# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shelx_a
_database_code_depnum_ccdc_archive 'CCDC 1970264'
loop_
_audit_author_name
_audit_author_address
'Hidehiro Uekusa'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2019-12-05 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
"anti-5-[2-(4-trifluoromethylphenyl)isoindoline-1,3-dionyl]methyl dispiro[tricyclo [3.3.1.13,7]decane-2,3'-[1,2]dioxetane-4',2''-tricyclo[3.3.1.13,7]decan]-5-carboxylate"
_chemical_formula_moiety         'C37 H36 F3 N O6'
_chemical_formula_sum            'C37 H36 F3 N O6'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane / CH2Cl2'
_chemical_melting_point          ?

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      93(2)
_chemical_formula_weight         647.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration ad

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'

_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.
;

_cell_length_a                   6.4039(4)
_cell_length_b                   49.826(3)
_cell_length_c                   9.4014(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.163(2)
_cell_angle_gamma                90
_cell_volume                     2999.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    29277
_cell_measurement_theta_min      3.207
_cell_measurement_theta_max      27.484
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.055
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.279
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   'abscor T.Higashi RIGAKU'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'rotating anode x-ray'
_diffrn_source_type              Rigaku
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            29277
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -64
_diffrn_reflns_limit_k_max       64
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.207
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6880
_reflns_number_gt                4464
_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       RAPID-AUTO
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0933P)²+1.2451P] 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         6880
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0649
_refine_ls_wR_factor_ref         0.1866
_refine_ls_wR_factor_gt          0.1608
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 -0.0284(3) 0.26970(3) 0.65028(18) 0.0308(4) Uani 1 1 d . . . . .
N1 N 1.0547(3) 0.50714(4) 0.7541(2) 0.0273(4) Uani 1 1 d . . . . .
F1 F 1.7645(3) 0.59593(4) 0.8421(2) 0.0562(5) Uani 1 1 d . . . . .
C1 C -0.0709(4) 0.29278(4) 0.5556(3) 0.0249(5) Uani 1 1 d . . . . .
O2 O -0.0936(3) 0.28645(3) 0.77500(18) 0.0296(4) Uani 1 1 d . . . . .
F2 F 1.5718(4) 0.61511(4) 0.6855(2) 0.0690(7) Uani 1 1 d . . . . .
C2 C 0.0879(4) 0.29349(5) 0.4351(3) 0.0292(5) Uani 1 1 d . . . . .
H2 H 0.230878 0.296700 0.474702 0.035 Uiso 1 1 calc R U . . .
C3 C 0.0328(4) 0.31565(5) 0.3266(3) 0.0312(6) Uani 1 1 d . . . . .
H3A H 0.037059 0.333399 0.373816 0.037 Uiso 1 1 calc R U . . .
H3B H 0.136834 0.315691 0.248860 0.037 Uiso 1 1 calc R U . . .
F3 F 1.4897(3) 0.61674(4) 0.9050(2) 0.0567(5) Uani 1 1 d . . . . .
O3 O 0.0238(4) 0.40402(4) 0.5268(2) 0.0536(6) Uani 1 1 d . . . . .
O4 O 0.2937(3) 0.40609(3) 0.67787(19) 0.0324(4) Uani 1 1 d . . . . .
C4 C -0.1861(4) 0.31074(5) 0.2647(3) 0.0308(5) Uani 1 1 d . . . . .
H4 H -0.220941 0.325211 0.194843 0.037 Uiso 1 1 calc R U . . .
C5 C -0.1911(5) 0.28332(6) 0.1896(3) 0.0356(6) Uani 1 1 d . . . . .
H5A H -0.331637 0.280102 0.149003 0.043 Uiso 1 1 calc R U . . .
H5B H -0.088779 0.283145 0.110861 0.043 Uiso 1 1 calc R U . . .
O5 O 1.1809(3) 0.48182(4) 0.9459(2) 0.0350(4) Uani 1 1 d . . . . .
C6 C -0.1378(5) 0.26129(5) 0.2963(3) 0.0358(6) Uani 1 1 d . . . . .
H6 H -0.141451 0.243449 0.247566 0.043 Uiso 1 1 calc R U . . .
O6 O 0.8453(3) 0.52003(3) 0.56086(19) 0.0323(4) Uani 1 1 d . . . . .
C7 C 0.0816(4) 0.26620(5) 0.3579(3) 0.0349(6) Uani 1 1 d . . . . .
H7A H 0.185595 0.266058 0.280226 0.042 Uiso 1 1 calc R U . . .
H7B H 0.117644 0.251677 0.425506 0.042 Uiso 1 1 calc R U . . .
C8 C -0.2975(4) 0.26157(5) 0.4176(3) 0.0329(6) Uani 1 1 d . . . . .
H8A H -0.264704 0.247076 0.486143 0.040 Uiso 1 1 calc R U . . .
H8B H -0.439124 0.258315 0.378871 0.040 Uiso 1 1 calc R U . . .
C9 C -0.2917(4) 0.28892(5) 0.4940(3) 0.0271(5) Uani 1 1 d . . . . .
H9 H -0.396338 0.289080 0.572812 0.033 Uiso 1 1 calc R U . . .
C12 C -0.2074(4) 0.33244(5) 0.7274(3) 0.0251(5) Uani 1 1 d . . . . .
H12 H -0.350018 0.326507 0.697286 0.030 Uiso 1 1 calc R U . . .
C11 C -0.0488(4) 0.31078(5) 0.6909(2) 0.0240(5) Uani 1 1 d . . . . .
C10 C -0.3458(4) 0.31089(5) 0.3853(3) 0.0298(5) Uani 1 1 d . . . . .
H10A H -0.487290 0.307690 0.346171 0.036 Uiso 1 1 calc R U . . .
H10B H -0.345367 0.328635 0.432640 0.036 Uiso 1 1 calc R U . . .
C13 C -0.2026(4) 0.33659(5) 0.8898(3) 0.0313(6) Uani 1 1 d . . . . .
H13A H -0.307856 0.350190 0.917065 0.038 Uiso 1 1 calc R U . . .
H13B H -0.237734 0.319549 0.938257 0.038 Uiso 1 1 calc R U . . .
C14 C 0.0146(4) 0.34594(5) 0.9364(3) 0.0308(6) Uani 1 1 d . . . . .
H14 H 0.016905 0.348480 1.041931 0.037 Uiso 1 1 calc R U . . .
C15 C 0.0679(4) 0.37255(5) 0.8631(3) 0.0293(5) Uani 1 1 d . . . . .
H15A H 0.208111 0.378652 0.893816 0.035 Uiso 1 1 calc R U . . .
H15B H -0.034899 0.386431 0.890704 0.035 Uiso 1 1 calc R U . . .
C16 C 0.0644(4) 0.36877(5) 0.7012(3) 0.0251(5) Uani 1 1 d . . . . .
C17 C 0.2266(4) 0.34720(4) 0.6596(3) 0.0255(5) Uani 1 1 d . . . . .
H17A H 0.226831 0.344795 0.555115 0.031 Uiso 1 1 calc R U . . .
H17B H 0.367883 0.353058 0.689414 0.031 Uiso 1 1 calc R U . . .
C18 C 0.1717(4) 0.32035(5) 0.7328(3) 0.0264(5) Uani 1 1 d . . . . .
H18 H 0.276642 0.306393 0.705957 0.032 Uiso 1 1 calc R U . . .
C19 C 0.1769(4) 0.32471(5) 0.8946(3) 0.0304(5) Uani 1 1 d . . . . .
H19A H 0.146029 0.307607 0.943844 0.036 Uiso 1 1 calc R U . . .
H19B H 0.317849 0.330720 0.924156 0.036 Uiso 1 1 calc R U . . .
C20 C -0.1525(4) 0.35922(5) 0.6532(3) 0.0262(5) Uani 1 1 d . . . . .
H20A H -0.153857 0.356702 0.548763 0.031 Uiso 1 1 calc R U . . .
H20B H -0.258157 0.372968 0.677455 0.031 Uiso 1 1 calc R U . . .
C21 C 0.1196(4) 0.39457(5) 0.6244(3) 0.0300(5) Uani 1 1 d . . . . .
C22 C 0.3546(5) 0.43056(5) 0.6078(3) 0.0351(6) Uani 1 1 d . . . . .
H22A H 0.236971 0.443445 0.609551 0.042 Uiso 1 1 calc R U . . .
H22B H 0.388652 0.426725 0.507184 0.042 Uiso 1 1 calc R U . . .
C23 C 0.5407(4) 0.44271(5) 0.6802(3) 0.0284(5) Uani 1 1 d . . . . .
C24 C 0.6392(4) 0.43128(5) 0.7993(3) 0.0307(6) Uani 1 1 d . . . . .
H24 H 0.586700 0.414968 0.837297 0.037 Uiso 1 1 calc R U . . .
C25 C 0.8121(4) 0.44331(5) 0.8629(3) 0.0306(5) Uani 1 1 d . . . . .
H25 H 0.878458 0.435463 0.943314 0.037 Uiso 1 1 calc R U . . .
C26 C 0.8836(4) 0.46710(5) 0.8049(3) 0.0265(5) Uani 1 1 d . . . . .
C27 C 0.7852(4) 0.47859(5) 0.6877(3) 0.0272(5) Uani 1 1 d . . . . .
C28 C 0.6157(4) 0.46689(5) 0.6237(3) 0.0286(5) Uani 1 1 d . . . . .
H28 H 0.550794 0.474940 0.543365 0.034 Uiso 1 1 calc R U . . .
