# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_jle296c
_database_code_depnum_ccdc_archive 'CCDC 2192929'
loop_
_audit_author_name
_audit_author_address
'Jorg-M. Neudorfl'
;Department Chemie, Organische Chemie, Universitaet zu Koeln
Germany
;
_audit_update_record             
;
2022-07-27 deposited with the CCDC.	2022-10-28 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         'C19 H18 O2'
_chemical_formula_sum            'C19 H18 O2'
_chemical_formula_weight         278.33

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                   13.1123(4)
_cell_length_b                   5.8889(2)
_cell_length_c                   19.6384(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.1592(11)
_cell_angle_gamma                90
_cell_volume                     1470.35(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9876
_cell_measurement_theta_min      3.48
_cell_measurement_theta_max      72.06

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.633
_shelx_estimated_absorpt_T_min   0.786
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5950
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17310
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.476
_diffrn_reflns_theta_max         72.116
_diffrn_reflns_theta_full        67.679
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2898
_reflns_number_gt                2561
_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 APEX 3'
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_reduction        'Bruker APEX 3'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'
_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)+(0.0295P)²+0.7578P] 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         2898
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0860
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.80364(7) 0.69235(16) 0.88513(4) 0.0214(2) Uani 1 1 d . . . . .
C1 C 0.91599(9) 0.7057(2) 0.89420(6) 0.0199(3) Uani 1 1 d . . . . .
H1A H 0.9496 0.7830 0.9388 0.024 Uiso 1 1 calc R U . . .
H1AB H 0.9334 0.7898 0.8549 0.024 Uiso 1 1 calc R U . . .
C2 C 0.95247(9) 0.4599(2) 0.89527(6) 0.0190(3) Uani 1 1 d . . . . .
H2A H 0.9595 0.3903 0.9421 0.023 Uiso 1 1 calc R U . . .
H2AB H 1.0204 0.4479 0.8820 0.023 Uiso 1 1 calc R U . . .
O2 O 0.87042(7) 0.03270(15) 0.72862(5) 0.0198(2) Uani 1 1 d . . . . .
C3 C 0.86353(9) 0.3506(2) 0.84026(6) 0.0157(2) Uani 1 1 d . . . . .
H3 H 0.8522 0.1855 0.8478 0.019 Uiso 1 1 calc R U . . .
C4 C 0.85698(9) 0.4183(2) 0.76321(6) 0.0135(2) Uani 1 1 d . . . . .
H4 H 0.9154 0.5251 0.7611 0.016 Uiso 1 1 calc R U . . .
C6 C 0.76721(9) 0.5053(2) 0.83975(6) 0.0168(2) Uani 1 1 d . . . . .
H6 H 0.7067 0.4228 0.8510 0.020 Uiso 1 1 calc R U . . .
C5 C 0.75205(9) 0.5558(2) 0.76000(6) 0.0143(2) Uani 1 1 d . . . . .
H5 H 0.7614 0.7210 0.7515 0.017 Uiso 1 1 calc R U . . .
C8 C 0.61227(9) 0.2522(2) 0.72291(7) 0.0187(3) Uani 1 1 d . . . . .
H8 H 0.6481 0.1606 0.7611 0.022 Uiso 1 1 calc R U . . .
C7 C 0.65305(9) 0.4650(2) 0.71202(6) 0.0146(2) Uani 1 1 d . . . . .
C9 C 0.51984(10) 0.1735(2) 0.67839(8) 0.0248(3) Uani 1 1 d . . . . .
H9 H 0.4926 0.0294 0.6866 0.030 Uiso 1 1 calc R U . . .
C10 C 0.46725(10) 0.3043(3) 0.62212(8) 0.0300(3) Uani 1 1 d . . . . .
H10 H 0.4040 0.2504 0.5918 0.036 Uiso 1 1 calc R U . . .
C11 C 0.50750(10) 0.5147(3) 0.61024(8) 0.0290(3) Uani 1 1 d . . . . .
H11 H 0.4722 0.6045 0.5714 0.035 Uiso 1 1 calc R U . . .
C12 C 0.59936(9) 0.5938(2) 0.65515(7) 0.0199(3) Uani 1 1 d . . . . .
H12 H 0.6261 0.7384 0.6469 0.024 Uiso 1 1 calc R U . . .
C13 C 0.85153(8) 0.2302(2) 0.71065(6) 0.0144(2) Uani 1 1 d . . . . .
C14 C 0.82182(9) 0.2923(2) 0.63456(6) 0.0142(2) Uani 1 1 d . . . . .
C15 C 0.77242(9) 0.1306(2) 0.58602(6) 0.0184(3) Uani 1 1 d . . . . .
H15 H 0.7573 -0.0152 0.6017 0.022 Uiso 1 1 calc R U . . .
C16 C 0.74507(10) 0.1807(2) 0.51478(7) 0.0224(3) Uani 1 1 d . . . . .
H16 H 0.7104 0.0702 0.4819 0.027 Uiso 1 1 calc R U . . .
C17 C 0.76855(10) 0.3934(2) 0.49163(6) 0.0199(3) Uani 1 1 d . . . . .
H17 H 0.7511 0.4272 0.4428 0.024 Uiso 1 1 calc R U . . .
C18 C 0.81729(10) 0.5553(2) 0.53964(6) 0.0198(3) Uani 1 1 d . . . . .
H18 H 0.8333 0.7002 0.5237 0.024 Uiso 1 1 calc R U . . .
C19 C 0.84303(9) 0.5071(2) 0.61122(6) 0.0176(2) Uani 1 1 d . . . . .
H19 H 0.8750 0.6201 0.6441 0.021 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 C6 1.4240(15) . ?
O1 C1 1.4421(15) . ?
C1 C2 1.5230(18) . ?
C1 H1A 0.9900 . ?
C1 H1AB 0.9900 . ?
C2 C3 1.5249(16) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
O2 C13 1.2228(15) . ?
C3 C4 1.5468(15) . ?
C3 C6 1.5553(16) . ?
C3 H3 1.0000 . ?
C4 C13 1.5036(16) . ?
C4 C5 1.5846(15) . ?
C4 H4 1.0000 . ?
C6 C5 1.5584(16) . ?
C6 H6 1.0000 . ?
C5 C7 1.5034(15) . ?
C5 H5 1.0000 . ?
C8 C9 1.3890(18) . ?
C8 C7 1.3995(17) . ?
C8 H8 0.9500 . ?
C7 C12 1.3904(17) . ?
C9 C10 1.385(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.3877(18) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.4947(16) . ?
C14 C15 1.3903(17) . ?
C14 C19 1.3963(17) . ?
C15 C16 1.3883(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.3922(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.3829(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.3923(17) . ?
C18 H18 0.9500 . ?
C19 H19 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 O1 C1 107.20(9) . . ?
O1 C1 C2 104.94(10) . . ?
O1 C1 H1A 110.8 . . ?
C2 C1 H1A 110.8 . . ?
O1 C1 H1AB 110.8 . . ?
C2 C1 H1AB 110.8 . . ?
H1A C1 H1AB 108.8 . . ?
C1 C2 C3 102.02(9) . . ?
C1 C2 H2A 111.4 . . ?
C3 C2 H2A 111.4 . . ?
C1 C2 H2AB 111.4 . . ?
C3 C2 H2AB 111.4 . . ?
H2A C2 H2AB 109.2 . . ?
C2 C3 C4 115.73(10) . . ?
C2 C3 C6 103.67(10) . . ?
C4 C3 C6 89.55(8) . . ?
C2 C3 H3 114.9 . . ?
C4 C3 H3 114.9 . . ?
C6 C3 H3 114.9 . . ?
C13 C4 C3 117.62(10) . . ?
C13 C4 C5 117.02(9) . . ?
C3 C4 C5 90.59(8) . . ?
C13 C4 H4 110.1 . . ?
C3 C4 H4 110.1 . . ?
C5 C4 H4 110.1 . . ?
O1 C6 C3 107.55(9) . . ?
O1 C6 C5 114.96(10) . . ?
C3 C6 C5 91.26(8) . . ?
O1 C6 H6 113.6 . . ?
C3 C6 H6 113.6 . . ?
C5 C6 H6 113.6 . . ?
C7 C5 C6 116.12(10) . . ?
C7 C5 C4 116.83(9) . . ?
C6 C5 C4 88.08(8) . . ?
C7 C5 H5 111.3 . . ?
C6 C5 H5 111.3 . . ?
C4 C5 H5 111.3 . . ?
C9 C8 C7 120.63(12) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C12 C7 C8 118.28(11) . . ?
C12 C7 C5 119.96(11) . . ?
C8 C7 C5 121.76(11) . . ?
C10 C9 C8 120.29(13) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 119.67(12) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 119.92(13) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 121.19(12) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
O2 C13 C14 120.41(11) . . ?
O2 C13 C4 122.02(10) . . ?
C14 C13 C4 117.57(10) . . ?
C15 C14 C19 119.48(11) . . ?
C15 C14 C13 118.78(11) . . ?
C19 C14 C13 121.73(11) . . ?
C16 C15 C14 120.51(12) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 119.80(12) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 119.99(11) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.35(12) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 119.84(11) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?

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 O1 C1 C2 -36.01(12) . . . . ?
O1 C1 C2 C3 37.94(12) . . . . ?
C1 C2 C3 C4 70.72(12) . . . . ?
C1 C2 C3 C6 -25.50(12) . . . . ?
C2 C3 C4 C13 128.40(11) . . . . ?
C6 C3 C4 C13 -126.62(10) . . . . ?
C2 C3 C4 C5 -110.40(11) . . . . ?
C6 C3 C4 C5 -5.41(9) . . . . ?
C1 O1 C6 C3 18.97(12) . . . . ?
C1 O1 C6 C5 -80.98(12) . . . . ?
C2 C3 C6 O1 5.19(12) . . . . ?
C4 C3 C6 O1 -111.22(10) . . . . ?
C2 C3 C6 C5 121.91(9) . . . . ?
C4 C3 C6 C5 5.50(9) . . . . ?
O1 C6 C5 C7 -136.21(10) . . . . ?
C3 C6 C5 C7 113.73(10) . . . . ?
O1 C6 C5 C4 104.68(10) . . . . ?
C3 C6 C5 C4 -5.37(9) . . . . ?
C13 C4 C5 C7 8.65(15) . . . . ?
C3 C4 C5 C7 -113.06(11) . . . . ?
C13 C4 C5 C6 127.12(10) . . . . ?
C3 C4 C5 C6 5.40(9) . . . . ?
C9 C8 C7 C12 -0.76(18) . . . . ?
C9 C8 C7 C5 179.08(11) . . . . ?
C6 C5 C7 C12 141.24(11) . . . . ?
C4 C5 C7 C12 -116.86(12) . . . . ?
C6 C5 C7 C8 -38.59(15) . . . . ?
C4 C5 C7 C8 63.30(15) . . . . ?
C7 C8 C9 C10 0.6(2) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C10 C11 C12 -0.7(2) . . . . ?
C10 C11 C12 C7 0.5(2) . . . . ?
C8 C7 C12 C11 0.20(19) . . . . ?
C5 C7 C12 C11 -179.64(12) . . . . ?
C3 C4 C13 O2 -13.02(16) . . . . ?
C5 C4 C13 O2 -119.28(12) . . . . ?
C3 C4 C13 C14 166.95(9) . . . . ?
C5 C4 C13 C14 60.69(13) . . . . ?
O2 C13 C14 C15 27.61(16) . . . . ?
C4 C13 C14 C15 -152.36(11) . . . . ?
O2 C13 C14 C19 -151.94(11) . . . . ?
C4 C13 C14 C19 28.08(15) . . . . ?
C19 C14 C15 C16 0.57(18) . . . . ?
C13 C14 C15 C16 -179.00(11) . . . . ?
C14 C15 C16 C17 0.89(19) . . . . ?
C15 C16 C17 C18 -1.15(19) . . . . ?
C16 C17 C18 C19 -0.07(19) . . . . ?
C17 C18 C19 C14 1.53(19) . . . . ?
C15 C14 C19 C18 -1.77(17) . . . . ?
C13 C14 C19 C18 177.78(11) . . . . ?

