# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_test_0m
_database_code_depnum_ccdc_archive 'CCDC 1888961'
loop_
_audit_author_name
_audit_author_address
'Yimin Hu'
;'?q?21?, 241002
China
;
_audit_update_record             
;
2019-01-06 deposited with the CCDC.	2019-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H24 F2 O5'
_chemical_formula_weight         502.49

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   14.1655(13)
_cell_length_b                   22.469(2)
_cell_length_c                   16.4190(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.4190(10)
_cell_angle_gamma                90.00
_cell_volume                     5169.7(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8750
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      20.71

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2096
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9781
_exptl_absorpt_correction_T_max  0.9809
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            51985
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         25.34
_reflns_number_total             9421
_reflns_number_gt                4904
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9421
_refine_ls_number_parameters     675
_refine_ls_number_restraints     1586
_refine_ls_R_factor_all          0.1689
_refine_ls_R_factor_gt           0.1089
_refine_ls_wR_factor_ref         0.3959
_refine_ls_wR_factor_gt          0.3402
_refine_ls_goodness_of_fit_ref   1.349
_refine_ls_restrained_S_all      1.443
_refine_ls_shift/su_max          0.034
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7821(5) 1.1053(3) 0.7491(4) 0.0873(15) Uani 1 1 d U . .
C2 C 0.8628(8) 1.1161(5) 0.8787(6) 0.185(4) Uani 1 1 d U . .
H2A H 0.8591 1.0863 0.9202 0.277 Uiso 1 1 calc R . .
H2B H 0.8123 1.1445 0.8797 0.277 Uiso 1 1 calc R . .
H2C H 0.9233 1.1360 0.8896 0.277 Uiso 1 1 calc R . .
C3 C 0.8170(5) 1.1451(3) 0.6185(4) 0.0882(15) Uani 1 1 d U . .
C4 C 0.9330(8) 1.2222(4) 0.6261(6) 0.153(3) Uani 1 1 d U . .
H4A H 0.9696 1.2083 0.5851 0.230 Uiso 1 1 calc R . .
H4B H 0.9743 1.2425 0.6688 0.230 Uiso 1 1 calc R . .
H4C H 0.8845 1.2490 0.6013 0.230 Uiso 1 1 calc R . .
C5 C 0.7793(4) 1.0918(3) 0.6599(3) 0.0773(13) Uani 1 1 d U . .
C6 C 0.6767(4) 1.0751(2) 0.6211(3) 0.0744(12) Uani 1 1 d U . .
H6A H 0.6298 1.0948 0.6493 0.089 Uiso 1 1 calc R . .
H6B H 0.6650 1.0855 0.5632 0.089 Uiso 1 1 calc R . .
C7 C 0.6740(4) 1.0090(2) 0.6327(3) 0.0694(11) Uani 1 1 d U . .
C8 C 0.5964(4) 0.9717(2) 0.6288(3) 0.0698(11) Uani 1 1 d U . .
C9 C 0.6110(4) 0.9107(2) 0.6405(3) 0.0727(12) Uani 1 1 d U . .
C10 C 0.7047(4) 0.8886(3) 0.6572(3) 0.0761(12) Uani 1 1 d U . .
C11 C 0.7846(4) 0.9259(3) 0.6595(3) 0.0739(12) Uani 1 1 d U . .
C12 C 0.7673(4) 0.9863(2) 0.6477(3) 0.0723(12) Uani 1 1 d U . .
C13 C 0.8376(4) 1.0354(3) 0.6459(4) 0.0790(13) Uani 1 1 d U . .
H13A H 0.8608 1.0370 0.5932 0.095 Uiso 1 1 calc R . .
H13B H 0.8914 1.0307 0.6893 0.095 Uiso 1 1 calc R . .
C14 C 0.4993(4) 0.9948(2) 0.6124(3) 0.0719(11) Uani 1 1 d U . .
C15 C 0.4179(4) 1.0098(2) 0.5994(3) 0.0719(12) Uani 1 1 d U . .
C16 C 0.3206(4) 1.0265(2) 0.5867(3) 0.0677(12) Uani 1 1 d U . .
C17 C 0.2895(4) 1.0823(3) 0.5586(3) 0.0746(13) Uani 1 1 d U . .
H17 H 0.3342 1.1104 0.5477 0.090 Uiso 1 1 calc R . .
C18 C 0.1952(4) 1.0971(3) 0.5466(4) 0.0841(14) Uani 1 1 d U . .
H18 H 0.1762 1.1351 0.5291 0.101 Uiso 1 1 calc R . .
C19 C 0.1298(4) 1.0562(3) 0.5602(4) 0.0862(15) Uani 1 1 d U . .
C20 C 0.1556(4) 1.0004(3) 0.5874(4) 0.0926(15) Uani 1 1 d U . .
H20 H 0.1094 0.9730 0.5973 0.111 Uiso 1 1 calc R . .
C21 C 0.2514(4) 0.9845(3) 0.6001(4) 0.0838(14) Uani 1 1 d U . .
H21 H 0.2696 0.9463 0.6174 0.101 Uiso 1 1 calc R . .
C22 C 0.5281(4) 0.8682(3) 0.6360(3) 0.0774(12) Uani 1 1 d U . .
C23 C 0.4762(5) 0.8616(3) 0.6951(4) 0.1007(14) Uani 1 1 d U . .
H23 H 0.4893 0.8844 0.7426 0.121 Uiso 1 1 calc R . .
C24 C 0.3984(5) 0.8191(4) 0.6871(5) 0.1156(18) Uani 1 1 d U . .
