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

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

data_DRH-02-103_a
_database_code_depnum_ccdc_archive 'CCDC 2408404'
loop_
_audit_author_name
_audit_author_address
'Denver Hopkins'
;Purdue University
United States of America
;
_audit_update_record             
;
2024-12-06 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
;
(3R,4aS,8R,9aR)-3-phenyl-1,3,4,8,9,9a-hexahydro-5H-4a,8-epoxycyclohepta[c]pyran-5-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 O3'
_chemical_formula_sum            'C16 H16 O3'
_chemical_formula_weight         256.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.5957(4)
_cell_length_b                   5.5652(2)
_cell_length_c                   17.3345(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1311.58(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9880
_cell_measurement_theta_min      2.9967
_cell_measurement_theta_max      32.4000

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.397
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.173
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6942
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_detector_type            
'PhotonII charge-integrating pixel array (CPAD)'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            28105
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.997
_diffrn_reflns_theta_max         33.172
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             4751
_reflns_number_gt                4206
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_max     0.894
_reflns_Friedel_fraction_full    0.934

_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       'Apex5 v2023.9-2 (Bruker, 2023)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_computing_structure_refinement  
;  
SHELXL-2019/2 (Sheldrick, 2015a, 2019), 
SHELXLE Rev1613 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
All hydrogens were placed automatically.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0516P)²+0.0986P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1718 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4751
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0927
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.71944(8) 0.44860(19) 0.43511(7) 0.0262(2) Uani 1 1 d . . . . .
O2 O 0.82600(7) 0.92426(18) 0.55568(7) 0.0246(2) Uani 1 1 d . . . . .
O3 O 0.62647(9) 0.7223(3) 0.66819(7) 0.0347(3) Uani 1 1 d . . . . .
C1 C 0.81172(11) 0.4426(3) 0.47421(9) 0.0252(3) Uani 1 1 d . . . . .
H1A H 0.857602 0.555124 0.448501 0.030 Uiso 1 1 calc R U . . .
H1B H 0.839801 0.278975 0.469956 0.030 Uiso 1 1 calc R U . . .
C2 C 0.80367(10) 0.5098(2) 0.55927(8) 0.0209(2) Uani 1 1 d . . . . .
H2 H 0.770660 0.380163 0.589702 0.025 Uiso 1 1 calc R U . . .
C3 C 0.90765(11) 0.5657(3) 0.59126(11) 0.0289(3) Uani 1 1 d . . . . .
H3A H 0.959255 0.523766 0.553278 0.035 Uiso 1 1 calc R U . . .
H3B H 0.920140 0.477312 0.639855 0.035 Uiso 1 1 calc R U . . .
C4 C 0.90385(11) 0.8406(3) 0.60541(10) 0.0283(3) Uani 1 1 d . . . . .
H4 H 0.967945 0.918411 0.592143 0.034 Uiso 1 1 calc R U . . .
C5 C 0.87573(12) 0.8895(3) 0.68739(11) 0.0320(3) Uani 1 1 d . . . . .
H5 H 0.924047 0.936876 0.723939 0.038 Uiso 1 1 calc R U . . .
C6 C 0.78149(13) 0.8655(3) 0.70847(10) 0.0307(3) Uani 1 1 d . . . . .
H6 H 0.761142 0.902603 0.759524 0.037 Uiso 1 1 calc R U . . .
C7 C 0.71015(11) 0.7802(3) 0.65079(9) 0.0242(3) Uani 1 1 d . . . . .
C8 C 0.74903(10) 0.7532(2) 0.56769(8) 0.0195(2) Uani 1 1 d . . . . .
C9 C 0.66608(10) 0.7912(3) 0.51059(9) 0.0228(3) Uani 1 1 d . . . . .
H9A H 0.652974 0.965676 0.506395 0.027 Uiso 1 1 calc R U . . .
H9B H 0.605902 0.714289 0.531205 0.027 Uiso 1 1 calc R U . . .
C10 C 0.68578(11) 0.6918(2) 0.42984(8) 0.0227(3) Uani 1 1 d . . . . .
H10 H 0.737150 0.791960 0.403925 0.027 Uiso 1 1 calc R U . . .