C29 C 0.8899(4) 0.50435(5) 0.6542(3) 0.0266(5) Uani 1 1 d . . . . .
C30 C 1.0587(4) 0.48483(5) 0.8489(3) 0.0272(5) Uani 1 1 d . . . . .
C31 C 1.1884(4) 0.53015(5) 0.7646(3) 0.0272(5) Uani 1 1 d . . . . .
C32 C 1.3900(4) 0.52777(5) 0.8182(3) 0.0311(6) Uani 1 1 d . . . . .
H32 H 1.442424 0.510708 0.845855 0.037 Uiso 1 1 calc R U . . .
C33 C 1.5152(4) 0.55059(5) 0.8313(3) 0.0318(6) Uani 1 1 d . . . . .
H33 H 1.652211 0.549100 0.869569 0.038 Uiso 1 1 calc R U . . .
C34 C 1.4398(4) 0.57546(5) 0.7884(3) 0.0296(5) Uani 1 1 d . . . . .
C35 C 1.2403(4) 0.57768(5) 0.7332(3) 0.0319(6) Uani 1 1 d . . . . .
H35 H 1.190127 0.594671 0.702623 0.038 Uiso 1 1 calc R U . . .
C36 C 1.1126(4) 0.55520(5) 0.7221(3) 0.0314(6) Uani 1 1 d . . . . .
H36 H 0.974684 0.556865 0.685699 0.038 Uiso 1 1 calc R U . . .
C37 C 1.5672(4) 0.60049(6) 0.8047(3) 0.0362(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.479(3) . ?
O1 O2 1.500(2) . ?
N1 C29 1.418(3) . ?
N1 C30 1.425(3) . ?
N1 C31 1.434(3) . ?
F1 C37 1.330(3) . ?
C1 C2 1.525(3) . ?
C1 C9 1.539(3) . ?
C1 C11 1.563(3) . ?
O2 C11 1.476(3) . ?
F2 C37 1.337(3) . ?
C2 C7 1.542(4) . ?
C2 C3 1.544(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.536(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
F3 C37 1.339(3) . ?
O3 C21 1.198(3) . ?
O4 C21 1.350(3) . ?
O4 C22 1.440(3) . ?
C4 C10 1.529(3) . ?
C4 C5 1.538(4) . ?
C4 H4 1.0000 . ?
C5 C6 1.525(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
O5 C30 1.209(3) . ?
C6 C8 1.534(4) . ?
C6 C7 1.538(4) . ?
C6 H6 1.0000 . ?
O6 C29 1.208(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.541(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.536(3) . ?
C9 H9 1.0000 . ?
C12 C11 1.522(3) . ?
C12 C13 1.541(3) . ?
C12 C20 1.547(3) . ?
C12 H12 1.0000 . ?
C11 C18 1.541(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C13 C14 1.530(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.533(3) . ?
C14 C19 1.535(4) . ?
C14 H14 1.0000 . ?
C15 C16 1.534(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.517(3) . ?
C16 C20 1.535(3) . ?
C16 C17 1.546(3) . ?
C17 C18 1.545(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.537(4) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C22 C23 1.498(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C28 1.402(3) . ?
C23 C24 1.404(4) . ?
C24 C25 1.393(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.391(3) . ?
C26 C30 1.485(4) . ?
C27 C28 1.370(4) . ?
C27 C29 1.483(3) . ?
C28 H28 0.9500 . ?
C31 C32 1.390(4) . ?
C31 C36 1.397(4) . ?
C32 C33 1.396(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.390(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.382(4) . ?
C34 C37 1.498(4) . ?
C35 C36 1.391(4) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 O2 89.23(14) . . ?
C29 N1 C30 110.5(2) . . ?
C29 N1 C31 124.5(2) . . ?
C30 N1 C31 124.8(2) . . ?
O1 C1 C2 110.08(19) . . ?
O1 C1 C9 107.26(19) . . ?
C2 C1 C9 109.7(2) . . ?
O1 C1 C11 86.59(16) . . ?
C2 C1 C11 122.1(2) . . ?
C9 C1 C11 117.3(2) . . ?
C11 O2 O1 89.05(14) . . ?
C1 C2 C7 108.2(2) . . ?
C1 C2 C3 110.9(2) . . ?
C7 C2 C3 108.3(2) . . ?
C1 C2 H2 109.8 . . ?
C7 C2 H2 109.8 . . ?
C3 C2 H2 109.8 . . ?
C4 C3 C2 110.1(2) . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3B 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.2 . . ?
C21 O4 C22 114.4(2) . . ?
C10 C4 C3 109.3(2) . . ?
C10 C4 C5 109.4(2) . . ?
C3 C4 C5 109.4(2) . . ?
C10 C4 H4 109.6 . . ?
C3 C4 H4 109.6 . . ?
C5 C4 H4 109.6 . . ?
C6 C5 C4 109.5(2) . . ?
C6 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
C5 C6 C8 109.5(2) . . ?
C5 C6 C7 109.6(2) . . ?
C8 C6 C7 109.2(2) . . ?
C5 C6 H6 109.5 . . ?
C8 C6 H6 109.5 . . ?
C7 C6 H6 109.5 . . ?
C6 C7 C2 109.9(2) . . ?
C6 C7 H7A 109.7 . . ?
C2 C7 H7A 109.7 . . ?
C6 C7 H7B 109.7 . . ?
C2 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C6 C8 C9 109.9(2) . . ?
C6 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C6 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C10 C9 C1 111.5(2) . . ?
C10 C9 C8 108.3(2) . . ?
C1 C9 C8 107.8(2) . . ?
C10 C9 H9 109.7 . . ?
C1 C9 H9 109.7 . . ?
C8 C9 H9 109.7 . . ?
C11 C12 C13 107.9(2) . . ?
C11 C12 C20 110.93(19) . . ?
C13 C12 C20 109.1(2) . . ?
C11 C12 H12 109.6 . . ?
C13 C12 H12 109.6 . . ?
C20 C12 H12 109.6 . . ?
O2 C11 C12 109.32(18) . . ?
O2 C11 C18 107.25(18) . . ?
C12 C11 C18 109.55(19) . . ?
O2 C11 C1 86.97(16) . . ?
C12 C11 C1 122.1(2) . . ?
C18 C11 C1 117.82(19) . . ?
C4 C10 C9 109.9(2) . . ?
C4 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
C4 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C14 C13 C12 109.9(2) . . ?
C14 C13 H13A 109.7 . . ?
C12 C13 H13A 109.7 . . ?
C14 C13 H13B 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C13 C14 C15 109.7(2) . . ?
C13 C14 C19 109.4(2) . . ?
C15 C14 C19 109.2(2) . . ?
C13 C14 H14 109.5 . . ?
C15 C14 H14 109.5 . . ?
C19 C14 H14 109.5 . . ?
C14 C15 C16 109.7(2) . . ?
C14 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C21 C16 C15 111.5(2) . . ?
C21 C16 C20 109.5(2) . . ?
C15 C16 C20 109.9(2) . . ?
C21 C16 C17 108.13(19) . . ?
C15 C16 C17 109.2(2) . . ?
C20 C16 C17 108.57(19) . . ?
C18 C17 C16 109.59(19) . . ?
C18 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
C19 C18 C11 108.3(2) . . ?
C19 C18 C17 108.3(2) . . ?
C11 C18 C17 111.32(19) . . ?
C19 C18 H18 109.6 . . ?
C11 C18 H18 109.6 . . ?
C17 C18 H18 109.6 . . ?
C14 C19 C18 109.8(2) . . ?
C14 C19 H19A 109.7 . . ?
C18 C19 H19A 109.7 . . ?
C14 C19 H19B 109.7 . . ?
C18 C19 H19B 109.7 . . ?
H19A C19 H19B 108.2 . . ?
C16 C20 C12 109.98(19) . . ?
C16 C20 H20A 109.7 . . ?
C12 C20 H20A 109.7 . . ?
C16 C20 H20B 109.7 . . ?
C12 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
O3 C21 O4 122.6(2) . . ?
O3 C21 C16 125.3(2) . . ?
O4 C21 C16 112.1(2) . . ?
O4 C22 C23 110.5(2) . . ?
O4 C22 H22A 109.5 . . ?
C23 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C28 C23 C24 119.8(2) . . ?
C28 C23 C22 116.6(2) . . ?
C24 C23 C22 123.6(2) . . ?
C25 C24 C23 121.6(2) . . ?
C25 C24 H24 119.2 . . ?
C23 C24 H24 119.2 . . ?
C26 C25 C24 117.6(2) . . ?
C26 C25 H25 121.2 . . ?
C24 C25 H25 121.2 . . ?
C25 C26 C27 121.0(2) . . ?
C25 C26 C30 130.6(2) . . ?
C27 C26 C30 108.4(2) . . ?
C28 C27 C26 122.0(2) . . ?
C28 C27 C29 129.3(2) . . ?
C26 C27 C29 108.7(2) . . ?
C27 C28 C23 118.1(2) . . ?
C27 C28 H28 120.9 . . ?
C23 C28 H28 120.9 . . ?
O6 C29 N1 126.3(2) . . ?
O6 C29 C27 127.4(2) . . ?
N1 C29 C27 106.3(2) . . ?
O5 C30 N1 125.4(2) . . ?
O5 C30 C26 128.5(2) . . ?
N1 C30 C26 106.1(2) . . ?
C32 C31 C36 120.1(2) . . ?
C32 C31 N1 120.7(2) . . ?
C36 C31 N1 119.2(2) . . ?
C31 C32 C33 119.7(2) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C34 C33 C32 120.1(3) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C35 C34 C33 120.0(2) . . ?
C35 C34 C37 118.3(2) . . ?
C33 C34 C37 121.6(2) . . ?
C34 C35 C36 120.5(2) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C35 C36 C31 119.6(2) . . ?
C35 C36 H36 120.2 . . ?
C31 C36 H36 120.2 . . ?
F1 C37 F2 107.0(2) . . ?
F1 C37 F3 105.7(2) . . ?
F2 C37 F3 105.7(2) . . ?
F1 C37 C34 113.7(2) . . ?
F2 C37 C34 112.4(2) . . ?
F3 C37 C34 111.9(2) . . ?

