# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1
_database_code_depnum_ccdc_archive 'CCDC 2179771'
_audit_update_record             
;
2022-06-17 deposited with the CCDC.	2022-11-30 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         ?
_chemical_formula_sum            'C9 H11 N O3'
_chemical_formula_weight         181.19

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'
N N 0.0061 0.0033 '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                   6.7100(9)
_cell_length_b                   9.9787(13)
_cell_length_c                   13.6067(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     911.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1769
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      25.21

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4607
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.385
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1582
_reflns_number_gt                1332
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0686P)²+0.0593P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.022(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 470 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.1(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1582
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_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
O2 O 0.3216(3) 0.3440(2) 0.90658(9) 0.0609(6) Uani 1 1 d G . . . .
H2A H 0.3687 0.3251 0.9629 0.091 Uiso 1 1 d G U . . .
H2B H 0.3921 0.3067 0.8624 0.091 Uiso 1 1 d G U . . .
O3 O 0.4487(3) 0.2862(2) 0.10023(9) 0.0664(6) Uani 1 1 d G . . . .
H3A H 0.4032 0.3064 0.0439 0.100 Uiso 1 1 d G U . . .
H3B H 0.3469 0.2857 0.1374 0.100 Uiso 1 1 d G U . . .
N1 N 0.6054(3) 0.2779(2) 0.69159(15) 0.0452(5) Uani 1 1 d . . . . .
O1 O 0.6024(3) 0.2317(2) 0.78330(12) 0.0673(6) Uani 1 1 d . . . . .
C8 C 0.6120(3) 0.2421(2) 0.51958(16) 0.0361(6) Uani 1 1 d . . . . .
C3 C 0.6087(4) 0.3811(2) 0.50229(16) 0.0373(6) Uani 1 1 d . . . . .
C9 C 0.6130(4) 0.1950(2) 0.61667(17) 0.0410(6) Uani 1 1 d . . . . .
H9 H 0.6192 0.1032 0.6283 0.049 Uiso 1 1 calc R U . . .
C7 C 0.6131(4) 0.1528(3) 0.43880(19) 0.0448(6) Uani 1 1 d . . . . .
H7 H 0.6151 0.0608 0.4494 0.054 Uiso 1 1 calc R U . . .
C2 C 0.6030(4) 0.4656(2) 0.58533(19) 0.0486(7) Uani 1 1 d . . . . .
H2 H 0.6014 0.5580 0.5767 0.058 Uiso 1 1 calc R U . . .
C4 C 0.6074(4) 0.4280(3) 0.40436(19) 0.0500(7) Uani 1 1 d . . . . .
H4 H 0.6062 0.5196 0.3919 0.060 Uiso 1 1 calc R U . . .
C1 C 0.5997(5) 0.4146(3) 0.6768(2) 0.0524(7) Uani 1 1 d . . . . .
H1 H 0.5935 0.4721 0.7305 0.063 Uiso 1 1 calc R U . . .
C6 C 0.6111(4) 0.2022(3) 0.34534(19) 0.0523(7) Uani 1 1 d . . . . .
H6 H 0.6119 0.1433 0.2924 0.063 Uiso 1 1 calc R U . . .
C5 C 0.6079(5) 0.3399(3) 0.3283(2) 0.0564(7) Uani 1 1 d . . . . .
H5 H 0.6061 0.3719 0.2641 0.068 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
O2 H2A 0.8500 . ?
O2 H2B 0.8500 . ?
O3 H3A 0.8500 . ?
O3 H3B 0.8501 . ?
N1 C9 1.314(3) . ?
N1 O1 1.330(3) . ?
N1 C1 1.380(4) . ?
C8 C9 1.402(3) . ?
C8 C3 1.407(4) . ?
C8 C7 1.415(3) . ?
C3 C2 1.410(3) . ?
C3 C4 1.412(3) . ?
C9 H9 0.9300 . ?
C7 C6 1.364(4) . ?
C7 H7 0.9300 . ?
C2 C1 1.344(4) . ?
C2 H2 0.9300 . ?
C4 C5 1.358(4) . ?
C4 H4 0.9300 . ?
C1 H1 0.9300 . ?
C6 C5 1.394(4) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H2A O2 H2B 109.5 . . ?
H3A O3 H3B 104.5 . . ?
C9 N1 O1 120.7(2) . . ?
C9 N1 C1 120.7(2) . . ?
O1 N1 C1 118.6(2) . . ?
C9 C8 C3 119.2(2) . . ?
C9 C8 C7 121.4(2) . . ?
C3 C8 C7 119.4(2) . . ?
C2 C3 C8 117.1(2) . . ?
C2 C3 C4 123.9(2) . . ?
C8 C3 C4 119.0(2) . . ?
N1 C9 C8 121.3(2) . . ?
N1 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C6 C7 C8 119.8(2) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C1 C2 C3 121.1(2) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C2 C1 N1 120.6(2) . . ?
C2 C1 H1 119.7 . . ?
N1 C1 H1 119.7 . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?

