O14 O 0.50478(7) 0.67657(14) 0.56196(5) 0.0255(3) Uani 1 1 d . . . . .
C22 C 0.46024(11) 0.8183(2) 0.49502(7) 0.0332(5) Uani 1 1 d . . . . .
H22A H 0.4668 0.9041 0.5139 0.050 Uiso 1 1 calc GR . . . .
H22B H 0.4205 0.8298 0.4723 0.050 Uiso 1 1 calc GR . . . .
H22C H 0.5030 0.7985 0.4766 0.050 Uiso 1 1 calc GR . . . .
C23 C 0.44554(10) 0.6992(2) 0.52922(6) 0.0231(4) Uani 1 1 d . . . . .
H23 H 0.4388 0.6131 0.5092 0.028 Uiso 1 1 calc R . . . .
C24 C 0.37896(11) 0.7241(2) 0.55774(7) 0.0313(5) Uani 1 1 d . . . . .
H24A H 0.3716 0.6467 0.5805 0.047 Uiso 1 1 calc GR . . . .
H24B H 0.3388 0.7304 0.5351 0.047 Uiso 1 1 calc GR . . . .
H24C H 0.3833 0.8113 0.5761 0.047 Uiso 1 1 calc GR . . . .
H14 H 0.5145(9) 0.766(2) 0.5742(6) 0.003(4) Uiso 1 1 d . . . . .
H3 H 0.7268(15) 1.052(3) 0.6574(10) 0.054(8) Uiso 1 1 d . . . . .
H13A H 0.7657(16) 0.784(3) 0.8298(11) 0.057(9) Uiso 1 1 d . . . . .
H9 H 0.547(2) 0.744(4) 0.6802(13) 0.085 Uiso 1 1 d R . . . .
H1 H 0.7013(16) 0.279(2) 0.5683(10) 0.051(8) Uiso 1 1 d D . . . .
H11 H 0.5194(17) 1.526(2) 0.5908(8) 0.077 Uiso 1 1 d DR . . . .


_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 C7 1.315(2) . ?
O1 H1 0.859(17) . ?
O2 C7 1.214(2) . ?
O3 C9 1.308(2) . ?
O3 H3 0.88(3) . ?
O4 C9 1.222(2) . ?
O5 H5 0.8400 . ?
O5 C8 1.280(2) . ?
O6 H6 0.8400 . ?
O6 C8 1.260(2) . ?
C1 C2 1.393(2) . ?
C1 C6 1.394(3) . ?
C1 C7 1.499(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.398(3) . ?
C3 C4 1.389(3) . ?
C3 C8 1.484(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(2) . ?
C5 C6 1.396(3) . ?
C5 C9 1.495(2) . ?
C6 H6A 0.9500 . ?
O7 H7 0.8400 . ?
O7 C16 1.274(2) . ?
O8 H8 0.8400 . ?
O8 C16 1.264(2) . ?
O9 C18 1.311(2) . ?
O9 H9 0.90(4) . ?
O10 C18 1.219(2) . ?
O11 C17 1.309(2) . ?
O11 H11 0.901(17) . ?
O12 C17 1.213(2) . ?
C10 C11 1.391(2) . ?
C10 C15 1.398(2) . ?
C10 C16 1.486(2) . ?
C11 H11A 0.9500 . ?
C11 C12 1.394(2) . ?
C12 C13 1.389(2) . ?
C12 C17 1.495(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.396(2) . ?
C14 C15 1.392(2) . ?
C14 C18 1.497(2) . ?
C15 H15 0.9500 . ?
O13 C20 1.452(2) . ?
O13 H13A 0.86(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 C20 1.513(3) . ?
C20 H20 1.0000 . ?
C20 C21 1.499(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O14 C23 1.449(2) . ?
O14 H14 0.940(19) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22 C23 1.506(3) . ?
C23 H23 1.0000 . ?
C23 C24 1.513(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 H1 115(2) . . ?
C9 O3 H3 107.0(19) . . ?