H24 H 0.3620 0.8145 0.7294 0.139 Uiso 1 1 calc R . .
C25 C 0.3809(5) 0.7892(3) 0.6238(5) 0.1010(17) Uani 1 1 d U . .
C26 C 0.4322(6) 0.7913(4) 0.5627(5) 0.1225(18) Uani 1 1 d U . .
H26 H 0.4208 0.7655 0.5181 0.147 Uiso 1 1 calc R . .
C27 C 0.5045(5) 0.8340(3) 0.5685(5) 0.1130(15) Uani 1 1 d U . .
H27 H 0.5376 0.8392 0.5241 0.136 Uiso 1 1 calc R . .
C28 C 0.7199(5) 0.8232(3) 0.6753(4) 0.0978(14) Uani 1 1 d U . .
C29 C 0.7510(6) 0.7876(3) 0.6188(5) 0.131(2) Uani 1 1 d U . .
H29A H 0.7643 0.7478 0.6309 0.157 Uiso 1 1 calc R . .
H29B H 0.7591 0.8028 0.5676 0.157 Uiso 1 1 calc R . .
C30 C 0.8845(4) 0.9035(3) 0.6739(4) 0.0935(17) Uani 1 1 d U . .
H30A H 0.9104 0.9038 0.6230 0.140 Uiso 1 1 calc R . .
H30B H 0.8852 0.8635 0.6948 0.140 Uiso 1 1 calc R . .
H30C H 0.9224 0.9286 0.7133 0.140 Uiso 1 1 calc R . .
C31 C 0.9234(4) 0.2793(2) 0.3412(3) 0.0654(12) Uani 1 1 d U . .
C32 C 0.9066(5) 0.1817(3) 0.3867(4) 0.105(2) Uani 1 1 d U . .
H32A H 0.9547 0.1946 0.4305 0.157 Uiso 1 1 calc R . .
H32B H 0.9247 0.1441 0.3660 0.157 Uiso 1 1 calc R . .
H32C H 0.8468 0.1775 0.4071 0.157 Uiso 1 1 calc R . .
C33 C 0.9479(4) 0.2934(2) 0.1964(3) 0.0682(12) Uani 1 1 d U . .
C34 C 1.0816(6) 0.2466(5) 0.1566(5) 0.152(3) Uani 1 1 d U . .
H34A H 1.0469 0.2125 0.1331 0.227 Uiso 1 1 calc R . .
H34B H 1.1447 0.2347 0.1806 0.227 Uiso 1 1 calc R . .
H34C H 1.0858 0.2756 0.1144 0.227 Uiso 1 1 calc R . .
C35 C 0.9072(3) 0.3206(2) 0.2663(3) 0.0613(11) Uani 1 1 d U . .
C36 C 0.9535(3) 0.3821(2) 0.2863(3) 0.0631(11) Uani 1 1 d U . .
H36A H 1.0031 0.3798 0.3337 0.076 Uiso 1 1 calc R . .
H36B H 0.9809 0.3975 0.2398 0.076 Uiso 1 1 calc R . .
C37 C 0.8712(3) 0.4207(2) 0.3046(3) 0.0571(10) Uani 1 1 d U . .
C38 C 0.8770(3) 0.4776(2) 0.3371(3) 0.0566(10) Uani 1 1 d U . .
C39 C 0.7921(3) 0.5069(2) 0.3488(3) 0.0599(10) Uani 1 1 d U . .
C40 C 0.7052(3) 0.4771(2) 0.3273(3) 0.0627(11) Uani 1 1 d U . .
C41 C 0.6997(3) 0.4199(2) 0.2932(3) 0.0629(11) Uani 1 1 d U . .
C42 C 0.7845(3) 0.3929(2) 0.2834(3) 0.0580(10) Uani 1 1 d U . .
C43 C 0.7987(3) 0.3317(2) 0.2463(3) 0.0621(11) Uani 1 1 d U . .
H43A H 0.7782 0.3319 0.1873 0.075 Uiso 1 1 calc R . .
H43B H 0.7632 0.3015 0.2711 0.075 Uiso 1 1 calc R . .
C44 C 0.9683(3) 0.5059(2) 0.3576(3) 0.0606(11) Uani 1 1 d U . .
C45 C 1.0452(4) 0.5290(2) 0.3757(3) 0.0616(11) Uani 1 1 d U . .
C46 C 1.1353(3) 0.5570(2) 0.3998(3) 0.0608(11) Uani 1 1 d U . .
C47 C 1.2146(4) 0.5411(3) 0.3634(3) 0.0765(13) Uani 1 1 d U . .
H47 H 1.2088 0.5117 0.3230 0.092 Uiso 1 1 calc R . .
C48 C 1.3007(4) 0.5683(3) 0.3864(4) 0.0859(14) Uani 1 1 d U . .
H48 H 1.3534 0.5585 0.3613 0.103 Uiso 1 1 calc R . .
C49 C 1.3075(4) 0.6097(3) 0.4467(4) 0.0860(15) Uani 1 1 d U . .
C50 C 1.2329(4) 0.6261(3) 0.4853(4) 0.0887(15) Uani 1 1 d U . .
H50 H 1.2404 0.6539 0.5277 0.106 Uiso 1 1 calc R . .
C51 C 1.1453(4) 0.5998(2) 0.4593(3) 0.0761(13) Uani 1 1 d U . .
H51 H 1.0924 0.6116 0.4828 0.091 Uiso 1 1 calc R . .
C52 C 0.7949(3) 0.5693(2) 0.3786(3) 0.0630(11) Uani 1 1 d U . .
