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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2432528'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro'
;Universidad Nacional de La Plata
Argentina
;
_audit_update_record             
;
2025-03-19 deposited with the CCDC.	2025-04-30 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'1,3,3-trimethyl-2-oxabicycle[2.2.2] octane-5,8-diol'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H20 O4'
_chemical_formula_weight         204.26
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
# start Validation Reply Form
_vrf_PLAT111_shelx               
;
PROBLEM: ADDSYM Detects New (Pseudo) Centre of Symmetry .        100 %Fit  
RESPONSE: Because optimization of inter-molecular OH...Ow, OH...OH and OwH...OH 
bonds, hydroxyl and water H-atoms slightly break the symmetry of the pseudo 
centric space group Pnma (#62 of IT) exhibited by the heavier atoms, reducing it 
to its non-centric subgroup Pn21a, which under the axes transformation a-->-a 
and b<-->c becomes the standard space group Pna21 (#33).
;
_vrf_PLAT113_shelx               
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group       Pnma Check 
RESPONSE: Because optimization of inter-molecular OH...Ow, OH...OH and OwH...OH 
bonds, hydroxyl and water H-atoms slightly break the symmetry of the pseudo 
space group Pnma (#62 of IT) exhibited by the heavier atoms, reducing it to its 
subgroup Pn21a, which under the axes transformation a-->-a and b<-->c becomes 
the standard space group Pna21 (#33).
;
# end Validation Reply Form  
_cell_length_a                   15.9487(8)
_cell_length_b                   7.4063(4)
_cell_length_c                   9.5158(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1124.01(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1311
_cell_measurement_theta_min      4.3140
_cell_measurement_theta_max      26.7700
_exptl_crystal_description       fragment
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.378
_exptl_crystal_size_mid          0.234
_exptl_crystal_size_min          0.194
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_T_min  0.93018
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.945
_oxdiff_exptl_absorpt_empirical_full_max 1.094
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            5157
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.033
_diffrn_reflns_theta_max         28.808
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.736
_diffrn_reflns_point_group_measured_fraction_full 0.883
_reflns_number_total             2156
_reflns_number_gt                1569
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.582
_reflns_Friedel_fraction_max     0.575
_reflns_Friedel_fraction_full    0.750
_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.0 
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0560P)²+0.1179P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
Flack x determined using 462 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   2.0(10)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2156
_refine_ls_number_parameters     146
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.74725(15) 0.4095(4) 0.6246(4) 0.0391(6) Uani 1 1 d . . . . .
C2 C 0.7143(2) 0.5242(6) 0.7448(4) 0.0512(10) Uani 1 1 d . . . . .
H2A H 0.7380 0.6446 0.7388 0.061 Uiso 1 1 calc R U . . .
H2B H 0.7313 0.4716 0.8337 0.061 Uiso 1 1 calc R U . . .
C3 C 0.6185(2) 0.5356(5) 0.7381(3) 0.0447(8) Uani 1 1 d . . . . .
H3 H 0.6034 0.6590 0.7109 0.054 Uiso 1 1 calc R U . . .
C4 C 0.58835(14) 0.4086(4) 0.6217(4) 0.0363(6) Uani 1 1 d . . . . .
H4 H 0.5269 0.4050 0.6209 0.044 Uiso 1 1 calc R U . . .
C5 C 0.6202(2) 0.4988(5) 0.4872(3) 0.0466(8) Uani 1 1 d . . . . .
H5 H 0.6061 0.6274 0.4920 0.056 Uiso 1 1 calc R U . . .
C6 C 0.7160(2) 0.4816(5) 0.4844(4) 0.0478(9) Uani 1 1 d . . . . .
H6A H 0.7326 0.4002 0.4095 0.057 Uiso 1 1 calc R U . . .
H6B H 0.7409 0.5987 0.4661 0.057 Uiso 1 1 calc R U . . .
C7 C 0.62312(15) 0.2165(4) 0.6389(4) 0.0427(7) Uani 1 1 d . . . . .