C11 C 0.59274(11) 0.6957(3) 0.38235(8) 0.0229(3) Uani 1 1 d . . . . .
C12 C 0.57317(12) 0.8915(3) 0.33472(9) 0.0277(3) Uani 1 1 d . . . . .
H12 H 0.619539 1.018642 0.331022 0.033 Uiso 1 1 calc R U . . .
C13 C 0.48619(12) 0.9023(3) 0.29250(10) 0.0295(3) Uani 1 1 d . . . . .
H13 H 0.473129 1.037673 0.260742 0.035 Uiso 1 1 calc R U . . .
C14 C 0.41868(12) 0.7166(3) 0.29659(10) 0.0287(3) Uani 1 1 d . . . . .
H14 H 0.360058 0.722595 0.266818 0.034 Uiso 1 1 calc R U . . .
C15 C 0.43706(12) 0.5215(3) 0.34443(10) 0.0288(3) Uani 1 1 d . . . . .
H15 H 0.390571 0.394510 0.347762 0.035 Uiso 1 1 calc R U . . .
C16 C 0.52347(11) 0.5115(3) 0.38757(9) 0.0270(3) Uani 1 1 d . . . . .
H16 H 0.535262 0.378574 0.420688 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 C1 1.4264(19) . ?
O1 C10 1.4319(17) . ?
O2 C8 1.4302(16) . ?
O2 C4 1.4423(19) . ?
O3 C7 1.2204(19) . ?
C1 C2 1.525(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.550(2) . ?
C2 C8 1.5516(18) . ?
C2 H2 1.0000 . ?
C3 C4 1.550(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.497(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.339(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.472(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.542(2) . ?
C8 C9 1.5153(19) . ?
C9 C10 1.529(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.510(2) . ?
C10 H10 1.0000 . ?
C11 C12 1.392(2) . ?
C11 C16 1.395(2) . ?
C12 C13 1.392(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(2) . ?
C15 H15 0.9500 . ?
C16 H16 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
C1 O1 C10 109.49(11) . . ?
C8 O2 C4 103.59(11) . . ?
O1 C1 C2 112.99(11) . . ?
O1 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
O1 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C1 C2 C3 109.24(12) . . ?
C1 C2 C8 109.84(11) . . ?
C3 C2 C8 103.18(11) . . ?
C1 C2 H2 111.4 . . ?
C3 C2 H2 111.4 . . ?
C8 C2 H2 111.4 . . ?
C2 C3 C4 102.95(11) . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
C4 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
O2 C4 C5 108.75(12) . . ?
O2 C4 C3 104.40(12) . . ?
C5 C4 C3 109.77(14) . . ?
O2 C4 H4 111.2 . . ?
C5 C4 H4 111.2 . . ?
C3 C4 H4 111.2 . . ?
C6 C5 C4 119.04(14) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C7 118.51(15) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
O3 C7 C6 122.11(14) . . ?
O3 C7 C8 121.65(14) . . ?
C6 C7 C8 116.13(13) . . ?
O2 C8 C9 110.89(11) . . ?
O2 C8 C7 108.77(11) . . ?
C9 C8 C7 109.97(11) . . ?
O2 C8 C2 102.54(10) . . ?
C9 C8 C2 114.63(11) . . ?
C7 C8 C2 109.71(11) . . ?
C8 C9 C10 114.65(11) . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
O1 C10 C11 108.43(11) . . ?
O1 C10 C9 109.85(11) . . ?
C11 C10 C9 110.33(11) . . ?
O1 C10 H10 109.4 . . ?
C11 C10 H10 109.4 . . ?
C9 C10 H10 109.4 . . ?
C12 C11 C16 118.98(14) . . ?
C12 C11 C10 119.65(13) . . ?
C16 C11 C10 121.32(13) . . ?
C13 C12 C11 120.52(14) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.29(14) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.66(14) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.22(15) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.31(14) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?

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
C10 O1 C1 C2 68.12(15) . . . . ?
O1 C1 C2 C3 -164.80(12) . . . . ?
O1 C1 C2 C8 -52.31(15) . . . . ?
C1 C2 C3 C4 110.59(14) . . . . ?
C8 C2 C3 C4 -6.22(15) . . . . ?