C53 C 0.8492(4) 0.5860(2) 0.4511(3) 0.0759(12) Uani 1 1 d U . .
H53 H 0.8812 0.5570 0.4850 0.091 Uiso 1 1 calc R . .
C54 C 0.8576(5) 0.6451(3) 0.4749(4) 0.0916(15) Uani 1 1 d U . .
H54 H 0.8956 0.6563 0.5236 0.110 Uiso 1 1 calc R . .
C55 C 0.8082(5) 0.6862(3) 0.4245(4) 0.0907(15) Uani 1 1 d U . .
C56 C 0.7530(5) 0.6729(3) 0.3543(4) 0.0890(15) Uani 1 1 d U . .
H56 H 0.7201 0.7023 0.3220 0.107 Uiso 1 1 calc R . .
C57 C 0.7461(4) 0.6132(2) 0.3308(3) 0.0779(13) Uani 1 1 d U . .
H57 H 0.7080 0.6027 0.2819 0.093 Uiso 1 1 calc R . .
C58 C 0.6132(4) 0.5070(2) 0.3404(4) 0.0773(13) Uani 1 1 d U . .
C59 C 0.5981(5) 0.5210(4) 0.4264(4) 0.111(2) Uani 1 1 d U . .
H59A H 0.5521 0.5524 0.4256 0.166 Uiso 1 1 calc R . .
H59B H 0.6574 0.5333 0.4577 0.166 Uiso 1 1 calc R . .
H59C H 0.5751 0.4861 0.4511 0.166 Uiso 1 1 calc R . .
C60 C 0.6059(4) 0.3863(3) 0.2695(4) 0.0836(16) Uani 1 1 d U . .
H60A H 0.5701 0.4044 0.2217 0.125 Uiso 1 1 calc R . .
H60B H 0.5694 0.3878 0.3144 0.125 Uiso 1 1 calc R . .
H60C H 0.6192 0.3455 0.2576 0.125 Uiso 1 1 calc R . .
F1 F 0.0365(2) 1.0714(2) 0.5467(3) 0.1355(16) Uani 1 1 d . . .
F2 F 0.3079(3) 0.7485(2) 0.6183(3) 0.1360(16) Uani 1 1 d . . .
F3 F 1.3950(3) 0.6351(2) 0.4731(3) 0.1362(16) Uani 1 1 d . . .
F4 F 0.8186(4) 0.74517(16) 0.4472(4) 0.156(2) Uani 1 1 d . . .
O1 O 0.7182(5) 1.1326(3) 0.7739(3) 0.155(2) Uani 1 1 d . . .
O2 O 0.8531(4) 1.0876(3) 0.7973(3) 0.143(2) Uani 1 1 d . . .
O3 O 0.7944(6) 1.1581(4) 0.5509(5) 0.221(4) Uani 1 1 d U . .
O4 O 0.8880(5) 1.1710(2) 0.6618(3) 0.147(2) Uani 1 1 d . . .
O5 O 0.7095(7) 0.8009(4) 0.7450(5) 0.192(3) Uani 1 1 d U . .
H5 H 0.6754 0.8228 0.7681 0.289 Uiso 1 1 calc R . .
O6 O 0.9511(4) 0.29468(19) 0.4104(2) 0.1036(14) Uani 1 1 d . . .
O7 O 0.8969(3) 0.22504(15) 0.3215(2) 0.0821(11) Uani 1 1 d . . .
O8 O 0.9097(4) 0.2915(2) 0.1265(3) 0.1195(17) Uani 1 1 d . . .
O9 O 1.0329(3) 0.2720(3) 0.2192(3) 0.1191(17) Uani 1 1 d . . .
O10 O 0.5530(3) 0.5196(3) 0.2822(4) 0.143(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.212(8) . ?
C1 O2 1.251(8) . ?
C1 C5 1.490(9) . ?
C2 O2 1.471(11) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 O3 1.147(8) . ?
C3 O4 1.284(7) . ?
C3 C5 1.511(8) . ?
C4 O4 1.476(9) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.546(7) . ?
C5 C13 1.548(8) . ?
C6 C7 1.498(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.377(7) . ?
C7 C12 1.405(7) . ?
C8 C9 1.396(7) . ?
C8 C14 1.458(7) . ?
C9 C10 1.406(7) . ?
C9 C22 1.507(7) . ?
C10 C11 1.404(7) . ?
C10 C28 1.509(9) . ?
C11 C12 1.388(8) . ?
C11 C30 1.489(7) . ?
C12 C13 1.489(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.190(7) . ?
C15 C16 1.415(7) . ?
C16 C17 1.384(7) . ?
C16 C21 1.400(7) . ?
C17 C18 1.362(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.346(8) . ?
C18 H18 0.9300 . ?
C19 F1 1.352(6) . ?
C19 C20 1.365(8) . ?
C20 C21 1.389(8) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.308(8) . ?
C22 C27 1.349(8) . ?
C23 C24 1.449(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.231(9) . ?
C24 H24 0.9300 . ?
C25 C26 1.323(9) . ?
C25 F2 1.373(7) . ?
C26 C27 1.397(9) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 O5 1.277(9) . ?
C28 C29 1.347(10) . ?
C29 H29A 0.9300 . ?
C29 H29B 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 O6 1.197(6) . ?
C31 O7 1.303(6) . ?
C31 C35 1.530(7) . ?
C32 O7 1.439(6) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 O8 1.196(6) . ?
C33 O9 1.300(7) . ?
C33 C35 1.489(7) . ?
C34 O9 1.438(9) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 C43 1.544(6) . ?