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.199
_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_jel708a
_database_code_depnum_ccdc_archive 'CCDC 2192931'
loop_
_audit_author_name
_audit_author_address
'Jorg-M. Neudorfl'
;Department Chemie, Organische Chemie, Universitaet zu Koeln
Germany
;
_audit_update_record             
;
2022-07-27 deposited with the CCDC.	2022-10-28 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         'C17 H17 F3 O2'
_chemical_formula_sum            'C17 H17 F3 O2'
_chemical_formula_weight         310.30

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'
F F 0.0727 0.0534 '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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   11.6102(2)
_cell_length_b                   11.1265(2)
_cell_length_c                   12.1841(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.7470(10)
_cell_angle_gamma                90
_cell_volume                     1429.41(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9773
_cell_measurement_theta_min      3.99
_cell_measurement_theta_max      72.04

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.019
_shelx_estimated_absorpt_T_min   0.785
_shelx_estimated_absorpt_T_max   0.862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6268
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus'
_diffrn_detector_type            'Bruker PhotonIII M14'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31812
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.418
_diffrn_reflns_theta_max         72.374
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2822
_reflns_number_gt                2752
_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 APEX 3'
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_reduction        'Bruker APEX 3'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'

_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)+(0.0440P)²+1.1996P] 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         2822
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0434
_refine_ls_wR_factor_ref         0.1063
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
F1 F 0.99826(10) 0.38513(12) 0.71127(10) 0.0432(3) Uani 1 1 d . . . . .
F2 F 1.03508(12) 0.22497(11) 0.81198(17) 0.0651(5) Uani 1 1 d . . . . .
F3 F 1.05880(10) 0.39364(16) 0.90066(11) 0.0600(4) Uani 1 1 d . . . . .
O1 O 0.34561(11) 0.53455(11) 0.89633(10) 0.0275(3) Uani 1 1 d . . . . .
O2 O 0.38157(11) 0.35356(10) 0.50965(9) 0.0228(3) Uani 1 1 d . . . . .
C1 C 0.39662(13) 0.42409(13) 0.75651(12) 0.0156(3) Uani 1 1 d . . . . .
H1 H 0.441375 0.496819 0.745627 0.019 Uiso 1 1 calc R U . . .
C2 C 0.37470(13) 0.43722(14) 0.86964(13) 0.0192(3) Uani 1 1 d . . . . .
C3 C 0.38649(15) 0.32722(15) 0.94601(14) 0.0234(3) Uani 1 1 d . . . . .
H3A H 0.301747 0.289951 0.920355 0.028 Uiso 1 1 calc R U . . .
H3AB H 0.415373 0.352227 1.031397 0.028 Uiso 1 1 calc R U . . .
C4 C 0.47867(14) 0.23330(14) 0.93764(13) 0.0204(3) Uani 1 1 d . . . . .
H4A H 0.566086 0.265739 0.973605 0.024 Uiso 1 1 calc R U . . .
H4AB H 0.476461 0.160482 0.983422 0.024 Uiso 1 1 calc R U . . .
C5 C 0.44163(14) 0.20080(13) 0.80572(13) 0.0199(3) Uani 1 1 d . . . . .
H5A H 0.351852 0.174803 0.768475 0.024 Uiso 1 1 calc R U . . .
H5AB H 0.494427 0.132698 0.801336 0.024 Uiso 1 1 calc R U . . .
C6 C 0.45934(13) 0.30844(13) 0.73409(12) 0.0162(3) Uani 1 1 d . . . . .
C7 C 0.35348(14) 0.30245(13) 0.60215(13) 0.0189(3) Uani 1 1 d . . . . .
H7 H 0.310721 0.222391 0.580350 0.023 Uiso 1 1 calc R U . . .
C8 C 0.35160(16) 0.47937(14) 0.49913(14) 0.0239(3) Uani 1 1 d . . . . .
H8A H 0.324022 0.506549 0.414527 0.029 Uiso 1 1 calc R U . . .
H8AB H 0.426422 0.527139 0.551487 0.029 Uiso 1 1 calc R U . . .
C9 C 0.24431(15) 0.49350(15) 0.53941(14) 0.0244(3) Uani 1 1 d . . . . .
H9A H 0.244496 0.574715 0.572679 0.029 Uiso 1 1 calc R U . . .
H9AB H 0.160660 0.478382 0.471820 0.029 Uiso 1 1 calc R U . . .
C10 C 0.27630(14) 0.39760(14) 0.63666(13) 0.0193(3) Uani 1 1 d . . . . .
H10 H 0.201920 0.365007 0.648309 0.023 Uiso 1 1 calc R U . . .
C11 C 0.59505(13) 0.31907(13) 0.75053(12) 0.0158(3) Uani 1 1 d . . . . .
C12 C 0.67942(14) 0.39843(13) 0.83382(13) 0.0176(3) Uani 1 1 d . . . . .
H12 H 0.650303 0.449857 0.879121 0.021 Uiso 1 1 calc R U . . .
C13 C 0.80584(14) 0.40354(13) 0.85172(13) 0.0185(3) Uani 1 1 d . . . . .
H13 H 0.862532 0.457987 0.908989 0.022 Uiso 1 1 calc R U . . .
C14 C 0.84867(14) 0.32890(13) 0.78568(13) 0.0184(3) Uani 1 1 d . . . . .
C15 C 0.76525(15) 0.24921(14) 0.70172(14) 0.0231(3) Uani 1 1 d . . . . .
H15 H 0.794475 0.198057 0.656301 0.028 Uiso 1 1 calc R U . . .
C16 C 0.64011(15) 0.24471(14) 0.68468(14) 0.0214(3) Uani 1 1 d . . . . .
H16 H 0.583687 0.190208 0.627271 0.026 Uiso 1 1 calc R U . . .
C17 C 0.98405(15) 0.33304(14) 0.80327(14) 0.0218(3) 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
F1 C17 1.3321(18) . ?
F2 C17 1.3249(19) . ?
F3 C17 1.324(2) . ?
O1 C2 1.2184(19) . ?
O2 C7 1.4169(18) . ?
O2 C8 1.4352(19) . ?
C1 C2 1.5100(19) . ?
C1 C6 1.5579(19) . ?
C1 C10 1.5693(19) . ?
C1 H1 1.0000 . ?
C2 C3 1.509(2) . ?
C3 C4 1.529(2) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C5 1.523(2) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C6 1.545(2) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 C11 1.5076(19) . ?
C6 C7 1.5637(19) . ?
C7 C10 1.554(2) . ?
C7 H7 1.0000 . ?
C8 C9 1.526(2) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.521(2) . ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 H10 1.0000 . ?
C11 C12 1.392(2) . ?
C11 C16 1.398(2) . ?
C12 C13 1.392(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.393(2) . ?
C14 C17 1.496(2) . ?
C15 C16 1.380(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
C7 O2 C8 109.55(11) . . ?
C2 C1 C6 120.64(12) . . ?
C2 C1 C10 116.30(12) . . ?
C6 C1 C10 88.91(11) . . ?
C2 C1 H1 109.8 . . ?
C6 C1 H1 109.8 . . ?
C10 C1 H1 109.8 . . ?
O1 C2 C3 121.35(13) . . ?
O1 C2 C1 120.07(14) . . ?
C3 C2 C1 118.56(13) . . ?
C2 C3 C4 113.49(12) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3AB 108.9 . . ?
C4 C3 H3AB 108.9 . . ?
H3A C3 H3AB 107.7 . . ?
C5 C4 C3 109.65(12) . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4AB 109.7 . . ?
C3 C4 H4AB 109.7 . . ?
H4A C4 H4AB 108.2 . . ?
C4 C5 C6 111.49(12) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5AB 109.3 . . ?
C6 C5 H5AB 109.3 . . ?
H5A C5 H5AB 108.0 . . ?
C11 C6 C5 111.38(12) . . ?
C11 C6 C1 116.81(12) . . ?
C5 C6 C1 111.02(11) . . ?
C11 C6 C7 117.90(12) . . ?
C5 C6 C7 108.33(12) . . ?
C1 C6 C7 89.52(11) . . ?
O2 C7 C10 107.01(12) . . ?
O2 C7 C6 117.20(12) . . ?
C10 C7 C6 89.24(10) . . ?
O2 C7 H7 113.6 . . ?
C10 C7 H7 113.6 . . ?
C6 C7 H7 113.6 . . ?
O2 C8 C9 105.77(12) . . ?
O2 C8 H8A 110.6 . . ?
C9 C8 H8A 110.6 . . ?
O2 C8 H8AB 110.6 . . ?
C9 C8 H8AB 110.6 . . ?
H8A C8 H8AB 108.7 . . ?
C10 C9 C8 102.26(12) . . ?
C10 C9 H9A 111.3 . . ?
C8 C9 H9A 111.3 . . ?
C10 C9 H9AB 111.3 . . ?
C8 C9 H9AB 111.3 . . ?
H9A C9 H9AB 109.2 . . ?
C9 C10 C7 104.34(12) . . ?
C9 C10 C1 115.16(12) . . ?
C7 C10 C1 89.44(11) . . ?
C9 C10 H10 114.9 . . ?
C7 C10 H10 114.9 . . ?
C1 C10 H10 114.9 . . ?
C12 C11 C16 118.42(14) . . ?
C12 C11 C6 121.61(12) . . ?
C16 C11 C6 119.93(13) . . ?
C11 C12 C13 120.95(13) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 119.73(14) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 119.98(14) . . ?
C13 C14 C17 120.63(14) . . ?
C15 C14 C17 119.39(13) . . ?
C16 C15 C14 119.88(14) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C11 121.04(14) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
F3 C17 F2 106.68(15) . . ?
F3 C17 F1 105.48(14) . . ?
F2 C17 F1 104.69(14) . . ?
F3 C17 C14 113.54(13) . . ?
F2 C17 C14 113.04(13) . . ?
F1 C17 C14 112.69(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 O1 167.77(13) . . . . ?
C10 C1 C2 O1 -86.68(17) . . . . ?
C6 C1 C2 C3 -13.72(19) . . . . ?
C10 C1 C2 C3 91.84(16) . . . . ?
O1 C2 C3 C4 -152.96(14) . . . . ?
C1 C2 C3 C4 28.55(19) . . . . ?
C2 C3 C4 C5 -54.23(17) . . . . ?
C3 C4 C5 C6 66.26(15) . . . . ?
C4 C5 C6 C11 82.71(15) . . . . ?
C4 C5 C6 C1 -49.31(16) . . . . ?
C4 C5 C6 C7 -146.07(12) . . . . ?
C2 C1 C6 C11 -105.68(15) . . . . ?
C10 C1 C6 C11 134.07(12) . . . . ?
C2 C1 C6 C5 23.50(18) . . . . ?
C10 C1 C6 C5 -96.75(12) . . . . ?
C2 C1 C6 C7 132.99(13) . . . . ?
C10 C1 C6 C7 12.74(11) . . . . ?
C8 O2 C7 C10 11.29(15) . . . . ?
C8 O2 C7 C6 -86.86(15) . . . . ?
C11 C6 C7 O2 -24.47(18) . . . . ?
C5 C6 C7 O2 -152.04(12) . . . . ?
C1 C6 C7 O2 95.93(13) . . . . ?
C11 C6 C7 C10 -133.26(13) . . . . ?
C5 C6 C7 C10 99.17(12) . . . . ?
C1 C6 C7 C10 -12.86(11) . . . . ?
C7 O2 C8 C9 -28.63(16) . . . . ?
O2 C8 C9 C10 33.66(15) . . . . ?
C8 C9 C10 C7 -26.09(15) . . . . ?
C8 C9 C10 C1 70.16(16) . . . . ?
O2 C7 C10 C9 10.34(15) . . . . ?
C6 C7 C10 C9 128.64(12) . . . . ?
O2 C7 C10 C1 -105.53(12) . . . . ?
C6 C7 C10 C1 12.77(11) . . . . ?
C2 C1 C10 C9 117.57(15) . . . . ?
C6 C1 C10 C9 -118.42(13) . . . . ?
C2 C1 C10 C7 -136.82(13) . . . . ?
C6 C1 C10 C7 -12.82(11) . . . . ?
C5 C6 C11 C12 -97.84(15) . . . . ?
C1 C6 C11 C12 31.17(19) . . . . ?
C7 C6 C11 C12 136.05(14) . . . . ?
C5 C6 C11 C16 79.56(16) . . . . ?
C1 C6 C11 C16 -151.43(13) . . . . ?
C7 C6 C11 C16 -46.54(19) . . . . ?
C16 C11 C12 C13 -0.3(2) . . . . ?
C6 C11 C12 C13 177.19(13) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C12 C13 C14 C17 179.88(13) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C17 C14 C15 C16 -179.94(14) . . . . ?
C14 C15 C16 C11 0.0(2) . . . . ?
C12 C11 C16 C15 0.2(2) . . . . ?
C6 C11 C16 C15 -177.29(14) . . . . ?
C13 C14 C17 F3 12.8(2) . . . . ?
C15 C14 C17 F3 -167.32(15) . . . . ?
C13 C14 C17 F2 134.53(16) . . . . ?
C15 C14 C17 F2 -45.6(2) . . . . ?
C13 C14 C17 F1 -107.02(17) . . . . ?
C15 C14 C17 F1 72.83(19) . . . . ?