C8 O2 C4 C5 -72.32(15) . . . . ?
C8 O2 C4 C3 44.80(14) . . . . ?
C2 C3 C4 O2 -22.20(16) . . . . ?
C2 C3 C4 C5 94.22(15) . . . . ?
O2 C4 C5 C6 36.8(2) . . . . ?
C3 C4 C5 C6 -76.82(18) . . . . ?
C4 C5 C6 C7 3.0(2) . . . . ?
C5 C6 C7 O3 169.64(16) . . . . ?
C5 C6 C7 C8 -6.7(2) . . . . ?
C4 O2 C8 C9 -171.37(11) . . . . ?
C4 O2 C8 C7 67.58(13) . . . . ?
C4 O2 C8 C2 -48.55(13) . . . . ?
O3 C7 C8 O2 154.11(14) . . . . ?
C6 C7 C8 O2 -29.52(16) . . . . ?
O3 C7 C8 C9 32.50(19) . . . . ?
C6 C7 C8 C9 -151.12(13) . . . . ?
O3 C7 C8 C2 -94.45(16) . . . . ?
C6 C7 C8 C2 81.92(16) . . . . ?
C1 C2 C8 O2 -83.52(13) . . . . ?
C3 C2 C8 O2 32.86(14) . . . . ?
C1 C2 C8 C9 36.74(16) . . . . ?
C3 C2 C8 C9 153.12(13) . . . . ?
C1 C2 C8 C7 161.02(12) . . . . ?
C3 C2 C8 C7 -82.60(14) . . . . ?
O2 C8 C9 C10 78.49(14) . . . . ?
C7 C8 C9 C10 -161.17(12) . . . . ?
C2 C8 C9 C10 -37.02(17) . . . . ?
C1 O1 C10 C11 175.16(11) . . . . ?
C1 O1 C10 C9 -64.21(14) . . . . ?
C8 C9 C10 O1 49.68(16) . . . . ?
C8 C9 C10 C11 169.16(12) . . . . ?
O1 C10 C11 C12 -145.82(14) . . . . ?
C9 C10 C11 C12 93.84(16) . . . . ?
O1 C10 C11 C16 36.97(18) . . . . ?
C9 C10 C11 C16 -83.37(17) . . . . ?
C16 C11 C12 C13 -0.5(2) . . . . ?
C10 C11 C12 C13 -177.79(14) . . . . ?
C11 C12 C13 C14 -0.9(2) . . . . ?
C12 C13 C14 C15 1.4(2) . . . . ?
C13 C14 C15 C16 -0.6(2) . . . . ?
C14 C15 C16 C11 -0.8(2) . . . . ?
C12 C11 C16 C15 1.3(2) . . . . ?
C10 C11 C16 C15 178.57(14) . . . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_Me_O-allyl_a
_database_code_depnum_ccdc_archive 'CCDC 2470759'
loop_
_audit_author_name
_audit_author_address
'Denver Hopkins'
;Purdue University
United States of America
;
_audit_update_record             
;
2025-07-07 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
;
(3S*,4aS*,8R*,9aR*)-3-methyl-1,3,4,8,9,9a-hexahydro-5H-4a,8-epoxycyclohepta[c]pyran-5-one
;
_chemical_formula_moiety         'C11 H14 O3'
_chemical_formula_sum            'C11 H14 O3'
_chemical_formula_weight         194.22

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      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                   8.8005(10)
_cell_length_b                   16.8892(19)
_cell_length_c                   6.6655(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.072(5)
_cell_angle_gamma                90
_cell_volume                     941.84(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9938
_cell_measurement_theta_min      5.2870
_cell_measurement_theta_max      80.1207

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.027
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.811
_shelx_estimated_absorpt_T_min   0.803
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6349
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'HELIOS multilayer Montel optics'
_diffrn_source                   'I-mu-S 3.0 microsource X-ray tube'
_diffrn_source_voltage           '50 kV'
_diffrn_source_current           '1.1 mA'
_diffrn_detector_type            
'PhotonIII_C14 charge-integrating and photon counting pixel array'
_diffrn_measurement_device       'four circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            25222
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         5.238
_diffrn_reflns_theta_max         80.463
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2057
_reflns_number_gt                1844
_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       'Apex5 v2023.9-2 (Bruker, 2023)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_computing_structure_refinement  
;  
SHELXL-2019/2 (Sheldrick, 2015a, 2019), 
SHELXLE Rev1613 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 All hydrogens were placed automatically.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0379P)²+0.3374P] 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         2057
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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 0.61134(10) 0.38531(5) 0.56364(13) 0.0278(2) Uani 1 1 d . . . . .
