# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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 2104642'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro'
;Universidad Nacional de La Plata
Argentina
;
_audit_update_record             
;
2021-08-21 deposited with the CCDC.	2022-02-24 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]oct-5-yl acetate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H20 O3'
_chemical_formula_weight         212.28

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_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'
_cell_length_a                   5.9803(5)
_cell_length_b                   7.9085(7)
_cell_length_c                   13.5905(12)
_cell_angle_alpha                88.056(7)
_cell_angle_beta                 87.341(7)
_cell_angle_gamma                70.216(8)
_cell_volume                     604.06(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1141
_cell_measurement_theta_min      3.8660
_cell_measurement_theta_max      24.0140
_exptl_crystal_description       fragment
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.466
_exptl_crystal_size_mid          0.352
_exptl_crystal_size_min          0.215
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_T_min  0.75917
_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 0.707
_oxdiff_exptl_absorpt_empirical_full_max 1.514
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(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            4757
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.002
_diffrn_reflns_theta_max         28.909
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.824
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.824
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.824
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2630
_reflns_number_gt                1637
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement. 
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection       '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)+(0.0731P)²+0.0103P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.110(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2630
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1578
_refine_ls_wR_factor_gt          0.1222
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.003
_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 0.2038(3) 0.2417(3) 0.15134(13) 0.0443(5) Uani 1 1 d . . . . .
C2 C 0.3729(4) 0.1602(3) 0.23366(14) 0.0522(5) Uani 1 1 d . . . . .
H2A H 0.5038 0.0580 0.2094 0.063 Uiso 1 1 calc R U . . .
H2B H 0.2900 0.1183 0.2869 0.063 Uiso 1 1 calc R U . . .
C3 C 0.4684(3) 0.3010(3) 0.27157(12) 0.0432(5) Uani 1 1 d . . . . .
H3 H 0.6300 0.2779 0.2438 0.052 Uiso 1 1 calc R U . . .
C4 C 0.3108(3) 0.4837(3) 0.23493(12) 0.0408(5) Uani 1 1 d . . . . .
H4 H 0.3476 0.5787 0.2681 0.049 Uiso 1 1 calc R U . . .
C5 C 0.3767(4) 0.4871(3) 0.12477(13) 0.0536(6) Uani 1 1 d . . . . .
H5A H 0.5444 0.4709 0.1153 0.064 Uiso 1 1 calc R U . . .
H5B H 0.2856 0.6018 0.0953 0.064 Uiso 1 1 calc R U . . .
C6 C 0.3210(4) 0.3341(3) 0.07616(13) 0.0577(6) Uani 1 1 d . . . . .
H6A H 0.2158 0.3822 0.0222 0.069 Uiso 1 1 calc R U . . .
H6B H 0.4669 0.2478 0.0497 0.069 Uiso 1 1 calc R U . . .
C7 C 0.0445(3) 0.5108(2) 0.24930(13) 0.0409(5) Uani 1 1 d . . . . .
C8 C -0.1120(4) 0.6932(3) 0.20984(17) 0.0636(6) Uani 1 1 d . . . . .
H8A H -0.0709 0.7059 0.1415 0.095 Uiso 1 1 calc R U . . .
H8B H -0.0878 0.7868 0.2464 0.095 Uiso 1 1 calc R U . . .
H8C H -0.2759 0.7016 0.2167 0.095 Uiso 1 1 calc R U . . .
C9 C -0.0334(3) 0.4901(3) 0.35532(14) 0.0557(6) Uani 1 1 d . . . . .
H9A H -0.2012 0.5105 0.3591 0.083 Uiso 1 1 calc R U . . .
H9B H 0.0007 0.5759 0.3950 0.083 Uiso 1 1 calc R U . . .
H9C H 0.0508 0.3707 0.3791 0.083 Uiso 1 1 calc R U . . .
C10 C 0.1129(4) 0.1062(3) 0.10614(16) 0.0677(7) Uani 1 1 d . . . . .
H10A H 0.0412 0.0517 0.1569 0.102 Uiso 1 1 calc R U . . .
H10B H 0.2430 0.0151 0.0743 0.102 Uiso 1 1 calc R U . . .
H10C H -0.0032 0.1658 0.0585 0.102 Uiso 1 1 calc R U . . .
C11 C 0.6559(4) 0.1711(3) 0.41970(15) 0.0532(6) Uani 1 1 d . . . . .
C12 C 0.6515(4) 0.1918(4) 0.52825(15) 0.0747(8) Uani 1 1 d . . . . .
H12A H 0.5170 0.1666 0.5578 0.112 Uiso 1 1 calc R U . . .
H12B H 0.6395 0.3126 0.5426 0.112 Uiso 1 1 calc R U . . .
H12C H 0.7950 0.1094 0.5544 0.112 Uiso 1 1 calc R U . . .
O1 O -0.0045(2) 0.37688(17) 0.19144(9) 0.0468(4) Uani 1 1 d . . . . .
O2 O 0.4749(2) 0.30047(19) 0.37853(8) 0.0505(4) Uani 1 1 d . . . . .
O3 O 0.7998(3) 0.0559(2) 0.37312(12) 0.0787(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 1.438(2) . ?
C1 C10 1.514(3) . ?
C1 C6 1.517(3) . ?
C1 C2 1.518(3) . ?
C2 C3 1.526(2) . ?
C3 O2 1.456(2) . ?
C3 C4 1.516(3) . ?
C4 C5 1.532(2) . ?
C4 C7 1.537(2) . ?
C5 C6 1.536(3) . ?
C7 O1 1.4539(19) . ?
C7 C9 1.515(3) . ?
C7 C8 1.524(3) . ?
C11 O3 1.196(2) . ?
C11 O2 1.341(2) . ?
C11 C12 1.488(3) . ?