_refine_diff_density_max         0.610
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.054



####################################################################### 
# 
# 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_jel725a
_database_code_depnum_ccdc_archive 'CCDC 2192932'
loop_
_audit_author_name
_audit_author_address
'Jorg-M. Neudorfl'
;Department Chemie, Organische Chemie, Universitaet zu Koeln
Germany
;
_audit_update_record             
;
2022-07-27 deposited with the CCDC.	2022-10-28 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         'C17 H22 O'
_chemical_formula_sum            'C17 H22 O'
_chemical_formula_weight         242.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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                   14.7574(5)
_cell_length_b                   6.6603(2)
_cell_length_c                   14.4105(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.2900(10)
_cell_angle_gamma                90
_cell_volume                     1383.93(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9804
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      72.06
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.534
_shelx_estimated_absorpt_T_min   0.901
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6554
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus'
_diffrn_detector_type            'Bruker PhotonIII M14'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34070
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.065
_diffrn_reflns_theta_max         72.082
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2723
_reflns_number_gt                2599
_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 APEX 3'
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_reduction        'Bruker APEX 3'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'

_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)+(0.0428P)²+0.4742P] 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         2723
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0896
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
O18 O 0.93431(5) 0.17597(12) 0.79342(6) 0.0305(2) Uani 1 1 d . . . . .
C1 C 0.76509(6) 0.60302(14) 0.74767(7) 0.0171(2) Uani 1 1 d . . . . .
C2 C 0.74305(7) 0.64546(15) 0.63692(7) 0.0185(2) Uani 1 1 d . . . . .
C3 C 0.82848(7) 0.51060(15) 0.63188(7) 0.0187(2) Uani 1 1 d . . . . .
H3 H 0.885736 0.595293 0.643615 0.022 Uiso 1 1 calc R U . . .
C4 C 0.81782(7) 0.41118(15) 0.72750(7) 0.0176(2) Uani 1 1 d . . . . .
H4 H 0.773561 0.295905 0.713884 0.021 Uiso 1 1 calc R U . . .
C5 C 0.90454(7) 0.34592(15) 0.79617(7) 0.0195(2) Uani 1 1 d . . . . .
C6 C 0.95526(7) 0.49731(17) 0.86584(7) 0.0242(2) Uani 1 1 d . . . . .
H6A H 1.003235 0.563354 0.837778 0.029 Uiso 1 1 calc R U . . .
H6AB H 0.987290 0.426034 0.923881 0.029 Uiso 1 1 calc R U . . .
C7 C 0.89228(7) 0.65860(16) 0.89370(7) 0.0235(2) Uani 1 1 d . . . . .
H7A H 0.850983 0.597603 0.931789 0.028 Uiso 1 1 calc R U . . .
H7AB H 0.930427 0.762503 0.932948 0.028 Uiso 1 1 calc R U . . .
C8 C 0.83415(7) 0.75471(15) 0.80440(7) 0.0206(2) Uani 1 1 d . . . . .
H8A H 0.875635 0.805132 0.763907 0.025 Uiso 1 1 calc R U . . .
H8AB H 0.799636 0.870541 0.822578 0.025 Uiso 1 1 calc R U . . .
C9 C 0.65164(7) 0.54978(17) 0.58657(7) 0.0235(2) Uani 1 1 d . . . . .
H9A H 0.647588 0.551358 0.517806 0.035 Uiso 1 1 calc R U . . .
H9B H 0.599679 0.625832 0.601437 0.035 Uiso 1 1 calc R U . . .
H9C H 0.649038 0.410797 0.608179 0.035 Uiso 1 1 calc R U . . .
C10 C 0.74668(7) 0.86143(16) 0.60282(8) 0.0241(2) Uani 1 1 d . . . . .
H10A H 0.739101 0.862894 0.533587 0.036 Uiso 1 1 calc R U . . .
H10B H 0.806622 0.921067 0.632243 0.036 Uiso 1 1 calc R U . . .
H10C H 0.696649 0.939136 0.620701 0.036 Uiso 1 1 calc R U . . .
C11 C 0.82783(8) 0.37627(16) 0.54670(7) 0.0248(2) Uani 1 1 d . . . . .
H11A H 0.824925 0.459306 0.490005 0.037 Uiso 1 1 calc R U . . .
H11B H 0.773629 0.287623 0.537150 0.037 Uiso 1 1 calc R U . . .
H11C H 0.884510 0.295120 0.557946 0.037 Uiso 1 1 calc R U . . .
C12 C 0.68339(7) 0.57725(16) 0.79494(7) 0.0200(2) Uani 1 1 d . . . . .
C13 C 0.66720(7) 0.40073(17) 0.84051(7) 0.0242(2) Uani 1 1 d . . . . .
H13 H 0.707904 0.289770 0.841800 0.029 Uiso 1 1 calc R U . . .
C14 C 0.59160(8) 0.3851(2) 0.88441(8) 0.0314(3) Uani 1 1 d . . . . .
H14 H 0.581554 0.264240 0.915745 0.038 Uiso 1 1 calc R U . . .
C15 C 0.53152(7) 0.5448(2) 0.88237(7) 0.0337(3) Uani 1 1 d . . . . .
H15 H 0.480050 0.533528 0.911972 0.040 Uiso 1 1 calc R U . . .
C16 C 0.54643(8) 0.7214(2) 0.83707(8) 0.0322(3) Uani 1 1 d . . . . .
H16 H 0.504956 0.831159 0.835137 0.039 Uiso 1 1 calc R U . . .
C17 C 0.62224(7) 0.73757(18) 0.79446(8) 0.0265(2) Uani 1 1 d . . . . .
H17 H 0.632651 0.859888 0.764466 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
O18 C5 1.2179(13) . ?
C1 C12 1.5156(13) . ?
C1 C8 1.5405(13) . ?
C1 C4 1.5552(13) . ?
C1 C2 1.5848(13) . ?
C2 C10 1.5247(14) . ?
C2 C9 1.5283(14) . ?
C2 C3 1.5622(13) . ?
C3 C11 1.5172(14) . ?
C3 C4 1.5666(13) . ?
C3 H3 1.0000 . ?
C4 C5 1.5056(13) . ?
C4 H4 1.0000 . ?
C5 C6 1.5049(14) . ?
C6 C7 1.5291(14) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.5270(14) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.3918(15) . ?
C12 C17 1.3971(15) . ?
C13 C14 1.3987(15) . ?
C13 H13 0.9500 . ?
C14 C15 1.3808(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.3854(19) . ?
C15 H15 0.9500 . ?
C16 C17 1.3902(15) . ?
C16 H16 0.9500 . ?
C17 H17 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
C12 C1 C8 109.60(8) . . ?
C12 C1 C4 117.94(8) . . ?
C8 C1 C4 109.70(8) . . ?
C12 C1 C2 117.42(8) . . ?
C8 C1 C2 112.84(8) . . ?
C4 C1 C2 87.82(7) . . ?
C10 C2 C9 109.17(8) . . ?
C10 C2 C3 116.32(8) . . ?
C9 C2 C3 112.19(8) . . ?
C10 C2 C1 118.63(8) . . ?
C9 C2 C1 112.02(8) . . ?
C3 C2 C1 87.11(7) . . ?
C11 C3 C2 120.70(8) . . ?
C11 C3 C4 118.54(8) . . ?
C2 C3 C4 88.22(7) . . ?
C11 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
C4 C3 H3 109.2 . . ?
C5 C4 C1 120.23(8) . . ?
C5 C4 C3 118.01(8) . . ?
C1 C4 C3 88.00(7) . . ?
C5 C4 H4 109.6 . . ?
C1 C4 H4 109.6 . . ?
C3 C4 H4 109.6 . . ?
O18 C5 C6 120.85(9) . . ?
O18 C5 C4 120.60(9) . . ?
C6 C5 C4 118.52(9) . . ?
C5 C6 C7 113.71(8) . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6AB 108.8 . . ?
C7 C6 H6AB 108.8 . . ?
H6A C6 H6AB 107.7 . . ?
C8 C7 C6 109.69(8) . . ?
C8 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
C8 C7 H7AB 109.7 . . ?
C6 C7 H7AB 109.7 . . ?
H7A C7 H7AB 108.2 . . ?
C7 C8 C1 111.21(8) . . ?
C7 C8 H8A 109.4 . . ?
C1 C8 H8A 109.4 . . ?
C7 C8 H8AB 109.4 . . ?
C1 C8 H8AB 109.4 . . ?
H8A C8 H8AB 108.0 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 118.19(9) . . ?
C13 C12 C1 122.72(9) . . ?
C17 C12 C1 119.08(9) . . ?
C12 C13 C14 120.64(11) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 120.23(11) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.89(10) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C17 119.82(11) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C12 121.22(11) . . ?
C16 C17 H17 119.4 . . ?
C12 C17 H17 119.4 . . ?

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
C12 C1 C2 C10 98.64(11) . . . . ?
C8 C1 C2 C10 -30.31(12) . . . . ?
C4 C1 C2 C10 -140.80(9) . . . . ?
C12 C1 C2 C9 -30.00(12) . . . . ?
C8 C1 C2 C9 -158.94(8) . . . . ?
C4 C1 C2 C9 90.57(9) . . . . ?
C12 C1 C2 C3 -142.79(9) . . . . ?
C8 C1 C2 C3 88.26(9) . . . . ?
C4 C1 C2 C3 -22.23(7) . . . . ?
C10 C2 C3 C11 -94.75(11) . . . . ?
C9 C2 C3 C11 31.93(12) . . . . ?
C1 C2 C3 C11 144.57(9) . . . . ?
C10 C2 C3 C4 142.74(9) . . . . ?
C9 C2 C3 C4 -90.58(8) . . . . ?
C1 C2 C3 C4 22.06(7) . . . . ?
C12 C1 C4 C5 -96.19(11) . . . . ?
C8 C1 C4 C5 30.20(11) . . . . ?
C2 C1 C4 C5 143.72(9) . . . . ?
C12 C1 C4 C3 142.24(8) . . . . ?
C8 C1 C4 C3 -91.37(8) . . . . ?
C2 C1 C4 C3 22.15(7) . . . . ?
C11 C3 C4 C5 89.64(11) . . . . ?
C2 C3 C4 C5 -145.99(9) . . . . ?
C11 C3 C4 C1 -146.85(9) . . . . ?
C2 C3 C4 C1 -22.48(7) . . . . ?
C1 C4 C5 O18 163.12(9) . . . . ?
C3 C4 C5 O18 -91.56(12) . . . . ?
C1 C4 C5 C6 -18.97(13) . . . . ?
C3 C4 C5 C6 86.34(11) . . . . ?
O18 C5 C6 C7 -152.77(10) . . . . ?
C4 C5 C6 C7 29.32(13) . . . . ?
C5 C6 C7 C8 -52.29(12) . . . . ?
C6 C7 C8 C1 66.38(11) . . . . ?
C12 C1 C8 C7 77.52(10) . . . . ?
C4 C1 C8 C7 -53.46(10) . . . . ?
C2 C1 C8 C7 -149.60(8) . . . . ?
C8 C1 C12 C13 -110.91(11) . . . . ?
C4 C1 C12 C13 15.53(14) . . . . ?
C2 C1 C12 C13 118.62(10) . . . . ?
C8 C1 C12 C17 68.03(11) . . . . ?
C4 C1 C12 C17 -165.53(9) . . . . ?
C2 C1 C12 C17 -62.43(12) . . . . ?
C17 C12 C13 C14 0.06(15) . . . . ?
C1 C12 C13 C14 179.02(9) . . . . ?
C12 C13 C14 C15 0.52(16) . . . . ?
C13 C14 C15 C16 -0.31(17) . . . . ?
C14 C15 C16 C17 -0.47(17) . . . . ?
C15 C16 C17 C12 1.07(17) . . . . ?
C13 C12 C17 C16 -0.86(16) . . . . ?
C1 C12 C17 C16 -179.85(10) . . . . ?