C35 C36 1.544(7) . ?
C36 C37 1.518(6) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C42 1.377(6) . ?
C37 C38 1.382(6) . ?
C38 C39 1.408(6) . ?
C38 C44 1.437(6) . ?
C39 C40 1.399(7) . ?
C39 C52 1.484(7) . ?
C40 C41 1.401(7) . ?
C40 C58 1.511(7) . ?
C41 C42 1.377(7) . ?
C41 C60 1.528(7) . ?
C42 C43 1.528(6) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 C45 1.204(6) . ?
C45 C46 1.425(7) . ?
C46 C51 1.364(7) . ?
C46 C47 1.394(7) . ?
C47 C48 1.368(7) . ?
C47 H47 0.9300 . ?
C48 C49 1.352(8) . ?
C48 H48 0.9300 . ?
C49 C50 1.361(9) . ?
C49 F3 1.376(6) . ?
C50 C51 1.384(7) . ?
C50 H50 0.9300 . ?
C51 H51 0.9300 . ?
C52 C53 1.372(7) . ?
C52 C57 1.382(7) . ?
C53 C54 1.383(7) . ?
C53 H53 0.9300 . ?
C54 C55 1.364(8) . ?
C54 H54 0.9300 . ?
C55 C56 1.328(8) . ?
C55 F4 1.378(7) . ?
C56 C57 1.396(8) . ?
C56 H56 0.9300 . ?
C57 H57 0.9300 . ?
C58 O10 1.216(7) . ?
C58 C59 1.491(9) . ?
C59 H59A 0.9600 . ?
C59 H59B 0.9600 . ?
C59 H59C 0.9600 . ?
C60 H60A 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60C 0.9600 . ?
O5 H5 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 121.3(7) . . ?
O1 C1 C5 121.3(7) . . ?
O2 C1 C5 117.5(6) . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O3 C3 O4 120.3(6) . . ?
O3 C3 C5 124.8(7) . . ?
O4 C3 C5 114.2(6) . . ?
O4 C4 H4A 109.5 . . ?
O4 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O4 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 C5 C3 108.8(5) . . ?
C1 C5 C6 110.0(5) . . ?
C3 C5 C6 112.3(5) . . ?
C1 C5 C13 111.9(5) . . ?
C3 C5 C13 110.5(5) . . ?
C6 C5 C13 103.3(4) . . ?
C7 C6 C5 103.2(4) . . ?
C7 C6 H6A 111.1 . . ?
C5 C6 H6A 111.1 . . ?
C7 C6 H6B 111.1 . . ?
C5 C6 H6B 111.1 . . ?
H6A C6 H6B 109.1 . . ?
C8 C7 C12 120.7(5) . . ?
C8 C7 C6 129.3(5) . . ?
C12 C7 C6 109.9(4) . . ?
C7 C8 C9 119.4(5) . . ?
C7 C8 C14 121.0(5) . . ?
C9 C8 C14 119.5(5) . . ?
C8 C9 C10 119.3(5) . . ?
C8 C9 C22 121.1(5) . . ?
C10 C9 C22 119.6(5) . . ?
C11 C10 C9 121.9(5) . . ?
C11 C10 C28 119.1(5) . . ?
C9 C10 C28 119.0(5) . . ?
C12 C11 C10 117.1(5) . . ?
C12 C11 C30 119.8(5) . . ?
C10 C11 C30 123.1(5) . . ?
C11 C12 C7 121.4(5) . . ?
C11 C12 C13 128.5(5) . . ?
C7 C12 C13 110.0(5) . . ?
C12 C13 C5 103.4(4) . . ?
C12 C13 H13A 111.1 . . ?
C5 C13 H13A 111.1 . . ?
C12 C13 H13B 111.1 . . ?
C5 C13 H13B 111.1 . . ?
H13A C13 H13B 109.1 . . ?
C15 C14 C8 175.5(6) . . ?
C14 C15 C16 177.8(6) . . ?
C17 C16 C21 117.8(5) . . ?
C17 C16 C15 123.0(5) . . ?
C21 C16 C15 119.1(5) . . ?
C18 C17 C16 121.7(5) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C19 C18 C17 119.6(6) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 F1 118.8(6) . . ?
C18 C19 C20 121.6(6) . . ?
F1 C19 C20 119.7(6) . . ?
C19 C20 C21 119.6(6) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C20 C21 C16 119.6(6) . . ?
C20 C21 H21 120.2 . . ?
C16 C21 H21 120.2 . . ?
C23 C22 C27 116.5(6) . . ?
C23 C22 C9 123.7(5) . . ?
C27 C22 C9 119.8(5) . . ?
C22 C23 C24 120.6(6) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 119.5(6) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 123.7(7) . . ?
C24 C25 F2 118.4(6) . . ?
C26 C25 F2 117.7(7) . . ?
C25 C26 C27 116.8(7) . . ?
C25 C26 H26 121.6 . . ?
C27 C26 H26 121.6 . . ?
C22 C27 C26 122.5(7) . . ?
C22 C27 H27 118.7 . . ?
C26 C27 H27 118.7 . . ?
O5 C28 C29 118.5(8) . . ?
O5 C28 C10 121.8(7) . . ?
C29 C28 C10 119.6(7) . . ?
C28 C29 H29A 120.0 . . ?
C28 C29 H29B 120.0 . . ?
H29A C29 H29B 120.0 . . ?
C11 C30 H30A 109.5 . . ?
C11 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C11 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O6 C31 O7 123.2(5) . . ?
O6 C31 C35 125.3(5) . . ?