C8 C 0.6016(3) 0.0890(6) 0.5189(5) 0.0701(13) Uani 1 1 d . . . . .
H8A H 0.6210 0.1394 0.4319 0.105 Uiso 1 1 calc R U . . .
H8B H 0.5419 0.0725 0.5148 0.105 Uiso 1 1 calc R U . . .
H8C H 0.6283 -0.0255 0.5345 0.105 Uiso 1 1 calc R U . . .
C9 C 0.5960(3) 0.1259(6) 0.7764(5) 0.0679(12) Uani 1 1 d . . . . .
H9A H 0.6163 0.0039 0.7784 0.102 Uiso 1 1 calc R U . . .
H9B H 0.5360 0.1256 0.7825 0.102 Uiso 1 1 calc R U . . .
H9C H 0.6189 0.1915 0.8546 0.102 Uiso 1 1 calc R U . . .
C10 C 0.84205(15) 0.3935(5) 0.6293(6) 0.0554(8) Uani 1 1 d . . . . .
H10A H 0.8586 0.3376 0.7160 0.083 Uiso 1 1 calc R U . . .
H10B H 0.8666 0.5116 0.6231 0.083 Uiso 1 1 calc R U . . .
H10C H 0.8609 0.3212 0.5518 0.083 Uiso 1 1 calc R U . . .
O1 O 0.71458(10) 0.2293(3) 0.6429(3) 0.0520(6) Uani 1 1 d . . . . .
O2 O 0.58470(16) 0.5030(4) 0.8739(3) 0.0649(8) Uani 1 1 d . . . . .
O3 O 0.58049(15) 0.4246(4) 0.3653(3) 0.0689(9) Uani 1 1 d . . . . .
O4W O 0.67360(16) 0.4350(4) 0.1261(4) 0.0588(6) Uani 1 1 d . . . . .
H2O H 0.534(3) 0.524(5) 0.874(6) 0.079(14) Uiso 1 1 d . . . . .
H3O H 0.606(4) 0.460(8) 0.285(8) 0.12(2) Uiso 1 1 d . . . . .
H4A H 0.710(3) 0.518(7) 0.122(8) 0.098(16) Uiso 1 1 d . . . . .
H4B H 0.645(3) 0.450(6) 0.041(5) 0.073(13) Uiso 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
C1 O1 1.443(3) . ?
C1 C10 1.517(3) . ?
C1 C2 1.518(5) . ?
C1 C6 1.521(5) . ?
C2 C3 1.533(6) . ?
C3 O2 1.420(4) . ?
C3 C4 1.530(5) . ?
C4 C5 1.530(5) . ?
C4 C7 1.535(4) . ?
C5 O3 1.431(5) . ?
C5 C6 1.534(5) . ?
C7 O1 1.462(3) . ?
C7 C8 1.521(5) . ?
C7 C9 1.533(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C10 106.5(2) . . ?
O1 C1 C2 107.6(3) . . ?
C10 C1 C2 111.5(3) . . ?
O1 C1 C6 108.1(3) . . ?
C10 C1 C6 112.3(3) . . ?
C2 C1 C6 110.6(2) . . ?
C1 C2 C3 110.2(3) . . ?
O2 C3 C4 115.8(3) . . ?
O2 C3 C2 109.4(3) . . ?
C4 C3 C2 108.0(2) . . ?
C5 C4 C3 103.5(2) . . ?
C5 C4 C7 111.9(3) . . ?
C3 C4 C7 112.3(3) . . ?
O3 C5 C4 111.3(3) . . ?
O3 C5 C6 113.2(3) . . ?
C4 C5 C6 108.0(3) . . ?
C1 C6 C5 109.9(3) . . ?
O1 C7 C8 106.6(3) . . ?
O1 C7 C9 106.7(3) . . ?
C8 C7 C9 107.8(3) . . ?
O1 C7 C4 107.6(2) . . ?
