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

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

data_Compound-1
_database_code_depnum_ccdc_archive 'CCDC 1584353'
_audit_update_record             
;
2017-11-07 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   10.4344(2)
_cell_length_b                   11.4942(2)
_cell_length_c                   11.5277(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1382.58(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    288.3(1)
_cell_measurement_reflns_used    4762
_cell_measurement_theta_min      5.3980
_cell_measurement_theta_max      73.2590

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.710
_shelx_estimated_absorpt_T_min   0.815
_shelx_estimated_absorpt_T_max   0.843
_exptl_absorpt_correction_T_min  0.51490
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      288.3(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            6802
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.435
_diffrn_reflns_theta_max         73.347
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measured_fraction_theta_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 0.936
_reflns_number_total             2513
_reflns_number_gt                2419
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.666
_reflns_Friedel_fraction_max     0.856
_reflns_Friedel_fraction_full    0.903

_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+0.1468P] 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 949 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(9)
_chemical_absolute_configuration .
_refine_ls_number_reflns         2513
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0804
_refine_ls_wR_factor_gt          0.0783
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.40902(13) 0.61107(12) 0.57198(11) 0.0172(3) Uani 1 1 d . . . . .
O2 O 0.22841(14) 0.20278(13) 0.31468(11) 0.0199(3) Uani 1 1 d . . . . .
O3 O 0.24937(13) 0.42911(12) 0.29281(10) 0.0156(3) Uani 1 1 d . . . . .
H3 H 0.212716 0.378005 0.255897 0.019 Uiso 1 1 calc R U . . .
C1 C 0.20095(19) 0.7539(2) 0.48458(17) 0.0199(5) Uani 1 1 d . . . . .
H1A H 0.117629 0.780762 0.458595 0.024 Uiso 1 1 calc R U . . .
H1B H 0.217024 0.763616 0.566889 0.024 Uiso 1 1 calc R U . . .
C2 C 0.3107(2) 0.76787(19) 0.40422(18) 0.0201(5) Uani 1 1 d . . . . .
H2A H 0.393560 0.786388 0.437666 0.024 Uiso 1 1 calc R U . . .
H2B H 0.294223 0.803524 0.329436 0.024 Uiso 1 1 calc R U . . .
C3 C 0.25774(19) 0.64738(19) 0.42511(16) 0.0164(4) Uani 1 1 d . . . . .
H3A H 0.207939 0.611372 0.362606 0.020 Uiso 1 1 calc R U . . .
C4 C 0.33526(17) 0.56946(19) 0.50061(14) 0.0133(4) Uani 1 1 d . . . . .
C5 C 0.17057(18) 0.42406(19) 0.53695(16) 0.0154(4) Uani 1 1 d . . . . .
H5A H 0.153343 0.343668 0.553251 0.023 Uiso 1 1 calc R U . . .
H5B H 0.114626 0.450505 0.476325 0.023 Uiso 1 1 calc R U . . .
H5C H 0.156268 0.469515 0.605607 0.023 Uiso 1 1 calc R U . . .
C6 C 0.31161(17) 0.43778(18) 0.49772(14) 0.0128(4) Uani 1 1 d . . . . .
C7 C 0.40173(17) 0.37926(18) 0.58494(15) 0.0137(4) Uani 1 1 d . . . . .
H7A H 0.489469 0.398991 0.565283 0.016 Uiso 1 1 calc R U . . .
H7B H 0.384340 0.410064 0.661675 0.016 Uiso 1 1 calc R U . . .
C8 C 0.38879(18) 0.24860(18) 0.58830(16) 0.0137(4) Uani 1 1 d . . . . .
C9 C 0.42702(18) 0.18754(18) 0.68738(16) 0.0155(4) Uani 1 1 d . . . . .
H9 H 0.463915 0.227462 0.749095 0.019 Uiso 1 1 calc R U . . .
C10 C 0.41048(18) 0.06829(19) 0.69446(16) 0.0175(4) Uani 1 1 d . . . . .
H10 H 0.435522 0.028829 0.761148 0.021 Uiso 1 1 calc R U . . .
C11 C 0.35680(19) 0.0073(2) 0.60279(16) 0.0178(4) Uani 1 1 d . . . . .
H11 H 0.345863 -0.072869 0.608140 0.021 Uiso 1 1 calc R U . . .
C12 C 0.31947(17) 0.06563(19) 0.50322(16) 0.0163(4) Uani 1 1 d . . . . .
H12 H 0.283645 0.024760 0.441604 0.020 Uiso 1 1 calc R U . . .
C13 C 0.33569(17) 0.18563(19) 0.49559(15) 0.0142(4) Uani 1 1 d . . . . .
C14 C 0.29204(19) 0.24928(19) 0.39100(15) 0.0150(4) Uani 1 1 d . . . . .
C15 C 0.33001(17) 0.37738(18) 0.37746(14) 0.0125(4) Uani 1 1 d . . . . .
C16 C 0.46927(18) 0.37845(19) 0.33102(15) 0.0175(4) Uani 1 1 d . . . . .
H16A H 0.523093 0.335824 0.384876 0.021 Uiso 1 1 calc R U . . .
H16B H 0.471240 0.337432 0.257510 0.021 Uiso 1 1 calc R U . . .
C17 C 0.52647(19) 0.49913(19) 0.31346(17) 0.0204(5) Uani 1 1 d . . . . .
H17A H 0.464786 0.548295 0.275843 0.031 Uiso 1 1 calc R U . . .
H17B H 0.601860 0.493324 0.266084 0.031 Uiso 1 1 calc R U . . .
H17C H 0.548793 0.531811 0.387385 0.031 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.224(2) . ?
O2 C14 1.225(2) . ?
O3 C15 1.419(2) . ?
O3 H3 0.8200 . ?
C1 C2 1.482(3) . ?
C1 C3 1.523(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.511(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.488(3) . ?
C3 H3A 0.9800 . ?
C4 C6 1.534(3) . ?
