# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_150914a
_database_code_depnum_ccdc_archive 'CCDC 1847632'
_audit_update_record             
;
2018-06-06 deposited with the CCDC.
2018-12-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 O2'
_chemical_formula_weight         276.32

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           Orthorhombic
_symmetry_space_group_name_H-M   Fdd2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   23.630(2)
_cell_length_b                   42.848(4)
_cell_length_c                   5.8546(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5927.9(9)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6044
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      26.29

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2336
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9828
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12522
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -54
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         27.54
_reflns_number_total             3374
_reflns_number_gt                2879
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0496P)²+1.4342P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(12)
_refine_ls_number_reflns         3374
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0922
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.26350(9) -0.09024(5) 0.6122(4) 0.0809(6) Uani 1 1 d . . .
H1A H 0.2666 -0.1051 0.4898 0.121 Uiso 1 1 calc R . .
H1B H 0.2446 -0.0998 0.7395 0.121 Uiso 1 1 calc R . .
H1C H 0.3006 -0.0837 0.6580 0.121 Uiso 1 1 calc R . .
O1 O 0.13013(4) 0.04143(2) 0.42783(19) 0.0507(3) Uani 1 1 d . . .
C2 C 0.23008(6) -0.06240(4) 0.5329(3) 0.0553(4) Uani 1 1 d . . .
O2 O 0.06356(7) 0.11341(3) 0.3241(3) 0.0938(5) Uani 1 1 d . . .
C3 C 0.22478(7) -0.03608(4) 0.6677(3) 0.0582(4) Uani 1 1 d . . .
H3 H 0.2438 -0.0353 0.8067 0.070 Uiso 1 1 calc R . .
C19 C 0.12500(10) 0.09968(4) 0.6269(4) 0.0795(6) Uani 1 1 d . . .
H19A H 0.1217 0.1214 0.6652 0.119 Uiso 1 1 calc R . .
H19B H 0.1639 0.0947 0.5975 0.119 Uiso 1 1 calc R . .
H19C H 0.1114 0.0872 0.7518 0.119 Uiso 1 1 calc R . .
C4 C 0.19217(7) -0.01100(4) 0.6022(3) 0.0537(4) Uani 1 1 d . . .
H4 H 0.1892 0.0064 0.6968 0.064 Uiso 1 1 calc R . .
C5 C 0.16359(6) -0.01163(3) 0.3934(3) 0.0463(3) Uani 1 1 d . . .
C6 C 0.17010(7) -0.03776(4) 0.2559(3) 0.0524(4) Uani 1 1 d . . .
H6 H 0.1520 -0.0385 0.1150 0.063 Uiso 1 1 calc R . .
C7 C 0.20287(7) -0.06270(4) 0.3240(3) 0.0569(4) Uani 1 1 d . . .
H7 H 0.2067 -0.0799 0.2283 0.068 Uiso 1 1 calc R . .
C8 C 0.12696(6) 0.01359(3) 0.3173(3) 0.0479(3) Uani 1 1 d . . .
C9 C 0.08681(6) 0.01522(3) 0.1520(3) 0.0498(4) Uani 1 1 d . . .
H9 H 0.0766 -0.0008 0.0532 0.060 Uiso 1 1 calc R . .
C10 C 0.06306(6) 0.04571(3) 0.1562(3) 0.0469(3) Uani 1 1 d . . .
C11 C 0.09127(7) 0.06120(3) 0.3276(3) 0.0500(4) Uani 1 1 d . . .
C12 C 0.01632(6) 0.05538(3) 0.0047(3) 0.0472(3) Uani 1 1 d . . .
C13 C 0.01099(7) 0.04106(4) -0.2066(3) 0.0543(4) Uani 1 1 d . . .
H13 H 0.0384 0.0269 -0.2539 0.065 Uiso 1 1 calc R . .
C14 C -0.03447(8) 0.04757(4) -0.3486(3) 0.0638(4) Uani 1 1 d . . .
H14 H -0.0374 0.0377 -0.4897 0.077 Uiso 1 1 calc R . .
C15 C -0.07501(8) 0.06844(4) -0.2814(4) 0.0654(5) Uani 1 1 d . . .
