# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mges210916
_database_code_depnum_ccdc_archive 'CCDC 2111415'
loop_
_audit_author_name
_audit_author_address
'Corinne Bailly'
;Service de Radiocristallographie Federation de Chimie Le Bel
France
;
_audit_update_record             
;
2021-09-23 deposited with the CCDC.	2025-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 O3'
_chemical_formula_sum            'C10 H10 O3'
_chemical_formula_weight         178.18

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/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1953(3)
_cell_length_b                   7.1751(3)
_cell_length_c                   14.7724(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.9270(10)
_cell_angle_gamma                90
_cell_volume                     852.90(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      31.97

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7192
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Mo-ImuS 3.0 microfocus tube'
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω shuterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28304
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.531
_diffrn_reflns_theta_max         32.014
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2964
_reflns_number_gt                2695
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0548P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_number_reflns         2964
_refine_ls_number_parameters     123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0340
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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 0.36961(9) 0.73837(10) 0.51376(5) 0.01379(13) Uani 1 1 d . . . . .
C2 C 0.51173(10) 0.72620(11) 0.47518(5) 0.01775(15) Uani 1 1 d . . . . .
H2 H 0.5049 0.7021 0.4113 0.021 Uiso 1 1 calc R U . . .
C3 C 0.66399(10) 0.75076(12) 0.53403(6) 0.01986(16) Uani 1 1 d . . . . .
H3 H 0.7638 0.7433 0.5104 0.024 Uiso 1 1 calc R U . . .
C4 C 0.67144(10) 0.78641(12) 0.62787(6) 0.01994(16) Uani 1 1 d . . . . .
H4 H 0.7769 0.8029 0.6668 0.024 Uiso 1 1 calc R U . . .
C5 C 0.52868(9) 0.79836(11) 0.66581(5) 0.01795(15) Uani 1 1 d . . . . .
H5 H 0.5348 0.8227 0.7296 0.022 Uiso 1 1 calc R U . . .
C6 C 0.37674(9) 0.77326(10) 0.60668(5) 0.01349(13) Uani 1 1 d . . . . .
C7 C 0.19378(9) 0.71617(10) 0.47066(5) 0.01508(14) Uani 1 1 d . . . . .
C8 C 0.20348(9) 0.77876(10) 0.62643(5) 0.01398(13) Uani 1 1 d . . . . .
C9 C 0.16834(9) 0.62198(10) 0.69004(5) 0.01659(14) Uani 1 1 d . . . . .
H9A H 0.2392 0.6391 0.7516 0.020 Uiso 1 1 calc R U . . .
H9B H 0.0509 0.6294 0.6973 0.020 Uiso 1 1 calc R U . . .
C10 C 0.15777(11) 0.96708(11) 0.66149(6) 0.02162(16) Uani 1 1 d . . . . .
H10A H 0.1848 1.0656 0.6208 0.032 Uiso 1 1 calc R U . . .
H10B H 0.2205 0.9872 0.7241 0.032 Uiso 1 1 calc R U . . .
H10C H 0.0385 0.9700 0.6622 0.032 Uiso 1 1 calc R U . . .
O1 O 0.09933(7) 0.74548(8) 0.53538(4) 0.01661(12) Uani 1 1 d . . . . .
O2 O 0.13131(7) 0.67880(9) 0.39151(4) 0.02123(14) Uani 1 1 d . . . . .
O3 O 0.19860(7) 0.44384(8) 0.65593(4) 0.01924(13) Uani 1 1 d . . . . .
H3A H 0.0999(18) 0.398(2) 0.6336(10) 0.040(4) 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 C6 1.3855(10) . ?
C1 C2 1.3931(10) . ?
C1 C7 1.4695(10) . ?
C2 C3 1.3902(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.3995(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.3924(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.3905(10) . ?
C5 H5 0.9500 . ?
C6 C8 1.5033(10) . ?
C7 O2 1.2141(9) . ?
C7 O1 1.3557(9) . ?
C8 O1 1.4696(9) . ?
C8 C10 1.5192(10) . ?
C8 C9 1.5278(10) . ?
C9 O3 1.4130(9) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O3 H3A 0.879(15) . ?

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 C1 C2 122.35(7) . . ?
C6 C1 C7 107.62(6) . . ?
C2 C1 C7 130.03(7) . . ?
C3 C2 C1 117.20(7) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 120.53(7) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 121.85(7) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C6 C5 C4 117.38(7) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C1 C6 C5 120.69(7) . . ?
C1 C6 C8 109.45(6) . . ?
C5 C6 C8 129.86(7) . . ?
O2 C7 O1 121.37(7) . . ?
O2 C7 C1 129.87(7) . . ?
O1 C7 C1 108.76(6) . . ?
O1 C8 C6 102.95(5) . . ?
O1 C8 C10 108.58(6) . . ?
C6 C8 C10 113.12(6) . . ?
O1 C8 C9 107.38(6) . . ?
C6 C8 C9 113.28(6) . . ?
C10 C8 C9 110.96(6) . . ?
O3 C9 C8 112.36(6) . . ?
O3 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
O3 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 O1 C8 111.13(5) . . ?
C9 O3 H3A 105.2(10) . . ?