O7 C31 C35 111.3(4) . . ?
O7 C32 H32A 109.5 . . ?
O7 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O7 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
O8 C33 O9 122.3(5) . . ?
O8 C33 C35 125.6(5) . . ?
O9 C33 C35 112.2(5) . . ?
O9 C34 H34A 109.5 . . ?
O9 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
O9 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C35 C31 110.0(4) . . ?
C33 C35 C43 112.9(4) . . ?
C31 C35 C43 107.3(4) . . ?
C33 C35 C36 109.3(4) . . ?
C31 C35 C36 111.2(4) . . ?
C43 C35 C36 106.2(4) . . ?
C37 C36 C35 103.8(4) . . ?
C37 C36 H36A 111.0 . . ?
C35 C36 H36A 111.0 . . ?
C37 C36 H36B 111.0 . . ?
C35 C36 H36B 111.0 . . ?
H36A C36 H36B 109.0 . . ?
C42 C37 C38 121.2(4) . . ?
C42 C37 C36 111.9(4) . . ?
C38 C37 C36 127.0(4) . . ?
C37 C38 C39 118.8(4) . . ?
C37 C38 C44 120.1(4) . . ?
C39 C38 C44 121.2(4) . . ?
C40 C39 C38 118.7(4) . . ?
C40 C39 C52 121.0(4) . . ?
C38 C39 C52 120.3(4) . . ?
C39 C40 C41 122.4(4) . . ?
C39 C40 C58 119.8(4) . . ?
C41 C40 C58 117.8(4) . . ?
C42 C41 C40 116.9(4) . . ?
C42 C41 C60 119.6(4) . . ?
C40 C41 C60 123.5(4) . . ?
C37 C42 C41 122.2(4) . . ?
C37 C42 C43 110.2(4) . . ?
C41 C42 C43 127.6(4) . . ?
C42 C43 C35 104.2(4) . . ?
C42 C43 H43A 110.9 . . ?
C35 C43 H43A 110.9 . . ?
C42 C43 H43B 110.9 . . ?
C35 C43 H43B 110.9 . . ?
H43A C43 H43B 108.9 . . ?
C45 C44 C38 178.9(5) . . ?
C44 C45 C46 177.9(5) . . ?
C51 C46 C47 118.8(5) . . ?
C51 C46 C45 120.4(5) . . ?
C47 C46 C45 120.8(5) . . ?
C48 C47 C46 120.6(5) . . ?
C48 C47 H47 119.7 . . ?
C46 C47 H47 119.7 . . ?
C49 C48 C47 118.4(6) . . ?
C49 C48 H48 120.8 . . ?
C47 C48 H48 120.8 . . ?
C48 C49 C50 123.4(5) . . ?
C48 C49 F3 118.8(6) . . ?
C50 C49 F3 117.7(6) . . ?
C49 C50 C51 117.6(6) . . ?
C49 C50 H50 121.2 . . ?
C51 C50 H50 121.2 . . ?
C46 C51 C50 121.2(6) . . ?
C46 C51 H51 119.4 . . ?
C50 C51 H51 119.4 . . ?
C53 C52 C57 117.9(5) . . ?
C53 C52 C39 122.0(4) . . ?
C57 C52 C39 120.0(4) . . ?
C52 C53 C54 121.5(5) . . ?
C52 C53 H53 119.2 . . ?
C54 C53 H53 119.2 . . ?
C55 C54 C53 117.6(5) . . ?
C55 C54 H54 121.2 . . ?
C53 C54 H54 121.2 . . ?
C56 C55 C54 123.9(6) . . ?
C56 C55 F4 118.5(6) . . ?
C54 C55 F4 117.5(6) . . ?
C55 C56 C57 117.8(5) . . ?
C55 C56 H56 121.1 . . ?
C57 C56 H56 121.1 . . ?
C52 C57 C56 121.3(5) . . ?
C52 C57 H57 119.3 . . ?
C56 C57 H57 119.3 . . ?
O10 C58 C59 120.9(6) . . ?
O10 C58 C40 120.7(6) . . ?
C59 C58 C40 118.4(5) . . ?
C58 C59 H59A 109.5 . . ?
C58 C59 H59B 109.5 . . ?
H59A C59 H59B 109.5 . . ?
C58 C59 H59C 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C41 C60 H60A 109.5 . . ?
C41 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
C41 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C1 O2 C2 113.4(7) . . ?
C3 O4 C4 118.9(6) . . ?
C28 O5 H5 109.5 . . ?
C31 O7 C32 117.1(5) . . ?