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.213
_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_jel646b_1
_database_code_depnum_ccdc_archive 'CCDC 2192933'
loop_
_audit_author_name
_audit_author_address
'Jorg-M. Neudorfl'
;Department Chemie, Organische Chemie, Universitaet zu Koeln
Germany
;
_audit_update_record             
;
2022-10-14 deposited with the CCDC.	2022-10-28 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         'C17 H20 O3'

_chemical_formula_sum            'C17 H20 O3'
_chemical_formula_weight         272.33

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.5051(4)
_cell_length_b                   20.1564(8)
_cell_length_c                   13.1906(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.0000(10)
_cell_angle_gamma                90
_cell_volume                     2793.04(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    171(2)
_cell_measurement_reflns_used    9027
_cell_measurement_theta_min      4.01
_cell_measurement_theta_max      72.08
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.703
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6253
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      171(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus'
_diffrn_detector_type            'Bruker PhotonIII M14'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42493
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_av_R_equivalents  0.0767
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.350
_diffrn_reflns_theta_max         72.070
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             10780
_reflns_number_gt                9716
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.909
_reflns_Friedel_fraction_max     0.962
_reflns_Friedel_fraction_full    0.982

_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 APEX 3'
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_reduction        
;
Bruker APEX 3
SADABS Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'

_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)+(0.0470P)²+0.1023P] 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_abs_structure_details 
;
 Flack x determined using 4044 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         10780
_refine_ls_number_parameters     725
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0923
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 1.47588(19) 0.35426(10) 0.50411(14) 0.0328(4) Uani 1 1 d . . . . .
C1 C 1.1263(2) 0.40853(13) 0.75908(19) 0.0285(5) Uani 1 1 d . . . . .
H1A H 1.083730 0.401326 0.693038 0.034 Uiso 1 1 calc R U . . .
H1B H 1.068404 0.394051 0.813999 0.034 Uiso 1 1 calc R U . . .
O3 O 0.80113(17) 0.52895(10) 0.40506(14) 0.0315(4) Uani 1 1 d . . . . .
O4 O 1.03362(17) 0.74208(9) 0.51790(12) 0.0273(4) Uani 1 1 d . . . . .
O5 O 1.3774(2) 0.84658(11) 0.25276(14) 0.0374(4) Uani 1 1 d . . . . .
O6 O 0.68789(17) 0.69360(10) 0.13978(14) 0.0314(4) Uani 1 1 d . . . . .
C5 C 1.4541(2) 0.40807(12) 0.54146(16) 0.0239(5) Uani 1 1 d . . . . .
O7 O 0.46403(17) 0.47151(9) 0.26794(12) 0.0259(3) Uani 1 1 d . . . . .
O8 O 0.1157(2) 0.36795(11) 0.00431(14) 0.0367(4) Uani 1 1 d . . . . .
O9 O 0.80969(18) 0.52932(10) -0.10561(14) 0.0325(4) Uani 1 1 d . . . . .
O10 O -0.34312(17) 0.23558(9) -0.01889(13) 0.0277(3) Uani 1 1 d . . . . .
O11 O -0.0178(2) 0.35329(11) 0.24740(14) 0.0364(4) Uani 1 1 d . . . . .
O12 O -0.69569(16) 0.17295(9) 0.34786(13) 0.0293(4) Uani 1 1 d . . . . .
O1 O 1.16073(17) 0.47720(9) 0.77149(13) 0.0267(3) Uani 1 1 d . . . . .
C2 C 1.2519(3) 0.37078(13) 0.76387(19) 0.0293(5) Uani 1 1 d . . . . .
H2A H 1.246706 0.328322 0.726383 0.035 Uiso 1 1 calc R U . . .
H2B H 1.277177 0.361764 0.834855 0.035 Uiso 1 1 calc R U . . .
C3 C 1.3443(2) 0.41876(12) 0.71287(16) 0.0225(4) Uani 1 1 d . . . . .
H3 H 1.433723 0.417015 0.738722 0.027 Uiso 1 1 calc R U . . .
C4 C 1.3310(2) 0.42114(11) 0.59487(16) 0.0211(4) Uani 1 1 d . . . . .
H4 H 1.263183 0.389978 0.571061 0.025 Uiso 1 1 calc R U . . .
C6 C 1.5515(3) 0.46333(14) 0.5364(2) 0.0353(6) Uani 1 1 d . . . . .
H6A H 1.566403 0.474694 0.464383 0.042 Uiso 1 1 calc R U . . .
H6B H 1.632867 0.446794 0.564627 0.042 Uiso 1 1 calc R U . . .
C7 C 1.5139(2) 0.52627(13) 0.5931(2) 0.0297(5) Uani 1 1 d . . . . .
H7A H 1.572151 0.562820 0.574131 0.036 Uiso 1 1 calc R U . . .
H7B H 1.521833 0.518797 0.667056 0.036 Uiso 1 1 calc R U . . .
C8 C 1.3769(2) 0.54580(12) 0.56768(19) 0.0248(5) Uani 1 1 d . . . . .
H8A H 1.369219 0.551768 0.493429 0.030 Uiso 1 1 calc R U . . .
H8B H 1.357416 0.588897 0.600175 0.030 Uiso 1 1 calc R U . . .
C9 C 1.2783(2) 0.49414(11) 0.60272(16) 0.0202(4) Uani 1 1 d . . . . .
C10 C 1.2785(2) 0.48736(12) 0.72167(17) 0.0222(4) Uani 1 1 d . . . . .
H10 H 1.332976 0.521368 0.755810 0.027 Uiso 1 1 calc R U . . .
C11 C 1.1524(2) 0.50456(11) 0.55004(17) 0.0201(4) Uani 1 1 d . . . . .
C12 C 1.1309(2) 0.47623(12) 0.45533(17) 0.0236(4) Uani 1 1 d . . . . .
H12 H 1.196693 0.450601 0.425184 0.028 Uiso 1 1 calc R U . . .
C13 C 1.0167(2) 0.48403(12) 0.40309(17) 0.0243(5) Uani 1 1 d . . . . .
H13 H 1.005561 0.464608 0.338062 0.029 Uiso 1 1 calc R U . . .
C14 C 0.9194(2) 0.52045(12) 0.44710(18) 0.0239(5) Uani 1 1 d . . . . .
C15 C 0.9389(2) 0.55022(12) 0.54106(19) 0.0267(5) Uani 1 1 d . . . . .
H15 H 0.872785 0.575657 0.571089 0.032 Uiso 1 1 calc R U . . .
C16 C 1.0544(2) 0.54299(12) 0.59125(18) 0.0242(5) Uani 1 1 d . . . . .
H16 H 1.067025 0.564494 0.654550 0.029 Uiso 1 1 calc R U . . .
C17 C 0.7812(3) 0.50090(15) 0.3068(2) 0.0371(6) Uani 1 1 d . . . . .
H17A H 0.692483 0.507793 0.286360 0.056 Uiso 1 1 calc R U . . .
H17B H 0.799474 0.453242 0.308952 0.056 Uiso 1 1 calc R U . . .
H17C H 0.837876 0.522419 0.257864 0.056 Uiso 1 1 calc R U . . .
C18 C 1.0109(3) 0.81148(13) 0.5033(2) 0.0302(5) Uani 1 1 d . . . . .
H18A H 0.953040 0.828923 0.556234 0.036 Uiso 1 1 calc R U . . .
H18B H 0.972568 0.819831 0.435943 0.036 Uiso 1 1 calc R U . . .
C19 C 1.1418(3) 0.84375(13) 0.5111(2) 0.0317(5) Uani 1 1 d . . . . .
H19A H 1.144788 0.886000 0.472907 0.038 Uiso 1 1 calc R U . . .
H19B H 1.165121 0.852268 0.582631 0.038 Uiso 1 1 calc R U . . .
C20 C 1.2285(2) 0.79211(12) 0.46384(17) 0.0246(5) Uani 1 1 d . . . . .
H20 H 1.316501 0.790365 0.492587 0.030 Uiso 1 1 calc R U . . .
C21 C 1.2209(2) 0.78881(11) 0.34548(17) 0.0218(4) Uani 1 1 d . . . . .
H21 H 1.159678 0.822555 0.318872 0.026 Uiso 1 1 calc R U . . .
C22 C 1.3472(2) 0.79501(13) 0.29381(17) 0.0262(5) Uani 1 1 d . . . . .
C23 C 1.4368(3) 0.73658(16) 0.2962(2) 0.0394(6) Uani 1 1 d . . . . .
H23A H 1.517519 0.750707 0.328289 0.047 Uiso 1 1 calc R U . . .
H23B H 1.456336 0.723454 0.225545 0.047 Uiso 1 1 calc R U . . .
C24 C 1.3861(3) 0.67586(14) 0.3529(2) 0.0328(6) Uani 1 1 d . . . . .
H24A H 1.391492 0.683668 0.426882 0.039 Uiso 1 1 calc R U . . .
H24B H 1.439093 0.636690 0.336441 0.039 Uiso 1 1 calc R U . . .
C25 C 1.2476(2) 0.66229(13) 0.32312(19) 0.0280(5) Uani 1 1 d . . . . .
H25A H 1.219254 0.620722 0.356126 0.034 Uiso 1 1 calc R U . . .
H25B H 1.243045 0.655557 0.248865 0.034 Uiso 1 1 calc R U . . .
C26 C 1.1559(2) 0.71871(11) 0.35301(17) 0.0212(4) Uani 1 1 d . . . . .
C27 C 1.1519(2) 0.72651(12) 0.47185(17) 0.0236(4) Uani 1 1 d . . . . .
H27 H 1.199259 0.690638 0.508164 0.028 Uiso 1 1 calc R U . . .
C28 C 1.0317(2) 0.71223(11) 0.29658(17) 0.0212(4) Uani 1 1 d . . . . .
C29 C 0.9292(2) 0.67574(12) 0.33401(18) 0.0265(5) Uani 1 1 d . . . . .
H29 H 0.936839 0.654268 0.397840 0.032 Uiso 1 1 calc R U . . .
C30 C 0.8168(3) 0.67012(13) 0.2802(2) 0.0285(5) Uani 1 1 d . . . . .
H30 H 0.747809 0.645606 0.307837 0.034 Uiso 1 1 calc R U . . .
C31 C 0.8040(2) 0.70009(12) 0.18586(19) 0.0246(5) Uani 1 1 d . . . . .
C32 C 0.9058(2) 0.73484(13) 0.14480(17) 0.0250(5) Uani 1 1 d . . . . .
H32 H 0.899309 0.754315 0.079422 0.030 Uiso 1 1 calc R U . . .
C33 C 1.0176(2) 0.74072(13) 0.20093(17) 0.0245(5) Uani 1 1 d . . . . .
H33 H 1.086696 0.765011 0.173010 0.029 Uiso 1 1 calc R U . . .
C34 C 0.6749(3) 0.71942(15) 0.0401(2) 0.0355(6) Uani 1 1 d . . . . .
H34A H 0.737713 0.698499 -0.004502 0.053 Uiso 1 1 calc R U . . .
H34B H 0.688867 0.767479 0.041273 0.053 Uiso 1 1 calc R U . . .
H34C H 0.588976 0.710084 0.014847 0.053 Uiso 1 1 calc R U . . .
C35 C 0.4889(2) 0.40215(13) 0.25235(19) 0.0287(5) Uani 1 1 d . . . . .
H35A H 0.546915 0.384871 0.305308 0.034 Uiso 1 1 calc R U . . .
H35B H 0.528183 0.394612 0.185092 0.034 Uiso 1 1 calc R U . . .
C36 C 0.3594(3) 0.36843(12) 0.2588(2) 0.0288(5) Uani 1 1 d . . . . .
H36A H 0.335945 0.358826 0.329971 0.035 Uiso 1 1 calc R U . . .
H36B H 0.358153 0.326626 0.219390 0.035 Uiso 1 1 calc R U . . .
C37 C 0.2707(2) 0.42008(12) 0.21236(17) 0.0232(4) Uani 1 1 d . . . . .
H37 H 0.182850 0.420951 0.241544 0.028 Uiso 1 1 calc R U . . .
C38 C 0.2768(2) 0.42468(11) 0.09404(17) 0.0219(4) Uani 1 1 d . . . . .
H38 H 0.337116 0.391083 0.065647 0.026 Uiso 1 1 calc R U . . .
C39 C 0.1482(2) 0.41922(13) 0.04513(17) 0.0258(5) Uani 1 1 d . . . . .
C40 C 0.0597(3) 0.47798(17) 0.0496(2) 0.0414(7) Uani 1 1 d . . . . .
H40A H -0.019604 0.464248 0.084305 0.050 Uiso 1 1 calc R U . . .
H40B H 0.036831 0.490742 -0.020559 0.050 Uiso 1 1 calc R U . . .
C41 C 0.1130(3) 0.53892(14) 0.1038(2) 0.0328(6) Uani 1 1 d . . . . .
H41A H 0.109430 0.532020 0.178005 0.039 Uiso 1 1 calc R U . . .
H41B H 0.060606 0.578246 0.087052 0.039 Uiso 1 1 calc R U . . .
C42 C 0.2506(2) 0.55106(12) 0.07131(18) 0.0255(5) Uani 1 1 d . . . . .
H42A H 0.280623 0.593133 0.101808 0.031 Uiso 1 1 calc R U . . .
H42B H 0.253560 0.556182 -0.003301 0.031 Uiso 1 1 calc R U . . .
C43 C 0.3419(2) 0.49460(11) 0.10276(16) 0.0199(4) Uani 1 1 d . . . . .
C44 C 0.3452(2) 0.48612(11) 0.22158(16) 0.0219(4) Uani 1 1 d . . . . .
H44 H 0.296440 0.521405 0.258085 0.026 Uiso 1 1 calc R U . . .
C45 C 0.4668(2) 0.50229(11) 0.04858(16) 0.0204(4) Uani 1 1 d . . . . .
C46 C 0.4859(2) 0.47149(12) -0.04507(17) 0.0228(4) Uani 1 1 d . . . . .
H46 H 0.420502 0.444232 -0.072210 0.027 Uiso 1 1 calc R U . . .
C47 C 0.5982(2) 0.47963(12) -0.09969(17) 0.0239(4) Uani 1 1 d . . . . .
H47 H 0.608469 0.458750 -0.163735 0.029 Uiso 1 1 calc R U . . .
C48 C 0.6952(2) 0.51861(12) -0.05965(18) 0.0236(5) Uani 1 1 d . . . . .
C49 C 0.6776(2) 0.54975(12) 0.03333(19) 0.0262(5) Uani 1 1 d . . . . .
H49 H 0.743692 0.576440 0.060811 0.031 Uiso 1 1 calc R U . . .
C50 C 0.5647(2) 0.54223(12) 0.08626(17) 0.0249(5) Uani 1 1 d . . . . .
H50 H 0.553683 0.564535 0.149090 0.030 Uiso 1 1 calc R U . . .
C51 C 0.8285(3) 0.50034(16) -0.2027(2) 0.0373(6) Uani 1 1 d . . . . .
H51A H 0.768982 0.520148 -0.251250 0.056 Uiso 1 1 calc R U . . .
H51B H 0.813297 0.452442 -0.198621 0.056 Uiso 1 1 calc R U . . .
H51C H 0.916029 0.508455 -0.225065 0.056 Uiso 1 1 calc R U . . .
C52 C -0.3763(3) 0.30426(14) -0.00483(19) 0.0306(5) Uani 1 1 d . . . . .
H52A H -0.418979 0.310913 0.061290 0.037 Uiso 1 1 calc R U . . .
