# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_mo_fa0516_3_kotora
_database_code_depnum_ccdc_archive 'CCDC 2240461'
loop_
_audit_author_name
_audit_author_address
'Ivana Cisarova'
;Charles Univerzity
Czech Republic
;
_audit_update_record             
;
2023-02-07 deposited with the CCDC.	2023-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 O2'
_chemical_formula_sum            'C18 H12 O2'
_chemical_formula_weight         260.28
_chemical_compound_source        'synthesized by the authors'

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                   7.3664(3)
_cell_length_b                   8.4028(3)
_cell_length_c                   20.5541(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1272.27(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9905
_cell_measurement_theta_min      3.1315
_cell_measurement_theta_max      30.0009

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.258
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTONIII CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            64599
_diffrn_reflns_av_unetI/netI     0.0085
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.619
_diffrn_reflns_theta_max         30.001
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3710
_reflns_number_gt                3670
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_max     0.999
_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 Instrument Service vV6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XS, VERSION 2013/1'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0558P)²+0.2225P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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 1549 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.24(12)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3710
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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 0.36323(18) 0.76769(17) 0.83136(6) 0.0189(2) Uani 1 1 d . . . . .
C2 C 0.29154(19) 0.91860(17) 0.85520(7) 0.0230(3) Uani 1 1 d . . . . .
H2 H 0.369124 1.008871 0.856323 0.028 Uiso 1 1 calc R U . . .
C3 C 0.11860(18) 0.93397(16) 0.87570(7) 0.0195(3) Uani 1 1 d . . . . .
H3 H 0.077276 1.035940 0.889082 0.023 Uiso 1 1 calc R U . . .
C4 C -0.00752(16) 0.80053(15) 0.87815(6) 0.0145(2) Uani 1 1 d . . . . .
C5 C 0.04918(17) 0.65366(15) 0.84519(6) 0.0146(2) Uani 1 1 d . . . . .
C6 C -0.07568(18) 0.53488(15) 0.82762(6) 0.0170(2) Uani 1 1 d . . . . .
H6 H -0.201396 0.550638 0.835664 0.020 Uiso 1 1 calc R U . . .
C7 C -0.0173(2) 0.39443(16) 0.79857(7) 0.0205(3) Uani 1 1 d . . . . .
H7 H -0.102849 0.313611 0.788376 0.025 Uiso 1 1 calc R U . . .
C8 C 0.1657(2) 0.37133(18) 0.78430(7) 0.0224(3) Uani 1 1 d . . . . .
H8 H 0.205764 0.273439 0.766167 0.027 Uiso 1 1 calc R U . . .
C9 C 0.28877(19) 0.49211(17) 0.79674(6) 0.0204(3) Uani 1 1 d . . . . .
H9 H 0.412679 0.478628 0.785171 0.024 Uiso 1 1 calc R U . . .
C10 C 0.23236(17) 0.63374(16) 0.82617(6) 0.0162(2) Uani 1 1 d . . . . .
C11 C -0.16331(17) 0.81242(15) 0.91504(6) 0.0144(2) Uani 1 1 d . . . . .
C12 C -0.25274(19) 0.66751(15) 0.94193(6) 0.0178(2) Uani 1 1 d . . . . .
H12 H -0.185818 0.570874 0.942411 0.021 Uiso 1 1 calc R U . . .
C13 C -0.24211(16) 0.96626(14) 0.93504(6) 0.0151(2) Uani 1 1 d . . . . .
C14 C -0.27289(18) 1.08573(15) 0.88899(7) 0.0190(2) Uani 1 1 d . . . . .
H14 H -0.240362 1.068612 0.844812 0.023 Uiso 1 1 calc R U . . .
C15 C -0.3510(2) 1.22963(17) 0.90753(8) 0.0235(3) Uani 1 1 d . . . . .
H15 H -0.372747 1.309596 0.875804 0.028 Uiso 1 1 calc R U . . .
C16 C -0.3973(2) 1.25721(17) 0.97212(9) 0.0262(3) Uani 1 1 d . . . . .
H16 H -0.448643 1.356239 0.984705 0.031 Uiso 1 1 calc R U . . .
C17 C -0.3678(2) 1.13869(18) 1.01820(8) 0.0251(3) Uani 1 1 d . . . . .
H17 H -0.399083 1.156922 1.062415 0.030 Uiso 1 1 calc R U . . .
C18 C -0.29272(19) 0.99351(17) 0.99977(6) 0.0196(3) Uani 1 1 d . . . . .
H18 H -0.275669 0.912302 1.031337 0.024 Uiso 1 1 calc R U . . .
O1 O 0.52227(14) 0.75346(15) 0.81370(5) 0.0268(2) Uani 1 1 d . . . . .
O2 O -0.40642(15) 0.66625(12) 0.96326(5) 0.0243(2) 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 1.2323(16) . ?
C1 C2 1.458(2) . ?
C1 C10 1.4858(19) . ?
C2 C3 1.3480(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.4570(17) . ?
C3 H3 0.9500 . ?
C4 C11 1.3791(17) . ?
C4 C5 1.4685(16) . ?