H15 H -0.1055 0.0728 -0.3764 0.078 Uiso 1 1 calc R . .
C16 C -0.07040(7) 0.08298(4) -0.0723(4) 0.0626(5) Uani 1 1 d . . .
H16 H -0.0980 0.0972 -0.0267 0.075 Uiso 1 1 calc R . .
C17 C -0.02518(7) 0.07668(4) 0.0705(3) 0.0556(4) Uani 1 1 d . . .
H17 H -0.0225 0.0867 0.2110 0.067 Uiso 1 1 calc R . .
C18 C 0.09062(7) 0.09299(4) 0.4190(4) 0.0625(5) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.504(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
O1 C8 1.3592(17) . ?
O1 C11 1.3803(19) . ?
C2 C7 1.382(3) . ?
C2 C3 1.382(2) . ?
O2 C18 1.218(2) . ?
C3 C4 1.377(2) . ?
C3 H3 0.9300 . ?
C19 C18 1.491(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C4 C5 1.397(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(2) . ?
C5 C8 1.454(2) . ?
C6 C7 1.379(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.357(2) . ?
C9 C10 1.422(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(2) . ?
C10 C12 1.476(2) . ?
C11 C18 1.464(2) . ?
C12 C13 1.387(2) . ?
C12 C17 1.394(2) . ?
C13 C14 1.387(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(2) . ?
C16 H16 0.9300 . ?
C17 H17 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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C8 O1 C11 107.43(11) . . ?
C7 C2 C3 118.09(15) . . ?
C7 C2 C1 120.68(17) . . ?
C3 C2 C1 121.21(17) . . ?
C4 C3 C2 121.90(16) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C4 C5 119.96(15) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 118.00(14) . . ?
C6 C5 C8 119.21(14) . . ?
C4 C5 C8 122.78(14) . . ?
C7 C6 C5 121.35(16) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C2 120.67(16) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
C9 C8 O1 109.44(13) . . ?
C9 C8 C5 132.28(14) . . ?
O1 C8 C5 118.26(13) . . ?
C8 C9 C10 108.12(13) . . ?
C8 C9 H9 125.9 . . ?
C10 C9 H9 125.9 . . ?
C11 C10 C9 105.34(14) . . ?
C11 C10 C12 131.72(14) . . ?
C9 C10 C12 122.89(14) . . ?
C10 C11 O1 109.67(12) . . ?
C10 C11 C18 135.31(15) . . ?
O1 C11 C18 114.99(14) . . ?
C13 C12 C17 118.17(15) . . ?
C13 C12 C10 118.68(15) . . ?
C17 C12 C10 122.99(15) . . ?
C12 C13 C14 121.09(16) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 120.08(19) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.72(17) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 120.64(17) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 120.29(18) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?
O2 C18 C11 120.49(17) . . ?
O2 C18 C19 121.35(16) . . ?
C11 C18 C19 118.15(16) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.127
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.032
####################################################################### 
# 
# 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_181009a
_database_code_depnum_ccdc_archive 'CCDC 1873152'
_audit_update_record             
;
2018-10-14 deposited with the CCDC.
2018-12-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 O3'
_chemical_formula_weight         306.34

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                   10.476(11)
_cell_length_b                   15.249(18)
_cell_length_c                   11.317(13)
_cell_angle_alpha                90
_cell_angle_beta                 116.28(3)
_cell_angle_gamma                90
_cell_volume                     1621(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9239
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      27.39

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23907
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.442
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_full        24.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2843
_reflns_number_gt                2226
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.0999P)²+1.1839P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2843
_refine_ls_number_parameters     222
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0682
_refine_ls_wR_factor_ref         0.2064
_refine_ls_wR_factor_gt          0.1841
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.067
_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 0.1868(3) 0.48579(18) 0.2567(3) 0.0621(8) Uani 1 1 d . . . . .
H1 H 0.184431 0.487219 0.173567 0.074 Uiso 1 1 calc R U . . .
C2 C 0.1150(3) 0.5450(2) 0.2953(4) 0.0787(10) Uani 1 1 d . . . . .