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
O2 O1 C1 C2 144.03(19) . . . . ?
O2 O1 C1 C9 -96.63(18) . . . . ?
O2 O1 C1 C11 20.95(15) . . . . ?
C1 O1 O2 C11 -22.20(17) . . . . ?
O1 C1 C2 C7 55.5(3) . . . . ?
C9 C1 C2 C7 -62.3(3) . . . . ?
C11 C1 C2 C7 154.4(2) . . . . ?
O1 C1 C2 C3 174.1(2) . . . . ?
C9 C1 C2 C3 56.3(3) . . . . ?
C11 C1 C2 C3 -87.0(3) . . . . ?
C1 C2 C3 C4 -58.8(3) . . . . ?
C7 C2 C3 C4 59.7(3) . . . . ?
C2 C3 C4 C10 59.7(3) . . . . ?
C2 C3 C4 C5 -60.1(3) . . . . ?
C10 C4 C5 C6 -59.9(3) . . . . ?
C3 C4 C5 C6 59.8(3) . . . . ?
C4 C5 C6 C8 59.7(3) . . . . ?
C4 C5 C6 C7 -60.0(3) . . . . ?
C5 C6 C7 C2 60.6(3) . . . . ?
C8 C6 C7 C2 -59.3(3) . . . . ?
C1 C2 C7 C6 60.4(3) . . . . ?
C3 C2 C7 C6 -59.8(3) . . . . ?
C5 C6 C8 C9 -60.3(3) . . . . ?
C7 C6 C8 C9 59.7(3) . . . . ?
O1 C1 C9 C10 -175.91(18) . . . . ?
C2 C1 C9 C10 -56.3(3) . . . . ?
C11 C1 C9 C10 88.9(2) . . . . ?
O1 C1 C9 C8 -57.1(2) . . . . ?
C2 C1 C9 C8 62.5(2) . . . . ?
C11 C1 C9 C8 -152.3(2) . . . . ?
C6 C8 C9 C10 60.0(3) . . . . ?
C6 C8 C9 C1 -60.8(3) . . . . ?
O1 O2 C11 C12 144.06(19) . . . . ?
O1 O2 C11 C18 -97.24(18) . . . . ?
O1 O2 C11 C1 20.98(16) . . . . ?
C13 C12 C11 O2 54.7(2) . . . . ?
C20 C12 C11 O2 174.15(18) . . . . ?
C13 C12 C11 C18 -62.5(2) . . . . ?
C20 C12 C11 C18 56.9(3) . . . . ?
C13 C12 C11 C1 153.6(2) . . . . ?
C20 C12 C11 C1 -87.0(3) . . . . ?
O1 C1 C11 O2 -21.33(16) . . . . ?
C2 C1 C11 O2 -133.0(2) . . . . ?
C9 C1 C11 O2 86.4(2) . . . . ?
O1 C1 C11 C12 -132.3(2) . . . . ?
C2 C1 C11 C12 116.1(3) . . . . ?
C9 C1 C11 C12 -24.6(3) . . . . ?
O1 C1 C11 C18 86.6(2) . . . . ?
C2 C1 C11 C18 -25.0(3) . . . . ?
C9 C1 C11 C18 -165.7(2) . . . . ?
C3 C4 C10 C9 -59.2(3) . . . . ?
C5 C4 C10 C9 60.6(3) . . . . ?
C1 C9 C10 C4 58.2(3) . . . . ?
C8 C9 C10 C4 -60.3(3) . . . . ?
C11 C12 C13 C14 61.2(3) . . . . ?
C20 C12 C13 C14 -59.4(3) . . . . ?
C12 C13 C14 C15 60.2(3) . . . . ?
C12 C13 C14 C19 -59.7(3) . . . . ?
C13 C14 C15 C16 -59.7(3) . . . . ?
C19 C14 C15 C16 60.2(3) . . . . ?
C14 C15 C16 C21 -179.2(2) . . . . ?
C14 C15 C16 C20 59.2(3) . . . . ?
C14 C15 C16 C17 -59.8(3) . . . . ?
C21 C16 C17 C18 -178.4(2) . . . . ?
C15 C16 C17 C18 60.2(3) . . . . ?
C20 C16 C17 C18 -59.7(3) . . . . ?
O2 C11 C18 C19 -56.3(2) . . . . ?
C12 C11 C18 C19 62.3(2) . . . . ?
C1 C11 C18 C19 -152.1(2) . . . . ?
O2 C11 C18 C17 -175.22(18) . . . . ?
C12 C11 C18 C17 -56.7(3) . . . . ?
C1 C11 C18 C17 89.0(2) . . . . ?
C16 C17 C18 C19 -60.4(3) . . . . ?
C16 C17 C18 C11 58.5(3) . . . . ?
C13 C14 C19 C18 59.1(3) . . . . ?
C15 C14 C19 C18 -61.1(3) . . . . ?
C11 C18 C19 C14 -59.9(2) . . . . ?
C17 C18 C19 C14 61.0(2) . . . . ?
C21 C16 C20 C12 178.24(19) . . . . ?
C15 C16 C20 C12 -59.0(2) . . . . ?
C17 C16 C20 C12 60.4(2) . . . . ?
C11 C12 C20 C16 -59.9(3) . . . . ?
C13 C12 C20 C16 58.8(2) . . . . ?
C22 O4 C21 O3 -0.1(4) . . . . ?
C22 O4 C21 C16 179.4(2) . . . . ?
C15 C16 C21 O3 -131.8(3) . . . . ?
C20 C16 C21 O3 -10.0(4) . . . . ?
C17 C16 C21 O3 108.2(3) . . . . ?
C15 C16 C21 O4 48.7(3) . . . . ?
C20 C16 C21 O4 170.6(2) . . . . ?
C17 C16 C21 O4 -71.3(3) . . . . ?
C21 O4 C22 C23 176.4(2) . . . . ?
O4 C22 C23 C28 -179.3(2) . . . . ?
O4 C22 C23 C24 0.2(4) . . . . ?
C28 C23 C24 C25 -0.5(4) . . . . ?
C22 C23 C24 C25 179.9(3) . . . . ?
C23 C24 C25 C26 0.2(4) . . . . ?
C24 C25 C26 C27 0.4(4) . . . . ?
C24 C25 C26 C30 178.7(2) . . . . ?
C25 C26 C27 C28 -0.7(4) . . . . ?
C30 C26 C27 C28 -179.4(2) . . . . ?
C25 C26 C27 C29 177.4(2) . . . . ?
C30 C26 C27 C29 -1.3(3) . . . . ?
C26 C27 C28 C23 0.4(4) . . . . ?
C29 C27 C28 C23 -177.2(2) . . . . ?
C24 C23 C28 C27 0.2(4) . . . . ?
C22 C23 C28 C27 179.8(2) . . . . ?
C30 N1 C29 O6 179.4(2) . . . . ?
C31 N1 C29 O6 3.8(4) . . . . ?
C30 N1 C29 C27 -0.5(3) . . . . ?
C31 N1 C29 C27 -176.2(2) . . . . ?
C28 C27 C29 O6 -0.9(4) . . . . ?
C26 C27 C29 O6 -178.8(2) . . . . ?
C28 C27 C29 N1 179.0(2) . . . . ?
C26 C27 C29 N1 1.1(3) . . . . ?
C29 N1 C30 O5 -179.3(2) . . . . ?
C31 N1 C30 O5 -3.7(4) . . . . ?
C29 N1 C30 C26 -0.3(3) . . . . ?
C31 N1 C30 C26 175.4(2) . . . . ?
C25 C26 C30 O5 1.5(5) . . . . ?
C27 C26 C30 O5 -180.0(3) . . . . ?
C25 C26 C30 N1 -177.5(3) . . . . ?
C27 C26 C30 N1 1.0(3) . . . . ?
C29 N1 C31 C32 -153.1(2) . . . . ?
C30 N1 C31 C32 31.8(4) . . . . ?
C29 N1 C31 C36 27.8(3) . . . . ?
C30 N1 C31 C36 -147.3(2) . . . . ?
C36 C31 C32 C33 1.0(4) . . . . ?
N1 C31 C32 C33 -178.2(2) . . . . ?
C31 C32 C33 C34 -1.2(4) . . . . ?
C32 C33 C34 C35 0.2(4) . . . . ?
C32 C33 C34 C37 178.2(2) . . . . ?
C33 C34 C35 C36 1.0(4) . . . . ?
C37 C34 C35 C36 -177.1(2) . . . . ?
C34 C35 C36 C31 -1.2(4) . . . . ?
C32 C31 C36 C35 0.2(4) . . . . ?
N1 C31 C36 C35 179.4(2) . . . . ?
C35 C34 C37 F1 -172.3(2) . . . . ?
C33 C34 C37 F1 9.7(4) . . . . ?
C35 C34 C37 F2 -50.6(3) . . . . ?
C33 C34 C37 F2 131.4(3) . . . . ?
C35 C34 C37 F3 68.1(3) . . . . ?
C33 C34 C37 F3 -109.9(3) . . . . ?