H52B H -0.433827 0.319552 -0.059469 0.037 Uiso 1 1 calc R U . . .
C53 C -0.2509(3) 0.34157(13) -0.00838(19) 0.0301(5) Uani 1 1 d . . . . .
H53A H -0.255753 0.383414 0.030739 0.036 Uiso 1 1 calc R U . . .
H53B H -0.226010 0.351795 -0.079069 0.036 Uiso 1 1 calc R U . . .
C54 C -0.1582(2) 0.29312(12) 0.04013(17) 0.0233(4) Uani 1 1 d . . . . .
H54 H -0.069347 0.295091 0.013031 0.028 Uiso 1 1 calc R U . . .
C55 C -0.1683(2) 0.28883(12) 0.15819(17) 0.0215(4) Uani 1 1 d . . . . .
H55 H -0.234394 0.320071 0.184562 0.026 Uiso 1 1 calc R U . . .
C56 C -0.0429(2) 0.30002(13) 0.20942(17) 0.0256(5) Uani 1 1 d . . . . .
C57 C 0.0529(3) 0.24428(16) 0.2099(2) 0.0403(6) Uani 1 1 d . . . . .
H57A H 0.071732 0.232354 0.281177 0.048 Uiso 1 1 calc R U . . .
H57B H 0.132964 0.260567 0.179081 0.048 Uiso 1 1 calc R U . . .
C58 C 0.0112(3) 0.18178(14) 0.1537(2) 0.0345(6) Uani 1 1 d . . . . .
H58A H 0.068651 0.144591 0.171407 0.041 Uiso 1 1 calc R U . . .
H58B H 0.016906 0.189285 0.079697 0.041 Uiso 1 1 calc R U . . .
C59 C -0.1256(2) 0.16384(12) 0.18229(19) 0.0271(5) Uani 1 1 d . . . . .
H59A H -0.131110 0.158465 0.256761 0.033 Uiso 1 1 calc R U . . .
H59B H -0.147733 0.120741 0.150902 0.033 Uiso 1 1 calc R U . . .
C60 C -0.2231(2) 0.21630(11) 0.14834(17) 0.0213(4) Uani 1 1 d . . . . .
C61 C -0.2243(2) 0.22451(12) 0.02983(17) 0.0226(4) Uani 1 1 d . . . . .
H61 H -0.170465 0.190889 -0.005773 0.027 Uiso 1 1 calc R U . . .
C62 C -0.3491(2) 0.20511(11) 0.20084(16) 0.0206(4) Uani 1 1 d . . . . .
C63 C -0.4424(2) 0.16268(12) 0.16210(17) 0.0243(5) Uani 1 1 d . . . . .
H63 H -0.427295 0.140175 0.099980 0.029 Uiso 1 1 calc R U . . .
C64 C -0.5565(2) 0.15280(12) 0.21247(19) 0.0265(5) Uani 1 1 d . . . . .
H64 H -0.619300 0.124337 0.184263 0.032 Uiso 1 1 calc R U . . .
C65 C -0.5794(2) 0.18465(11) 0.30469(17) 0.0216(4) Uani 1 1 d . . . . .
C66 C -0.4862(2) 0.22577(12) 0.34619(17) 0.0231(4) Uani 1 1 d . . . . .
H66 H -0.499907 0.246928 0.409610 0.028 Uiso 1 1 calc R U . . .
C67 C -0.3732(2) 0.23542(12) 0.29376(17) 0.0231(4) Uani 1 1 d . . . . .
H67 H -0.310161 0.263639 0.322188 0.028 Uiso 1 1 calc R U . . .
C68 C -0.7204(3) 0.20474(15) 0.4424(2) 0.0351(6) Uani 1 1 d . . . . .
H68A H -0.706768 0.252616 0.435338 0.053 Uiso 1 1 calc R U . . .
H68B H -0.662608 0.187083 0.494114 0.053 Uiso 1 1 calc R U . . .
H68C H -0.808654 0.196361 0.462650 0.053 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 C5 1.213(3) . ?
C1 O1 1.440(3) . ?
C1 C2 1.524(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
O3 C14 1.372(3) . ?
O3 C17 1.429(4) . ?
O4 C27 1.418(3) . ?
O4 C18 1.432(3) . ?
O5 C22 1.214(3) . ?
O6 C31 1.369(3) . ?
O6 C34 1.420(4) . ?
C5 C4 1.497(3) . ?
C5 C6 1.514(4) . ?
O7 C44 1.421(3) . ?
O7 C35 1.437(3) . ?
O8 C39 1.214(3) . ?
O9 C48 1.364(3) . ?
O9 C51 1.421(3) . ?
O10 C61 1.421(3) . ?
O10 C52 1.439(3) . ?
O11 C56 1.214(3) . ?
O12 C65 1.369(3) . ?
O12 C68 1.426(3) . ?
O1 C10 1.416(3) . ?
C2 C3 1.526(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C10 1.550(3) . ?
C3 C4 1.564(3) . ?
C3 H3 1.0000 . ?
C4 C9 1.576(3) . ?
C4 H4 1.0000 . ?
C6 C7 1.525(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.530(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.540(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C11 1.509(3) . ?
C9 C10 1.575(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.392(3) . ?
C11 C16 1.398(3) . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(4) . ?
C15 C16 1.390(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.524(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.517(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C27 1.551(3) . ?
C20 C21 1.565(3) . ?
C20 H20 1.0000 . ?
C21 C22 1.496(3) . ?
C21 C26 1.573(3) . ?
C21 H21 1.0000 . ?
C22 C23 1.508(4) . ?
C23 C24 1.530(4) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.532(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.541(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C28 1.508(3) . ?
C26 C27 1.576(3) . ?
C27 H27 1.0000 . ?
C28 C29 1.394(3) . ?
C28 C33 1.394(3) . ?
C29 C30 1.383(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.389(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.388(3) . ?
C32 C33 1.393(3) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.524(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.526(3) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C44 1.549(3) . ?
C37 C38 1.565(3) . ?
C37 H37 1.0000 . ?
C38 C39 1.502(3) . ?
C38 C43 1.570(3) . ?
C38 H38 1.0000 . ?
C39 C40 1.507(4) . ?
C40 C41 1.527(4) . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 C42 1.527(4) . ?
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 C43 1.545(3) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C45 1.502(3) . ?
C43 C44 1.577(3) . ?
C44 H44 1.0000 . ?
C45 C46 1.397(3) . ?
C45 C50 1.398(3) . ?
C46 C47 1.392(3) . ?
C46 H46 0.9500 . ?
C47 C48 1.391(3) . ?
C47 H47 0.9500 . ?
C48 C49 1.390(4) . ?
C49 C50 1.384(4) . ?
C49 H49 0.9500 . ?
C50 H50 0.9500 . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C52 C53 1.518(4) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 C54 1.520(3) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C54 C61 1.554(3) . ?
C54 C55 1.563(3) . ?
C54 H54 1.0000 . ?
C55 C56 1.497(3) . ?
C55 C60 1.577(3) . ?
C55 H55 1.0000 . ?
C56 C57 1.509(4) . ?
C57 C58 1.526(4) . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
C58 C59 1.529(4) . ?
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
C59 C60 1.539(3) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
C60 C62 1.511(3) . ?
C60 C61 1.572(3) . ?
C61 H61 1.0000 . ?
C62 C67 1.393(3) . ?
C62 C63 1.398(3) . ?
C63 C64 1.385(3) . ?
C63 H63 0.9500 . ?
C64 C65 1.396(3) . ?
C64 H64 0.9500 . ?
C65 C66 1.395(3) . ?
C66 C67 1.388(3) . ?
C66 H66 0.9500 . ?
C67 H67 0.9500 . ?
C68 H68A 0.9800 . ?
C68 H68B 0.9800 . ?
C68 H68C 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
O1 C1 C2 104.9(2) . . ?
O1 C1 H1A 110.8 . . ?
C2 C1 H1A 110.8 . . ?
O1 C1 H1B 110.8 . . ?
C2 C1 H1B 110.8 . . ?
H1A C1 H1B 108.8 . . ?
C14 O3 C17 116.7(2) . . ?
C27 O4 C18 107.74(18) . . ?
C31 O6 C34 117.5(2) . . ?
O2 C5 C4 120.8(2) . . ?
O2 C5 C6 120.9(2) . . ?
C4 C5 C6 118.4(2) . . ?
C44 O7 C35 107.46(18) . . ?
C48 O9 C51 117.2(2) . . ?
C61 O10 C52 107.77(18) . . ?
C65 O12 C68 116.66(19) . . ?
C10 O1 C1 107.79(18) . . ?
C1 C2 C3 102.5(2) . . ?
C1 C2 H2A 111.3 . . ?
C3 C2 H2A 111.3 . . ?
C1 C2 H2B 111.3 . . ?
C3 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
C2 C3 C10 104.40(19) . . ?
C2 C3 C4 113.7(2) . . ?
C10 C3 C4 90.41(16) . . ?
C2 C3 H3 115.1 . . ?
C10 C3 H3 115.1 . . ?
C4 C3 H3 115.1 . . ?
C5 C4 C3 112.68(19) . . ?
C5 C4 C9 119.9(2) . . ?
C3 C4 C9 89.70(16) . . ?
C5 C4 H4 110.9 . . ?
C3 C4 H4 110.9 . . ?
C9 C4 H4 110.9 . . ?
C5 C6 C7 114.6(2) . . ?
C5 C6 H6A 108.6 . . ?
C7 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
C7 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C6 C7 C8 110.5(2) . . ?
C6 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 C9 113.2(2) . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
C11 C9 C8 110.94(19) . . ?
C11 C9 C10 118.19(19) . . ?
C8 C9 C10 110.89(18) . . ?
C11 C9 C4 114.06(18) . . ?
C8 C9 C4 112.06(19) . . ?
C10 C9 C4 89.07(16) . . ?
O1 C10 C3 107.18(19) . . ?
O1 C10 C9 118.26(18) . . ?
C3 C10 C9 90.21(16) . . ?
O1 C10 H10 113.0 . . ?
C3 C10 H10 113.0 . . ?
C9 C10 H10 113.0 . . ?
C12 C11 C16 117.2(2) . . ?
C12 C11 C9 119.9(2) . . ?
C16 C11 C9 122.9(2) . . ?
C11 C12 C13 122.5(2) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C14 C13 C12 119.2(2) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
O3 C14 C13 124.4(2) . . ?
O3 C14 C15 116.1(2) . . ?
C13 C14 C15 119.5(2) . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C11 121.0(2) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 C19 104.9(2) . . ?
O4 C18 H18A 110.8 . . ?
C19 C18 H18A 110.8 . . ?
O4 C18 H18B 110.8 . . ?
C19 C18 H18B 110.8 . . ?
H18A C18 H18B 108.8 . . ?
C20 C19 C18 102.8(2) . . ?
C20 C19 H19A 111.2 . . ?
C18 C19 H19A 111.2 . . ?
C20 C19 H19B 111.2 . . ?
C18 C19 H19B 111.2 . . ?
H19A C19 H19B 109.1 . . ?
C19 C20 C27 104.2(2) . . ?
C19 C20 C21 114.1(2) . . ?
C27 C20 C21 90.31(17) . . ?
C19 C20 H20 115.1 . . ?
C27 C20 H20 115.1 . . ?
C21 C20 H20 115.1 . . ?
C22 C21 C20 113.96(19) . . ?
C22 C21 C26 119.3(2) . . ?
C20 C21 C26 89.84(16) . . ?
C22 C21 H21 110.7 . . ?
C20 C21 H21 110.7 . . ?
C26 C21 H21 110.7 . . ?
O5 C22 C21 120.4(2) . . ?
O5 C22 C23 121.0(2) . . ?
C21 C22 C23 118.6(2) . . ?
C22 C23 C24 114.7(2) . . ?
C22 C23 H23A 108.6 . . ?
C24 C23 H23A 108.6 . . ?
C22 C23 H23B 108.6 . . ?
C24 C23 H23B 108.6 . . ?
H23A C23 H23B 107.6 . . ?
C23 C24 C25 110.3(2) . . ?
C23 C24 H24A 109.6 . . ?
C25 C24 H24A 109.6 . . ?
C23 C24 H24B 109.6 . . ?
C25 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
C24 C25 C26 113.3(2) . . ?
C24 C25 H25A 108.9 . . ?
C26 C25 H25A 108.9 . . ?
C24 C25 H25B 108.9 . . ?
C26 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C28 C26 C25 110.52(19) . . ?
C28 C26 C21 114.99(18) . . ?
C25 C26 C21 112.1(2) . . ?
C28 C26 C27 118.44(19) . . ?
C25 C26 C27 110.18(19) . . ?
C21 C26 C27 89.13(17) . . ?
O4 C27 C20 107.16(19) . . ?
O4 C27 C26 118.15(19) . . ?
C20 C27 C26 90.19(17) . . ?
O4 C27 H27 113.0 . . ?
C20 C27 H27 113.0 . . ?
C26 C27 H27 113.0 . . ?
C29 C28 C33 117.1(2) . . ?
C29 C28 C26 122.6(2) . . ?
C33 C28 C26 120.2(2) . . ?
C30 C29 C28 121.4(2) . . ?
C30 C29 H29 119.3 . . ?
C28 C29 H29 119.3 . . ?
C29 C30 C31 120.4(2) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
O6 C31 C32 124.1(2) . . ?
O6 C31 C30 116.2(2) . . ?
C32 C31 C30 119.6(2) . . ?
C31 C32 C33 119.0(2) . . ?
C31 C32 H32 120.5 . . ?
C33 C32 H32 120.5 . . ?
C32 C33 C28 122.4(2) . . ?
C32 C33 H33 118.8 . . ?
C28 C33 H33 118.8 . . ?
O6 C34 H34A 109.5 . . ?
O6 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O6 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O7 C35 C36 105.3(2) . . ?
O7 C35 H35A 110.7 . . ?
C36 C35 H35A 110.7 . . ?
O7 C35 H35B 110.7 . . ?
C36 C35 H35B 110.7 . . ?
H35A C35 H35B 108.8 . . ?
C35 C36 C37 102.64(19) . . ?
C35 C36 H36A 111.2 . . ?
C37 C36 H36A 111.2 . . ?
C35 C36 H36B 111.2 . . ?
C37 C36 H36B 111.2 . . ?
H36A C36 H36B 109.2 . . ?
C36 C37 C44 104.26(19) . . ?
C36 C37 C38 114.6(2) . . ?
C44 C37 C38 90.38(17) . . ?
C36 C37 H37 114.9 . . ?
C44 C37 H37 114.9 . . ?
C38 C37 H37 114.9 . . ?
C39 C38 C37 112.77(19) . . ?
C39 C38 C43 119.3(2) . . ?
C37 C38 C43 89.89(17) . . ?
C39 C38 H38 111.1 . . ?
C37 C38 H38 111.1 . . ?
C43 C38 H38 111.1 . . ?
O8 C39 C38 120.4(2) . . ?
O8 C39 C40 120.9(2) . . ?
C38 C39 C40 118.7(2) . . ?
C39 C40 C41 115.1(2) . . ?
C39 C40 H40A 108.5 . . ?
C41 C40 H40A 108.5 . . ?
C39 C40 H40B 108.5 . . ?
C41 C40 H40B 108.5 . . ?
H40A C40 H40B 107.5 . . ?
C40 C41 C42 110.2(2) . . ?
C40 C41 H41A 109.6 . . ?
C42 C41 H41A 109.6 . . ?
C40 C41 H41B 109.6 . . ?
C42 C41 H41B 109.6 . . ?