C5 C6 1.548(2) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.532(2) . ?
C6 C15 1.562(2) . ?
C7 C8 1.508(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.399(3) . ?
C8 C13 1.405(3) . ?
C9 C10 1.384(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.387(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.482(3) . ?
C14 C15 1.533(3) . ?
C15 C16 1.549(3) . ?
C16 C17 1.524(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O3 H3 109.5 . . ?
C2 C1 C3 60.33(14) . . ?
C2 C1 H1A 117.7 . . ?
C3 C1 H1A 117.7 . . ?
C2 C1 H1B 117.7 . . ?
C3 C1 H1B 117.7 . . ?
H1A C1 H1B 114.9 . . ?
C1 C2 C3 61.19(14) . . ?
C1 C2 H2A 117.6 . . ?
C3 C2 H2A 117.6 . . ?
C1 C2 H2B 117.6 . . ?
C3 C2 H2B 117.6 . . ?
H2A C2 H2B 114.8 . . ?
C4 C3 C2 116.49(17) . . ?
C4 C3 C1 115.60(16) . . ?
C2 C3 C1 58.47(14) . . ?
C4 C3 H3A 117.7 . . ?
C2 C3 H3A 117.7 . . ?
C1 C3 H3A 117.7 . . ?
O1 C4 C3 120.0(2) . . ?
O1 C4 C6 120.09(17) . . ?
C3 C4 C6 119.59(16) . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C6 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 108.68(15) . . ?
C7 C6 C5 110.32(14) . . ?
C4 C6 C5 104.31(16) . . ?
C7 C6 C15 108.17(15) . . ?
C4 C6 C15 115.97(15) . . ?
C5 C6 C15 109.32(14) . . ?
C8 C7 C6 113.52(16) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C13 118.37(18) . . ?
C9 C8 C7 119.67(17) . . ?
C13 C8 C7 121.93(18) . . ?
C10 C9 C8 120.64(18) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.43(18) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 119.86(18) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C8 120.69(18) . . ?
C12 C13 C14 120.20(17) . . ?
C8 C13 C14 119.07(19) . . ?
O2 C14 C13 122.38(19) . . ?
O2 C14 C15 119.09(17) . . ?
C13 C14 C15 118.53(16) . . ?
O3 C15 C14 108.62(15) . . ?
O3 C15 C16 108.38(14) . . ?
C14 C15 C16 106.58(16) . . ?
O3 C15 C6 110.56(15) . . ?
C14 C15 C6 107.75(14) . . ?
C16 C15 C6 114.74(15) . . ?
C17 C16 C15 114.88(17) . . ?
C17 C16 H16A 108.5 . . ?
C15 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C15 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.040



####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1585557'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 O3'
_chemical_formula_sum            'C20 H20 O3'
_chemical_formula_weight         308.36

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4310(6)
_cell_length_b                   8.6965(5)
_cell_length_c                   11.7742(5)
_cell_angle_alpha                80.603(4)
_cell_angle_beta                 87.055(4)
_cell_angle_gamma                65.920(6)
_cell_volume                     777.47(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    2971
_cell_measurement_theta_min      3.8030
_cell_measurement_theta_max      72.2850

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.701
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.86741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            5036
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.806
_diffrn_reflns_theta_max         73.290
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3022
_reflns_number_gt                2658
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+0.3093P] 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         3022
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0912
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.44995(11) 0.73369(11) 0.37305(8) 0.0207(2) Uani 1 1 d . . . . .
H1 H 0.457683 0.667791 0.432957 0.025 Uiso 1 1 calc R U . . .
O2 O 0.61386(12) 0.39948(11) 0.40348(8) 0.0228(2) Uani 1 1 d . . . . .
O3 O 0.63388(12) 0.99159(12) 0.11671(8) 0.0250(2) Uani 1 1 d . . . . .
C1 C 0.78104(15) 0.47387(16) 0.12203(11) 0.0182(3) Uani 1 1 d . . . . .
C2 C 0.87293(16) 0.38230(17) 0.03567(11) 0.0213(3) Uani 1 1 d . . . . .
H2 H 0.885450 0.440664 -0.035397 0.026 Uiso 1 1 calc R U . . .
C3 C 0.94573(16) 0.20572(17) 0.05437(12) 0.0227(3) Uani 1 1 d . . . . .
H3 H 1.009174 0.146738 -0.003417 0.027 Uiso 1 1 calc R U . . .
C4 C 0.92458(16) 0.11569(17) 0.15923(12) 0.0226(3) Uani 1 1 d . . . . .
H4 H 0.973441 -0.002895 0.171447 0.027 Uiso 1 1 calc R U . . .
C5 C 0.83071(16) 0.20385(16) 0.24460(11) 0.0202(3) Uani 1 1 d . . . . .
H5 H 0.814239 0.144688 0.314223 0.024 Uiso 1 1 calc R U . . .
C6 C 0.76004(15) 0.38247(16) 0.22667(11) 0.0178(3) Uani 1 1 d . . . . .
C7 C 0.65760(15) 0.47328(16) 0.31901(10) 0.0170(3) Uani 1 1 d . . . . .
C8 C 0.60298(15) 0.66779(15) 0.30918(10) 0.0165(3) Uani 1 1 d . . . . .
C9 C 0.55931(15) 0.75331(15) 0.18012(10) 0.0173(3) Uani 1 1 d . . . . .
C10 C 0.71331(16) 0.66548(16) 0.10444(11) 0.0188(3) Uani 1 1 d . . . . .
H10A H 0.678202 0.708820 0.024331 0.023 Uiso 1 1 calc R U . . .
H10B H 0.807369 0.696742 0.119596 0.023 Uiso 1 1 calc R U . . .
C11 C 0.39582(16) 0.73838(17) 0.13999(12) 0.0226(3) Uani 1 1 d . . . . .
H11A H 0.365530 0.797137 0.062619 0.034 Uiso 1 1 calc R U . . .