_refine_diff_density_max         0.532
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.106


_chemical_properties_physical    Heat-sensitive
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_shelx_a_pl
_database_code_depnum_ccdc_archive 'CCDC 1970265'
loop_
_audit_author_name
_audit_author_address
'Hidehiro Uekusa'
;Tokyo Institute of Technology
Japan
;

_audit_update_record             
;
2020-02-12 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;
_publcif_datablock.id            {498dcac5-38a1-403f-8d5f-1dfb962f14cc}

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
"Syn-5-[2-(4-trifluoromethylphenyl)isoindoline-1,3-dionyl]methyl dispiro[tricyclo [3.3.1.13,7]decane-2,3'-[1,2]dioxetane-4',2''-tricyclo[3.3.1.13,7]decan]-5-carboxylate"
_chemical_name_common            
"Syn-5-[2-(4-trifluoromethylphenyl)isoindoline-1,3-dionyl]methyl dispiro[tricyclo [3.3.1.13,7]decane-2,3'-[1,2]dioxetane-4',2''-tricyclo[3.3.1.13,7]decan]-5-carboxylate"
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H36 F3 N O6'
_chemical_formula_sum            'C37 H36 F3 N O6'
_chemical_formula_weight         647.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   6.847(2)
_cell_length_b                   9.989(3)
_cell_length_c                   23.661(8)
_cell_angle_alpha                81.861(13)
_cell_angle_beta                 81.721(11)
_cell_angle_gamma                71.02(2)
_cell_volume                     1506.6(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    9677
_cell_measurement_theta_min      3.164
_cell_measurement_theta_max      27.686