H41A C41 H41B 108.1 . . ?
C41 C42 C43 113.2(2) . . ?
C41 C42 H42A 108.9 . . ?
C43 C42 H42A 108.9 . . ?
C41 C42 H42B 108.9 . . ?
C43 C42 H42B 108.9 . . ?
H42A C42 H42B 107.7 . . ?
C45 C43 C42 109.78(18) . . ?
C45 C43 C38 115.98(19) . . ?
C42 C43 C38 111.80(19) . . ?
C45 C43 C44 117.70(19) . . ?
C42 C43 C44 111.12(18) . . ?
C38 C43 C44 89.15(16) . . ?
O7 C44 C37 107.44(18) . . ?
O7 C44 C43 117.99(18) . . ?
C37 C44 C43 90.22(16) . . ?
O7 C44 H44 113.0 . . ?
C37 C44 H44 113.0 . . ?
C43 C44 H44 113.0 . . ?
C46 C45 C50 117.7(2) . . ?
C46 C45 C43 120.0(2) . . ?
C50 C45 C43 122.2(2) . . ?
C47 C46 C45 121.8(2) . . ?
C47 C46 H46 119.1 . . ?
C45 C46 H46 119.1 . . ?
C48 C47 C46 119.4(2) . . ?
C48 C47 H47 120.3 . . ?
C46 C47 H47 120.3 . . ?
O9 C48 C49 115.9(2) . . ?
O9 C48 C47 124.5(2) . . ?
C49 C48 C47 119.5(2) . . ?
C50 C49 C48 120.6(2) . . ?
C50 C49 H49 119.7 . . ?
C48 C49 H49 119.7 . . ?
C49 C50 C45 120.9(2) . . ?
C49 C50 H50 119.5 . . ?
C45 C50 H50 119.5 . . ?
O9 C51 H51A 109.5 . . ?
O9 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
O9 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
O10 C52 C53 105.2(2) . . ?
O10 C52 H52A 110.7 . . ?
C53 C52 H52A 110.7 . . ?
O10 C52 H52B 110.7 . . ?
C53 C52 H52B 110.7 . . ?
H52A C52 H52B 108.8 . . ?
C52 C53 C54 103.0(2) . . ?
C52 C53 H53A 111.2 . . ?
C54 C53 H53A 111.2 . . ?
C52 C53 H53B 111.2 . . ?
C54 C53 H53B 111.2 . . ?
H53A C53 H53B 109.1 . . ?
C53 C54 C61 104.39(19) . . ?
C53 C54 C55 114.3(2) . . ?
C61 C54 C55 90.43(17) . . ?
C53 C54 H54 114.9 . . ?
C61 C54 H54 114.9 . . ?
C55 C54 H54 114.9 . . ?
C56 C55 C54 112.43(19) . . ?
C56 C55 C60 119.9(2) . . ?
C54 C55 C60 89.66(17) . . ?
C56 C55 H55 111.0 . . ?
C54 C55 H55 111.0 . . ?
C60 C55 H55 111.0 . . ?
O11 C56 C55 120.7(2) . . ?
O11 C56 C57 120.8(2) . . ?
C55 C56 C57 118.5(2) . . ?
C56 C57 C58 114.9(2) . . ?
C56 C57 H57A 108.5 . . ?
C58 C57 H57A 108.5 . . ?
C56 C57 H57B 108.5 . . ?
C58 C57 H57B 108.5 . . ?
H57A C57 H57B 107.5 . . ?
C57 C58 C59 110.2(2) . . ?
C57 C58 H58A 109.6 . . ?
C59 C58 H58A 109.6 . . ?
C57 C58 H58B 109.6 . . ?
C59 C58 H58B 109.6 . . ?
H58A C58 H58B 108.1 . . ?
C58 C59 C60 113.0(2) . . ?
C58 C59 H59A 109.0 . . ?
C60 C59 H59A 109.0 . . ?
C58 C59 H59B 109.0 . . ?
C60 C59 H59B 109.0 . . ?
H59A C59 H59B 107.8 . . ?
C62 C60 C59 110.31(19) . . ?
C62 C60 C61 117.66(19) . . ?
C59 C60 C61 111.55(19) . . ?
C62 C60 C55 114.88(19) . . ?
C59 C60 C55 111.73(19) . . ?
C61 C60 C55 89.27(17) . . ?
O10 C61 C54 107.01(19) . . ?
O10 C61 C60 118.26(18) . . ?
C54 C61 C60 90.17(17) . . ?
O10 C61 H61 113.0 . . ?
C54 C61 H61 113.0 . . ?
C60 C61 H61 113.0 . . ?
C67 C62 C63 117.5(2) . . ?
C67 C62 C60 119.8(2) . . ?
C63 C62 C60 122.6(2) . . ?
C64 C63 C62 121.3(2) . . ?
C64 C63 H63 119.3 . . ?
C62 C63 H63 119.3 . . ?
C63 C64 C65 120.0(2) . . ?
C63 C64 H64 120.0 . . ?
C65 C64 H64 120.0 . . ?
O12 C65 C66 124.5(2) . . ?
O12 C65 C64 115.9(2) . . ?
C66 C65 C64 119.6(2) . . ?
C67 C66 C65 119.2(2) . . ?
C67 C66 H66 120.4 . . ?
C65 C66 H66 120.4 . . ?
C66 C67 C62 122.2(2) . . ?
C66 C67 H67 118.9 . . ?
C62 C67 H67 118.9 . . ?
O12 C68 H68A 109.5 . . ?
O12 C68 H68B 109.5 . . ?
H68A C68 H68B 109.5 . . ?
O12 C68 H68C 109.5 . . ?
H68A C68 H68C 109.5 . . ?
H68B C68 H68C 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
C2 C1 O1 C10 36.1(2) . . . . ?
O1 C1 C2 C3 -34.9(2) . . . . ?
C1 C2 C3 C10 21.2(2) . . . . ?
C1 C2 C3 C4 -75.7(2) . . . . ?
O2 C5 C4 C3 101.9(3) . . . . ?
C6 C5 C4 C3 -77.4(3) . . . . ?
O2 C5 C4 C9 -154.6(2) . . . . ?
C6 C5 C4 C9 26.2(3) . . . . ?
C2 C3 C4 C5 -125.5(2) . . . . ?
C10 C3 C4 C5 128.5(2) . . . . ?
C2 C3 C4 C9 111.9(2) . . . . ?
C10 C3 C4 C9 5.95(17) . . . . ?
O2 C5 C6 C7 -175.9(2) . . . . ?
C4 C5 C6 C7 3.3(3) . . . . ?
C5 C6 C7 C8 -46.9(3) . . . . ?
C6 C7 C8 C9 63.9(3) . . . . ?
C7 C8 C9 C11 -163.0(2) . . . . ?
C7 C8 C9 C10 63.5(3) . . . . ?
C7 C8 C9 C4 -34.3(3) . . . . ?
C5 C4 C9 C11 117.2(2) . . . . ?
C3 C4 C9 C11 -126.53(19) . . . . ?
C5 C4 C9 C8 -9.9(3) . . . . ?
C3 C4 C9 C8 106.4(2) . . . . ?
C5 C4 C9 C10 -122.1(2) . . . . ?
C3 C4 C9 C10 -5.85(17) . . . . ?
C1 O1 C10 C3 -21.9(2) . . . . ?
C1 O1 C10 C9 78.0(2) . . . . ?
C2 C3 C10 O1 -0.8(2) . . . . ?
C4 C3 C10 O1 113.83(18) . . . . ?
C2 C3 C10 C9 -120.54(19) . . . . ?
C4 C3 C10 C9 -5.95(17) . . . . ?
C11 C9 C10 O1 13.2(3) . . . . ?
C8 C9 C10 O1 142.9(2) . . . . ?
C4 C9 C10 O1 -103.8(2) . . . . ?
C11 C9 C10 C3 122.9(2) . . . . ?
C8 C9 C10 C3 -107.4(2) . . . . ?
C4 C9 C10 C3 5.91(17) . . . . ?
C8 C9 C11 C12 85.7(3) . . . . ?
C10 C9 C11 C12 -144.7(2) . . . . ?
C4 C9 C11 C12 -42.0(3) . . . . ?
C8 C9 C11 C16 -93.1(3) . . . . ?
C10 C9 C11 C16 36.5(3) . . . . ?
C4 C9 C11 C16 139.2(2) . . . . ?
C16 C11 C12 C13 -1.2(3) . . . . ?
C9 C11 C12 C13 179.9(2) . . . . ?
C11 C12 C13 C14 -1.0(4) . . . . ?
C17 O3 C14 C13 -3.5(3) . . . . ?
C17 O3 C14 C15 177.6(2) . . . . ?
C12 C13 C14 O3 -176.9(2) . . . . ?
C12 C13 C14 C15 2.0(4) . . . . ?
O3 C14 C15 C16 178.2(2) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C14 C15 C16 C11 -1.5(4) . . . . ?
C12 C11 C16 C15 2.4(4) . . . . ?
C9 C11 C16 C15 -178.7(2) . . . . ?
C27 O4 C18 C19 -35.9(2) . . . . ?
O4 C18 C19 C20 35.0(3) . . . . ?
C18 C19 C20 C27 -21.3(2) . . . . ?
C18 C19 C20 C21 75.6(3) . . . . ?
C19 C20 C21 C22 126.5(2) . . . . ?
C27 C20 C21 C22 -127.8(2) . . . . ?
C19 C20 C21 C26 -111.2(2) . . . . ?
C27 C20 C21 C26 -5.52(18) . . . . ?
C20 C21 C22 O5 -103.9(3) . . . . ?
C26 C21 C22 O5 151.9(2) . . . . ?
C20 C21 C22 C23 74.6(3) . . . . ?
C26 C21 C22 C23 -29.6(3) . . . . ?
O5 C22 C23 C24 178.6(2) . . . . ?
C21 C22 C23 C24 0.1(4) . . . . ?
C22 C23 C24 C25 44.8(3) . . . . ?
C23 C24 C25 C26 -63.4(3) . . . . ?
C24 C25 C26 C28 163.7(2) . . . . ?
C24 C25 C26 C21 34.0(3) . . . . ?
C24 C25 C26 C27 -63.6(3) . . . . ?
C22 C21 C26 C28 -115.7(2) . . . . ?
C20 C21 C26 C28 126.66(19) . . . . ?
C22 C21 C26 C25 11.6(3) . . . . ?
C20 C21 C26 C25 -106.0(2) . . . . ?
C22 C21 C26 C27 123.1(2) . . . . ?
C20 C21 C26 C27 5.43(18) . . . . ?
C18 O4 C27 C20 21.8(2) . . . . ?
C18 O4 C27 C26 -77.9(2) . . . . ?
C19 C20 C27 O4 0.9(2) . . . . ?
C21 C20 C27 O4 -114.15(18) . . . . ?
C19 C20 C27 C26 120.53(19) . . . . ?
C21 C20 C27 C26 5.51(18) . . . . ?
C28 C26 C27 O4 -14.0(3) . . . . ?
C25 C26 C27 O4 -142.6(2) . . . . ?
C21 C26 C27 O4 104.2(2) . . . . ?
C28 C26 C27 C20 -123.7(2) . . . . ?
C25 C26 C27 C20 107.8(2) . . . . ?
C21 C26 C27 C20 -5.48(18) . . . . ?
C25 C26 C28 C29 89.6(3) . . . . ?
C21 C26 C28 C29 -142.3(2) . . . . ?
C27 C26 C28 C29 -38.8(3) . . . . ?
C25 C26 C28 C33 -87.3(3) . . . . ?
C21 C26 C28 C33 40.7(3) . . . . ?
C27 C26 C28 C33 144.2(2) . . . . ?
C33 C28 C29 C30 -2.3(4) . . . . ?
C26 C28 C29 C30 -179.4(2) . . . . ?
C28 C29 C30 C31 1.1(4) . . . . ?
C34 O6 C31 C32 5.5(4) . . . . ?
C34 O6 C31 C30 -175.4(2) . . . . ?
C29 C30 C31 O6 -178.0(2) . . . . ?
C29 C30 C31 C32 1.2(4) . . . . ?
O6 C31 C32 C33 177.0(2) . . . . ?
C30 C31 C32 C33 -2.1(4) . . . . ?
C31 C32 C33 C28 0.8(4) . . . . ?
C29 C28 C33 C32 1.4(4) . . . . ?
C26 C28 C33 C32 178.5(2) . . . . ?
C44 O7 C35 C36 -35.7(2) . . . . ?
O7 C35 C36 C37 34.5(2) . . . . ?
C35 C36 C37 C44 -20.8(2) . . . . ?
C35 C36 C37 C38 76.3(2) . . . . ?
C36 C37 C38 C39 127.6(2) . . . . ?
C44 C37 C38 C39 -126.5(2) . . . . ?
C36 C37 C38 C43 -110.5(2) . . . . ?
C44 C37 C38 C43 -4.57(17) . . . . ?
C37 C38 C39 O8 -103.4(3) . . . . ?
C43 C38 C39 O8 153.1(2) . . . . ?
C37 C38 C39 C40 75.4(3) . . . . ?
C43 C38 C39 C40 -28.1(3) . . . . ?
O8 C39 C40 C41 179.7(2) . . . . ?
C38 C39 C40 C41 0.9(4) . . . . ?
C39 C40 C41 C42 43.6(3) . . . . ?
C40 C41 C42 C43 -64.2(3) . . . . ?
C41 C42 C43 C45 167.2(2) . . . . ?
C41 C42 C43 C38 37.0(3) . . . . ?
C41 C42 C43 C44 -60.9(3) . . . . ?
C39 C38 C43 C45 -118.6(2) . . . . ?
C37 C38 C43 C45 125.1(2) . . . . ?
C39 C38 C43 C42 8.3(3) . . . . ?
C37 C38 C43 C42 -107.98(19) . . . . ?
C39 C38 C43 C44 120.8(2) . . . . ?
C37 C38 C43 C44 4.49(17) . . . . ?
C35 O7 C44 C37 21.8(2) . . . . ?
C35 O7 C44 C43 -78.1(2) . . . . ?
C36 C37 C44 O7 0.5(2) . . . . ?
C38 C37 C44 O7 -115.00(18) . . . . ?
C36 C37 C44 C43 120.05(19) . . . . ?
C38 C37 C44 C43 4.55(17) . . . . ?
C45 C43 C44 O7 -13.7(3) . . . . ?
C42 C43 C44 O7 -141.5(2) . . . . ?
C38 C43 C44 O7 105.4(2) . . . . ?
C45 C43 C44 C37 -123.7(2) . . . . ?
C42 C43 C44 C37 108.6(2) . . . . ?
C38 C43 C44 C37 -4.53(17) . . . . ?
C42 C43 C45 C46 -90.7(2) . . . . ?
C38 C43 C45 C46 37.2(3) . . . . ?
C44 C43 C45 C46 140.9(2) . . . . ?
C42 C43 C45 C50 86.2(3) . . . . ?
C38 C43 C45 C50 -145.9(2) . . . . ?
C44 C43 C45 C50 -42.2(3) . . . . ?
C50 C45 C46 C47 0.2(3) . . . . ?
C43 C45 C46 C47 177.3(2) . . . . ?
C45 C46 C47 C48 1.0(4) . . . . ?
C51 O9 C48 C49 -177.5(2) . . . . ?
C51 O9 C48 C47 2.3(4) . . . . ?
C46 C47 C48 O9 179.0(2) . . . . ?
C46 C47 C48 C49 -1.1(4) . . . . ?
O9 C48 C49 C50 179.9(2) . . . . ?
C47 C48 C49 C50 0.1(4) . . . . ?
C48 C49 C50 C45 1.2(4) . . . . ?
C46 C45 C50 C49 -1.3(3) . . . . ?
C43 C45 C50 C49 -178.3(2) . . . . ?
C61 O10 C52 C53 35.2(2) . . . . ?
O10 C52 C53 C54 -34.2(2) . . . . ?
C52 C53 C54 C61 20.8(2) . . . . ?
C52 C53 C54 C55 -76.4(2) . . . . ?
C53 C54 C55 C56 -126.4(2) . . . . ?
C61 C54 C55 C56 127.6(2) . . . . ?
C53 C54 C55 C60 111.2(2) . . . . ?
C61 C54 C55 C60 5.18(17) . . . . ?
C54 C55 C56 O11 101.1(3) . . . . ?
C60 C55 C56 O11 -155.7(2) . . . . ?
C54 C55 C56 C57 -77.1(3) . . . . ?
C60 C55 C56 C57 26.2(3) . . . . ?
O11 C56 C57 C58 -176.4(2) . . . . ?
C55 C56 C57 C58 1.8(4) . . . . ?
C56 C57 C58 C59 -45.6(3) . . . . ?
C57 C58 C59 C60 64.6(3) . . . . ?
C58 C59 C60 C62 -165.6(2) . . . . ?
C58 C59 C60 C61 61.7(3) . . . . ?
C58 C59 C60 C55 -36.5(3) . . . . ?
C56 C55 C60 C62 118.6(2) . . . . ?
C54 C55 C60 C62 -125.5(2) . . . . ?
C56 C55 C60 C59 -8.0(3) . . . . ?
C54 C55 C60 C59 107.9(2) . . . . ?
C56 C55 C60 C61 -121.0(2) . . . . ?
C54 C55 C60 C61 -5.12(17) . . . . ?
C52 O10 C61 C54 -21.3(2) . . . . ?
C52 O10 C61 C60 78.4(2) . . . . ?
C53 C54 C61 O10 -0.7(2) . . . . ?
C55 C54 C61 O10 114.55(18) . . . . ?
C53 C54 C61 C60 -120.44(19) . . . . ?
C55 C54 C61 C60 -5.19(17) . . . . ?
C62 C60 C61 O10 13.6(3) . . . . ?
C59 C60 C61 O10 142.5(2) . . . . ?
C55 C60 C61 O10 -104.3(2) . . . . ?
C62 C60 C61 C54 123.1(2) . . . . ?
C59 C60 C61 C54 -108.0(2) . . . . ?
C55 C60 C61 C54 5.15(17) . . . . ?
C59 C60 C62 C67 89.6(3) . . . . ?
C61 C60 C62 C67 -140.9(2) . . . . ?
C55 C60 C62 C67 -37.8(3) . . . . ?
C59 C60 C62 C63 -87.5(3) . . . . ?
C61 C60 C62 C63 42.0(3) . . . . ?
C55 C60 C62 C63 145.1(2) . . . . ?
C67 C62 C63 C64 2.1(4) . . . . ?
C60 C62 C63 C64 179.3(2) . . . . ?
C62 C63 C64 C65 -1.1(4) . . . . ?
C68 O12 C65 C66 -0.9(3) . . . . ?
C68 O12 C65 C64 179.6(2) . . . . ?
C63 C64 C65 O12 178.7(2) . . . . ?
C63 C64 C65 C66 -0.7(4) . . . . ?
O12 C65 C66 C67 -178.0(2) . . . . ?
C64 C65 C66 C67 1.4(4) . . . . ?
C65 C66 C67 C62 -0.3(4) . . . . ?
C63 C62 C67 C66 -1.4(3) . . . . ?
C60 C62 C67 C66 -178.7(2) . . . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.037