H11B H 0.301356 0.788385 0.189904 0.034 Uiso 1 1 calc R U . . .
H11C H 0.418705 0.620312 0.142430 0.034 Uiso 1 1 calc R U . . .
C12 C 0.52915(16) 0.94342(16) 0.16662(10) 0.0181(3) Uani 1 1 d . . . . .
C13 C 0.36417(17) 1.06869(16) 0.21178(12) 0.0238(3) Uani 1 1 d . . . . .
H13A H 0.333868 1.013208 0.282607 0.029 Uiso 1 1 calc R U . . .
H13B H 0.270779 1.100185 0.156251 0.029 Uiso 1 1 calc R U . . .
C14 C 0.37814(19) 1.23038(18) 0.23507(13) 0.0285(3) Uani 1 1 d . . . . .
H14A H 0.458062 1.202381 0.298039 0.043 Uiso 1 1 calc R U . . .
H14B H 0.265918 1.310218 0.254271 0.043 Uiso 1 1 calc R U . . .
H14C H 0.419214 1.280207 0.167536 0.043 Uiso 1 1 calc R U . . .
C15 C 0.74983(16) 0.70033(15) 0.35943(10) 0.0173(3) Uani 1 1 d . . . . .
C16 C 0.70573(17) 0.82560(16) 0.43004(11) 0.0223(3) Uani 1 1 d . . . . .
H16 H 0.589734 0.885053 0.447051 0.027 Uiso 1 1 calc R U . . .
C17 C 0.83274(19) 0.86264(17) 0.47522(12) 0.0265(3) Uani 1 1 d . . . . .
H17 H 0.801079 0.946215 0.522311 0.032 Uiso 1 1 calc R U . . .
C18 C 1.00566(19) 0.77629(18) 0.45074(12) 0.0274(3) Uani 1 1 d . . . . .
H18 H 1.090223 0.802719 0.480028 0.033 Uiso 1 1 calc R U . . .
C19 C 1.05219(18) 0.64952(17) 0.38195(12) 0.0262(3) Uani 1 1 d . . . . .
H19 H 1.168558 0.589909 0.365903 0.031 Uiso 1 1 calc R U . . .
C20 C 0.92551(16) 0.61132(16) 0.33695(11) 0.0218(3) Uani 1 1 d . . . . .
H20 H 0.958074 0.525706 0.291467 0.026 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 C8 1.4129(14) . ?
O1 H1 0.8200 . ?
O2 C7 1.2181(15) . ?
O3 C12 1.2119(15) . ?
C1 C2 1.3958(17) . ?
C1 C6 1.3977(18) . ?
C1 C10 1.5063(17) . ?
C2 C3 1.3848(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.3944(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.3782(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.4011(18) . ?
C5 H5 0.9300 . ?
C6 C7 1.4762(17) . ?
C7 C8 1.5468(17) . ?
C8 C15 1.5424(17) . ?
C8 C9 1.5693(17) . ?
C9 C10 1.5353(17) . ?
C9 C11 1.5405(17) . ?
C9 C12 1.5487(17) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.5102(17) . ?
C13 C14 1.5266(19) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.3964(17) . ?
C15 C20 1.3979(17) . ?
C16 C17 1.3890(19) . ?
C16 H16 0.9300 . ?
C17 C18 1.381(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.390(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.3916(18) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 H1 109.5 . . ?
C2 C1 C6 118.16(12) . . ?
C2 C1 C10 120.74(11) . . ?
C6 C1 C10 121.05(11) . . ?
C3 C2 C1 120.90(12) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.48(12) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.47(12) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.11(12) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 120.85(11) . . ?
C1 C6 C7 120.30(11) . . ?
C5 C6 C7 118.82(11) . . ?
O2 C7 C6 121.89(11) . . ?
O2 C7 C8 118.51(10) . . ?
C6 C7 C8 119.60(10) . . ?
O1 C8 C15 110.16(10) . . ?
O1 C8 C7 107.72(9) . . ?
C15 C8 C7 109.03(9) . . ?
O1 C8 C9 107.96(9) . . ?
C15 C8 C9 112.27(10) . . ?
C7 C8 C9 109.60(10) . . ?
C10 C9 C11 109.75(10) . . ?
C10 C9 C12 107.52(10) . . ?
C11 C9 C12 109.90(10) . . ?
C10 C9 C8 109.73(10) . . ?
C11 C9 C8 109.87(10) . . ?
C12 C9 C8 110.04(10) . . ?
C1 C10 C9 114.89(10) . . ?
C1 C10 H10A 108.5 . . ?
C9 C10 H10A 108.5 . . ?
C1 C10 H10B 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 C13 120.59(11) . . ?
O3 C12 C9 120.22(11) . . ?
C13 C12 C9 119.13(10) . . ?
C12 C13 C14 113.59(11) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 118.19(12) . . ?
C16 C15 C8 118.65(11) . . ?
C20 C15 C8 123.16(11) . . ?
C17 C16 C15 120.90(12) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 120.48(12) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 119.40(13) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C18 C19 C20 120.33(13) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C15 120.68(12) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.205
_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_data
_database_code_depnum_ccdc_archive 'CCDC 1585556'
_audit_update_record             
;
2017-11-14 deposited with the CCDC.
2018-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H21 F O3'
_chemical_formula_weight         388.42

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/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                   9.8733(7)
_cell_length_b                   10.3877(7)
_cell_length_c                   37.781(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.893(6)
_cell_angle_gamma                90
_cell_volume                     3846.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.0(6)
_cell_measurement_reflns_used    2906
_cell_measurement_theta_min      4.3980
_cell_measurement_theta_max      72.8480

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.763
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.30077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(6)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            22968
_diffrn_reflns_av_unetI/netI     0.1562
_diffrn_reflns_av_R_equivalents  0.1712
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         4.417
_diffrn_reflns_theta_max         66.581
_diffrn_reflns_theta_full        66.581
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             6725
_reflns_number_gt                4051
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0609P)²] 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     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.00046(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6725
_refine_ls_number_parameters     526
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1466
_refine_ls_R_factor_gt           0.0889
_refine_ls_wR_factor_ref         0.1914
_refine_ls_wR_factor_gt          0.1572
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.027
_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 0.5371(2) 0.1039(2) 0.55059(6) 0.0295(6) Uani 1 1 d . U . . .