O2 O 0.23214(10) 0.30370(5) 0.57273(13) 0.0255(2) Uani 1 1 d . . . . .
O3 O 0.24547(11) 0.48296(6) 0.84994(15) 0.0365(2) Uani 1 1 d . . . . .
C1 C 0.47008(14) 0.38258(7) 0.38670(19) 0.0280(3) Uani 1 1 d . . . . .
H1A H 0.450384 0.327035 0.338117 0.034 Uiso 1 1 calc R U . . .
H1B H 0.488040 0.413798 0.270381 0.034 Uiso 1 1 calc R U . . .
C2 C 0.32060(14) 0.41429(7) 0.43122(17) 0.0237(2) Uani 1 1 d . . . . .
H2 H 0.320132 0.473478 0.434578 0.028 Uiso 1 1 calc R U . . .
C3 C 0.16979(15) 0.38161(7) 0.26260(19) 0.0280(3) Uani 1 1 d . . . . .
H3A H 0.093350 0.424631 0.200086 0.034 Uiso 1 1 calc R U . . .
H3B H 0.198392 0.353750 0.148675 0.034 Uiso 1 1 calc R U . . .
C4 C 0.09944(14) 0.32352(7) 0.39044(19) 0.0281(3) Uani 1 1 d . . . . .
H4 H 0.054577 0.275262 0.305850 0.034 Uiso 1 1 calc R U . . .
C5 C -0.02462(15) 0.36433(8) 0.4656(2) 0.0315(3) Uani 1 1 d . . . . .
H5 H -0.135184 0.355466 0.396851 0.038 Uiso 1 1 calc R U . . .
C6 C 0.02300(15) 0.41319(7) 0.6304(2) 0.0306(3) Uani 1 1 d . . . . .
H6 H -0.052644 0.436866 0.687123 0.037 Uiso 1 1 calc R U . . .
C7 C 0.19465(14) 0.42982(7) 0.72272(18) 0.0263(3) Uani 1 1 d . . . . .
C8 C 0.30755(13) 0.37884(6) 0.64012(18) 0.0224(2) Uani 1 1 d . . . . .
C9 C 0.46574(14) 0.36686(7) 0.81176(18) 0.0253(2) Uani 1 1 d . . . . .
H9A H 0.501441 0.418124 0.882782 0.030 Uiso 1 1 calc R U . . .
H9B H 0.449818 0.329735 0.918432 0.030 Uiso 1 1 calc R U . . .
C10 C 0.59549(14) 0.33465(7) 0.72884(19) 0.0257(3) Uani 1 1 d . . . . .
H10 H 0.565164 0.280261 0.670943 0.031 Uiso 1 1 calc R U . . .
C11 C 0.75574(15) 0.33123(8) 0.8987(2) 0.0324(3) Uani 1 1 d . . . . .
H11A H 0.837570 0.313650 0.836935 0.049 Uiso 1 1 calc R U . . .
H11B H 0.750139 0.293870 1.008704 0.049 Uiso 1 1 calc R U . . .
H11C H 0.783425 0.383951 0.960687 0.049 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 C1 1.4244(14) . ?
O1 C10 1.4351(14) . ?
O2 C8 1.4380(13) . ?
O2 C4 1.4394(14) . ?
O3 C7 1.2203(15) . ?
C1 C2 1.5321(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.5504(16) . ?
C2 C8 1.5523(15) . ?
C2 H2 1.0000 . ?
C3 C4 1.5490(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5025(18) . ?
C4 H4 1.0000 . ?
C5 C6 1.3330(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.4706(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.5398(15) . ?
C8 C9 1.5165(16) . ?
C9 C10 1.5156(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5111(16) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
C1 O1 C10 110.39(9) . . ?
C8 O2 C4 103.49(8) . . ?