C8 C7 C4 114.5(3) . . ?
C9 C7 C4 113.2(3) . . ?
C1 O1 C7 114.63(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -62.8(4) . . . . ?
C10 C1 C2 C3 -179.2(3) . . . . ?
C6 C1 C2 C3 55.1(3) . . . . ?
C1 C2 C3 O2 133.3(3) . . . . ?
C1 C2 C3 C4 6.5(4) . . . . ?
O2 C3 C4 C5 168.9(3) . . . . ?
C2 C3 C4 C5 -68.1(3) . . . . ?
O2 C3 C4 C7 -70.2(3) . . . . ?
C2 C3 C4 C7 52.7(3) . . . . ?
C3 C4 C5 O3 -165.4(3) . . . . ?
C7 C4 C5 O3 73.5(3) . . . . ?
C3 C4 C5 C6 69.7(3) . . . . ?
C7 C4 C5 C6 -51.4(4) . . . . ?
O1 C1 C6 C5 64.1(3) . . . . ?
C10 C1 C6 C5 -178.7(3) . . . . ?
C2 C1 C6 C5 -53.5(3) . . . . ?
O3 C5 C6 C1 -132.8(3) . . . . ?
C4 C5 C6 C1 -9.1(4) . . . . ?
C5 C4 C7 O1 59.4(4) . . . . ?
C3 C4 C7 O1 -56.5(4) . . . . ?
C5 C4 C7 C8 -58.9(3) . . . . ?
C3 C4 C7 C8 -174.8(3) . . . . ?
C5 C4 C7 C9 177.0(3) . . . . ?
C3 C4 C7 C9 61.2(3) . . . . ?
C10 C1 O1 C7 -179.0(3) . . . . ?
C2 C1 O1 C7 61.4(4) . . . . ?
C6 C1 O1 C7 -58.1(4) . . . . ?
C8 C7 O1 C1 120.9(3) . . . . ?
C9 C7 O1 C1 -124.2(3) . . . . ?
C4 C7 O1 C1 -2.4(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
C8 H8A O3 0.96 2.30 2.903(6) 120.3 .
C9 H9C O2 0.96 2.38 2.948(5) 117.6 .
O2 H2O O3 0.83(4) 1.86(4) 2.690(3) 177(5) 2_665
O3 H3O O4W 0.91(7) 1.86(8) 2.719(4) 157(5) .
O4W H4A O1 0.84(5) 1.99(5) 2.821(3) 170(6) 4_654
O4W H4B O2 0.94(5) 1.90(5) 2.833(4) 175(4) 1_554

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.057


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2432529'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro'
;Universidad Nacional de La Plata
Argentina
;
_audit_update_record             
;
2025-03-19 deposited with the CCDC.	2025-04-30 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
1,3,3-trimethyl-2-oxabicycle[2.2.2]octane-5-acetyl-8-oxo
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H18 O4'
_chemical_formula_weight         226.26
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.7247(3)
_cell_length_b                   8.6013(4)
_cell_length_c                   18.5304(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1231.20(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1593
_cell_measurement_theta_min      4.1690
_cell_measurement_theta_max      23.4270
_exptl_crystal_description       fragment
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.532
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.119
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_T_min  0.87214
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.866
_oxdiff_exptl_absorpt_empirical_full_max 1.176
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            6440
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.232
_diffrn_reflns_theta_max         28.689
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2658
_reflns_number_gt                2036
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.650
_reflns_Friedel_fraction_max     0.781
_reflns_Friedel_fraction_full    0.999
_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement. 
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0516P)²+0.0584P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 638 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(7)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         2658
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1070
_refine_ls_wR_factor_gt          0.0950
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3125(3) 0.3624(3) 0.58758(15) 0.0448(7) Uani 1 1 d . . . . .
C2 C 0.1462(3) 0.4555(3) 0.59430(15) 0.0453(6) Uani 1 1 d . . . . .