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 105.14(14) . . ?
O1 C1 C6 107.33(16) . . ?
C10 C1 C6 113.03(16) . . ?
O1 C1 C2 109.04(14) . . ?
C10 C1 C2 112.48(18) . . ?
C6 C1 C2 109.54(15) . . ?
C1 C2 C3 109.61(16) . . ?
O2 C3 C4 109.56(14) . . ?
O2 C3 C2 113.20(16) . . ?
C4 C3 C2 107.85(13) . . ?
C3 C4 C5 104.45(15) . . ?
C3 C4 C7 112.72(15) . . ?
C5 C4 C7 109.76(14) . . ?
C4 C5 C6 108.16(16) . . ?
C1 C6 C5 109.89(14) . . ?
O1 C7 C9 108.25(15) . . ?
O1 C7 C8 106.15(13) . . ?
C9 C7 C8 108.32(16) . . ?
O1 C7 C4 107.69(13) . . ?
C9 C7 C4 113.86(14) . . ?
C8 C7 C4 112.22(17) . . ?
O3 C11 O2 122.99(18) . . ?
O3 C11 C12 125.7(2) . . ?
O2 C11 C12 111.27(18) . . ?
C1 O1 C7 114.45(12) . . ?
C11 O2 C3 116.39(15) . . ?

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 -67.08(18) . . . . ?
C10 C1 C2 C3 176.70(16) . . . . ?
C6 C1 C2 C3 50.1(2) . . . . ?
C1 C2 C3 O2 137.22(16) . . . . ?
C1 C2 C3 C4 15.84(19) . . . . ?
O2 C3 C4 C5 163.33(13) . . . . ?
C2 C3 C4 C5 -73.05(17) . . . . ?
O2 C3 C4 C7 -77.57(17) . . . . ?
C2 C3 C4 C7 46.05(18) . . . . ?
C3 C4 C5 C6 60.98(18) . . . . ?
C7 C4 C5 C6 -60.1(2) . . . . ?
O1 C1 C6 C5 56.65(19) . . . . ?
C10 C1 C6 C5 172.11(17) . . . . ?
C2 C1 C6 C5 -61.6(2) . . . . ?
C4 C5 C6 C1 4.2(2) . . . . ?
C3 C4 C7 O1 -62.10(17) . . . . ?
C5 C4 C7 O1 53.9(2) . . . . ?
C3 C4 C7 C9 57.9(2) . . . . ?
C5 C4 C7 C9 173.90(16) . . . . ?
C3 C4 C7 C8 -178.56(14) . . . . ?
C5 C4 C7 C8 -62.6(2) . . . . ?
C10 C1 O1 C7 172.99(16) . . . . ?
C6 C1 O1 C7 -66.42(17) . . . . ?
C2 C1 O1 C7 52.16(19) . . . . ?
C9 C7 O1 C1 -113.91(16) . . . . ?
C8 C7 O1 C1 129.98(17) . . . . ?
C4 C7 O1 C1 9.61(19) . . . . ?
O3 C11 O2 C3 -3.5(3) . . . . ?
C12 C11 O2 C3 176.42(17) . . . . ?
C4 C3 O2 C11 -161.10(15) . . . . ?
C2 C3 O2 C11 78.48(19) . . . . ?