O1 C1 C2 114.18(9) . . ?
O1 C1 H1A 108.7 . . ?
C2 C1 H1A 108.7 . . ?
O1 C1 H1B 108.7 . . ?
C2 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C1 C2 C3 109.18(9) . . ?
C1 C2 C8 110.23(9) . . ?
C3 C2 C8 103.18(9) . . ?
C1 C2 H2 111.3 . . ?
C3 C2 H2 111.3 . . ?
C8 C2 H2 111.3 . . ?
C4 C3 C2 103.00(9) . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3B 111.2 . . ?
C2 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
O2 C4 C5 107.97(10) . . ?
O2 C4 C3 104.69(9) . . ?
C5 C4 C3 110.41(10) . . ?
O2 C4 H4 111.2 . . ?
C5 C4 H4 111.2 . . ?
C3 C4 H4 111.2 . . ?
C6 C5 C4 118.91(11) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C7 118.86(11) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
O3 C7 C6 122.60(11) . . ?
O3 C7 C8 121.44(11) . . ?
C6 C7 C8 115.88(10) . . ?
O2 C8 C9 110.16(9) . . ?
O2 C8 C7 108.59(9) . . ?
C9 C8 C7 110.36(9) . . ?
O2 C8 C2 102.45(8) . . ?
C9 C8 C2 114.97(9) . . ?
C7 C8 C2 109.91(9) . . ?
C10 C9 C8 113.07(9) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
O1 C10 C11 107.91(9) . . ?
O1 C10 C9 109.23(9) . . ?
C11 C10 C9 111.96(10) . . ?
O1 C10 H10 109.2 . . ?
C11 C10 H10 109.2 . . ?
C9 C10 H10 109.2 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
C10 O1 C1 C2 63.87(12) . . . . ?
O1 C1 C2 C3 -159.71(9) . . . . ?
O1 C1 C2 C8 -47.03(13) . . . . ?
C1 C2 C3 C4 110.68(10) . . . . ?
C8 C2 C3 C4 -6.55(11) . . . . ?
C8 O2 C4 C5 -73.13(11) . . . . ?
C8 O2 C4 C3 44.51(11) . . . . ?
C2 C3 C4 O2 -21.96(11) . . . . ?
C2 C3 C4 C5 94.00(11) . . . . ?
O2 C4 C5 C6 36.90(15) . . . . ?
C3 C4 C5 C6 -77.00(14) . . . . ?
C4 C5 C6 C7 4.39(18) . . . . ?
C5 C6 C7 O3 167.90(12) . . . . ?
C5 C6 C7 C8 -8.88(16) . . . . ?
C4 O2 C8 C9 -171.16(9) . . . . ?
C4 O2 C8 C7 67.87(10) . . . . ?
C4 O2 C8 C2 -48.37(10) . . . . ?
O3 C7 C8 O2 155.18(11) . . . . ?
C6 C7 C8 O2 -28.00(13) . . . . ?
O3 C7 C8 C9 34.34(15) . . . . ?
C6 C7 C8 C9 -148.84(10) . . . . ?
O3 C7 C8 C2 -93.49(13) . . . . ?
C6 C7 C8 C2 83.33(12) . . . . ?
C1 C2 C8 O2 -83.56(10) . . . . ?
C3 C2 C8 O2 32.93(11) . . . . ?
C1 C2 C8 C9 35.92(13) . . . . ?
C3 C2 C8 C9 152.41(9) . . . . ?
C1 C2 C8 C7 161.15(9) . . . . ?
C3 C2 C8 C7 -82.36(11) . . . . ?
O2 C8 C9 C10 73.94(12) . . . . ?
C7 C8 C9 C10 -166.16(9) . . . . ?
C2 C8 C9 C10 -41.16(13) . . . . ?
C1 O1 C10 C11 172.34(9) . . . . ?
C1 O1 C10 C9 -65.72(12) . . . . ?
C8 C9 C10 O1 54.66(12) . . . . ?
C8 C9 C10 C11 174.12(10) . . . . ?