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.032
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.001
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_process_details   'abscor T.Higashi RIGAKU'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode x-ray'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            9677
_diffrn_reflns_av_unetI/netI     0.8840
_diffrn_reflns_av_R_equivalents  0.3365
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.164
_diffrn_reflns_theta_max         27.686
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measured_fraction_theta_full 0.866
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_Laue_measured_fraction_full 0.866
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_point_group_measured_fraction_full 0.866
_reflns_number_total             5899
_reflns_number_gt                791
_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       RAPID-AUTO
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_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)+(0.1176P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5899
_refine_ls_number_parameters     424
_refine_ls_number_restraints     270
_refine_ls_R_factor_all          0.4605
_refine_ls_R_factor_gt           0.1103
_refine_ls_wR_factor_ref         0.3699
_refine_ls_wR_factor_gt          0.2366
_refine_ls_goodness_of_fit_ref   0.719
_refine_ls_restrained_S_all      0.718
_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 1.1301(15) 0.3292(14) 1.0308(4) 0.119(3) Uani 1 1 d . U . . .
F2 F 1.2564(18) 0.1144(16) 1.0396(4) 0.151(4) Uani 1 1 d . U . . .
F3 F 1.4376(14) 0.2400(14) 0.9985(3) 0.128(4) Uani 1 1 d . U . . .
O1 O 0.6191(13) 0.0802(11) 0.2624(3) 0.062(3) Uani 1 1 d . . . . .
O2 O 0.5164(14) 0.1092(12) 0.3217(3) 0.080(4) Uani 1 1 d . . . . .
O3 O 0.3662(15) 0.1715(15) 0.5185(4) 0.116(5) Uani 1 1 d . . . . .
O4 O 0.6723(13) 0.1708(11) 0.5310(3) 0.075(4) Uani 1 1 d . . . . .
O5 O 1.2444(12) 0.3074(11) 0.7324(3) 0.065(3) Uani 1 1 d . . . . .
O6 O 0.7542(12) 0.0937(11) 0.8165(3) 0.061(3) Uani 1 1 d . . . . .
N1 N 1.0123(14) 0.2031(13) 0.7890(4) 0.062(4) Uani 1 1 d . . . . .
C1 C 0.6020(19) 0.2340(18) 0.2492(5) 0.065(3) Uani 1 1 d . U . . .
C2 C 0.7881(18) 0.2526(17) 0.2087(5) 0.063(3) Uani 1 1 d . U . . .
H2 H 0.917531 0.208625 0.228263 0.076 Uiso 1 1 calc R U . . .
C3 C 0.7590(18) 0.4141(16) 0.1909(4) 0.061(3) Uani 1 1 d . U . . .
H3A H 0.746918 0.463422 0.225307 0.073 Uiso 1 1 calc R U . . .
H3B H 0.880168 0.425895 0.164744 0.073 Uiso 1 1 calc R U . . .
C4 C 0.5672(18) 0.4756(18) 0.1616(5) 0.070(3) Uani 1 1 d . U . . .
H4 H 0.545966 0.579512 0.150949 0.084 Uiso 1 1 calc R U . . .
C5 C 0.590(2) 0.4061(18) 0.1072(5) 0.072(3) Uani 1 1 d . U . . .
H5A H 0.714105 0.414913 0.081880 0.087 Uiso 1 1 calc R U . . .
H5B H 0.465979 0.451824 0.086020 0.087 Uiso 1 1 calc R U . . .
C6 C 0.610(2) 0.2498(18) 0.1258(5) 0.073(3) Uani 1 1 d . U . . .
H6 H 0.620532 0.200334 0.091047 0.088 Uiso 1 1 calc R U . . .
C7 C 0.8068(19) 0.1811(18) 0.1554(5) 0.072(3) Uani 1 1 d . U . . .
H7A H 0.826252 0.078352 0.165712 0.086 Uiso 1 1 calc R U . . .
H7B H 0.928710 0.191291 0.129191 0.086 Uiso 1 1 calc R U . . .
C8 C 0.4223(17) 0.2344(17) 0.1671(5) 0.070(3) Uani 1 1 d . U . . .
H8A H 0.293764 0.279990 0.148105 0.084 Uiso 1 1 calc R U . . .
H8B H 0.436334 0.132288 0.177065 0.084 Uiso 1 1 calc R U . . .
C9 C 0.407(2) 0.3006(19) 0.2194(5) 0.073(3) Uani 1 1 d . U . . .
H9 H 0.284972 0.288927 0.245814 0.088 Uiso 1 1 calc R U . . .
C10 C 0.3786(19) 0.4585(18) 0.2031(5) 0.075(3) Uani 1 1 d . U . . .
H10A H 0.367054 0.505856 0.238007 0.090 Uiso 1 1 calc R U . . .
H10B H 0.249384 0.503720 0.184347 0.090 Uiso 1 1 calc R U . . .
C11 C 0.5845(19) 0.2381(18) 0.3142(5) 0.059(3) Uani 1 1 d . U . . .
C12 C 0.7822(19) 0.1940(16) 0.3433(4) 0.064(3) Uani 1 1 d . U . . .
H12 H 0.891688 0.117329 0.323313 0.077 Uiso 1 1 calc R U . . .
C13 C 0.8584(19) 0.3259(17) 0.3419(5) 0.065(3) Uani 1 1 d . U . . .
H13A H 0.989311 0.297598 0.360047 0.078 Uiso 1 1 calc R U . . .
H13B H 0.885171 0.364335 0.301643 0.078 Uiso 1 1 calc R U . . .
C14 C 0.695(2) 0.4368(18) 0.3736(5) 0.066(3) Uani 1 1 d . U . . .
H14 H 0.745457 0.520151 0.373441 0.079 Uiso 1 1 calc R U . . .
C15 C 0.651(2) 0.3791(17) 0.4360(4) 0.070(3) Uani 1 1 d . U . . .
H15A H 0.779471 0.349940 0.455180 0.084 Uiso 1 1 calc R U . . .
H15B H 0.545878 0.455263 0.456634 0.084 Uiso 1 1 calc R U . . .
C16 C 0.572(2) 0.2540(18) 0.4392(5) 0.066(3) Uani 1 1 d . U . . .
C17 C 0.3726(19) 0.3030(17) 0.4079(4) 0.072(3) Uani 1 1 d . U . . .
H17A H 0.315416 0.223042 0.409816 0.086 Uiso 1 1 calc R U . . .
H17B H 0.266161 0.381549 0.426749 0.086 Uiso 1 1 calc R U . . .
C18 C 0.424(2) 0.3520(17) 0.3468(5) 0.065(3) Uani 1 1 d . U . . .
H18 H 0.294223 0.383189 0.327306 0.078 Uiso 1 1 calc R U . . .
C19 C 0.506(2) 0.4839(17) 0.3434(5) 0.069(3) Uani 1 1 d . U . . .
H19A H 0.537973 0.517717 0.302853 0.082 Uiso 1 1 calc R U . . .
H19B H 0.398369 0.562740 0.361918 0.082 Uiso 1 1 calc R U . . .
C20 C 0.736(2) 0.1404(18) 0.4051(4) 0.067(3) Uani 1 1 d . U . . .
H20A H 0.865606 0.107803 0.423894 0.080 Uiso 1 1 calc R U . . .
H20B H 0.685710 0.057518 0.406099 0.080 Uiso 1 1 calc R U . . .
C21 C 0.518(2) 0.2057(19) 0.4997(5) 0.073(4) Uani 1 1 d . U . . .
C22 C 0.6499(18) 0.1064(16) 0.5868(4) 0.059(3) Uani 1 1 d . U . . .
H22A H 0.702138 0.001611 0.586657 0.071 Uiso 1 1 calc R U . . .
H22B H 0.501149 0.133606 0.601754 0.071 Uiso 1 1 calc R U . . .
C23 C 0.7690(18) 0.1519(17) 0.6248(5) 0.056(3) Uani 1 1 d . U . . .
C24 C 0.9265(18) 0.2137(16) 0.6009(5) 0.059(3) Uani 1 1 d . U . . .
H24 H 0.948238 0.232157 0.560333 0.071 Uiso 1 1 calc R U . . .
C25 C 1.0464(18) 0.2470(16) 0.6339(5) 0.058(3) Uani 1 1 d . U . . .
H25 H 1.152795 0.286649 0.617273 0.069 Uiso 1 1 calc R U . . .
C26 C 1.0090(17) 0.2219(15) 0.6908(5) 0.051(3) Uani 1 1 d . U . . .
C27 C 0.8597(18) 0.1594(16) 0.7160(5) 0.054(3) Uani 1 1 d . U . . .
C28 C 0.7435(17) 0.1220(16) 0.6830(5) 0.055(3) Uani 1 1 d . U . . .
H28 H 0.645432 0.075473 0.700165 0.066 Uiso 1 1 calc R U . . .
C29 C 0.8591(18) 0.1458(17) 0.7798(5) 0.061(3) Uani 1 1 d . U . . .
C30 C 1.1060(19) 0.2549(16) 0.7359(5) 0.059(3) Uani 1 1 d . U . . .
C31 C 1.0692(18) 0.2036(16) 0.8438(5) 0.058(3) Uani 1 1 d . U . . .
C32 C 0.9184(19) 0.2505(17) 0.8904(5) 0.066(3) Uani 1 1 d . U . . .
H32 H 0.774677 0.279700 0.885608 0.080 Uiso 1 1 calc R U . . .
C33 C 0.9809(19) 0.2535(18) 0.9423(5) 0.072(3) Uani 1 1 d . U . . .
H33 H 0.882034 0.282292 0.974282 0.086 Uiso 1 1 calc R U . . .
C34 C 1.189(2) 0.2141(18) 0.9472(5) 0.068(3) Uani 1 1 d . U . . .
C35 C 1.3361(19) 0.1658(16) 0.9019(5) 0.063(3) Uani 1 1 d . U . . .
H35 H 1.479383 0.133693 0.907384 0.076 Uiso 1 1 calc R U . . .
C36 C 1.2781(17) 0.1639(15) 0.8501(5) 0.061(3) Uani 1 1 d . U . . .
H36 H 1.379188 0.135757 0.818434 0.073 Uiso 1 1 calc R U . . .
C37 C 1.265(2) 0.217(2) 1.0028(6) 0.078(4) Uani 1 1 d . 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 C37 1.38(2) . ?
F2 C37 1.256(18) . ?
F3 C37 1.265(13) . ?
O6 C29 1.215(11) . ?
O5 C30 1.212(11) . ?
O4 C21 1.302(13) . ?
O4 C22 1.395(11) . ?
O3 C21 1.206(11) . ?
O2 C11 1.487(15) . ?
O2 O1 1.498(11) . ?
O1 C1 1.493(18) . ?
N1 C29 1.402(12) . ?
N1 C31 1.409(13) . ?
N1 C30 1.434(12) . ?
C37 C34 1.491(16) . ?
C34 C33 1.366(16) . ?
C34 C35 1.385(18) . ?
C33 C32 1.363(14) . ?
C33 H33 0.9500 . ?
C32 C31 1.416(18) . ?
C32 H32 0.9500 . ?
C31 C36 1.379(14) . ?
C36 C35 1.346(13) . ?
C36 H36 0.9500 . ?
C35 H35 0.9500 . ?
C29 C27 1.495(15) . ?
C27 C28 1.356(13) . ?
C27 C26 1.387(13) . ?
C26 C25 1.338(13) . ?
C26 C30 1.461(15) . ?
C28 C23 1.364(13) . ?
C28 H28 0.9500 . ?
C23 C24 1.423(13) . ?
C23 C22 1.500(14) . ?
C24 C25 1.353(14) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C21 C16 1.477(15) . ?
C16 C15 1.502(17) . ?
C16 C20 1.54(2) . ?
C16 C17 1.552(15) . ?
C15 C14 1.532(13) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C14 C19 1.479(15) . ?
C14 C13 1.49(2) . ?
C14 H14 1.0000 . ?
C13 C12 1.562(17) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C12 C20 1.509(14) . ?
C12 C11 1.515(15) . ?
C12 H12 1.0000 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C19 C18 1.576(17) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C17 C18 1.490(13) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C11 1.51(2) . ?
C18 H18 1.0000 . ?
C11 C1 1.531(15) . ?
C1 C9 1.509(16) . ?
C1 C2 1.526(14) . ?
C2 C7 1.505(18) . ?
C2 C3 1.56(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.483(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.513(18) . ?
C4 C10 1.546(14) . ?
C4 H4 1.0000 . ?
C10 C9 1.52(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C9 C8 1.458(18) . ?
C9 H9 1.0000 . ?
C7 C6 1.518(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C6 1.537(14) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C6 C5 1.53(2) . ?
C6 H6 1.0000 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?