C5 C6 1.4045(17) . ?
C5 C10 1.4148(16) . ?
C6 C7 1.3908(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.393(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.3981(18) . ?
C9 H9 0.9500 . ?
C11 C13 1.4755(17) . ?
C11 C12 1.4907(17) . ?
C12 O2 1.2141(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3984(18) . ?
C13 C18 1.4004(17) . ?
C14 C15 1.3921(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.3920(19) . ?
C17 H17 0.9500 . ?
C18 H18 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
O1 C1 C2 121.84(13) . . ?
O1 C1 C10 121.48(13) . . ?
C2 C1 C10 116.61(11) . . ?
C3 C2 C1 122.04(12) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 122.66(12) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C11 C4 C3 119.60(11) . . ?
C11 C4 C5 123.45(11) . . ?
C3 C4 C5 116.71(11) . . ?
C6 C5 C10 118.00(11) . . ?
C6 C5 C4 121.98(11) . . ?
C10 C5 C4 119.88(11) . . ?
C7 C6 C5 120.72(12) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 120.53(13) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 119.50(13) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.61(13) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C5 120.25(12) . . ?
C9 C10 C1 118.88(12) . . ?
C5 C10 C1 120.62(11) . . ?
C4 C11 C13 122.96(11) . . ?
C4 C11 C12 120.83(11) . . ?
C13 C11 C12 116.00(10) . . ?
O2 C12 C11 123.58(12) . . ?
O2 C12 H12 118.2 . . ?
C11 C12 H12 118.2 . . ?
C14 C13 C18 118.85(12) . . ?
C14 C13 C11 120.27(11) . . ?
C18 C13 C11 120.85(11) . . ?
C15 C14 C13 120.34(13) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.51(13) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 119.50(13) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 120.27(13) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 120.51(13) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_mo_fa0529_kotora
_database_code_depnum_ccdc_archive 'CCDC 2240462'
loop_
_audit_author_name
_audit_author_address
'Ivana Cisarova'
;Charles Univerzity
Czech Republic
;
_audit_update_record             
;
2023-02-07 deposited with the CCDC.	2023-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 O3'
_chemical_formula_sum            'C16 H14 O3'
_chemical_formula_weight         254.27
_chemical_compound_source        'synthesized by the authors'

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                   12.4042(4)
_cell_length_b                   8.1827(2)
_cell_length_c                   12.1889(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.9100(10)
_cell_angle_gamma                90
_cell_volume                     1218.71(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9995
_cell_measurement_theta_min      2.9960
_cell_measurement_theta_max      27.4815

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.179
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTONIII CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            76544
_diffrn_reflns_av_unetI/netI     0.0063
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.996
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2792
_reflns_number_gt                2723
_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 Instrument Service vV6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+0.6323P] 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         2792
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.12841(7) 0.29874(10) 0.51549(7) 0.02613(19) Uani 1 1 d . . . . .
O2 O 0.30668(6) 0.57227(10) 0.19705(6) 0.02218(18) Uani 1 1 d . . . . .
O3 O 0.09451(6) 0.65594(9) 0.21577(6) 0.01660(16) Uani 1 1 d . . . . .
C1 C 0.27598(8) 0.54365(12) 0.28475(8) 0.0153(2) Uani 1 1 d . . . . .
C2 C 0.17217(8) 0.62470(12) 0.31161(8) 0.01382(19) Uani 1 1 d . . . . .
C3 C 0.12621(8) 0.54640(13) 0.41293(8) 0.0159(2) Uani 1 1 d . . . . .
H3 H 0.0483(12) 0.5355(17) 0.3989(11) 0.024 Uiso 1 1 d . U . . .
C4 C 0.17785(8) 0.39332(13) 0.46521(8) 0.0167(2) Uani 1 1 d . . . . .
C5 C 0.29520(8) 0.36477(12) 0.45687(8) 0.0168(2) Uani 1 1 d . . . . .
C6 C 0.35861(9) 0.26112(13) 0.53327(9) 0.0218(2) Uani 1 1 d . . . . .
H6 H 0.328327 0.214261 0.592491 0.026 Uiso 1 1 calc R U . . .
C7 C 0.46587(10) 0.22671(14) 0.52253(10) 0.0264(3) Uani 1 1 d . . . . .
H7 H 0.509180 0.157523 0.575202 0.032 Uiso 1 1 calc R U . . .
C8 C 0.51033(9) 0.29286(14) 0.43518(10) 0.0262(2) Uani 1 1 d . . . . .
H8 H 0.583415 0.267411 0.427633 0.031 Uiso 1 1 calc R U . . .
C9 C 0.44807(9) 0.39593(14) 0.35909(9) 0.0213(2) Uani 1 1 d . . . . .
H9 H 0.478626 0.440859 0.299432 0.026 Uiso 1 1 calc R U . . .
C10 C 0.34031(8) 0.43413(12) 0.36979(8) 0.0162(2) Uani 1 1 d . . . . .
C11 C 0.19796(8) 0.77493(12) 0.38579(8) 0.0156(2) Uani 1 1 d . . . . .