C33 O9 C34 117.5(5) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.994
_refine_diff_density_min         -0.672
_refine_diff_density_rms         0.072
####################################################################### 
# 
# 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_mo_20190225a_0m
_database_code_depnum_ccdc_archive 'CCDC 1903151'
loop_
_audit_author_name
_audit_author_address
'Yimin Hu'
;Anhui Normal University
China
;
_audit_update_record             
;
2019-03-14 deposited with the CCDC.	2019-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 F O3'
_chemical_formula_weight         259.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   9.9135(4)
_cell_length_b                   11.2232(4)
_cell_length_c                   13.3885(5)
_cell_angle_alpha                94.007(2)
_cell_angle_beta                 107.0200(10)
_cell_angle_gamma                109.9160(10)
_cell_volume                     1315.15(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51276
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.124
_diffrn_reflns_theta_max         27.559
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             6013
_reflns_number_gt                4718
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1359P)²+0.4109P] 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         6013
_refine_ls_number_parameters     422
_refine_ls_number_restraints     286
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.2261
_refine_ls_wR_factor_gt          0.2028
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8181(12) 1.2221(6) 0.8602(8) 0.139(3) Uani 0.525(4) 1 d D U P A 1
H1A H 0.850152 1.237957 0.799685 0.209 Uiso 0.525(4) 1 calc R U P A 1
H1B H 0.888247 1.287723 0.920860 0.209 Uiso 0.525(4) 1 calc R U P A 1
H1C H 0.718046 1.223693 0.845479 0.209 Uiso 0.525(4) 1 calc R U P A 1
C2 C 0.7233(5) 0.9942(4) 0.8068(3) 0.0786(14) Uani 0.525(4) 1 d D U P A 1
C3 C 0.4731(17) 0.7372(12) 0.9876(9) 0.113(4) Uani 0.525(4) 1 d D U P A 1
H3A H 0.465145 0.651321 0.996985 0.169 Uiso 0.525(4) 1 calc R U P A 1
H3B H 0.373998 0.741567 0.969736 0.169 Uiso 0.525(4) 1 calc R U P A 1
H3C H 0.539836 0.797030 1.052468 0.169 Uiso 0.525(4) 1 calc R U P A 1
C4 C 0.6819(4) 0.8272(9) 0.9187(3) 0.070(2) Uani 0.525(4) 1 d D U P A 1
C5 C 0.7339(2) 0.87212(16) 0.83364(13) 0.0505(4) Uani 1 1 d . . . . .
C6 C 0.9006(2) 0.88406(19) 0.85322(13) 0.0538(4) Uani 1 1 d . . . . .
H6A H 0.971693 0.971921 0.884583 0.065 Uiso 1 1 calc R U . . .
H6B H 0.926740 0.826800 0.899603 0.065 Uiso 1 1 calc R U . . .
C7 C 0.9013(2) 0.84495(16) 0.74340(13) 0.0485(4) Uani 1 1 d . . . . .
C8 C 1.0271(2) 0.85754(17) 0.71283(14) 0.0524(4) Uani 1 1 d . . . . .
C9 C 0.9988(2) 0.81066(17) 0.60568(14) 0.0515(4) Uani 1 1 d . . . . .
C10 C 0.8515(2) 0.75380(16) 0.53153(13) 0.0490(4) Uani 1 1 d . . . . .
C11 C 0.7260(2) 0.74110(16) 0.56520(12) 0.0481(4) Uani 1 1 d . . . . .
C12 C 0.7535(2) 0.78693(16) 0.67184(12) 0.0464(4) Uani 1 1 d . . . . .
C13 C 0.6378(2) 0.77758(18) 0.72593(12) 0.0518(4) Uani 1 1 d . . . . .
H13A H 0.591729 0.690358 0.736667 0.062 Uiso 1 1 calc R U . . .
H13B H 0.558238 0.804089 0.684901 0.062 Uiso 1 1 calc R U . . .
C14 C 0.5741(2) 0.68324(18) 0.49001(13) 0.0527(4) Uani 1 1 d . . . . .
C15 C 0.4525(2) 0.63326(19) 0.42173(14) 0.0555(4) Uani 1 1 d . . . . .
C16 C 0.3144(2) 0.56775(17) 0.33366(14) 0.0537(4) Uani 1 1 d . U . . .
C17 C 0.3234(2) 0.5404(2) 0.23324(15) 0.0614(5) Uani 1 1 d . U . . .
H17 H 0.418033 0.566432 0.224227 0.074 Uiso 1 1 calc R U . . .
C18 C 0.1927(3) 0.4749(2) 0.14683(19) 0.0793(7) Uani 1 1 d . U . . .
H18 H 0.198041 0.457325 0.079504 0.095 Uiso 1 1 calc R U . . .
C19 C 0.0571(3) 0.4371(3) 0.1626(2) 0.0875(8) Uani 1 1 d . U . . .
C20 C 0.0422(3) 0.4611(3) 0.2585(3) 0.0873(8) Uani 1 1 d . U . . .
H20 H -0.053568 0.433032 0.265858 0.105 Uiso 1 1 calc R U . . .
C21 C 0.1723(3) 0.5284(2) 0.3459(2) 0.0691(5) Uani 1 1 d . U . . .
H21 H 0.164287 0.546948 0.412183 0.083 Uiso 1 1 calc R U . . .
C22 C 0.8249(2) 0.70509(18) 0.41794(13) 0.0529(4) Uani 1 1 d . . . . .
C23 C 0.8716(3) 0.7895(2) 0.35300(16) 0.0708(6) Uani 1 1 d . . . . .
H23 H 0.920701 0.877520 0.380425 0.085 Uiso 1 1 calc R U . . .
C24 C 0.8456(4) 0.7437(3) 0.24725(18) 0.0859(8) Uani 1 1 d . . . . .
H24 H 0.878092 0.799847 0.203654 0.103 Uiso 1 1 calc R U . . .
C25 C 0.7713(3) 0.6144(3) 0.20900(16) 0.0781(7) Uani 1 1 d . . . . .
C26 C 0.7223(3) 0.5280(2) 0.26967(17) 0.0685(5) Uani 1 1 d . . . . .
H26 H 0.671972 0.440287 0.241082 0.082 Uiso 1 1 calc R U . . .
C27 C 0.7497(2) 0.5745(2) 0.37506(15) 0.0612(5) Uani 1 1 d . . . . .
H27 H 0.717055 0.517216 0.417865 0.073 Uiso 1 1 calc R U . . .
C28 C 1.1317(2) 0.8166(2) 0.57185(16) 0.0604(5) Uani 1 1 d . . . . .