F2 F 1.1259(2) -0.0891(2) 0.45354(6) 0.0270(6) Uani 1 1 d . U . . .
O1 O 0.1744(3) 0.5877(3) 0.45034(8) 0.0264(7) Uani 1 1 d . . . . .
O2 O 0.1800(3) 0.4319(2) 0.35887(7) 0.0185(6) Uani 1 1 d . . . . .
H2O H 0.190010 0.430893 0.337635 0.022 Uiso 1 1 calc R U . . .
O3 O 0.3953(3) 0.5026(3) 0.32643(7) 0.0274(7) Uani 1 1 d . . . . .
O4 O 0.9411(3) 0.0180(3) 0.20655(7) 0.0261(7) Uani 1 1 d . . . . .
O5 O 0.7343(3) 0.0252(3) 0.24563(7) 0.0253(7) Uani 1 1 d . . . . .
H5O H 0.736770 -0.003322 0.225478 0.030 Uiso 1 1 calc R U . . .
O6 O 0.7556(3) 0.2777(3) 0.31780(8) 0.0279(7) Uani 1 1 d . . . . .
C1 C 0.4940(4) 0.1529(4) 0.51739(10) 0.0212(9) Uani 1 1 d . U . . .
C2 C 0.3607(4) 0.1325(4) 0.50253(10) 0.0214(9) Uani 1 1 d . . . . .
H1 H 0.301457 0.084461 0.514643 0.026 Uiso 1 1 calc R U . . .
C3 C 0.5862(4) 0.2173(4) 0.50008(10) 0.0200(9) Uani 1 1 d . . . . .
H3 H 0.676574 0.226353 0.509988 0.024 Uiso 1 1 calc R U . . .
C4 C 0.5395(4) 0.2690(4) 0.46691(10) 0.0183(9) Uani 1 1 d . . . . .
H4 H 0.600701 0.313877 0.454608 0.022 Uiso 1 1 calc R U . . .
C5 C 0.3163(4) 0.1849(4) 0.46924(10) 0.0178(9) Uani 1 1 d . . . . .
H5 H 0.226932 0.171648 0.459053 0.021 Uiso 1 1 calc R U . . .
C6 C 0.4041(4) 0.2564(3) 0.45121(10) 0.0168(9) Uani 1 1 d . . . . .
C7 C 0.3550(4) 0.3188(4) 0.41525(10) 0.0165(8) Uani 1 1 d . . . . .
H7A H 0.277524 0.270118 0.404123 0.020 Uiso 1 1 calc R U . . .
H7B H 0.427229 0.311154 0.400085 0.020 Uiso 1 1 calc R U . . .
C8 C 0.3129(4) 0.4623(3) 0.41635(9) 0.0146(8) Uani 1 1 d . U . . .
C9 C 0.4292(4) 0.5462(4) 0.43550(10) 0.0162(8) Uani 1 1 d . . . . .
H9A H 0.395445 0.633234 0.437657 0.019 Uiso 1 1 calc R U . . .
H9B H 0.453494 0.512957 0.459408 0.019 Uiso 1 1 calc R U . . .
C10 C 0.5540(4) 0.5509(3) 0.41709(10) 0.0178(9) Uani 1 1 d . . . . .
C11 C 0.6830(4) 0.5736(4) 0.43630(10) 0.0195(9) Uani 1 1 d . . . . .
H11 H 0.689817 0.585811 0.460830 0.023 Uiso 1 1 calc R U . . .
C12 C 0.7990(4) 0.5781(4) 0.41964(11) 0.0226(9) Uani 1 1 d . . . . .
H12 H 0.883393 0.594039 0.432653 0.027 Uiso 1 1 calc R U . . .
C13 C 0.7885(4) 0.5583(4) 0.38275(11) 0.0254(10) Uani 1 1 d . . . . .
H13 H 0.866481 0.558906 0.371183 0.030 Uiso 1 1 calc R U . . .
C14 C 0.6611(4) 0.5376(4) 0.36335(11) 0.0226(9) Uani 1 1 d . . . . .
H14 H 0.654750 0.524723 0.338846 0.027 Uiso 1 1 calc R U . . .
C15 C 0.5440(4) 0.5360(3) 0.38015(10) 0.0155(8) Uani 1 1 d . . . . .
C16 C 0.4085(4) 0.5143(4) 0.35913(10) 0.0180(9) Uani 1 1 d . . . . .
C17 C 0.2794(4) 0.5140(3) 0.37742(10) 0.0151(8) Uani 1 1 d . . . . .
C18 C 0.2258(4) 0.6523(3) 0.37505(10) 0.0212(9) Uani 1 1 d . . . . .
H18A H 0.140757 0.656571 0.384929 0.032 Uiso 1 1 calc R U . . .
H18B H 0.212156 0.678788 0.350544 0.032 Uiso 1 1 calc R U . . .
H18C H 0.290924 0.708244 0.388208 0.032 Uiso 1 1 calc R U . . .
C19 C 0.1868(4) 0.4834(4) 0.43617(10) 0.0166(8) Uani 1 1 d . . . . .
C20 C 0.0833(4) 0.3823(4) 0.44030(10) 0.0167(9) Uani 1 1 d . . . . .
C21 C 0.0236(4) 0.3023(4) 0.41257(10) 0.0189(9) Uani 1 1 d . . . . .
H21 H 0.047769 0.311671 0.389661 0.023 Uiso 1 1 calc R U . . .
C22 C -0.0701(4) 0.2105(4) 0.41933(11) 0.0250(10) Uani 1 1 d . . . . .