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_DRH_05_156_0m_4
_database_code_depnum_ccdc_archive 'CCDC 2411050'
loop_
_audit_author_name
_audit_author_address
'Denver Hopkins'
;Purdue University
United States of America
;
_audit_update_record             
;
2024-12-17 deposited with the CCDC.	2025-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        
;
2-phenyl-1,2,3,7,8,8a-hexahydro-4H-3a,7-epoxyazulen-4-one
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 O2'
_chemical_formula_sum            'C16 H16 O2'
_chemical_formula_weight         240.29

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      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                   10.2958(11)
_cell_length_b                   10.1721(10)
_cell_length_c                   12.0183(16)
_cell_angle_alpha                90
_cell_angle_beta                 97.742(9)
_cell_angle_gamma                90
_cell_volume                     1247.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6502
_cell_measurement_theta_min      6.1437
_cell_measurement_theta_max      79.0292

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   0.626708
_exptl_transmission_factor_max   0.754299
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.660
_shelx_estimated_absorpt_T_min   0.863
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
TWINABS 2012/1: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.
(2015). J. Appl. Cryst. 48 3-10.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'HELIOS multilayer Montel optics'
_diffrn_source                   'I-mu-S 3.0 microsource X-ray tube'
_diffrn_source_voltage           '50 kV'
_diffrn_source_current           '1.1 mA'
_diffrn_detector_type            
'PhotonIII_C14 charge-integrating and photon counting pixel array'
_diffrn_measurement_device       'four circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            2672
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         5.720
_diffrn_reflns_theta_max         80.097
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2672
_reflns_number_gt                2081
_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       'Apex5 v2023.9-2 (Bruker, 2023)'
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2020)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2020)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015b)'
_computing_structure_refinement  
;  
SHELXL-2019/2 (Sheldrick, 2015a, 2019), 
SHELXLE Rev1613 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin. Hydrogens were placed automatically.
The crystal under investigation was found to be non-merohedrally 
twinned. The orientation matrices for the two components were 
identified with cell_now, with the two components 
being related by a 180 degree rotation around the real
C axis. The two components were integrated using Saint and 
corrected for absorption using twinabs, resulting in the following statistics

     9683 data (   1927 unique ) involve domain  1 only,  mean I/sigma  10.9
     9638 data (   1920 unique ) involve domain  2 only,  mean I/sigma   6.5
     5061 data (   1313 unique ) involve   2 domains,  mean I/sigma  14.4

The structure was solved using dual methods using 2833 corrected 
reflections written to the hklf 4 type file. The structure was 
refined using the hklf 4 routine based on these reflections.

The Rint value given is for all reflections and is based on 
agreement between observed single and composite intensities 
and those calculated from refined unique intensities and twin 
fractions (TWINABS (Sheldrick, 2012)). 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0725P)²+0.7022P] 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         2672
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1657
_refine_ls_wR_factor_gt          0.1518
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_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 0.18119(17) 0.91879(15) 0.73371(15) 0.0447(4) Uani 1 1 d . . . . .
O2 O 0.33682(13) 0.61708(14) 0.79739(12) 0.0312(3) Uani 1 1 d . . . . .
C1 C 0.4277(2) 0.7950(2) 0.69643(17) 0.0312(4) Uani 1 1 d . . . . .
H1A H 0.504081 0.765184 0.749375 0.037 Uiso 1 1 calc R U . . .
H1B H 0.415917 0.890618 0.706914 0.037 Uiso 1 1 calc R U . . .
C2 C 0.30445(19) 0.72023(18) 0.71661(16) 0.0271(4) Uani 1 1 d . . . . .
C3 C 0.19430(19) 0.8019(2) 0.75409(16) 0.0299(4) Uani 1 1 d . . . . .
C4 C 0.0983(2) 0.7267(2) 0.80830(18) 0.0357(5) Uani 1 1 d . . . . .
H4 H 0.028822 0.770435 0.837604 0.043 Uiso 1 1 calc R U . . .
C5 C 0.1099(2) 0.5964(2) 0.81591(18) 0.0362(5) Uani 1 1 d . . . . .
H5 H 0.044796 0.545889 0.845340 0.043 Uiso 1 1 calc R U . . .
C6 C 0.2263(2) 0.5301(2) 0.77770(19) 0.0341(5) Uani 1 1 d . . . . .