####################################################################### 
# 
# 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_jel660a
_database_code_depnum_ccdc_archive 'CCDC 2192930'
loop_
_audit_author_name
_audit_author_address
'Jorg-M. Neudorfl'
;Department Chemie, Organische Chemie, Universitaet zu Koeln
Germany
;
_audit_update_record             
;
2022-07-27 deposited with the CCDC.	2022-10-28 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 H18 O2'
_chemical_formula_sum            'C16 H18 O2'
_chemical_formula_weight         242.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   7.7154(2)
_cell_length_b                   15.6790(5)
_cell_length_c                   20.7193(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2506.41(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9813
_cell_measurement_theta_min      5.64
_cell_measurement_theta_max      72.06
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.657
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6357
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro focus'
_diffrn_detector_type            'Bruker PhotonIII M14'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            73371
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.267
_diffrn_reflns_theta_max         72.123
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2474
_reflns_number_gt                2332
_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 APEX 3'
_computing_cell_refinement       'Bruker APEX 3'
_computing_data_reduction        
;
Bruker APEX 3
SADABS Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_computing_structure_refinement  
;
SHELXL-2014/7 (Sheldrick, 2014)
SHELXLE (C. B. Huebschle 2016)'
;
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2015)'


_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)+(0.0679P)²+2.5862P] 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         2474
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1432
_refine_ls_wR_factor_gt          0.1413
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 0.1837(2) 0.58711(10) 0.24198(7) 0.0408(4) Uani 1 1 d . . . . .
O2 O 0.10111(16) 0.39192(8) 0.45841(6) 0.0278(3) Uani 1 1 d . . . . .
C1 C 0.2272(2) 0.58068(12) 0.29826(9) 0.0257(4) Uani 1 1 d . . . . .
C2 C 0.3166(2) 0.65348(11) 0.33283(9) 0.0259(4) Uani 1 1 d . . . . .
H2A H 0.237685 0.703270 0.333248 0.031 Uiso 1 1 calc R U . . .
H2AB H 0.421027 0.669759 0.307963 0.031 Uiso 1 1 calc R U . . .
C3 C 0.3708(3) 0.63388(11) 0.40220(9) 0.0256(4) Uani 1 1 d . . . . .
H3A H 0.268277 0.636427 0.430877 0.031 Uiso 1 1 calc R U . . .
H3AB H 0.455578 0.676952 0.417142 0.031 Uiso 1 1 calc R U . . .
C4 C 0.4521(2) 0.54474(11) 0.40537(8) 0.0225(4) Uani 1 1 d . . . . .
H4A H 0.499924 0.535498 0.449154 0.027 Uiso 1 1 calc R U . . .
H4AB H 0.549512 0.541803 0.374347 0.027 Uiso 1 1 calc R U . . .
C5 C 0.3216(2) 0.47254(11) 0.38989(8) 0.0197(4) Uani 1 1 d . . . . .
C6 C 0.1695(2) 0.47234(11) 0.43972(8) 0.0221(4) Uani 1 1 d . . . . .
H6 H 0.189251 0.511722 0.476961 0.027 Uiso 1 1 calc R U . . .
C7 C -0.0130(2) 0.36326(12) 0.40807(10) 0.0307(4) Uani 1 1 d . . . . .
H7A H -0.100796 0.323263 0.425336 0.037 Uiso 1 1 calc R U . . .
H7AB H 0.052915 0.334330 0.373413 0.037 Uiso 1 1 calc R U . . .
C8 C -0.0987(2) 0.44417(13) 0.38278(10) 0.0290(4) Uani 1 1 d . . . . .
H8A H -0.137050 0.437078 0.337503 0.035 Uiso 1 1 calc R U . . .
H8AB H -0.199384 0.460498 0.409688 0.035 Uiso 1 1 calc R U . . .
C9 C 0.0461(2) 0.50971(11) 0.38794(8) 0.0237(4) Uani 1 1 d . . . . .
H9 H 0.006715 0.569462 0.396293 0.028 Uiso 1 1 calc R U . . .
C10 C 0.1920(2) 0.50080(11) 0.33578(8) 0.0213(4) Uani 1 1 d . . . . .
H10 H 0.166475 0.452215 0.305996 0.026 Uiso 1 1 calc R U . . .
C11 C 0.4185(2) 0.39009(10) 0.37783(8) 0.0184(4) Uani 1 1 d . . . . .
C12 C 0.4808(2) 0.37244(11) 0.31606(9) 0.0236(4) Uani 1 1 d . . . . .
H12 H 0.453640 0.409923 0.281487 0.028 Uiso 1 1 calc R U . . .
C13 C 0.5822(2) 0.30071(12) 0.30438(10) 0.0287(4) Uani 1 1 d . . . . .
H13 H 0.625111 0.290130 0.262168 0.034 Uiso 1 1 calc R U . . .
C14 C 0.6207(2) 0.24474(11) 0.35391(10) 0.0290(4) Uani 1 1 d . . . . .
H14 H 0.688431 0.195312 0.345737 0.035 Uiso 1 1 calc R U . . .
C15 C 0.5597(2) 0.26132(11) 0.41562(10) 0.0258(4) Uani 1 1 d . . . . .
H15 H 0.586272 0.223228 0.449880 0.031 Uiso 1 1 calc R U . . .
C16 C 0.4596(2) 0.33365(11) 0.42761(8) 0.0210(4) Uani 1 1 d . . . . .
H16 H 0.418928 0.344607 0.470090 0.025 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 1.218(2) . ?
O2 C6 1.421(2) . ?
O2 C7 1.437(2) . ?
C1 C10 1.499(2) . ?
C1 C2 1.514(3) . ?
C2 C3 1.528(2) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.533(2) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C5 1.548(2) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C11 1.514(2) . ?
C5 C6 1.563(2) . ?
C5 C10 1.566(2) . ?
C6 C9 1.549(2) . ?
C6 H6 1.0000 . ?
C7 C8 1.523(3) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C9 1.522(3) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.567(2) . ?
C9 H9 1.0000 . ?
C10 H10 1.0000 . ?
C11 C12 1.395(2) . ?
C11 C16 1.396(2) . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(3) . ?
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
C6 O2 C7 107.89(13) . . ?
O1 C1 C10 121.05(17) . . ?
O1 C1 C2 121.10(17) . . ?
C10 C1 C2 117.84(15) . . ?
C1 C2 C3 114.72(15) . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2AB 108.6 . . ?
C3 C2 H2AB 108.6 . . ?
H2A C2 H2AB 107.6 . . ?
C2 C3 C4 109.61(14) . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3AB 109.7 . . ?
C4 C3 H3AB 109.7 . . ?
H3A C3 H3AB 108.2 . . ?
C3 C4 C5 113.04(14) . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4AB 109.0 . . ?
C5 C4 H4AB 109.0 . . ?
H4A C4 H4AB 107.8 . . ?
C11 C5 C4 109.73(13) . . ?
C11 C5 C6 118.54(14) . . ?
C4 C5 C6 110.66(13) . . ?
C11 C5 C10 116.01(14) . . ?
C4 C5 C10 110.89(14) . . ?
C6 C5 C10 89.65(12) . . ?
O2 C6 C9 107.23(14) . . ?
O2 C6 C5 117.45(14) . . ?
C9 C6 C5 90.19(13) . . ?
O2 C6 H6 113.2 . . ?
C9 C6 H6 113.2 . . ?
C5 C6 H6 113.2 . . ?
O2 C7 C8 104.78(15) . . ?
O2 C7 H7A 110.8 . . ?
C8 C7 H7A 110.8 . . ?
O2 C7 H7AB 110.8 . . ?
C8 C7 H7AB 110.8 . . ?
H7A C7 H7AB 108.9 . . ?
C9 C8 C7 102.69(14) . . ?
C9 C8 H8A 111.2 . . ?
C7 C8 H8A 111.2 . . ?
C9 C8 H8AB 111.2 . . ?
C7 C8 H8AB 111.2 . . ?
H8A C8 H8AB 109.1 . . ?
C8 C9 C6 104.15(14) . . ?
C8 C9 C10 114.76(15) . . ?
C6 C9 C10 90.14(13) . . ?
C8 C9 H9 114.9 . . ?
C6 C9 H9 114.9 . . ?
C10 C9 H9 114.9 . . ?
C1 C10 C5 119.46(15) . . ?
C1 C10 C9 114.43(14) . . ?
C5 C10 C9 89.44(13) . . ?
C1 C10 H10 110.6 . . ?
C5 C10 H10 110.6 . . ?
C9 C10 H10 110.6 . . ?
C12 C11 C16 118.29(16) . . ?
C12 C11 C5 119.41(15) . . ?
C16 C11 C5 122.11(15) . . ?
C13 C12 C11 120.92(17) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.33(17) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.49(16) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C16 120.30(17) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.66(16) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?