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
C3 H3 O1 0.98 2.62 3.521(2) 152.7 1_655
C9 H9C O2 0.96 2.41 2.926(2) 113.7 .
C12 H12C O3 0.96 2.56 3.504(3) 168.9 2_756

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.037


_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 2104643'
loop_
_audit_author_name
_audit_author_address
'Oscar Enrique Piro'
;Universidad Nacional de La Plata
Argentina
;
_audit_update_record             
;
2021-08-21 deposited with the CCDC.	2022-02-24 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]oct-5,8-yl acetate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H22 O5'
_chemical_formula_weight         270.31
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.6744(4)
_cell_length_b                   19.7633(9)
_cell_length_c                   10.3173(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.582(6)
_cell_angle_gamma                90
_cell_volume                     1474.33(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1847
_cell_measurement_theta_min      4.3190
_cell_measurement_theta_max      25.7280
_exptl_crystal_description       fragment
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.496
_exptl_crystal_size_mid          0.449
_exptl_crystal_size_min          0.262
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_T_min  0.97716
_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 0.929
_oxdiff_exptl_absorpt_empirical_full_max 1.048
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(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            8068
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.000
_diffrn_reflns_theta_max         28.957
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3255
_reflns_number_gt                2092
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement. 
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection       '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)+(0.0793P)²+0.2208P] 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_number_reflns         3255
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0562
_refine_ls_wR_factor_ref         0.1661
_refine_ls_wR_factor_gt          0.1401
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.020
_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 0.4209(2) 0.28435(11) 0.5394(2) 0.0506(5) Uani 1 1 d . . . . .
C2 C 0.5238(3) 0.31613(11) 0.6793(2) 0.0581(6) Uani 1 1 d . . . . .
H2A H 0.5258 0.2846 0.7519 0.070 Uiso 1 1 calc R U . . .
H2B H 0.6506 0.3255 0.6861 0.070 Uiso 1 1 calc R U . . .
C3 C 0.4298(3) 0.38163(11) 0.6979(2) 0.0497(5) Uani 1 1 d . . . . .