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
C21 O4 C22 119.3(9) . . ?
C11 O2 O1 87.6(7) . . ?
C1 O1 O2 89.3(9) . . ?
C29 N1 C31 123.2(8) . . ?
C29 N1 C30 111.5(9) . . ?
C31 N1 C30 125.3(8) . . ?
F2 C37 F3 112.2(16) . . ?
F2 C37 F1 100.4(13) . . ?
F3 C37 F1 103.5(14) . . ?
F2 C37 C34 114.5(14) . . ?
F3 C37 C34 114.9(11) . . ?
F1 C37 C34 109.6(14) . . ?
C33 C34 C35 121.8(12) . . ?
C33 C34 C37 120.6(13) . . ?
C35 C34 C37 117.6(11) . . ?
C32 C33 C34 118.6(12) . . ?
C32 C33 H33 120.7 . . ?
C34 C33 H33 120.7 . . ?
C33 C32 C31 119.5(11) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C36 C31 N1 117.6(11) . . ?
C36 C31 C32 120.7(11) . . ?
N1 C31 C32 121.6(10) . . ?
C35 C36 C31 118.7(12) . . ?
C35 C36 H36 120.6 . . ?
C31 C36 H36 120.6 . . ?
C36 C35 C34 120.6(11) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
O6 C29 N1 126.3(10) . . ?
O6 C29 C27 128.6(10) . . ?
N1 C29 C27 105.1(9) . . ?
C28 C27 C26 120.4(10) . . ?
C28 C27 C29 130.8(10) . . ?
C26 C27 C29 108.8(9) . . ?
C25 C26 C27 122.5(10) . . ?
C25 C26 C30 128.5(10) . . ?
C27 C26 C30 109.0(9) . . ?
O5 C30 N1 124.1(10) . . ?
O5 C30 C26 130.2(10) . . ?
N1 C30 C26 105.6(9) . . ?
C27 C28 C23 119.2(10) . . ?
C27 C28 H28 120.4 . . ?
C23 C28 H28 120.4 . . ?
C28 C23 C24 118.3(10) . . ?
C28 C23 C22 120.7(9) . . ?
C24 C23 C22 120.7(9) . . ?
C25 C24 C23 122.2(10) . . ?
C25 C24 H24 118.9 . . ?
C23 C24 H24 118.9 . . ?
C26 C25 C24 117.3(10) . . ?
C26 C25 H25 121.4 . . ?
C24 C25 H25 121.4 . . ?
O4 C22 C23 110.0(9) . . ?
O4 C22 H22A 109.7 . . ?
C23 C22 H22A 109.7 . . ?
O4 C22 H22B 109.7 . . ?
C23 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
O3 C21 O4 118.5(11) . . ?
O3 C21 C16 126.1(11) . . ?
O4 C21 C16 113.8(11) . . ?
C21 C16 C15 110.3(11) . . ?
C21 C16 C20 115.0(13) . . ?
C15 C16 C20 107.6(10) . . ?
C21 C16 C17 108.7(10) . . ?
C15 C16 C17 107.9(12) . . ?
C20 C16 C17 107.1(10) . . ?
C16 C15 C14 111.3(10) . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C19 C14 C13 108.7(11) . . ?
C19 C14 C15 111.4(10) . . ?
C13 C14 C15 110.7(13) . . ?
C19 C14 H14 108.7 . . ?
C13 C14 H14 108.7 . . ?
C15 C14 H14 108.7 . . ?
C14 C13 C12 108.9(10) . . ?
C14 C13 H13A 109.9 . . ?
C12 C13 H13A 109.9 . . ?
C14 C13 H13B 109.9 . . ?
C12 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C20 C12 C11 108.7(9) . . ?
C20 C12 C13 108.9(10) . . ?
C11 C12 C13 109.3(11) . . ?
C20 C12 H12 110.0 . . ?
C11 C12 H12 110.0 . . ?
C13 C12 H12 110.0 . . ?
C12 C20 C16 113.0(13) . . ?
C12 C20 H20A 109.0 . . ?
C16 C20 H20A 109.0 . . ?
C12 C20 H20B 109.0 . . ?
C16 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C14 C19 C18 107.4(12) . . ?
C14 C19 H19A 110.2 . . ?
C18 C19 H19A 110.2 . . ?
C14 C19 H19B 110.2 . . ?
C18 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
C18 C17 C16 109.2(10) . . ?
C18 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
C17 C18 C11 113.6(13) . . ?
C17 C18 C19 110.0(11) . . ?
C11 C18 C19 108.8(9) . . ?
C17 C18 H18 108.1 . . ?
C11 C18 H18 108.1 . . ?
C19 C18 H18 108.1 . . ?
O2 C11 C18 108.7(9) . . ?
O2 C11 C12 105.2(11) . . ?
C18 C11 C12 107.6(11) . . ?
O2 C11 C1 88.3(9) . . ?
C18 C11 C1 124.2(11) . . ?
C12 C11 C1 118.6(11) . . ?
O1 C1 C9 105.3(9) . . ?
O1 C1 C2 110.8(13) . . ?
C9 C1 C2 109.2(9) . . ?
O1 C1 C11 86.2(8) . . ?
C9 C1 C11 118.0(12) . . ?
C2 C1 C11 123.1(8) . . ?
C7 C2 C1 109.4(9) . . ?
C7 C2 C3 108.6(9) . . ?
C1 C2 C3 110.2(13) . . ?
C7 C2 H2 109.5 . . ?
C1 C2 H2 109.5 . . ?
C3 C2 H2 109.5 . . ?
C4 C3 C2 108.1(9) . . ?
C4 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
C4 C3 H3B 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
C3 C4 C5 110.3(13) . . ?
C3 C4 C10 109.6(9) . . ?
C5 C4 C10 111.7(10) . . ?
C3 C4 H4 108.4 . . ?
C5 C4 H4 108.4 . . ?
C10 C4 H4 108.4 . . ?
C9 C10 C4 109.1(14) . . ?
C9 C10 H10A 109.9 . . ?
C4 C10 H10A 109.9 . . ?
C9 C10 H10B 109.9 . . ?
C4 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C8 C9 C1 110.8(14) . . ?
C8 C9 C10 108.5(10) . . ?
C1 C9 C10 109.2(10) . . ?
C8 C9 H9 109.5 . . ?
C1 C9 H9 109.5 . . ?
C10 C9 H9 109.5 . . ?
C2 C7 C6 109.0(14) . . ?
C2 C7 H7A 109.9 . . ?
C6 C7 H7A 109.9 . . ?
C2 C7 H7B 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C9 C8 C6 110.6(10) . . ?
C9 C8 H8A 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C7 C6 C5 109.1(10) . . ?
C7 C6 C8 109.3(9) . . ?
C5 C6 C8 111.1(14) . . ?
C7 C6 H6 109.1 . . ?
C5 C6 H6 109.1 . . ?
C8 C6 H6 109.1 . . ?
C4 C5 C6 106.4(10) . . ?
C4 C5 H5A 110.4 . . ?
C6 C5 H5A 110.4 . . ?
C4 C5 H5B 110.4 . . ?
C6 C5 H5B 110.4 . . ?
H5A C5 H5B 108.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 O2 O1 C1 -22.3(7) . . . . ?
F2 C37 C34 C33 77(2) . . . . ?
F3 C37 C34 C33 -150.6(18) . . . . ?
F1 C37 C34 C33 -35(2) . . . . ?
F2 C37 C34 C35 -100.5(18) . . . . ?
F3 C37 C34 C35 32(2) . . . . ?