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
C6 C1 C2 C3 -0.03(11) . . . . ?
C7 C1 C2 C3 -178.86(7) . . . . ?
C1 C2 C3 C4 -0.11(12) . . . . ?
C2 C3 C4 C5 0.10(13) . . . . ?
C3 C4 C5 C6 0.05(12) . . . . ?
C2 C1 C6 C5 0.18(11) . . . . ?
C7 C1 C6 C5 179.24(7) . . . . ?
C2 C1 C6 C8 179.75(7) . . . . ?
C7 C1 C6 C8 -1.19(8) . . . . ?
C4 C5 C6 C1 -0.19(11) . . . . ?
C4 C5 C6 C8 -179.65(7) . . . . ?
C6 C1 C7 O2 -177.54(8) . . . . ?
C2 C1 C7 O2 1.43(14) . . . . ?
C6 C1 C7 O1 2.66(8) . . . . ?
C2 C1 C7 O1 -178.37(7) . . . . ?
C1 C6 C8 O1 -0.55(7) . . . . ?
C5 C6 C8 O1 178.96(7) . . . . ?
C1 C6 C8 C10 -117.54(7) . . . . ?
C5 C6 C8 C10 61.98(10) . . . . ?
C1 C6 C8 C9 115.08(7) . . . . ?
C5 C6 C8 C9 -65.40(10) . . . . ?
O1 C8 C9 O3 57.34(7) . . . . ?
C6 C8 C9 O3 -55.64(8) . . . . ?
C10 C8 C9 O3 175.86(6) . . . . ?
O2 C7 O1 C8 177.08(7) . . . . ?
C1 C7 O1 C8 -3.10(8) . . . . ?
C6 C8 O1 C7 2.28(7) . . . . ?
C10 C8 O1 C7 122.44(6) . . . . ?
C9 C8 O1 C7 -117.52(6) . . . . ?

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
O3 H3A O2 0.879(15) 1.940(15) 2.8031(8) 167.2(13) 3_566

_refine_diff_density_max         0.447
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.048



####################################################################### 
# 
# 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_mges220617
_database_code_depnum_ccdc_archive 'CCDC 2384274'
loop_
_audit_author_name
_audit_author_address
'Lydia KARMAZIN'
;University of Strasbourg
France
;
_audit_update_record             
;
2024-09-16 deposited with the CCDC.	2025-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 O3'
_chemical_formula_sum            'C11 H12 O3'
_chemical_formula_weight         192.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.3853(2)
_cell_length_b                   6.7196(2)
_cell_length_c                   26.2878(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     951.28(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9989
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      66.56