H22 H -0.109533 0.157971 0.400986 0.030 Uiso 1 1 calc R U . . .
C23 C -0.1056(4) 0.1963(4) 0.45319(11) 0.0263(10) Uani 1 1 d . . . . .
H23 H -0.167851 0.133140 0.457822 0.032 Uiso 1 1 calc R U . . .
C24 C -0.0486(4) 0.2762(4) 0.48054(11) 0.0245(10) Uani 1 1 d . . . . .
H24 H -0.073396 0.266578 0.503372 0.029 Uiso 1 1 calc R U . . .
C25 C 0.0446(4) 0.3698(4) 0.47399(10) 0.0194(9) Uani 1 1 d . . . . .
H25 H 0.081099 0.424214 0.492245 0.023 Uiso 1 1 calc R U . . .
C26 C 0.4912(4) -0.0775(4) 0.36234(12) 0.0300(11) Uani 1 1 d . . . . .
H26 H 0.436042 -0.130084 0.374461 0.036 Uiso 1 1 calc R U . . .
C27 C 0.5402(4) 0.0383(4) 0.37727(11) 0.0274(10) Uani 1 1 d . . . . .
H27 H 0.514772 0.064199 0.399090 0.033 Uiso 1 1 calc R U . . .
C28 C 0.5252(4) -0.1139(4) 0.32937(12) 0.0288(11) Uani 1 1 d . . . . .
H28 H 0.489689 -0.189215 0.318657 0.035 Uiso 1 1 calc R U . . .
C29 C 0.6124(4) -0.0378(4) 0.31238(11) 0.0230(9) Uani 1 1 d . . . . .
H29 H 0.635533 -0.062215 0.290199 0.028 Uiso 1 1 calc R U . . .
C30 C 0.6254(4) 0.1150(4) 0.36036(10) 0.0194(9) Uani 1 1 d . . . . .
H30 H 0.655808 0.193164 0.370371 0.023 Uiso 1 1 calc R U . . .
C31 C 0.6657(4) 0.0751(4) 0.32821(10) 0.0179(9) Uani 1 1 d . . . . .
C32 C 0.7665(4) 0.1616(4) 0.31363(10) 0.0158(8) Uani 1 1 d . . . . .
C33 C 0.8871(4) 0.1106(4) 0.29511(10) 0.0153(8) Uani 1 1 d . U . . .
C34 C 0.9344(4) -0.0272(3) 0.30663(9) 0.0149(8) Uani 1 1 d . . . . .
H34A H 0.858687 -0.085648 0.300278 0.018 Uiso 1 1 calc R U . . .
H34B H 1.006935 -0.052072 0.292841 0.018 Uiso 1 1 calc R U . . .
C35 C 0.9852(4) -0.0468(3) 0.34609(10) 0.0155(8) Uani 1 1 d . . . . .
C36 C 1.1179(4) -0.0111(4) 0.36032(10) 0.0177(9) Uani 1 1 d . . . . .
H36 H 1.175722 0.023632 0.345135 0.021 Uiso 1 1 calc R U . . .
C37 C 1.1665(4) -0.0258(4) 0.39651(10) 0.0190(9) Uani 1 1 d . . . . .
H37 H 1.254413 -0.001089 0.405538 0.023 Uiso 1 1 calc R U . . .
C38 C 1.0795(4) -0.0778(4) 0.41774(10) 0.0198(9) Uani 1 1 d . . . . .
C39 C 0.9512(4) -0.1194(4) 0.40506(10) 0.0207(9) Uani 1 1 d . . . . .
H39 H 0.895998 -0.157498 0.420392 0.025 Uiso 1 1 calc R U . . .
C40 C 0.9036(4) -0.1043(4) 0.36881(11) 0.0208(9) Uani 1 1 d . . . . .
H40 H 0.816860 -0.133023 0.360044 0.025 Uiso 1 1 calc R U . . .
C41 C 1.0059(4) 0.2075(4) 0.30356(10) 0.0169(8) Uani 1 1 d . . . . .
H41A H 0.971841 0.293992 0.298518 0.020 Uiso 1 1 calc R U . . .
H41B H 1.038603 0.202947 0.328791 0.020 Uiso 1 1 calc R U . . .
C42 C 1.1229(4) 0.1829(3) 0.28255(10) 0.0173(9) Uani 1 1 d . . . . .
C43 C 1.2558(4) 0.2214(4) 0.29618(11) 0.0193(9) Uani 1 1 d . . . . .
H43 H 1.271030 0.260308 0.318481 0.023 Uiso 1 1 calc R U . . .
C44 C 1.3630(4) 0.2021(4) 0.27678(11) 0.0250(10) Uani 1 1 d . . . . .
H44 H 1.450325 0.228951 0.285720 0.030 Uiso 1 1 calc R U . . .
C45 C 1.3403(4) 0.1416(4) 0.24340(11) 0.0267(10) Uani 1 1 d . . . . .
H45 H 1.412823 0.127485 0.230284 0.032 Uiso 1 1 calc R U . . .
C46 C 1.2088(4) 0.1024(4) 0.22982(11) 0.0266(10) Uani 1 1 d . . . . .
H46 H 1.193924 0.062033 0.207723 0.032 Uiso 1 1 calc R U . . .
C47 C 1.1011(4) 0.1237(4) 0.24923(10) 0.0188(9) Uani 1 1 d . . . . .
C48 C 0.9626(4) 0.0794(4) 0.23443(10) 0.0183(9) Uani 1 1 d . . . . .
C49 C 0.8412(4) 0.1151(4) 0.25366(10) 0.0160(8) Uani 1 1 d . . . . .
C50 C 0.7936(4) 0.2475(4) 0.23948(11) 0.0244(10) Uani 1 1 d . . . . .
H50A H 0.714682 0.273298 0.250287 0.037 Uiso 1 1 calc R U . . .
H50B H 0.770767 0.243165 0.214080 0.037 Uiso 1 1 calc R U . . .