C29 C 1.3293(4) 0.9496(4) 0.5175(3) 0.1144(12) Uani 1 1 d . . . . .
H29A H 1.414515 0.956158 0.577815 0.172 Uiso 1 1 calc R U . . .
H29B H 1.353475 1.027358 0.489072 0.172 Uiso 1 1 calc R U . . .
H29C H 1.307061 0.877470 0.463994 0.172 Uiso 1 1 calc R U . . .
C30 C 1.1863(3) 0.9161(3) 0.79157(18) 0.0729(6) Uani 1 1 d . . . . .
H30A H 1.236577 1.000984 0.780005 0.109 Uiso 1 1 calc R U . . .
H30B H 1.241699 0.863122 0.782546 0.109 Uiso 1 1 calc R U . . .
H30C H 1.182371 0.921749 0.862471 0.109 Uiso 1 1 calc R U . . .
C1' C 0.7565(14) 1.1897(6) 0.7703(8) 0.132(3) Uani 0.475(4) 1 d D U P A 2
H1'1 H 0.762524 1.217624 0.705071 0.198 Uiso 0.475(4) 1 calc R U P A 2
H1'2 H 0.837349 1.251636 0.829278 0.198 Uiso 0.475(4) 1 calc R U P A 2
H1'3 H 0.660078 1.182106 0.776694 0.198 Uiso 0.475(4) 1 calc R U P A 2
C2' C 0.7215(6) 1.0039(4) 0.8418(3) 0.0656(13) Uani 0.475(4) 1 d D U P A 2
C3' C 0.4742(15) 0.7864(13) 0.9838(11) 0.094(3) Uani 0.475(4) 1 d D U P A 2
H3'1 H 0.365804 0.741039 0.953529 0.141 Uiso 0.475(4) 1 calc R U P A 2
H3'2 H 0.496446 0.863833 1.031485 0.141 Uiso 0.475(4) 1 calc R U P A 2
H3'3 H 0.519038 0.732391 1.022197 0.141 Uiso 0.475(4) 1 calc R U P A 2
C4' C 0.6806(4) 0.8292(7) 0.9289(5) 0.0552(16) Uani 0.475(4) 1 d D U P A 2
F1 F 0.7461(3) 0.5686(2) 0.10559(12) 0.1213(7) Uani 1 1 d . . . . .
F2 F -0.0708(2) 0.3712(2) 0.07743(19) 0.1449(9) Uani 1 1 d . . . . .
O1 O 0.8151(6) 1.0973(3) 0.8823(4) 0.1175(17) Uani 0.525(4) 1 d D U P A 1
O2 O 0.6380(7) 1.0180(4) 0.7307(4) 0.137(2) Uani 0.525(4) 1 d D U P A 1
O3 O 0.5338(4) 0.7698(5) 0.9029(5) 0.0808(16) Uani 0.525(4) 1 d D U P A 1
O4 O 0.7644(7) 0.8432(8) 1.0112(4) 0.0823(17) Uani 0.525(4) 1 d D U P A 1
O5 O 1.1971(2) 0.93098(18) 0.55018(16) 0.0825(5) Uani 1 1 d . . . . .
O6 O 1.1758(2) 0.73070(19) 0.56722(19) 0.0989(6) Uani 1 1 d . . . . .
O1' O 0.7710(6) 1.0652(4) 0.7703(3) 0.0961(13) Uani 0.475(4) 1 d D U P A 2
O2' O 0.7134(7) 1.0588(4) 0.9214(3) 0.1181(18) Uani 0.475(4) 1 d D U P A 2
O3' O 0.5362(4) 0.8191(6) 0.9001(6) 0.0760(15) Uani 0.475(4) 1 d D U P A 2
O4' O 0.7622(9) 0.8025(7) 1.0052(5) 0.093(2) Uani 0.475(4) 1 d D U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.444(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O2 1.2299(2) . ?
C2 O1 1.3299(2) . ?
C2 C5 1.471(5) . ?
C3 O3 1.446(9) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 O4 1.2300(2) . ?
C4 O3 1.3300(2) . ?
C4 C5 1.436(5) . ?
C5 C2' 1.524(4) . ?
C5 C6 1.551(3) . ?
C5 C13 1.551(2) . ?
C5 C4' 1.564(6) . ?
C6 C7 1.507(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.389(3) . ?
C7 C12 1.389(2) . ?
C8 C9 1.404(2) . ?
C8 C30 1.502(3) . ?
C9 C10 1.397(3) . ?
C9 C28 1.497(3) . ?
C10 C11 1.411(2) . ?
C10 C22 1.494(2) . ?
C11 C12 1.397(2) . ?
C11 C14 1.434(2) . ?
C12 C13 1.506(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.194(3) . ?
C15 C16 1.433(3) . ?
C16 C21 1.388(3) . ?
C16 C17 1.393(3) . ?
C17 C18 1.383(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.350(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.354(4) . ?
C19 F2 1.361(3) . ?
C20 C21 1.390(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.385(3) . ?
C22 C27 1.386(3) . ?
C23 C24 1.389(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.363(4) . ?
C24 H24 0.9300 . ?
C25 F1 1.362(2) . ?
C25 C26 1.363(4) . ?
C26 C27 1.383(3) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 O6 1.192(3) . ?
C28 O5 1.322(3) . ?
C29 O5 1.454(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C1' O1' 1.453(7) . ?
C1' H1'1 0.9600 . ?
C1' H1'2 0.9600 . ?
C1' H1'3 0.9600 . ?
C2' O2' 1.2299(2) . ?