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
O1 C1 C2 C3 -177.15(18) . . . . ?
C10 C1 C2 C3 3.6(2) . . . . ?
C1 C2 C3 C4 43.5(2) . . . . ?
C2 C3 C4 C5 -65.68(19) . . . . ?
C3 C4 C5 C11 166.16(14) . . . . ?
C3 C4 C5 C6 -61.18(18) . . . . ?
C3 C4 C5 C10 36.70(19) . . . . ?
C7 O2 C6 C9 20.44(18) . . . . ?
C7 O2 C6 C5 -79.05(18) . . . . ?
C11 C5 C6 O2 -15.9(2) . . . . ?
C4 C5 C6 O2 -143.94(15) . . . . ?
C10 C5 C6 O2 103.80(16) . . . . ?
C11 C5 C6 C9 -125.52(15) . . . . ?
C4 C5 C6 C9 106.46(14) . . . . ?
C10 C5 C6 C9 -5.80(13) . . . . ?
C6 O2 C7 C8 -35.41(18) . . . . ?
O2 C7 C8 C9 35.49(18) . . . . ?
C7 C8 C9 C6 -22.59(18) . . . . ?
C7 C8 C9 C10 74.24(18) . . . . ?
O2 C6 C9 C8 2.49(18) . . . . ?
C5 C6 C9 C8 121.42(14) . . . . ?
O2 C6 C9 C10 -113.13(14) . . . . ?
C5 C6 C9 C10 5.79(13) . . . . ?
O1 C1 C10 C5 147.81(18) . . . . ?
C2 C1 C10 C5 -33.0(2) . . . . ?
O1 C1 C10 C9 -108.1(2) . . . . ?
C2 C1 C10 C9 71.2(2) . . . . ?
C11 C5 C10 C1 -114.35(17) . . . . ?
C4 C5 C10 C1 11.7(2) . . . . ?
C6 C5 C10 C1 123.73(16) . . . . ?
C11 C5 C10 C9 127.65(15) . . . . ?
C4 C5 C10 C9 -106.32(14) . . . . ?
C6 C5 C10 C9 5.73(13) . . . . ?
C8 C9 C10 C1 126.15(17) . . . . ?
C6 C9 C10 C1 -128.18(15) . . . . ?
C8 C9 C10 C5 -111.46(15) . . . . ?
C6 C9 C10 C5 -5.78(13) . . . . ?
C4 C5 C11 C12 -86.17(18) . . . . ?
C6 C5 C11 C12 145.38(16) . . . . ?
C10 C5 C11 C12 40.4(2) . . . . ?
C4 C5 C11 C16 88.80(18) . . . . ?
C6 C5 C11 C16 -39.6(2) . . . . ?
C10 C5 C11 C16 -144.58(16) . . . . ?
C16 C11 C12 C13 -0.4(3) . . . . ?
C5 C11 C12 C13 174.80(16) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C11 0.3(3) . . . . ?
C12 C11 C16 C15 -0.3(2) . . . . ?
C5 C11 C16 C15 -175.33(15) . . . . ?

_refine_diff_density_max         0.679
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.055