H50C H 0.865346 0.309109 0.245170 0.037 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
F1 C1 1.373(4) . ?
F2 C38 1.380(4) . ?
O1 C19 1.221(4) . ?
O2 C17 1.420(4) . ?
O2 H2O 0.8200 . ?
O3 C16 1.232(4) . ?
O4 C48 1.228(4) . ?
O5 C49 1.414(4) . ?
O5 H5O 0.8200 . ?
O6 C32 1.222(4) . ?
C1 C3 1.359(6) . ?
C1 C2 1.384(6) . ?
C2 C5 1.392(5) . ?
C2 H1 0.9300 . ?
C3 C4 1.391(5) . ?
C3 H3 0.9300 . ?
C4 C6 1.403(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.530(5) . ?
C7 C8 1.549(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C19 1.544(5) . ?
C8 C9 1.550(5) . ?
C8 C17 1.564(5) . ?
C9 C10 1.486(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.396(5) . ?
C10 C11 1.409(5) . ?
C11 C12 1.372(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.400(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.394(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.488(5) . ?
C16 C17 1.522(5) . ?
C17 C18 1.530(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.486(5) . ?
C20 C25 1.378(5) . ?
C20 C21 1.410(5) . ?
C21 C22 1.374(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.374(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.390(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.382(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C28 1.381(6) . ?
C26 C27 1.391(6) . ?
C26 H26 0.9300 . ?
C27 C30 1.370(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.382(5) . ?
C28 H28 0.9300 . ?
C29 C31 1.391(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.387(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.494(5) . ?
C32 C33 1.546(5) . ?
C33 C41 1.550(5) . ?
C33 C34 1.552(5) . ?
C33 C49 1.578(5) . ?
C34 C35 1.529(5) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 C40 1.381(5) . ?
C35 C36 1.404(5) . ?
C36 C37 1.402(5) . ?
C36 H36 0.9300 . ?
C37 C38 1.355(5) . ?
C37 H37 0.9300 . ?
C38 C39 1.369(6) . ?
C39 C40 1.402(5) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
C41 C42 1.500(5) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C47 1.394(5) . ?
C42 C43 1.409(5) . ?
C43 C44 1.373(5) . ?
C43 H43 0.9300 . ?
C44 C45 1.403(6) . ?
C44 H44 0.9300 . ?
C45 C46 1.398(6) . ?
C45 H45 0.9300 . ?
C46 C47 1.380(5) . ?
C46 H46 0.9300 . ?
C47 C48 1.487(6) . ?
C48 C49 1.520(5) . ?
C49 C50 1.530(5) . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O2 H2O 109.5 . . ?
C49 O5 H5O 109.5 . . ?
C3 C1 F1 118.0(4) . . ?
C3 C1 C2 122.6(4) . . ?
F1 C1 C2 119.3(4) . . ?
C1 C2 C5 119.2(4) . . ?
C1 C2 H1 120.4 . . ?
C5 C2 H1 120.4 . . ?
C1 C3 C4 117.1(4) . . ?
C1 C3 H3 121.5 . . ?
C4 C3 H3 121.5 . . ?
C3 C4 C6 122.7(4) . . ?
C3 C4 H4 118.6 . . ?
C6 C4 H4 118.6 . . ?
C6 C5 C2 120.5(4) . . ?
C6 C5 H5 119.7 . . ?
C2 C5 H5 119.7 . . ?
C5 C6 C4 117.7(4) . . ?
C5 C6 C7 121.0(4) . . ?
C4 C6 C7 121.3(3) . . ?
C6 C7 C8 116.1(3) . . ?
C6 C7 H7A 108.2 . . ?
C8 C7 H7A 108.2 . . ?
C6 C7 H7B 108.2 . . ?
C8 C7 H7B 108.2 . . ?
H7A C7 H7B 107.4 . . ?
C19 C8 C7 112.6(3) . . ?
C19 C8 C9 106.8(3) . . ?
C7 C8 C9 111.6(3) . . ?
C19 C8 C17 108.4(3) . . ?
C7 C8 C17 109.4(3) . . ?
C9 C8 C17 107.9(3) . . ?
C10 C9 C8 114.1(3) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C15 C10 C11 119.0(4) . . ?
C15 C10 C9 120.1(4) . . ?
C11 C10 C9 120.9(4) . . ?
C12 C11 C10 121.5(4) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 119.0(4) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 120.0(4) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.7(4) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C10 119.6(4) . . ?
C14 C15 C16 120.3(3) . . ?
C10 C15 C16 120.1(4) . . ?
O3 C16 C15 122.0(4) . . ?
O3 C16 C17 117.4(4) . . ?
C15 C16 C17 120.4(3) . . ?
O2 C17 C16 110.1(3) . . ?
O2 C17 C18 108.8(3) . . ?
C16 C17 C18 105.9(3) . . ?
O2 C17 C8 108.3(3) . . ?
C16 C17 C8 109.5(3) . . ?
C18 C17 C8 114.2(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C19 C20 118.4(3) . . ?
O1 C19 C8 117.9(3) . . ?
C20 C19 C8 123.7(3) . . ?
C25 C20 C21 119.5(4) . . ?
C25 C20 C19 115.7(3) . . ?
C21 C20 C19 124.7(3) . . ?
C22 C21 C20 120.1(4) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 120.0(4) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C22 C23 C24 120.1(4) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 120.4(4) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C20 C25 C24 119.7(4) . . ?
C20 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C28 C26 C27 119.5(4) . . ?
C28 C26 H26 120.3 . . ?
C27 C26 H26 120.3 . . ?
C30 C27 C26 121.1(4) . . ?
C30 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
C26 C28 C29 119.6(4) . . ?
C26 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C28 C29 C31 120.5(4) . . ?
C28 C29 H29 119.8 . . ?
C31 C29 H29 119.8 . . ?
C27 C30 C31 119.4(4) . . ?
C27 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
C30 C31 C29 119.7(4) . . ?
C30 C31 C32 114.7(3) . . ?