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
C9 C8 C3 C2 -1.1(3) . . . . ?
C7 C8 C3 C2 178.5(2) . . . . ?
C9 C8 C3 C4 -179.9(2) . . . . ?
C7 C8 C3 C4 -0.3(4) . . . . ?
O1 N1 C9 C8 178.6(2) . . . . ?
C1 N1 C9 C8 -1.1(4) . . . . ?
C3 C8 C9 N1 1.9(3) . . . . ?
C7 C8 C9 N1 -177.7(2) . . . . ?
C9 C8 C7 C6 179.7(2) . . . . ?
C3 C8 C7 C6 0.1(3) . . . . ?
C8 C3 C2 C1 -0.4(4) . . . . ?
C4 C3 C2 C1 178.4(3) . . . . ?
C2 C3 C4 C5 -178.2(3) . . . . ?
C8 C3 C4 C5 0.5(4) . . . . ?
C3 C2 C1 N1 1.2(4) . . . . ?
C9 N1 C1 C2 -0.4(4) . . . . ?
O1 N1 C1 C2 179.9(2) . . . . ?
C8 C7 C6 C5 -0.1(4) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C7 C6 C5 C4 0.2(5) . . . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2182218'
_audit_update_record             
;
2022-06-26 deposited with the CCDC.	2022-11-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 O3'
_chemical_formula_weight         252.26

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.490(6)
_cell_length_b                   8.098(6)
_cell_length_c                   11.691(8)
_cell_angle_alpha                74.674(12)
_cell_angle_beta                 81.853(13)
_cell_angle_gamma                65.253(11)
_cell_volume                     620.7(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    897
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      25.19