C12 C 0.16565(8) 0.70406(13) 0.47330(8) 0.0184(2) Uani 1 1 d . . . . .
H12 H 0.160266 0.739273 0.547765 0.022 Uiso 1 1 d R U . . .
C13 C 0.23814(9) 0.93823(13) 0.36485(9) 0.0196(2) Uani 1 1 d . . . . .
H13 H 0.256641 1.001523 0.430649 0.023 Uiso 1 1 d R U . . .
C14 C 0.19193(9) 1.02688(14) 0.25780(9) 0.0226(2) Uani 1 1 d . . . . .
H14A H 0.139169 0.966588 0.206224 0.027 Uiso 1 1 d R U . . .
H14B H 0.179869 1.141388 0.264724 0.027 Uiso 1 1 d R U . . .
C15 C 0.30788(9) 0.97044(14) 0.27660(10) 0.0244(2) Uani 1 1 d . . . . .
H15B H 0.367539 1.052089 0.295451 0.029 Uiso 1 1 d R U . . .
H15A H 0.323439 0.876689 0.234651 0.029 Uiso 1 1 d R U . . .
C16 C 0.05563(9) 0.51049(13) 0.15556(9) 0.0211(2) Uani 1 1 d . . . . .
H16A H -0.007996 0.537281 0.098898 0.032 Uiso 1 1 calc R U . . .
H16B H 0.034594 0.429646 0.207323 0.032 Uiso 1 1 calc R U . . .
H16C H 0.113793 0.465360 0.119411 0.032 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.2166(13) . ?
O2 C1 1.2176(12) . ?
O3 C2 1.4038(11) . ?
O3 C16 1.4373(12) . ?
C1 C10 1.4931(14) . ?
C1 C2 1.5330(13) . ?
C2 C11 1.5269(13) . ?
C2 C3 1.5822(13) . ?
C3 C4 1.4983(14) . ?
C3 C12 1.5236(14) . ?
C3 H3 0.956(14) . ?
C4 C5 1.4948(14) . ?
C5 C6 1.3975(14) . ?
C5 C10 1.4022(14) . ?
C6 C7 1.3881(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3903(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.3861(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.4005(14) . ?
C9 H9 0.9500 . ?
C11 C12 1.3349(14) . ?
C11 C13 1.4638(14) . ?
C12 H12 0.9655 . ?
C13 C15 1.5150(15) . ?
C13 C14 1.5165(15) . ?
C13 H13 0.9491 . ?
C14 C15 1.4902(15) . ?
C14 H14A 0.9620 . ?
C14 H14B 0.9549 . ?
C15 H15B 0.9941 . ?
C15 H15A 0.9598 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C2 O3 C16 113.33(8) . . ?
O2 C1 C10 120.96(9) . . ?
O2 C1 C2 120.35(9) . . ?
C10 C1 C2 118.66(8) . . ?
O3 C2 C11 112.95(8) . . ?
O3 C2 C1 112.49(8) . . ?
C11 C2 C1 112.13(8) . . ?
O3 C2 C3 115.81(8) . . ?
C11 C2 C3 86.03(7) . . ?
C1 C2 C3 114.85(8) . . ?
C4 C3 C12 115.10(8) . . ?
C4 C3 C2 119.04(8) . . ?
C12 C3 C2 84.56(7) . . ?
C4 C3 H3 110.1(9) . . ?
C12 C3 H3 113.3(8) . . ?
C2 C3 H3 112.8(8) . . ?
O1 C4 C5 121.06(10) . . ?
O1 C4 C3 122.03(9) . . ?
C5 C4 C3 116.86(8) . . ?
C6 C5 C10 119.86(10) . . ?
C6 C5 C4 119.51(9) . . ?
C10 C5 C4 120.55(9) . . ?
C7 C6 C5 119.93(10) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.41(10) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.04(10) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.28(10) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C9 C10 C5 119.46(10) . . ?
C9 C10 C1 118.28(9) . . ?
C5 C10 C1 122.22(9) . . ?
C12 C11 C13 133.94(9) . . ?
C12 C11 C2 93.57(8) . . ?
C13 C11 C2 132.42(9) . . ?
C11 C12 C3 95.60(8) . . ?
C11 C12 H12 134.5 . . ?
C3 C12 H12 129.7 . . ?
C11 C13 C15 122.40(9) . . ?
C11 C13 C14 119.80(9) . . ?
C15 C13 C14 58.89(7) . . ?
C11 C13 H13 113.0 . . ?
C15 C13 H13 114.9 . . ?
C14 C13 H13 117.8 . . ?
C15 C14 C13 60.50(7) . . ?
C15 C14 H14A 118.1 . . ?
C13 C14 H14A 115.5 . . ?
C15 C14 H14B 116.9 . . ?
C13 C14 H14B 115.8 . . ?
H14A C14 H14B 117.5 . . ?
C14 C15 C13 60.61(7) . . ?
C14 C15 H15B 119.2 . . ?
C13 C15 H15B 116.5 . . ?
C14 C15 H15A 116.3 . . ?
C13 C15 H15A 115.5 . . ?
H15B C15 H15A 116.8 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         0.372
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.039