C2' O1' 1.3299(2) . ?
C3' O3' 1.441(10) . ?
C3' H3'1 0.9600 . ?
C3' H3'2 0.9600 . ?
C3' H3'3 0.9600 . ?
C4' O4' 1.2300(2) . ?
C4' O3' 1.3300(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 113.6(4) . . ?
O2 C2 C5 132.0(3) . . ?
O1 C2 C5 114.2(3) . . ?
O3 C3 H3A 109.5 . . ?
O3 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O3 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O4 C4 O3 114.1(6) . . ?
O4 C4 C5 125.0(5) . . ?
O3 C4 C5 120.8(4) . . ?
C4 C5 C2 117.2(5) . . ?
C4 C5 C6 111.8(2) . . ?
C2 C5 C6 107.6(2) . . ?
C2' C5 C6 111.7(2) . . ?
C4 C5 C13 111.9(3) . . ?
C2 C5 C13 101.67(17) . . ?
C2' C5 C13 116.0(2) . . ?
C6 C5 C13 105.71(13) . . ?
C2' C5 C4' 97.8(3) . . ?
C6 C5 C4' 111.48(19) . . ?
C13 C5 C4' 114.2(3) . . ?
C7 C6 C5 103.51(13) . . ?
C7 C6 H6A 111.1 . . ?
C5 C6 H6A 111.1 . . ?
C7 C6 H6B 111.1 . . ?
C5 C6 H6B 111.1 . . ?
H6A C6 H6B 109.0 . . ?
C8 C7 C12 121.73(15) . . ?
C8 C7 C6 127.48(16) . . ?
C12 C7 C6 110.75(15) . . ?
C7 C8 C9 117.11(16) . . ?
C7 C8 C30 121.39(17) . . ?
C9 C8 C30 121.48(17) . . ?
C10 C9 C8 122.43(16) . . ?
C10 C9 C28 119.29(16) . . ?
C8 C9 C28 118.21(17) . . ?
C9 C10 C11 119.15(15) . . ?
C9 C10 C22 121.25(16) . . ?
C11 C10 C22 119.60(16) . . ?
C12 C11 C10 118.64(16) . . ?
C12 C11 C14 121.51(16) . . ?
C10 C11 C14 119.85(14) . . ?
C7 C12 C11 120.92(15) . . ?
C7 C12 C13 111.41(14) . . ?
C11 C12 C13 127.62(16) . . ?
C12 C13 C5 103.03(14) . . ?
C12 C13 H13A 111.2 . . ?
C5 C13 H13A 111.2 . . ?
C12 C13 H13B 111.2 . . ?
C5 C13 H13B 111.2 . . ?
H13A C13 H13B 109.1 . . ?
C15 C14 C11 174.94(18) . . ?
C14 C15 C16 173.93(19) . . ?
C21 C16 C17 119.08(19) . . ?
C21 C16 C15 121.95(19) . . ?
C17 C16 C15 118.96(18) . . ?
C18 C17 C16 120.5(2) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 118.4(2) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
C18 C19 C20 123.4(2) . . ?
C18 C19 F2 118.0(3) . . ?
C20 C19 F2 118.6(3) . . ?
C19 C20 C21 118.9(2) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 H20 120.5 . . ?
C16 C21 C20 119.7(2) . . ?
C16 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C23 C22 C27 118.83(17) . . ?
C23 C22 C10 120.80(17) . . ?
C27 C22 C10 120.36(16) . . ?
C22 C23 C24 120.5(2) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 118.3(2) . . ?
C25 C24 H24 120.8 . . ?
C23 C24 H24 120.8 . . ?
F1 C25 C26 118.1(2) . . ?
F1 C25 C24 118.7(2) . . ?
C26 C25 C24 123.16(19) . . ?
C25 C26 C27 118.0(2) . . ?
C25 C26 H26 121.0 . . ?
C27 C26 H26 121.0 . . ?
C26 C27 C22 121.12(19) . . ?
C26 C27 H27 119.4 . . ?
C22 C27 H27 119.4 . . ?
O6 C28 O5 124.0(2) . . ?
O6 C28 C9 124.67(19) . . ?
O5 C28 C9 111.33(17) . . ?
O5 C29 H29A 109.5 . . ?
O5 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O5 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C8 C30 H30A 109.5 . . ?
C8 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C8 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O1' C1' H1'1 109.5 . . ?
O1' C1' H1'2 109.5 . . ?
H1'1 C1' H1'2 109.5 . . ?
O1' C1' H1'3 109.5 . . ?
H1'1 C1' H1'3 109.5 . . ?
H1'2 C1' H1'3 109.5 . . ?
O2' C2' O1' 123.6(4) . . ?
O2' C2' C5 123.4(4) . . ?
O1' C2' C5 109.5(3) . . ?
O3' C3' H3'1 109.5 . . ?
O3' C3' H3'2 109.5 . . ?
H3'1 C3' H3'2 109.5 . . ?
O3' C3' H3'3 109.5 . . ?
H3'1 C3' H3'3 109.5 . . ?
H3'2 C3' H3'3 109.5 . . ?
O4' C4' O3' 132.9(7) . . ?
O4' C4' C5 121.8(6) . . ?
O3' C4' C5 104.9(5) . . ?
C2 O1 C1 117.9(5) . . ?
C4 O3 C3 123.5(8) . . ?
C28 O5 C29 116.7(2) . . ?
C2' O1' C1' 112.6(5) . . ?
C4' O3' C3' 110.9(8) . . ?

_refine_diff_density_max         0.436
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.041



