# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_x8_12116_0m


_symmetry_space_group_name_hall  ?
#Added by publCIF



_audit_update_record             
;
2014-03-27 # Formatted by publCIF

;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H30 O6'
_chemical_formula_weight         606.64

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   12.8251(19)
_cell_length_b                   17.633(3)
_cell_length_c                   13.342(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.491(3)
_cell_angle_gamma                90.00
_cell_volume                     3011.7(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1272
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      100(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            90592
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         31.62
_reflns_number_total             10090
_reflns_number_gt                8435
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0769P)²+1.0819P] 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         10090
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1361
_refine_ls_wR_factor_gt          0.1263
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.06607(6) 0.18867(4) 1.09844(6) 0.01898(15) Uani 1 1 d . . .
O2 O 0.08687(6) 0.19756(4) 1.02499(6) 0.02236(16) Uani 1 1 d . . .
O3 O 0.54930(7) -0.10126(5) 0.56229(6) 0.02504(17) Uani 1 1 d . . .
C2 C 0.08073(7) 0.04565(6) 0.97401(7) 0.01530(17) Uani 1 1 d . . .
H2 H 0.1366 0.0774 0.9564 0.018 Uiso 1 1 calc R . .
C8 C 0.40437(8) -0.14637(6) 0.64165(8) 0.02018(19) Uani 1 1 d . . .
H8 H 0.4064 -0.1902 0.6004 0.024 Uiso 1 1 calc R . .
C5 C 0.24075(8) -0.06391(6) 0.83731(8) 0.01768(18) Uani 1 1 d . . .
C13 C 0.01300(8) 0.16014(6) 1.04916(7) 0.01606(17) Uani 1 1 d . . .
C3 C 0.08296(7) -0.03119(6) 0.94645(7) 0.01478(17) Uani 1 1 d . . .
C1 C 0.00065(7) 0.07748(5) 1.02587(7) 0.01460(17) Uani 1 1 d . . .
C11 C 0.39790(8) -0.01727(6) 0.76091(8) 0.01900(19) Uani 1 1 d . . .
H11 H 0.3956 0.0270 0.8012 0.023 Uiso 1 1 calc R . .
C9 C 0.47827(8) -0.08914(6) 0.63312(8) 0.01794(18) Uani 1 1 d . . .
C6 C 0.32307(8) -0.07407(6) 0.77078(7) 0.01617(17) Uani 1 1 d . . .
C17 C -0.24376(9) 0.33534(6) 1.31596(8) 0.0224(2) Uani 1 1 d . . .
H17 H -0.2427 0.3478 1.3853 0.027 Uiso 1 1 calc R . .
C16 C -0.15278(9) 0.31063(6) 1.27390(8) 0.0207(2) Uani 1 1 d . . .
H16 H -0.0900 0.3058 1.3150 0.025 Uiso 1 1 calc R . .
C18 C -0.33576(9) 0.34170(6) 1.25641(9) 0.0223(2) Uani 1 1 d . . .
H18 H -0.3977 0.3587 1.2850 0.027 Uiso 1 1 calc R . .
C4 C 0.16844(8) -0.05448(6) 0.88953(8) 0.01683(18) Uani 1 1 d . . .
C10 C 0.47555(8) -0.02446(6) 0.69316(8) 0.01949(19) Uani 1 1 d . . .
H10 H 0.5263 0.0143 0.6878 0.023 Uiso 1 1 calc R . .
C7 C 0.32753(8) -0.13937(6) 0.71064(8) 0.01968(19) Uani 1 1 d . . .
H7 H 0.2780 -0.1789 0.7171 0.024 Uiso 1 1 calc R . .
C14 C -0.05433(9) 0.26820(6) 1.12691(9) 0.0211(2) Uani 1 1 d . . .
H14A H -0.0418 0.2994 1.0671 0.025 Uiso 1 1 calc R . .