H2 H 0.061678 0.588656 0.236880 0.094 Uiso 1 1 calc R U . . .
C3 C 0.1198(3) 0.5414(2) 0.4271(4) 0.0810(11) Uani 1 1 d . . . . .
H3 H 0.070003 0.583843 0.448668 0.097 Uiso 1 1 calc R U . . .
C4 C 0.1938(3) 0.4789(2) 0.5206(4) 0.0747(10) Uani 1 1 d . . . . .
H4 H 0.194465 0.477557 0.603072 0.090 Uiso 1 1 calc R U . . .
C5 C 0.2655(3) 0.4195(2) 0.4835(3) 0.0601(7) Uani 1 1 d . . . . .
H5 H 0.316787 0.375521 0.542282 0.072 Uiso 1 1 calc R U . . .
C6 C 0.2648(2) 0.42232(16) 0.3520(3) 0.0457(6) Uani 1 1 d . . . . .
C7 C 0.3402(2) 0.35911(15) 0.30499(18) 0.0425(6) Uani 1 1 d D . . . .
C8 C 0.5157(3) 0.4441(2) 0.2014(4) 0.0794(10) Uani 1 1 d . . . . .
H8A H 0.494666 0.468699 0.268894 0.119 Uiso 1 1 calc R U . . .
H8B H 0.541785 0.490177 0.158511 0.119 Uiso 1 1 calc R U . . .
H8C H 0.593177 0.403374 0.240310 0.119 Uiso 1 1 calc R U . . .
C9 C 0.3915(3) 0.39900(18) 0.1059(3) 0.0545(7) Uani 1 1 d . . . . .
C10 C 0.3139(2) 0.35933(15) 0.16204(17) 0.0470(6) Uani 1 1 d D . . . .
C11 C 0.1940(2) 0.31175(17) 0.0544(2) 0.0548(7) Uani 1 1 d D . . . .
C12 C 0.108(2) 0.2606(12) 0.098(2) 0.085(6) Uani 0.54(5) 1 d D . P A 1
H12A H 0.024319 0.293144 0.084921 0.128 Uiso 0.54(5) 1 calc R U P A 1
H12B H 0.161692 0.247593 0.190444 0.128 Uiso 0.54(5) 1 calc R U P A 1
H12C H 0.080907 0.206855 0.049259 0.128 Uiso 0.54(5) 1 calc R U P A 1
C12' C 0.119(2) 0.2620(11) 0.115(2) 0.074(6) Uani 0.46(5) 1 d D . P A 2
H12D H 0.028184 0.243060 0.047337 0.111 Uiso 0.46(5) 1 calc R U P A 2
H12E H 0.104026 0.298511 0.176624 0.111 Uiso 0.46(5) 1 calc R U P A 2
H12F H 0.174194 0.211720 0.159338 0.111 Uiso 0.46(5) 1 calc R U P A 2
C13 C 0.4330(2) 0.30773(17) 0.4047(2) 0.0473(6) Uani 1 1 d . . . . .
H13 H 0.445820 0.315790 0.490711 0.057 Uiso 1 1 calc R U . . .
C14 C 0.5108(3) 0.24058(17) 0.3740(2) 0.0469(6) Uani 1 1 d . . . . .
C15 C 0.6361(2) 0.21066(16) 0.4947(2) 0.0451(6) Uani 1 1 d . . . . .
C16 C 0.6980(3) 0.1373(2) 0.4758(3) 0.0627(8) Uani 1 1 d . . . . .
H16 H 0.665418 0.110416 0.393807 0.075 Uiso 1 1 calc R U . . .
C17 C 0.8111(3) 0.1056(2) 0.5848(3) 0.0732(9) Uani 1 1 d . . . . .
H17 H 0.854668 0.054376 0.576349 0.088 Uiso 1 1 calc R U . . .
C18 C 0.8667(3) 0.1474(2) 0.7123(3) 0.0709(9) Uani 1 1 d . . . . .
H18 H 0.945244 0.122990 0.782209 0.085 Uiso 1 1 calc R U . . .
C19 C 0.8080(3) 0.2203(3) 0.7324(3) 0.0814(11) Uani 1 1 d . . . . .