C29 C31 C32 125.7(4) . . ?
O6 C32 C31 118.2(3) . . ?
O6 C32 C33 118.7(3) . . ?
C31 C32 C33 123.0(3) . . ?
C32 C33 C41 106.8(3) . . ?
C32 C33 C34 114.3(3) . . ?
C41 C33 C34 110.3(3) . . ?
C32 C33 C49 107.1(3) . . ?
C41 C33 C49 107.8(3) . . ?
C34 C33 C49 110.3(3) . . ?
C35 C34 C33 116.7(3) . . ?
C35 C34 H34A 108.1 . . ?
C33 C34 H34A 108.1 . . ?
C35 C34 H34B 108.1 . . ?
C33 C34 H34B 108.1 . . ?
H34A C34 H34B 107.3 . . ?
C40 C35 C36 117.6(4) . . ?
C40 C35 C34 121.1(3) . . ?
C36 C35 C34 121.3(3) . . ?
C37 C36 C35 122.6(4) . . ?
C37 C36 H36 118.7 . . ?
C35 C36 H36 118.7 . . ?
C38 C37 C36 116.9(4) . . ?
C38 C37 H37 121.5 . . ?
C36 C37 H37 121.5 . . ?
C37 C38 C39 122.9(4) . . ?
C37 C38 F2 117.0(4) . . ?
C39 C38 F2 120.0(3) . . ?
C38 C39 C40 119.6(4) . . ?
C38 C39 H39 120.2 . . ?
C40 C39 H39 120.2 . . ?
C35 C40 C39 120.2(4) . . ?
C35 C40 H40 119.9 . . ?
C39 C40 H40 119.9 . . ?
C42 C41 C33 113.1(3) . . ?
C42 C41 H41A 109.0 . . ?
C33 C41 H41A 109.0 . . ?
C42 C41 H41B 109.0 . . ?
C33 C41 H41B 109.0 . . ?
H41A C41 H41B 107.8 . . ?
C47 C42 C43 119.5(4) . . ?
C47 C42 C41 120.5(4) . . ?
C43 C42 C41 120.0(3) . . ?
C44 C43 C42 120.5(4) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C43 C44 C45 119.7(4) . . ?
C43 C44 H44 120.2 . . ?
C45 C44 H44 120.2 . . ?
C46 C45 C44 120.1(4) . . ?
C46 C45 H45 119.9 . . ?
C44 C45 H45 119.9 . . ?
C47 C46 C45 119.9(4) . . ?
C47 C46 H46 120.0 . . ?
C45 C46 H46 120.0 . . ?
C46 C47 C42 120.3(4) . . ?
C46 C47 C48 118.9(4) . . ?
C42 C47 C48 120.8(4) . . ?
O4 C48 C47 122.7(4) . . ?
O4 C48 C49 118.1(4) . . ?
C47 C48 C49 119.1(3) . . ?
O5 C49 C48 110.3(3) . . ?
O5 C49 C50 109.1(3) . . ?
C48 C49 C50 106.2(3) . . ?
O5 C49 C33 108.2(3) . . ?
C48 C49 C33 108.6(3) . . ?
C50 C49 C33 114.4(3) . . ?
C49 C50 H50A 109.5 . . ?
C49 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
C49 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 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
C3 C1 C2 C5 -3.1(6) . . . . ?
F1 C1 C2 C5 178.5(3) . . . . ?
F1 C1 C3 C4 -178.3(3) . . . . ?
C2 C1 C3 C4 3.2(6) . . . . ?
C1 C3 C4 C6 -0.3(6) . . . . ?
C1 C2 C5 C6 -0.1(6) . . . . ?
C2 C5 C6 C4 2.8(6) . . . . ?
C2 C5 C6 C7 -177.7(3) . . . . ?
C3 C4 C6 C5 -2.7(6) . . . . ?
C3 C4 C6 C7 177.8(3) . . . . ?
C5 C6 C7 C8 96.8(4) . . . . ?
C4 C6 C7 C8 -83.6(4) . . . . ?
C6 C7 C8 C19 -64.9(4) . . . . ?
C6 C7 C8 C9 55.2(4) . . . . ?
C6 C7 C8 C17 174.6(3) . . . . ?
C19 C8 C9 C10 -172.5(3) . . . . ?
C7 C8 C9 C10 64.0(4) . . . . ?
C17 C8 C9 C10 -56.2(4) . . . . ?
C8 C9 C10 C15 28.6(5) . . . . ?
C8 C9 C10 C11 -153.1(3) . . . . ?
C15 C10 C11 C12 -1.7(6) . . . . ?
C9 C10 C11 C12 180.0(4) . . . . ?
C10 C11 C12 C13 -0.7(6) . . . . ?
C11 C12 C13 C14 1.6(6) . . . . ?
C12 C13 C14 C15 -0.2(6) . . . . ?
C13 C14 C15 C10 -2.2(6) . . . . ?
C13 C14 C15 C16 179.8(4) . . . . ?
C11 C10 C15 C14 3.1(5) . . . . ?
C9 C10 C15 C14 -178.5(4) . . . . ?
C11 C10 C15 C16 -178.9(3) . . . . ?
C9 C10 C15 C16 -0.5(5) . . . . ?
C14 C15 C16 O3 -3.1(6) . . . . ?
C10 C15 C16 O3 178.9(4) . . . . ?
C14 C15 C16 C17 -179.3(3) . . . . ?
C10 C15 C16 C17 2.6(5) . . . . ?
O3 C16 C17 O2 33.3(5) . . . . ?
C15 C16 C17 O2 -150.3(3) . . . . ?
O3 C16 C17 C18 -84.2(4) . . . . ?
C15 C16 C17 C18 92.2(4) . . . . ?
O3 C16 C17 C8 152.3(3) . . . . ?
C15 C16 C17 C8 -31.3(5) . . . . ?
C19 C8 C17 O2 -68.9(4) . . . . ?
C7 C8 C17 O2 54.2(4) . . . . ?