H14B H 0.0058 0.2744 1.1763 0.025 Uiso 1 1 calc R . .
C15 C -0.15325(8) 0.29293(6) 1.17205(8) 0.01846(18) Uani 1 1 d . . .
C19 C -0.33768(9) 0.32327(7) 1.15491(9) 0.0250(2) Uani 1 1 d . . .
H19 H -0.4010 0.3270 1.1145 0.030 Uiso 1 1 calc R . .
C20 C -0.24643(9) 0.29935(7) 1.11265(8) 0.0234(2) Uani 1 1 d . . .
H20 H -0.2476 0.2874 1.0432 0.028 Uiso 1 1 calc R . .
C12 C 0.63019(9) -0.04642(7) 0.55503(9) 0.0248(2) Uani 1 1 d . . .
H12A H 0.5992 0.0032 0.5386 0.037 Uiso 1 1 calc R . .
H12B H 0.6758 -0.0615 0.5022 0.037 Uiso 1 1 calc R . .
H12C H 0.6712 -0.0432 0.6193 0.037 Uiso 1 1 calc R . .
O4 O 0.37088(6) 0.18130(4) 0.04450(6) 0.01904(15) Uani 1 1 d . . .
O6 O -0.07114(7) 0.09172(5) 0.42093(7) 0.02650(18) Uani 1 1 d . . .
O5 O 0.53479(7) 0.20643(5) 0.00133(7) 0.02644(18) Uani 1 1 d . . .
C22 C 0.48045(7) 0.07757(5) 0.01452(7) 0.01400(16) Uani 1 1 d . . .
C29 C 0.00526(8) 0.07720(6) 0.35642(8) 0.01796(18) Uani 1 1 d . . .
C27 C 0.10145(8) -0.00258(6) 0.24837(8) 0.01746(18) Uani 1 1 d . . .
H27 H 0.1118 -0.0506 0.2182 0.021 Uiso 1 1 calc R . .
C25 C 0.25275(8) 0.04742(6) 0.16447(7) 0.01652(17) Uani 1 1 d . . .
C35 C 0.32137(8) 0.28246(5) 0.15426(8) 0.01637(17) Uani 1 1 d . . .
C33 C 0.46710(8) 0.16195(6) 0.02060(7) 0.01640(17) Uani 1 1 d . . .
C24 C 0.32426(8) 0.04020(6) 0.11009(7) 0.01614(17) Uani 1 1 d . . .
C31 C 0.15262(8) 0.12821(6) 0.27502(8) 0.01867(19) Uani 1 1 d . . .
H31 H 0.1974 0.1696 0.2623 0.022 Uiso 1 1 calc R . .
C30 C 0.07197(9) 0.13784(6) 0.33875(8) 0.0204(2) Uani 1 1 d . . .
H30 H 0.0622 0.1854 0.3702 0.025 Uiso 1 1 calc R . .
C21 C 0.56724(7) 0.05335(5) -0.03449(7) 0.01484(17) Uani 1 1 d . . .
H21 H 0.6139 0.0905 -0.0574 0.018 Uiso 1 1 calc R . .
C23 C 0.41101(7) 0.02343(5) 0.05168(7) 0.01430(16) Uani 1 1 d . . .
C26 C 0.16865(7) 0.05760(6) 0.22901(7) 0.01523(17) Uani 1 1 d . . .
C40 C 0.23158(8) 0.32382(6) 0.17166(8) 0.01925(19) Uani 1 1 d . . .
H40 H 0.1858 0.3391 0.1167 0.023 Uiso 1 1 calc R . .
C36 C 0.38801(8) 0.26040(6) 0.23554(8) 0.02044(19) Uani 1 1 d . . .
H36 H 0.4497 0.2327 0.2243 0.025 Uiso 1 1 calc R . .
C39 C 0.20868(9) 0.34286(6) 0.26933(8) 0.0223(2) Uani 1 1 d . . .
H39 H 0.1476 0.3714 0.2806 0.027 Uiso 1 1 calc R . .
C34 C 0.34497(9) 0.26167(6) 0.04849(8) 0.0202(2) Uani 1 1 d . . .
H34A H 0.2835 0.2725 0.0022 0.024 Uiso 1 1 calc R . .
H34B H 0.4044 0.2923 0.0271 0.024 Uiso 1 1 calc R . .
C28 C 0.01977(8) 0.00696(6) 0.31117(8) 0.01812(18) Uani 1 1 d . . .
H28 H -0.0258 -0.0341 0.3232 0.022 Uiso 1 1 calc R . .
C37 C 0.36458(9) 0.27880(6) 0.33309(8) 0.0225(2) Uani 1 1 d . . .
H37 H 0.4099 0.2630 0.3881 0.027 Uiso 1 1 calc R . .
C32 C -0.14259(9) 0.03196(7) 0.43988(9) 0.0250(2) Uani 1 1 d . . .
H32A H -0.1795 0.0165 0.3767 0.037 Uiso 1 1 calc R . .
H32B H -0.1933 0.0498 0.4867 0.037 Uiso 1 1 calc R . .
H32C H -0.1040 -0.0114 0.4693 0.037 Uiso 1 1 calc R . .
C38 C 0.27506(9) 0.32024(6) 0.35046(8) 0.0227(2) Uani 1 1 d . . .
H38 H 0.2593 0.3330 0.4171 0.027 Uiso 1 1 calc R . .