H19 H 0.843140 0.247717 0.814161 0.098 Uiso 1 1 calc R U . . .
C20 C 0.6926(3) 0.2518(2) 0.6245(3) 0.0675(9) Uani 1 1 d . . . . .
H20 H 0.647923 0.301999 0.634493 0.081 Uiso 1 1 calc R U . . .
O1 O 0.3645(2) 0.39929(16) -0.0267(2) 0.0731(7) Uani 1 1 d . . . . .
H1A H 0.293469 0.369791 -0.069648 0.110 Uiso 1 1 calc R U . . .
O2 O 0.1645(2) 0.31395(17) -0.07454(19) 0.0739(7) Uani 1 1 d . . . . .
O3 O 0.4750(2) 0.20834(14) 0.25708(19) 0.0656(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.365(4) . ?
C1 C6 1.410(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.470(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.357(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.485(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.486(3) . ?
C7 C13 1.364(3) . ?
C7 C10 1.516(2) . ?
C8 C9 1.445(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.375(3) . ?
C9 O1 1.398(4) . ?
C10 C11 1.4941(15) . ?
C11 O2 1.351(4) . ?
C11 C12 1.437(10) . ?
C11 C12' 1.464(11) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12' H12D 0.9600 . ?
C12' H12E 0.9600 . ?
C12' H12F 0.9600 . ?
C13 C14 1.444(4) . ?
C13 H13 0.9300 . ?
C14 O3 1.302(3) . ?
C14 C15 1.486(4) . ?
C15 C16 1.356(4) . ?
C15 C20 1.460(4) . ?
C16 C17 1.366(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.444(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.338(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.369(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
O1 H1A 0.8200 . ?

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 C1 C6 115.1(3) . . ?
C2 C1 H1 122.5 . . ?
C6 C1 H1 122.5 . . ?
C1 C2 C3 121.6(3) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 124.1(3) . . ?
C4 C3 H3 118.0 . . ?
C2 C3 H3 118.0 . . ?
C5 C4 C3 115.0(3) . . ?
C5 C4 H4 122.5 . . ?
C3 C4 H4 122.5 . . ?
C4 C5 C6 122.2(3) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C5 122.0(2) . . ?
C1 C6 C7 113.0(2) . . ?
C5 C6 C7 124.9(2) . . ?
C13 C7 C6 111.9(2) . . ?
C13 C7 C10 127.6(2) . . ?
C6 C7 C10 120.4(2) . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 O1 128.1(2) . . ?
C10 C9 C8 112.6(3) . . ?
O1 C9 C8 119.2(3) . . ?
C9 C10 C11 107.0(2) . . ?
C9 C10 C7 129.0(2) . . ?
C11 C10 C7 124.0(2) . . ?
O2 C11 C12 120.6(9) . . ?
O2 C11 C12' 127.1(9) . . ?
O2 C11 C10 125.2(2) . . ?
C12 C11 C10 114.2(9) . . ?
C12' C11 C10 107.7(9) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C12' H12D 109.5 . . ?
C11 C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C11 C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
C7 C13 C14 118.7(2) . . ?
C7 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
O3 C14 C13 125.0(2) . . ?
O3 C14 C15 123.9(2) . . ?
C13 C14 C15 111.1(2) . . ?
C16 C15 C20 120.3(2) . . ?
C16 C15 C14 113.4(2) . . ?
C20 C15 C14 126.3(2) . . ?
C15 C16 C17 115.7(3) . . ?
C15 C16 H16 122.1 . . ?
C17 C16 H16 122.1 . . ?
C16 C17 C18 123.4(3) . . ?
C16 C17 H17 118.3 . . ?
C18 C17 H17 118.3 . . ?
C19 C18 C17 121.7(3) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 115.5(3) . . ?
C18 C19 H19 122.3 . . ?
C20 C19 H19 122.3 . . ?
C19 C20 C15 123.4(3) . . ?
C19 C20 H20 118.3 . . ?
C15 C20 H20 118.3 . . ?
C9 O1 H1A 109.5 . . ?

_refine_diff_density_max         0.799
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.046