C8 O5 H5 109.5 . . ?
C8 O6 H6 109.5 . . ?
C2 C1 C6 120.31(17) . . ?
C2 C1 C7 120.38(16) . . ?
C6 C1 C7 119.29(15) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 119.90(16) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C8 119.41(16) . . ?
C4 C3 C2 120.10(16) . . ?
C4 C3 C8 120.41(16) . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.76(17) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.55(16) . . ?
C4 C5 C9 117.64(16) . . ?
C6 C5 C9 121.75(15) . . ?
C1 C6 C5 119.35(16) . . ?
C1 C6 H6A 120.3 . . ?
C5 C6 H6A 120.3 . . ?
O1 C7 C1 112.41(15) . . ?
O2 C7 O1 124.83(17) . . ?
O2 C7 C1 122.76(16) . . ?
O5 C8 C3 117.55(16) . . ?
O6 C8 O5 124.17(16) . . ?
O6 C8 C3 118.28(16) . . ?
O3 C9 C5 114.92(16) . . ?
O4 C9 O3 124.38(17) . . ?
O4 C9 C5 120.70(16) . . ?
C16 O7 H7 109.5 . . ?
C16 O8 H8 109.5 . . ?
C18 O9 H9 120(2) . . ?
C17 O11 H11 107.2(16) . . ?
C11 C10 C15 119.68(15) . . ?
C11 C10 C16 120.62(16) . . ?
C15 C10 C16 119.64(15) . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 C12 120.03(16) . . ?
C12 C11 H11A 120.0 . . ?
C11 C12 C17 117.76(16) . . ?
C13 C12 C11 120.53(16) . . ?
C13 C12 C17 121.67(15) . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.42(16) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C18 119.27(15) . . ?
C15 C14 C13 120.31(16) . . ?
C15 C14 C18 120.40(16) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 119.99(16) . . ?
C14 C15 H15 120.0 . . ?
O7 C16 C10 117.31(15) . . ?
O8 C16 O7 124.30(15) . . ?
O8 C16 C10 118.39(15) . . ?
O11 C17 C12 114.89(15) . . ?
O12 C17 O11 124.31(16) . . ?
O12 C17 C12 120.79(16) . . ?
O9 C18 C14 112.55(15) . . ?
O10 C18 O9 124.49(17) . . ?
O10 C18 C14 122.96(17) . . ?
C20 O13 H13A 109(2) . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
O13 C20 C19 110.55(15) . . ?
O13 C20 H20 108.8 . . ?
O13 C20 C21 106.64(15) . . ?
C19 C20 H20 108.8 . . ?
C21 C20 C19 113.01(16) . . ?
C21 C20 H20 108.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 O14 H14 103.4(11) . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
O14 C23 C22 110.53(16) . . ?
O14 C23 H23 108.1 . . ?
O14 C23 C24 110.71(15) . . ?
C22 C23 H23 108.1 . . ?
C22 C23 C24 111.24(17) . . ?
C24 C23 H23 108.1 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 O8 0.84 1.79 2.6202(18) 169.5 6_575
O6 H6 O7 0.84 1.79 2.6056(18) 163.8 6_575
O7 H7 O6 0.84 1.78 2.6056(18) 168.8 6_576
O8 H8 O5 0.84 1.80 2.6202(19) 165.1 6_576
O14 H14 O10 0.940(19) 1.909(19) 2.8251(19) 164.2(16) .
O3 H3 O13 0.88(3) 1.70(3) 2.5795(19) 174(3) 4_656
O13 H13A O2 0.86(3) 1.94(3) 2.7993(19) 176(3) 4_656
O9 H9 O12 0.90(4) 1.71(4) 2.5989(19) 167(4) 1_545
O1 H1 O4 0.859(17) 1.765(19) 2.6023(19) 164(3) 1_545
O11 H11 O14 0.901(17) 1.671(16) 2.5658(18) 172(3) 1_565

_olex2_submission_special_instructions 'No special instructions were received'