H3 H 0.5117 0.4197 0.6978 0.060 Uiso 1 1 calc R U . . .
C4 C 0.2506(2) 0.38946(10) 0.57525(19) 0.0442(4) Uani 1 1 d . . . . .
H4 H 0.1817 0.4292 0.5879 0.053 Uiso 1 1 calc R U . . .
C5 C 0.3276(3) 0.40182(10) 0.4571(2) 0.0492(5) Uani 1 1 d . . . . .
H5 H 0.4267 0.4355 0.4869 0.059 Uiso 1 1 calc R U . . .
C6 C 0.4083(3) 0.33541(12) 0.4259(2) 0.0590(6) Uani 1 1 d . . . . .
H6A H 0.3299 0.3177 0.3380 0.071 Uiso 1 1 calc R U . . .
H6B H 0.5303 0.3434 0.4205 0.071 Uiso 1 1 calc R U . . .
C7 C 0.1275(2) 0.32597(9) 0.5512(2) 0.0461(5) Uani 1 1 d . . . . .
C8 C -0.0438(3) 0.33159(12) 0.4219(2) 0.0604(6) Uani 1 1 d . . . . .
H8A H -0.0060 0.3364 0.3426 0.091 Uiso 1 1 calc R U . . .
H8B H -0.1151 0.3704 0.4294 0.091 Uiso 1 1 calc R U . . .
H8C H -0.1176 0.2915 0.4125 0.091 Uiso 1 1 calc R U . . .
C9 C 0.0616(3) 0.30908(11) 0.6708(2) 0.0578(6) Uani 1 1 d . . . . .
H9A H -0.0144 0.2693 0.6492 0.087 Uiso 1 1 calc R U . . .
H9B H -0.0089 0.3463 0.6869 0.087 Uiso 1 1 calc R U . . .
H9C H 0.1666 0.3010 0.7518 0.087 Uiso 1 1 calc R U . . .
C10 C 0.5051(3) 0.21807(12) 0.5186(3) 0.0679(6) Uani 1 1 d . . . . .
H10A H 0.5101 0.1878 0.5925 0.102 Uiso 1 1 calc R U . . .
H10B H 0.6280 0.2258 0.5173 0.102 Uiso 1 1 calc R U . . .
H10C H 0.4310 0.1984 0.4328 0.102 Uiso 1 1 calc R U . . .
C11 C 0.5274(4) 0.40371(12) 0.9374(2) 0.0640(6) Uani 1 1 d . . . . .
C12 C 0.4792(5) 0.39669(15) 1.0649(3) 0.0885(9) Uani 1 1 d . . . . .
H12A H 0.5369 0.3568 1.1138 0.133 Uiso 1 1 calc R U . . .
H12B H 0.3474 0.3930 1.0411 0.133 Uiso 1 1 calc R U . . .
H12C H 0.5221 0.4357 1.1222 0.133 Uiso 1 1 calc R U . . .
C13 C 0.1463(3) 0.49119(11) 0.3220(2) 0.0531(5) Uani 1 1 d . . . . .
C14 C 0.0057(3) 0.50751(13) 0.1864(2) 0.0718(7) Uani 1 1 d . . . . .
H14A H -0.0899 0.5349 0.2000 0.108 Uiso 1 1 calc R U . . .
H14B H -0.0472 0.4663 0.1405 0.108 Uiso 1 1 calc R U . . .
H14C H 0.0635 0.5318 0.1311 0.108 Uiso 1 1 calc R U . . .
O1 O 0.23516(17) 0.26843(7) 0.53331(16) 0.0571(4) Uani 1 1 d . . . . .
O2 O 0.39227(18) 0.38211(8) 0.82664(14) 0.0582(4) Uani 1 1 d . . . . .
O3 O 0.6710(3) 0.42424(13) 0.9330(2) 0.1091(8) Uani 1 1 d . . . . .
O4 O 0.18987(18) 0.42505(7) 0.33052(14) 0.0545(4) Uani 1 1 d . . . . .
O5 O 0.2145(2) 0.53086(8) 0.41272(18) 0.0735(5) 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(2) . ?
C1 C10 1.508(3) . ?
C1 C6 1.524(3) . ?
C1 C2 1.529(3) . ?
C2 C3 1.525(3) . ?
C3 O2 1.450(2) . ?
C3 C4 1.533(3) . ?
C4 C7 1.540(3) . ?
C4 C5 1.541(3) . ?
C5 O4 1.452(2) . ?
C5 C6 1.531(3) . ?
C7 O1 1.453(2) . ?
C7 C9 1.520(3) . ?
C7 C8 1.531(3) . ?
C11 O3 1.189(3) . ?
C11 O2 1.330(3) . ?
C11 C12 1.488(3) . ?
C13 O5 1.199(3) . ?
C13 O4 1.345(2) . ?
C13 C14 1.488(3) . ?