_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 C13 1.3398(12) . ?
O1 C14 1.4583(12) . ?
O2 C13 1.2141(12) . ?
O3 C9 1.3687(12) . ?
O3 C12 1.4258(14) . ?
C2 C1 1.3911(13) . ?
C2 C3 1.4048(14) . ?
C8 C7 1.3944(14) . ?
C8 C9 1.3939(15) . ?
C5 C4 1.2049(14) . ?
C5 C6 1.4315(14) . ?
C13 C1 1.4966(14) . ?
C3 C1 1.4145(13) 3_557 ?
C3 C4 1.4313(14) . ?
C1 C3 1.4145(13) 3_557 ?
C11 C10 1.3909(14) . ?
C11 C6 1.3990(14) . ?
C9 C10 1.3955(15) . ?
C6 C7 1.4065(14) . ?
C17 C18 1.3863(16) . ?
C17 C16 1.3950(15) . ?
C16 C15 1.3939(15) . ?
C18 C19 1.3913(16) . ?
C14 C15 1.5019(15) . ?
C15 C20 1.3978(16) . ?
C19 C20 1.3949(16) . ?
O4 C33 1.3376(12) . ?
O4 C34 1.4573(12) . ?
O6 C29 1.3672(12) . ?
O6 C32 1.4292(14) . ?
O5 C33 1.2091(13) . ?
C22 C21 1.3920(13) . ?
C22 C23 1.4157(13) . ?
C22 C33 1.5005(13) . ?
C29 C28 1.3951(14) . ?
C29 C30 1.3985(15) . ?
C27 C28 1.3909(14) . ?
C27 C26 1.4011(14) . ?
C25 C24 1.2103(14) . ?
C25 C26 1.4318(13) . ?
C35 C36 1.3945(14) . ?
C35 C40 1.3945(14) . ?
C35 C34 1.5066(14) . ?
C24 C23 1.4277(13) . ?
C31 C30 1.3888(14) . ?
C31 C26 1.4088(14) . ?
C21 C23 1.4039(13) 3_655 ?
C23 C21 1.4039(13) 3_655 ?
C40 C39 1.3942(15) . ?
C36 C37 1.3918(15) . ?
C39 C38 1.3941(16) . ?
C37 C38 1.3922(16) . ?