H6 H 0.245230 0.444152 0.817014 0.041 Uiso 1 1 calc R U . . .
C7 C 0.2051(2) 0.5119(2) 0.64898(19) 0.0363(5) Uani 1 1 d . . . . .
H7A H 0.256137 0.436456 0.626114 0.044 Uiso 1 1 calc R U . . .
H7B H 0.111237 0.498606 0.620549 0.044 Uiso 1 1 calc R U . . .
C8 C 0.25560(19) 0.6425(2) 0.60661(16) 0.0295(4) Uani 1 1 d . . . . .
H8 H 0.184443 0.691105 0.558659 0.035 Uiso 1 1 calc R U . . .
C9 C 0.37962(19) 0.6331(2) 0.54970(17) 0.0313(4) Uani 1 1 d . . . . .
H9A H 0.435963 0.559739 0.581635 0.038 Uiso 1 1 calc R U . . .
H9B H 0.357022 0.618948 0.467878 0.038 Uiso 1 1 calc R U . . .
C10 C 0.4490(2) 0.7650(2) 0.57348(17) 0.0309(4) Uani 1 1 d . . . . .
H10 H 0.401074 0.832853 0.523559 0.037 Uiso 1 1 calc R U . . .
C11 C 0.5917(2) 0.76624(19) 0.55465(16) 0.0293(4) Uani 1 1 d . . . . .
C12 C 0.6335(2) 0.8493(2) 0.47519(17) 0.0337(5) Uani 1 1 d . . . . .
H12 H 0.571586 0.903204 0.430556 0.040 Uiso 1 1 calc R U . . .
C13 C 0.7650(2) 0.8548(2) 0.45999(19) 0.0403(5) Uani 1 1 d . . . . .
H13 H 0.792622 0.912237 0.405462 0.048 Uiso 1 1 calc R U . . .
C14 C 0.8556(2) 0.7758(2) 0.5249(2) 0.0401(5) Uani 1 1 d . . . . .
H14 H 0.945820 0.780354 0.516057 0.048 Uiso 1 1 calc R U . . .
C15 C 0.8139(2) 0.6907(2) 0.6023(2) 0.0383(5) Uani 1 1 d . . . . .
H15 H 0.875326 0.634868 0.645394 0.046 Uiso 1 1 calc R U . . .
C16 C 0.6833(2) 0.6863(2) 0.61743(18) 0.0341(5) Uani 1 1 d . . . . .
H16 H 0.655932 0.627927 0.671411 0.041 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 C3 1.218(3) . ?
O2 C6 1.436(2) . ?
O2 C2 1.438(2) . ?
C1 C2 1.527(3) . ?
C1 C10 1.553(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.522(3) . ?
C2 C8 1.564(3) . ?
C3 C4 1.469(3) . ?
C4 C5 1.332(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.501(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.544(3) . ?
C6 H6 1.0000 . ?
C7 C8 1.537(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.531(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.529(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.516(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.387(3) . ?
C11 C16 1.389(3) . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(3) . ?
C15 H15 0.9500 . ?
C16 H16 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
C6 O2 C2 103.42(14) . . ?
C2 C1 C10 106.23(16) . . ?
C2 C1 H1A 110.5 . . ?
C10 C1 H1A 110.5 . . ?
C2 C1 H1B 110.5 . . ?
C10 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
O2 C2 C3 108.21(16) . . ?
O2 C2 C1 110.41(16) . . ?
C3 C2 C1 116.34(16) . . ?
O2 C2 C8 102.74(15) . . ?
C3 C2 C8 111.01(16) . . ?
C1 C2 C8 107.29(16) . . ?
O1 C3 C4 122.31(19) . . ?
O1 C3 C2 122.68(18) . . ?
C4 C3 C2 114.81(17) . . ?
C5 C4 C3 119.27(19) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 119.61(19) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
O2 C6 C5 108.67(17) . . ?
O2 C6 C7 103.93(16) . . ?
C5 C6 C7 110.44(17) . . ?
O2 C6 H6 111.2 . . ?
C5 C6 H6 111.2 . . ?
C7 C6 H6 111.2 . . ?
C8 C7 C6 102.72(16) . . ?
C8 C7 H7A 111.2 . . ?