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9735
_exptl_absorpt_correction_T_max  0.9807
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2876
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_sigmaI/netI    0.0886
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2132
_reflns_number_gt                1148
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.0000P] 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_number_reflns         2132
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1225
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1613
_refine_ls_wR_factor_gt          0.1471
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.057
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1834(4) 0.2494(4) 0.2313(2) 0.0495(7) Uani 1 1 d U . .
C2 C 0.1528(4) 0.4005(4) 0.1364(3) 0.0628(9) Uani 1 1 d . . .
H2A H 0.1485 0.3904 0.0595 0.075 Uiso 1 1 calc R . .
C3 C 0.1288(4) 0.5676(4) 0.1595(3) 0.0690(9) Uani 1 1 d . . .
H3A H 0.1065 0.6724 0.0974 0.083 Uiso 1 1 calc R . .
C4 C 0.1377(4) 0.5806(4) 0.2744(3) 0.0663(9) Uani 1 1 d . . .
H4A H 0.1207 0.6945 0.2880 0.080 Uiso 1 1 calc R . .
C5 C 0.1712(4) 0.4284(4) 0.3688(3) 0.0580(8) Uani 1 1 d . . .
H5A H 0.1787 0.4376 0.4455 0.070 Uiso 1 1 calc R . .
C6 C 0.1936(4) 0.2594(4) 0.3458(2) 0.0464(7) Uani 1 1 d . . .
C7 C 0.2284(4) 0.0747(4) 0.4242(3) 0.0524(8) Uani 1 1 d . . .
C8 C 0.2128(5) 0.0558(4) 0.2343(3) 0.0600(8) Uani 1 1 d U . .
C9 C 0.2503(4) 0.0167(4) 0.5401(2) 0.0512(8) Uani 1 1 d . . .
H9A H 0.2382 0.1094 0.5774 0.061 Uiso 1 1 calc R . .
C10 C 0.2903(4) -0.1666(4) 0.6212(2) 0.0486(7) Uani 1 1 d . . .
C11 C 0.3059(4) -0.3254(4) 0.5859(3) 0.0551(8) Uani 1 1 d . . .
H11A H 0.2897 -0.3160 0.5067 0.066 Uiso 1 1 calc R . .
C12 C 0.3445(4) -0.4946(4) 0.6658(3) 0.0630(9) Uani 1 1 d . . .
H12A H 0.3564 -0.5980 0.6400 0.076 Uiso 1 1 calc R . .
C13 C 0.3655(4) -0.5105(4) 0.7833(3) 0.0636(9) Uani 1 1 d . . .
H13A H 0.3914 -0.6248 0.8370 0.076 Uiso 1 1 calc R . .
C14 C 0.3483(4) -0.3571(4) 0.8224(2) 0.0604(8) Uani 1 1 d . . .
H14A H 0.3606 -0.3677 0.9024 0.072 Uiso 1 1 calc R . .
C15 C 0.3126(4) -0.1869(4) 0.7416(2) 0.0526(8) Uani 1 1 d . . .
C16 C 0.2970(5) -0.0331(4) 0.8948(2) 0.0762(10) Uani 1 1 d . . .
H16A H 0.2911 0.0835 0.9038 0.114 Uiso 1 1 calc R . .
H16B H 0.4133 -0.1330 0.9305 0.114 Uiso 1 1 calc R . .
H16C H 0.1829 -0.0526 0.9330 0.114 Uiso 1 1 calc R . .
O1 O 0.2167(4) -0.0173(3) 0.15660(18) 0.0872(8) Uani 1 1 d . . .
O2 O 0.2398(3) -0.0433(2) 0.35171(16) 0.0598(6) Uani 1 1 d . . .
O3 O 0.3026(3) -0.0293(3) 0.77230(16) 0.0694(7) 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 C6 1.377(4) . ?
C1 C2 1.379(4) . ?
C1 C8 1.480(4) . ?
C2 C3 1.383(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.388(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.379(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.401(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.471(4) . ?
C7 C9 1.321(4) . ?
C7 O2 1.407(3) . ?
C8 O1 1.200(3) . ?
C8 O2 1.389(3) . ?
C9 C10 1.469(4) . ?
C9 H9A 0.9300 . ?
C10 C15 1.400(4) . ?
C10 C11 1.406(4) . ?
C11 C12 1.379(4) . ?
C11 H11A 0.9300 . ?
C12 C13 1.370(4) . ?
C12 H12A 0.9300 . ?
C13 C14 1.385(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.392(4) . ?
C14 H14A 0.9300 . ?
C15 O3 1.384(3) . ?
C16 O3 1.420(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 122.5(3) . . ?
C6 C1 C8 107.6(2) . . ?
C2 C1 C8 129.9(3) . . ?
C1 C2 C3 117.7(3) . . ?
C1 C2 H2A 121.2 . . ?
C3 C2 H2A 121.2 . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C5 C4 C3 121.4(3) . . ?
C5 C4 H4A 119.3 . . ?
C3 C4 H4A 119.3 . . ?
C4 C5 C6 118.0(3) . . ?
C4 C5 H5A 121.0 . . ?
C6 C5 H5A 121.0 . . ?
C1 C6 C5 119.8(2) . . ?
C1 C6 C7 108.3(2) . . ?
C5 C6 C7 131.9(3) . . ?
C9 C7 O2 122.9(3) . . ?
C9 C7 C6 130.3(3) . . ?
O2 C7 C6 106.8(2) . . ?
O1 C8 O2 121.4(3) . . ?
O1 C8 C1 131.3(3) . . ?
O2 C8 C1 107.3(2) . . ?
C7 C9 C10 132.0(3) . . ?
C7 C9 H9A 114.0 . . ?
C10 C9 H9A 114.0 . . ?
C15 C10 C11 117.0(2) . . ?
C15 C10 C9 118.8(3) . . ?
C11 C10 C9 124.1(3) . . ?
C12 C11 C10 121.7(3) . . ?
C12 C11 H11A 119.2 . . ?
C10 C11 H11A 119.2 . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C12 C13 C14 120.3(3) . . ?
C12 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
C13 C14 C15 119.8(3) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
O3 C15 C14 123.5(3) . . ?
O3 C15 C10 115.4(2) . . ?
C14 C15 C10 121.1(3) . . ?
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 . . ?
C8 O2 C7 109.8(2) . . ?
C15 O3 C16 117.9(2) . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.052