C9 C8 C17 O2 175.8(3) . . . . ?
C19 C8 C17 C16 171.0(3) . . . . ?
C7 C8 C17 C16 -65.9(4) . . . . ?
C9 C8 C17 C16 55.7(4) . . . . ?
C19 C8 C17 C18 52.4(4) . . . . ?
C7 C8 C17 C18 175.6(3) . . . . ?
C9 C8 C17 C18 -62.9(4) . . . . ?
C7 C8 C19 O1 153.0(3) . . . . ?
C9 C8 C19 O1 30.2(5) . . . . ?
C17 C8 C19 O1 -85.9(4) . . . . ?
C7 C8 C19 C20 -24.2(5) . . . . ?
C9 C8 C19 C20 -147.0(4) . . . . ?
C17 C8 C19 C20 97.0(4) . . . . ?
O1 C19 C20 C25 -42.9(5) . . . . ?
C8 C19 C20 C25 134.2(4) . . . . ?
O1 C19 C20 C21 136.4(4) . . . . ?
C8 C19 C20 C21 -46.5(6) . . . . ?
C25 C20 C21 C22 -1.5(6) . . . . ?
C19 C20 C21 C22 179.2(4) . . . . ?
C20 C21 C22 C23 -0.2(6) . . . . ?
C21 C22 C23 C24 1.1(6) . . . . ?
C22 C23 C24 C25 -0.4(6) . . . . ?
C21 C20 C25 C24 2.2(6) . . . . ?
C19 C20 C25 C24 -178.4(4) . . . . ?
C23 C24 C25 C20 -1.3(6) . . . . ?
C28 C26 C27 C30 -2.2(7) . . . . ?
C27 C26 C28 C29 2.9(7) . . . . ?
C26 C28 C29 C31 -0.1(7) . . . . ?
C26 C27 C30 C31 -1.4(7) . . . . ?
C27 C30 C31 C29 4.2(6) . . . . ?
C27 C30 C31 C32 -175.7(4) . . . . ?
C28 C29 C31 C30 -3.5(6) . . . . ?
C28 C29 C31 C32 176.4(4) . . . . ?
C30 C31 C32 O6 -36.4(5) . . . . ?
C29 C31 C32 O6 143.7(4) . . . . ?
C30 C31 C32 C33 140.7(4) . . . . ?
C29 C31 C32 C33 -39.2(6) . . . . ?
O6 C32 C33 C41 29.5(5) . . . . ?
C31 C32 C33 C41 -147.6(3) . . . . ?
O6 C32 C33 C34 151.8(3) . . . . ?
C31 C32 C33 C34 -25.4(5) . . . . ?
O6 C32 C33 C49 -85.8(4) . . . . ?
C31 C32 C33 C49 97.1(4) . . . . ?
C32 C33 C34 C35 -60.6(4) . . . . ?
C41 C33 C34 C35 59.7(4) . . . . ?
C49 C33 C34 C35 178.7(3) . . . . ?
C33 C34 C35 C40 102.3(4) . . . . ?
C33 C34 C35 C36 -79.8(5) . . . . ?
C40 C35 C36 C37 -3.2(6) . . . . ?
C34 C35 C36 C37 178.8(3) . . . . ?
C35 C36 C37 C38 0.5(6) . . . . ?
C36 C37 C38 C39 2.4(6) . . . . ?
C36 C37 C38 F2 -178.3(3) . . . . ?
C37 C38 C39 C40 -2.4(6) . . . . ?
F2 C38 C39 C40 178.3(3) . . . . ?
C36 C35 C40 C39 3.2(5) . . . . ?
C34 C35 C40 C39 -178.9(3) . . . . ?
C38 C39 C40 C35 -0.5(6) . . . . ?
C32 C33 C41 C42 -170.6(3) . . . . ?
C34 C33 C41 C42 64.6(4) . . . . ?
C49 C33 C41 C42 -55.8(4) . . . . ?
C33 C41 C42 C47 27.6(5) . . . . ?
C33 C41 C42 C43 -153.5(3) . . . . ?
C47 C42 C43 C44 0.5(6) . . . . ?
C41 C42 C43 C44 -178.4(4) . . . . ?
C42 C43 C44 C45 -1.0(6) . . . . ?
C43 C44 C45 C46 0.7(6) . . . . ?
C44 C45 C46 C47 0.2(6) . . . . ?
C45 C46 C47 C42 -0.7(6) . . . . ?
C45 C46 C47 C48 -179.1(4) . . . . ?
C43 C42 C47 C46 0.4(6) . . . . ?
C41 C42 C47 C46 179.3(4) . . . . ?
C43 C42 C47 C48 178.7(4) . . . . ?
C41 C42 C47 C48 -2.3(6) . . . . ?
C46 C47 C48 O4 4.3(6) . . . . ?
C42 C47 C48 O4 -174.1(4) . . . . ?
C46 C47 C48 C49 -173.5(4) . . . . ?
C42 C47 C48 C49 8.1(5) . . . . ?
O4 C48 C49 O5 26.7(5) . . . . ?
C47 C48 C49 O5 -155.4(3) . . . . ?
O4 C48 C49 C50 -91.4(4) . . . . ?
C47 C48 C49 C50 86.5(4) . . . . ?
O4 C48 C49 C33 145.1(3) . . . . ?
C47 C48 C49 C33 -37.0(4) . . . . ?
C32 C33 C49 O5 -66.4(4) . . . . ?
C41 C33 C49 O5 179.0(3) . . . . ?
C34 C33 C49 O5 58.5(4) . . . . ?
C32 C33 C49 C48 173.9(3) . . . . ?
C41 C33 C49 C48 59.3(4) . . . . ?
C34 C33 C49 C48 -61.2(4) . . . . ?
C32 C33 C49 C50 55.5(4) . . . . ?
C41 C33 C49 C50 -59.1(4) . . . . ?
C34 C33 C49 C50 -179.6(3) . . . . ?

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.075