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 105.62(16) . . ?
O1 C1 C6 107.72(16) . . ?
C10 C1 C6 112.70(18) . . ?
O1 C1 C2 108.73(16) . . ?
C10 C1 C2 112.37(18) . . ?
C6 C1 C2 109.47(18) . . ?
C3 C2 C1 110.53(16) . . ?
O2 C3 C2 111.58(17) . . ?
O2 C3 C4 110.92(14) . . ?
C2 C3 C4 108.25(16) . . ?
C3 C4 C7 112.53(16) . . ?
C3 C4 C5 101.16(14) . . ?
C7 C4 C5 112.23(16) . . ?
O4 C5 C6 107.80(16) . . ?
O4 C5 C4 113.91(15) . . ?
C6 C5 C4 108.65(16) . . ?
C1 C6 C5 109.38(17) . . ?
O1 C7 C9 106.79(16) . . ?
O1 C7 C8 107.75(16) . . ?
C9 C7 C8 107.53(15) . . ?
O1 C7 C4 108.31(13) . . ?
C9 C7 C4 113.65(16) . . ?
C8 C7 C4 112.51(17) . . ?
O3 C11 O2 122.8(2) . . ?
O3 C11 C12 125.0(2) . . ?
O2 C11 C12 112.1(2) . . ?
O5 C13 O4 123.4(2) . . ?
O5 C13 C14 125.6(2) . . ?
O4 C13 C14 110.99(19) . . ?
C1 O1 C7 114.81(14) . . ?
C11 O2 C3 116.86(16) . . ?
C13 O4 C5 117.15(16) . . ?

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 -61.4(2) . . . . ?
C10 C1 C2 C3 -177.96(17) . . . . ?
C6 C1 C2 C3 56.0(2) . . . . ?
C1 C2 C3 O2 128.34(17) . . . . ?
C1 C2 C3 C4 6.0(2) . . . . ?
O2 C3 C4 C7 -70.9(2) . . . . ?
C2 C3 C4 C7 51.9(2) . . . . ?
O2 C3 C4 C5 169.20(15) . . . . ?
C2 C3 C4 C5 -68.07(19) . . . . ?
C3 C4 C5 O4 -167.95(16) . . . . ?
C7 C4 C5 O4 71.9(2) . . . . ?
C3 C4 C5 C6 71.89(19) . . . . ?
C7 C4 C5 C6 -48.3(2) . . . . ?
O1 C1 C6 C5 65.8(2) . . . . ?
C10 C1 C6 C5 -178.12(17) . . . . ?
C2 C1 C6 C5 -52.3(2) . . . . ?
O4 C5 C6 C1 -135.31(16) . . . . ?
C4 C5 C6 C1 -11.4(2) . . . . ?
C3 C4 C7 O1 -56.4(2) . . . . ?
C5 C4 C7 O1 56.9(2) . . . . ?
C3 C4 C7 C9 62.1(2) . . . . ?
C5 C4 C7 C9 175.43(16) . . . . ?
C3 C4 C7 C8 -175.38(16) . . . . ?
C5 C4 C7 C8 -62.1(2) . . . . ?
C10 C1 O1 C7 180.00(17) . . . . ?
C6 C1 O1 C7 -59.3(2) . . . . ?
C2 C1 O1 C7 59.2(2) . . . . ?
C9 C7 O1 C1 -123.96(17) . . . . ?
C8 C7 O1 C1 120.77(18) . . . . ?
C4 C7 O1 C1 -1.2(2) . . . . ?
O3 C11 O2 C3 2.7(4) . . . . ?
C12 C11 O2 C3 -175.33(19) . . . . ?
C2 C3 O2 C11 86.5(2) . . . . ?
C4 C3 O2 C11 -152.77(19) . . . . ?
O5 C13 O4 C5 -0.3(3) . . . . ?
C14 C13 O4 C5 179.33(16) . . . . ?
C6 C5 O4 C13 -158.67(16) . . . . ?
C4 C5 O4 C13 80.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8A O4 0.96 2.34 2.941(3) 120.2 .
C9 H9C O2 0.96 2.30 2.894(3) 119.7 .
C14 H14C O3 0.96 2.50 3.397(3) 155.6 3_666

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.046


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