F1 C37 C34 C35 147.6(14) . . . . ?
C35 C34 C33 C32 -3(2) . . . . ?
C37 C34 C33 C32 179.4(14) . . . . ?
C34 C33 C32 C31 2(2) . . . . ?
C29 N1 C31 C36 135.0(14) . . . . ?
C30 N1 C31 C36 -42.6(19) . . . . ?
C29 N1 C31 C32 -48.5(19) . . . . ?
C30 N1 C31 C32 134.0(13) . . . . ?
C33 C32 C31 C36 -1(2) . . . . ?
C33 C32 C31 N1 -177.9(12) . . . . ?
N1 C31 C36 C35 178.9(11) . . . . ?
C32 C31 C36 C35 2(2) . . . . ?
C31 C36 C35 C34 -3(2) . . . . ?
C33 C34 C35 C36 4(2) . . . . ?
C37 C34 C35 C36 -178.3(13) . . . . ?
C31 N1 C29 O6 2(2) . . . . ?
C30 N1 C29 O6 179.8(13) . . . . ?
C31 N1 C29 C27 -176.5(13) . . . . ?
C30 N1 C29 C27 1.4(15) . . . . ?
O6 C29 C27 C28 2(3) . . . . ?
N1 C29 C27 C28 -179.8(15) . . . . ?
O6 C29 C27 C26 -178.2(14) . . . . ?
N1 C29 C27 C26 0.1(15) . . . . ?
C28 C27 C26 C25 -1(2) . . . . ?
C29 C27 C26 C25 179.6(14) . . . . ?
C28 C27 C26 C30 178.3(13) . . . . ?
C29 C27 C26 C30 -1.6(15) . . . . ?
C29 N1 C30 O5 -178.9(13) . . . . ?
C31 N1 C30 O5 -1(2) . . . . ?
C29 N1 C30 C26 -2.3(15) . . . . ?
C31 N1 C30 C26 175.5(13) . . . . ?
C25 C26 C30 O5 -3(2) . . . . ?
C27 C26 C30 O5 178.7(15) . . . . ?
C25 C26 C30 N1 -178.9(14) . . . . ?
C27 C26 C30 N1 2.4(14) . . . . ?
C26 C27 C28 C23 -3(2) . . . . ?
C29 C27 C28 C23 177.2(16) . . . . ?
C27 C28 C23 C24 4(2) . . . . ?
C27 C28 C23 C22 177.3(14) . . . . ?
C28 C23 C24 C25 -2(2) . . . . ?
C22 C23 C24 C25 -175.4(15) . . . . ?
C27 C26 C25 C24 2(2) . . . . ?
C30 C26 C25 C24 -176.2(15) . . . . ?
C23 C24 C25 C26 -1(2) . . . . ?
C21 O4 C22 C23 -146.3(14) . . . . ?
C28 C23 C22 O4 169.1(14) . . . . ?
C24 C23 C22 O4 -17.6(17) . . . . ?
C22 O4 C21 O3 -5(2) . . . . ?
C22 O4 C21 C16 -171.8(13) . . . . ?
O3 C21 C16 C15 137.1(17) . . . . ?
O4 C21 C16 C15 -57.7(19) . . . . ?
O3 C21 C16 C20 -100.9(18) . . . . ?
O4 C21 C16 C20 64.3(17) . . . . ?
O3 C21 C16 C17 19(2) . . . . ?
O4 C21 C16 C17 -175.7(14) . . . . ?
C21 C16 C15 C14 -176.5(12) . . . . ?
C20 C16 C15 C14 57.2(14) . . . . ?
C17 C16 C15 C14 -58.0(16) . . . . ?
C16 C15 C14 C19 59.9(18) . . . . ?
C16 C15 C14 C13 -61.2(14) . . . . ?
C19 C14 C13 C12 -63.3(12) . . . . ?
C15 C14 C13 C12 59.4(11) . . . . ?
C14 C13 C12 C20 -57.7(13) . . . . ?
C14 C13 C12 C11 60.9(13) . . . . ?
C11 C12 C20 C16 -61.0(15) . . . . ?
C13 C12 C20 C16 58.0(13) . . . . ?
C21 C16 C20 C12 178.9(9) . . . . ?
C15 C16 C20 C12 -57.7(12) . . . . ?
C17 C16 C20 C12 58.0(13) . . . . ?
C13 C14 C19 C18 64.3(12) . . . . ?
C15 C14 C19 C18 -58.0(16) . . . . ?
C21 C16 C17 C18 -180.0(13) . . . . ?
C15 C16 C17 C18 60.4(16) . . . . ?
C20 C16 C17 C18 -55.2(15) . . . . ?
C16 C17 C18 C11 60.1(15) . . . . ?
C16 C17 C18 C19 -62.1(16) . . . . ?
C14 C19 C18 C17 60.8(15) . . . . ?
C14 C19 C18 C11 -64.2(12) . . . . ?
O1 O2 C11 C18 147.5(9) . . . . ?
O1 O2 C11 C12 -97.5(10) . . . . ?
O1 O2 C11 C1 21.8(8) . . . . ?
C17 C18 C11 O2 52.2(12) . . . . ?
C19 C18 C11 O2 175.1(7) . . . . ?
C17 C18 C11 C12 -61.2(13) . . . . ?
C19 C18 C11 C12 61.7(12) . . . . ?
C17 C18 C11 C1 153.4(9) . . . . ?
C19 C18 C11 C1 -83.7(12) . . . . ?
C20 C12 C11 O2 -57.1(15) . . . . ?
C13 C12 C11 O2 -175.8(10) . . . . ?
C20 C12 C11 C18 58.6(15) . . . . ?
C13 C12 C11 C18 -60.0(13) . . . . ?
C20 C12 C11 C1 -153.7(12) . . . . ?
C13 C12 C11 C1 87.6(15) . . . . ?
O2 O1 C1 C9 -96.3(9) . . . . ?
O2 O1 C1 C2 145.7(8) . . . . ?
O2 O1 C1 C11 21.7(7) . . . . ?
O2 C11 C1 O1 -21.9(8) . . . . ?
C18 C11 C1 O1 -133.5(11) . . . . ?
C12 C11 C1 O1 84.5(13) . . . . ?
O2 C11 C1 C9 83.5(13) . . . . ?
C18 C11 C1 C9 -28.2(17) . . . . ?
C12 C11 C1 C9 -170.1(13) . . . . ?
O2 C11 C1 C2 -134.2(14) . . . . ?
C18 C11 C1 C2 114.1(15) . . . . ?
C12 C11 C1 C2 -28(2) . . . . ?
O1 C1 C2 C7 55.6(12) . . . . ?
C9 C1 C2 C7 -60.0(17) . . . . ?
C11 C1 C2 C7 154.9(14) . . . . ?
O1 C1 C2 C3 175.0(8) . . . . ?
C9 C1 C2 C3 59.4(14) . . . . ?
C11 C1 C2 C3 -85.7(15) . . . . ?
C7 C2 C3 C4 60.0(13) . . . . ?
C1 C2 C3 C4 -59.9(12) . . . . ?
C2 C3 C4 C5 -62.8(13) . . . . ?
C2 C3 C4 C10 60.5(15) . . . . ?
C3 C4 C10 C9 -62.3(15) . . . . ?
C5 C4 C10 C9 60.2(14) . . . . ?
O1 C1 C9 C8 -59.6(12) . . . . ?
C2 C1 C9 C8 59.4(15) . . . . ?
C11 C1 C9 C8 -153.5(11) . . . . ?
O1 C1 C9 C10 -179.0(11) . . . . ?
C2 C1 C9 C10 -60.0(16) . . . . ?
C11 C1 C9 C10 87.2(14) . . . . ?
C4 C10 C9 C8 -59.9(12) . . . . ?
C4 C10 C9 C1 60.9(13) . . . . ?
C1 C2 C7 C6 60.5(14) . . . . ?
C3 C2 C7 C6 -59.9(12) . . . . ?
C1 C9 C8 C6 -58.8(15) . . . . ?
C10 C9 C8 C6 61.1(15) . . . . ?
C2 C7 C6 C5 62.7(13) . . . . ?
C2 C7 C6 C8 -59.0(15) . . . . ?
C9 C8 C6 C7 58.6(17) . . . . ?
C9 C8 C6 C5 -61.9(14) . . . . ?
C3 C4 C5 C6 64.3(12) . . . . ?
C10 C4 C5 C6 -57.8(15) . . . . ?
C7 C6 C5 C4 -62.9(14) . . . . ?
C8 C6 C5 C4 57.7(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C36 H36 O6 0.95 2.46 3.110(13) 125.8 1_655 yes