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.803
_shelx_estimated_absorpt_T_min   0.882
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6003
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Cu-ImuS Diamond microfocus tube'
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω shuterless scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21157
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.362
_diffrn_reflns_theta_max         66.553
_diffrn_reflns_theta_full        66.553
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1670
_reflns_number_gt                1603
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.638
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'Bruker APEX4'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+0.2086P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1670
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0840
_refine_ls_wR_factor_gt          0.0827
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8509(4) 0.5874(3) 0.62238(7) 0.0265(4) Uani 1 1 d . . . . .
C2 C 1.0136(4) 0.7447(3) 0.61347(8) 0.0326(5) Uani 1 1 d . . . . .
H2 H 1.0287 0.8481 0.6379 0.039 Uiso 1 1 calc R U . . .
C3 C 1.1534(5) 0.7519(4) 0.56937(9) 0.0424(6) Uani 1 1 d . . . . .
H3 H 1.2637 0.8599 0.5637 0.051 Uiso 1 1 calc R U . . .
C4 C 1.1326(5) 0.6014(4) 0.53346(8) 0.0482(7) Uani 1 1 d . . . . .
H4 H 1.2287 0.6060 0.5032 0.058 Uiso 1 1 calc R U . . .
C5 C 0.9718(5) 0.4451(4) 0.54197(8) 0.0430(6) Uani 1 1 d . . . . .
H5 H 0.9562 0.3428 0.5172 0.052 Uiso 1 1 calc R U . . .
C6 C 0.8313(4) 0.4359(3) 0.58666(7) 0.0320(5) Uani 1 1 d . . . . .
C7 C 0.6650(4) 0.2613(3) 0.59645(8) 0.0348(5) Uani 1 1 d . . . . .
H7A H 0.5819 0.2248 0.5642 0.042 Uiso 1 1 calc R U . . .
H7B H 0.7691 0.1469 0.6069 0.042 Uiso 1 1 calc R U . . .
C8 C 0.4703(4) 0.2935(3) 0.63613(8) 0.0297(5) Uani 1 1 d . . . . .
C9 C 0.7085(4) 0.5718(3) 0.67201(7) 0.0271(5) Uani 1 1 d . . . . .
C10 C 0.6180(4) 0.7705(3) 0.69234(9) 0.0389(5) Uani 1 1 d . . . . .
H10A H 0.5237 0.8397 0.6658 0.058 Uiso 1 1 calc R U . . .
H10B H 0.7609 0.8519 0.7024 0.058 Uiso 1 1 calc R U . . .
H10C H 0.5111 0.7482 0.7220 0.058 Uiso 1 1 calc R U . . .
C11 C 0.8608(4) 0.4651(3) 0.71282(7) 0.0320(5) Uani 1 1 d . . . . .
H11A H 1.0253 0.5298 0.7158 0.038 Uiso 1 1 calc R U . . .
H11B H 0.7756 0.4777 0.7460 0.038 Uiso 1 1 calc R U . . .
O1 O 0.2950(3) 0.1820(2) 0.64097(7) 0.0414(4) Uani 1 1 d . . . . .
O2 O 0.4806(3) 0.4548(2) 0.66570(5) 0.0307(4) Uani 1 1 d . . . . .
O3 O 0.8939(3) 0.2619(2) 0.70140(6) 0.0369(4) Uani 1 1 d . . . . .
H3O H 1.034(6) 0.244(4) 0.6823(10) 0.047(8) 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 C6 1.389(3) . ?
C1 C2 1.393(3) . ?
C1 C9 1.517(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.498(3) . ?
C7 C8 1.495(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O1 1.212(3) . ?
C8 O2 1.335(2) . ?
C9 O2 1.467(2) . ?
C9 C10 1.519(3) . ?
C9 C11 1.529(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O3 1.409(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
O3 H3O 0.92(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
C6 C1 C2 119.36(19) . . ?
C6 C1 C9 119.48(18) . . ?
C2 C1 C9 121.02(17) . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.6(2) . . ?
C1 C6 C7 120.20(18) . . ?
C5 C6 C7 120.1(2) . . ?
C8 C7 C6 115.20(18) . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
O1 C8 O2 118.3(2) . . ?
O1 C8 C7 121.99(18) . . ?
O2 C8 C7 119.67(18) . . ?
O2 C9 C1 111.28(15) . . ?
O2 C9 C10 104.05(17) . . ?
C1 C9 C10 113.81(17) . . ?
O2 C9 C11 106.09(16) . . ?
C1 C9 C11 111.38(17) . . ?
C10 C9 C11 109.73(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 C9 111.88(16) . . ?
O3 C11 H11A 109.2 . . ?
C9 C11 H11A 109.2 . . ?
O3 C11 H11B 109.2 . . ?
C9 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C8 O2 C9 122.39(16) . . ?
C11 O3 H3O 110.5(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
C6 C1 C2 C3 0.5(3) . . . . ?
C9 C1 C2 C3 176.3(2) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C9 C1 C6 C5 -176.9(2) . . . . ?
C2 C1 C6 C7 177.58(19) . . . . ?
C9 C1 C6 C7 1.8(3) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C4 C5 C6 C7 -177.5(2) . . . . ?
C1 C6 C7 C8 19.1(3) . . . . ?
C5 C6 C7 C8 -162.3(2) . . . . ?
C6 C7 C8 O1 165.3(2) . . . . ?
C6 C7 C8 O2 -11.2(3) . . . . ?
C6 C1 C9 O2 -28.7(3) . . . . ?
C2 C1 C9 O2 155.56(18) . . . . ?
C6 C1 C9 C10 -145.9(2) . . . . ?
C2 C1 C9 C10 38.4(3) . . . . ?
C6 C1 C9 C11 89.4(2) . . . . ?
C2 C1 C9 C11 -86.3(2) . . . . ?
O2 C9 C11 O3 52.7(2) . . . . ?
C1 C9 C11 O3 -68.6(2) . . . . ?
C10 C9 C11 O3 164.49(18) . . . . ?
O1 C8 O2 C9 164.73(18) . . . . ?
C7 C8 O2 C9 -18.6(3) . . . . ?
C1 C9 O2 C8 38.3(2) . . . . ?
C10 C9 O2 C8 161.21(17) . . . . ?
C11 C9 O2 C8 -83.0(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
O3 H3O O1 0.92(3) 1.82(3) 2.735(3) 173(3) 1_655

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.033