H2A H 0.0511 0.3867 0.6065 0.054 Uiso 1 1 calc R U . . .
H2B H 0.1198 0.5050 0.5486 0.054 Uiso 1 1 calc R U . . .
C3 C 0.1669(3) 0.5785(3) 0.65275(13) 0.0375(6) Uani 1 1 d . . . . .
H3 H 0.1008 0.5468 0.6954 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3588(3) 0.5915(3) 0.67307(13) 0.0361(5) Uani 1 1 d . . . . .
H4 H 0.3787 0.6801 0.7052 0.043 Uiso 1 1 calc R U . . .
C5 C 0.3952(3) 0.4404(3) 0.71109(14) 0.0461(6) Uani 1 1 d . . . . .
C6 C 0.3665(4) 0.3041(3) 0.66227(15) 0.0535(7) Uani 1 1 d . . . . .
H6A H 0.2767 0.2377 0.6820 0.064 Uiso 1 1 calc R U . . .
H6B H 0.4721 0.2436 0.6585 0.064 Uiso 1 1 calc R U . . .
C7 C 0.4806(3) 0.5980(3) 0.60703(13) 0.0410(6) Uani 1 1 d . . . . .
C8 C 0.6685(3) 0.5869(4) 0.63112(18) 0.0617(8) Uani 1 1 d . . . . .
H8A H 0.6862 0.4909 0.6565 0.092 Uiso 1 1 calc R U . . .
H8B H 0.6952 0.6725 0.6624 0.092 Uiso 1 1 calc R U . . .
H8C H 0.7428 0.5901 0.5896 0.092 Uiso 1 1 calc R U . . .
C9 C 0.4561(4) 0.7438(4) 0.56234(14) 0.0551(7) Uani 1 1 d . . . . .
H9A H 0.5378 0.7443 0.5233 0.083 Uiso 1 1 calc R U . . .
H9B H 0.4742 0.8336 0.5921 0.083 Uiso 1 1 calc R U . . .
H9C H 0.3406 0.7458 0.5432 0.083 Uiso 1 1 calc R U . . .
C10 C 0.3003(4) 0.2341(4) 0.53219(17) 0.0646(9) Uani 1 1 d . . . . .
H10A H 0.2799 0.2785 0.4854 0.097 Uiso 1 1 calc R U . . .
H10B H 0.2066 0.1657 0.5445 0.097 Uiso 1 1 calc R U . . .
H10C H 0.4068 0.1765 0.5314 0.097 Uiso 1 1 calc R U . . .
C11 C 0.0348(3) 0.8254(3) 0.67421(15) 0.0449(6) Uani 1 1 d . . . . .
C12 C -0.0404(4) 0.9651(3) 0.63820(17) 0.0626(8) Uani 1 1 d . . . . .
H12A H -0.1644 0.9612 0.6413 0.094 Uiso 1 1 calc R U . . .
H12B H -0.0061 0.9667 0.5884 0.094 Uiso 1 1 calc R U . . .
H12C H 0.0008 1.0574 0.6617 0.094 Uiso 1 1 calc R U . . .
O1 O 0.4462(2) 0.4648(2) 0.56158(9) 0.0515(5) Uani 1 1 d . . . . .
O2 O 0.0978(2) 0.72480(19) 0.62598(9) 0.0423(4) Uani 1 1 d . . . . .
O3 O 0.0360(3) 0.8024(2) 0.73773(10) 0.0698(7) Uani 1 1 d . . . . .
O4 O 0.4417(3) 0.4305(2) 0.77324(10) 0.0673(6) 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
C1 O1 1.440(3) . ?
C1 C10 1.510(4) . ?
C1 C2 1.519(4) . ?
C1 C6 1.530(4) . ?
C2 C3 1.523(4) . ?
C3 O2 1.454(3) . ?
C3 C4 1.533(3) . ?
C4 C5 1.505(4) . ?
C4 C7 1.545(3) . ?
C5 O4 1.209(3) . ?