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.086


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?

# start Validation Reply Form
_vrf_RINTA01_shelx_a_pl          
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: The crystals were needle-like crystals and a crystal had a small size
 of 142 x 32 x 20 micro mm. Preliminary measurements revealed that the crystals
 had a fragile property, in which decomposition reaction was caused by X-ray
 irradiation and the crystallinity was deteriorated. For these reasons, it was
 necessary to use a MoKa line having a shorter wavelength instead of CuKa in
 order to reduce damage to the crystal as much as possible. Because of the
 measurement conditions, the diffraction intensities were weak overall, and
 particularly high-angle reflection could not be measured. As the result, four
 Alert_A and three Alert_B were recorded. The solved molecular structure is the
 same as the structure predicted from the synthesis scheme, and there is little
 possibility of the other molecular structure. Then, we concluded that the
 molecular structure is correct. In the discussion of the crystal structure, the
 difference in the molecular structure and intermolecular distances was not
 talked about, but rather the orientation and packing of molecules were mainly
 discussed. Therefore, a relatively large R factor does not hinder the essential
 discussion.
;
_vrf_PLAT020_shelx_a_pl          
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.336 Report
RESPONSE: The crystals were needle-like crystals and a crystal had a small size
 of 142 x 32 x 20 micro mm. Preliminary measurements revealed that the crystals
 had a fragile property, in which decomposition reaction was caused by X-ray
 irradiation and the crystallinity was deteriorated. For these reasons, it was
 necessary to use a MoKa line having a shorter wavelength instead of CuKa in
 order to reduce damage to the crystal as much as possible. Because of the
 measurement conditions, the diffraction intensities were weak overall, and
 particularly high-angle reflection could not be measured. As the result, four
 Alert_A and three Alert_B were recorded. The solved molecular structure is the
 same as the structure predicted from the synthesis scheme, and there is little
 possibility of the other molecular structure. Then, we concluded that the
 molecular structure is correct. In the discussion of the crystal structure, the
 difference in the molecular structure and intermolecular distances was not
 talked about, but rather the orientation and packing of molecules were mainly
 discussed. Therefore, a relatively large R factor does not hinder the essential
 discussion.
;
_vrf_PLAT026_shelx_a_pl          
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        13% Check 
RESPONSE: The crystals were needle-like crystals and a crystal had a small size
 of 142 x 32 x 20 micro mm. Preliminary measurements revealed that the crystals
 had a fragile property, in which decomposition reaction was caused by X-ray
 irradiation and the crystallinity was deteriorated. For these reasons, it was
 necessary to use a MoKa line having a shorter wavelength instead of CuKa in
 order to reduce damage to the crystal as much as possible. Because of the
 measurement conditions, the diffraction intensities were weak overall, and
 particularly high-angle reflection could not be measured. As the result, four
 Alert_A and three Alert_B were recorded. The solved molecular structure is the
 same as the structure predicted from the synthesis scheme, and there is little
 possibility of the other molecular structure. Then, we concluded that the
 molecular structure is correct. In the discussion of the crystal structure, the
 difference in the molecular structure and intermolecular distances was not
 talked about, but rather the orientation and packing of molecules were mainly
 discussed. Therefore, a relatively large R factor does not hinder the essential
 discussion.
;
_vrf_PLAT029_shelx_a_pl          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.866 Why?  
RESPONSE: The crystals were needle-like crystals and a crystal had a small size
 of 142 x 32 x 20 micro mm. Preliminary measurements revealed that the crystals
 had a fragile property, in which decomposition reaction was caused by X-ray
 irradiation and the crystallinity was deteriorated. For these reasons, it was
 necessary to use a MoKa line having a shorter wavelength instead of CuKa in
 order to reduce damage to the crystal as much as possible. Because of the
 measurement conditions, the diffraction intensities were weak overall, and
 particularly high-angle reflection could not be measured. As the result, four
 Alert_A and three Alert_B were recorded. The solved molecular structure is the
 same as the structure predicted from the synthesis scheme, and there is little
 possibility of the other molecular structure. Then, we concluded that the
 molecular structure is correct. In the discussion of the crystal structure, the
 difference in the molecular structure and intermolecular distances was not
 talked about, but rather the orientation and packing of molecules were mainly
 discussed. Therefore, a relatively large R factor does not hinder the essential
 discussion.
;



_publcif_funding_html            
;
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane / CH2Cl2'
_chemical_properties_physical    Heat-sensitive
_exptl_crystal_preparation       Luminescent