C6 C7 H7A 111.2 . . ?
C8 C7 H7B 111.2 . . ?
C6 C7 H7B 111.2 . . ?
H7A C7 H7B 109.1 . . ?
C9 C8 C7 115.71(17) . . ?
C9 C8 C2 102.51(15) . . ?
C7 C8 C2 103.97(16) . . ?
C9 C8 H8 111.3 . . ?
C7 C8 H8 111.3 . . ?
C2 C8 H8 111.3 . . ?
C10 C9 C8 104.97(16) . . ?
C10 C9 H9A 110.8 . . ?
C8 C9 H9A 110.8 . . ?
C10 C9 H9B 110.8 . . ?
C8 C9 H9B 110.8 . . ?
H9A C9 H9B 108.8 . . ?
C11 C10 C9 114.64(17) . . ?
C11 C10 C1 113.80(16) . . ?
C9 C10 C1 103.23(16) . . ?
C11 C10 H10 108.3 . . ?
C9 C10 H10 108.3 . . ?
C1 C10 H10 108.3 . . ?
C12 C11 C16 118.64(19) . . ?
C12 C11 C10 120.34(18) . . ?
C16 C11 C10 121.01(18) . . ?
C11 C12 C13 120.9(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C11 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 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
C6 O2 C2 C3 71.51(18) . . . . ?
C6 O2 C2 C1 -160.11(16) . . . . ?
C6 O2 C2 C8 -45.95(18) . . . . ?
C10 C1 C2 O2 113.01(17) . . . . ?
C10 C1 C2 C3 -123.18(18) . . . . ?
C10 C1 C2 C8 1.8(2) . . . . ?
O2 C2 C3 O1 149.49(19) . . . . ?
C1 C2 C3 O1 24.6(3) . . . . ?
C8 C2 C3 O1 -98.5(2) . . . . ?
O2 C2 C3 C4 -35.5(2) . . . . ?
C1 C2 C3 C4 -160.45(18) . . . . ?
C8 C2 C3 C4 76.5(2) . . . . ?
O1 C3 C4 C5 171.9(2) . . . . ?
C2 C3 C4 C5 -3.1(3) . . . . ?
C3 C4 C5 C6 5.0(3) . . . . ?
C2 O2 C6 C5 -69.80(19) . . . . ?
C2 O2 C6 C7 47.82(19) . . . . ?
C4 C5 C6 O2 32.0(3) . . . . ?
C4 C5 C6 C7 -81.4(2) . . . . ?
O2 C6 C7 C8 -29.2(2) . . . . ?
C5 C6 C7 C8 87.2(2) . . . . ?
C6 C7 C8 C9 113.16(19) . . . . ?
C6 C7 C8 C2 1.6(2) . . . . ?
O2 C2 C8 C9 -94.63(17) . . . . ?
C3 C2 C8 C9 149.90(16) . . . . ?
C1 C2 C8 C9 21.8(2) . . . . ?
O2 C2 C8 C7 26.24(19) . . . . ?
C3 C2 C8 C7 -89.23(19) . . . . ?
C1 C2 C8 C7 142.65(17) . . . . ?
C7 C8 C9 C10 -150.06(17) . . . . ?
C2 C8 C9 C10 -37.65(19) . . . . ?
C8 C9 C10 C11 163.48(16) . . . . ?
C8 C9 C10 C1 39.2(2) . . . . ?
C2 C1 C10 C11 -149.63(17) . . . . ?
C2 C1 C10 C9 -24.8(2) . . . . ?
C9 C10 C11 C12 118.7(2) . . . . ?
C1 C10 C11 C12 -122.8(2) . . . . ?
C9 C10 C11 C16 -62.4(3) . . . . ?
C1 C10 C11 C16 56.1(3) . . . . ?
C16 C11 C12 C13 -1.3(3) . . . . ?
C10 C11 C12 C13 177.67(19) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 1.3(3) . . . . ?
C13 C14 C15 C16 -1.7(3) . . . . ?
C14 C15 C16 C11 0.6(3) . . . . ?
C12 C11 C16 C15 0.9(3) . . . . ?
C10 C11 C16 C15 -178.04(19) . . . . ?

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.058