C5 C6 1.497(4) . ?
C7 O1 1.447(3) . ?
C7 C9 1.514(4) . ?
C7 C8 1.522(4) . ?
C11 O3 1.194(3) . ?
C11 O2 1.336(3) . ?
C11 C12 1.492(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
O1 C1 C10 105.3(2) . . ?
O1 C1 C2 108.1(2) . . ?
C10 C1 C2 112.9(2) . . ?
O1 C1 C6 107.9(2) . . ?
C10 C1 C6 113.1(2) . . ?
C2 C1 C6 109.2(2) . . ?
C1 C2 C3 109.6(2) . . ?
O2 C3 C2 108.7(2) . . ?
O2 C3 C4 112.08(19) . . ?
C2 C3 C4 109.07(19) . . ?
C5 C4 C3 103.5(2) . . ?
C5 C4 C7 106.8(2) . . ?
C3 C4 C7 113.4(2) . . ?
O4 C5 C6 124.4(2) . . ?
O4 C5 C4 124.2(2) . . ?
C6 C5 C4 111.5(2) . . ?
C5 C6 C1 109.3(2) . . ?
O1 C7 C9 108.32(19) . . ?
O1 C7 C8 107.2(2) . . ?
C9 C7 C8 109.4(2) . . ?
O1 C7 C4 108.69(19) . . ?
C9 C7 C4 112.8(2) . . ?
C8 C7 C4 110.3(2) . . ?
O3 C11 O2 123.3(2) . . ?
O3 C11 C12 125.3(3) . . ?
O2 C11 C12 111.4(2) . . ?
C1 O1 C7 114.93(17) . . ?
C11 O2 C3 117.78(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -65.8(3) . . . . ?
C10 C1 C2 C3 178.1(2) . . . . ?
C6 C1 C2 C3 51.4(3) . . . . ?
C1 C2 C3 O2 135.0(2) . . . . ?
C1 C2 C3 C4 12.6(3) . . . . ?
O2 C3 C4 C5 170.25(19) . . . . ?
C2 C3 C4 C5 -69.4(3) . . . . ?
O2 C3 C4 C7 -74.5(3) . . . . ?
C2 C3 C4 C7 45.9(3) . . . . ?
C3 C4 C5 O4 -118.6(3) . . . . ?
C7 C4 C5 O4 121.5(3) . . . . ?
C3 C4 C5 C6 61.4(3) . . . . ?
C7 C4 C5 C6 -58.5(3) . . . . ?
O4 C5 C6 C1 -178.7(3) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
O1 C1 C6 C5 57.3(3) . . . . ?
C10 C1 C6 C5 173.4(2) . . . . ?
C2 C1 C6 C5 -60.0(3) . . . . ?
C5 C4 C7 O1 58.8(2) . . . . ?
C3 C4 C7 O1 -54.5(3) . . . . ?
C5 C4 C7 C9 178.9(2) . . . . ?
C3 C4 C7 C9 65.7(3) . . . . ?
C5 C4 C7 C8 -58.5(3) . . . . ?
C3 C4 C7 C8 -171.7(2) . . . . ?
C10 C1 O1 C7 -179.9(2) . . . . ?
C2 C1 O1 C7 59.2(3) . . . . ?
C6 C1 O1 C7 -58.8(3) . . . . ?
C9 C7 O1 C1 -122.9(2) . . . . ?
C8 C7 O1 C1 119.2(2) . . . . ?
C4 C7 O1 C1 0.0(3) . . . . ?
O3 C11 O2 C3 1.7(4) . . . . ?
C12 C11 O2 C3 -176.6(2) . . . . ?
C2 C3 O2 C11 151.8(2) . . . . ?
C4 C3 O2 C11 -87.6(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
C4 H4 O4 0.98 2.59 3.445(3) 145.5 3_656
C9 H9C O2 0.96 2.43 3.013(3) 118.9 .

_refine_diff_density_max         0.122
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.034


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