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
C13 O1 C14 114.81(8) . . ?
C9 O3 C12 117.30(9) . . ?
C1 C2 C3 123.16(9) . . ?
C7 C8 C9 120.08(9) . . ?
C4 C5 C6 176.97(11) . . ?
O2 C13 O1 123.54(9) . . ?
O2 C13 C1 123.27(9) . . ?
O1 C13 C1 113.19(8) . . ?
C2 C3 C1 117.41(9) . 3_557 ?
C2 C3 C4 116.37(9) . . ?
C1 C3 C4 126.18(9) 3_557 . ?
C2 C1 C3 119.43(9) . 3_557 ?
C2 C1 C13 115.10(9) . . ?
C3 C1 C13 125.46(9) 3_557 . ?
C10 C11 C6 121.22(9) . . ?
O3 C9 C10 124.40(10) . . ?
O3 C9 C8 115.33(9) . . ?
C10 C9 C8 120.26(9) . . ?
C11 C6 C7 118.72(9) . . ?
C11 C6 C5 120.32(9) . . ?
C7 C6 C5 120.89(9) . . ?
C18 C17 C16 119.88(10) . . ?
C15 C16 C17 120.53(10) . . ?
C17 C18 C19 120.20(10) . . ?
C5 C4 C3 171.03(11) . . ?
C11 C10 C9 119.44(10) . . ?
C8 C7 C6 120.27(10) . . ?
O1 C14 C15 107.90(8) . . ?
C16 C15 C20 119.18(10) . . ?
C16 C15 C14 120.15(10) . . ?
C20 C15 C14 120.67(10) . . ?
C18 C19 C20 119.90(11) . . ?
C19 C20 C15 120.30(10) . . ?
C33 O4 C34 118.19(8) . . ?
C29 O6 C32 117.72(9) . . ?
C21 C22 C23 119.72(8) . . ?
C21 C22 C33 115.26(8) . . ?
C23 C22 C33 124.99(9) . . ?
O6 C29 C28 123.94(9) . . ?
O6 C29 C30 115.60(9) . . ?
C28 C29 C30 120.45(9) . . ?
C28 C27 C26 120.92(9) . . ?
C24 C25 C26 178.81(11) . . ?
C36 C35 C40 119.32(9) . . ?
C36 C35 C34 120.80(9) . . ?
C40 C35 C34 119.88(9) . . ?
O5 C33 O4 124.76(9) . . ?
O5 C33 C22 123.09(9) . . ?
O4 C33 C22 112.07(8) . . ?
C25 C24 C23 173.31(10) . . ?
C30 C31 C26 120.58(9) . . ?
C31 C30 C29 119.72(9) . . ?
C22 C21 C23 123.03(9) . 3_655 ?
C21 C23 C22 117.23(8) 3_655 . ?
C21 C23 C24 117.27(9) 3_655 . ?
C22 C23 C24 125.40(9) . . ?
C27 C26 C31 118.77(9) . . ?
C27 C26 C25 120.69(9) . . ?
C31 C26 C25 120.54(9) . . ?
C39 C40 C35 120.31(10) . . ?
C37 C36 C35 120.35(10) . . ?
C40 C39 C38 120.23(10) . . ?
O4 C34 C35 109.27(8) . . ?
C27 C28 C29 119.55(9) . . ?
C38 C37 C36 120.34(10) . . ?
C37 C38 C39 119.45(10) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        31.62
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.691
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.058

_database_code_depnum_ccdc_archive 'CCDC 1003637'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_x8_12160_0m
# publcif _publ_body_element loop end

_audit_update_record             
;
2013-08-08 # Formatted by publCIF
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H42 O6'
_chemical_formula_weight         618.74

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   6.6014(4)
_cell_length_b                   17.3786(11)
_cell_length_c                   13.6759(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.0420(10)
_cell_angle_gamma                90.00
_cell_volume                     1557.11(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.051
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'

_exptl_special_details           
; 
 Bruker X8 Kappa DUO four-circle diffractometer, Bruker APEX2 CCD.  
 The instrument was purchased with the help of funding from the
 National Science Foundation (NSF) under Grant Number 
 CHE-0946721.  Please acknowledge this grant in all publications 
 of this structure.
 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'I\mS micro-focus sealed tube'
_diffrn_radiation_monochromator  'Incoatech I\mS multilayer optics'
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            44002
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         30.51
_reflns_number_total             4772
_reflns_number_gt                3769
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2011)'
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0543P)²+0.6680P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4772
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.1101
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.45737(12) 0.61507(5) -0.03591(6) 0.01629(17) Uani 1 1 d . . .
O1 O 0.32655(14) 0.65889(5) 0.09761(6) 0.02042(19) Uani 1 1 d . . .
O3 O -0.85628(13) 0.58678(5) 0.50839(6) 0.02102(19) Uani 1 1 d . . .
C15 C 0.73677(17) 0.67691(6) -0.10371(8) 0.0147(2) Uani 1 1 d . . .
H15 H 0.7954 0.6245 -0.1113 0.018 Uiso 1 1 calc R . .
C13 C 0.32285(17) 0.61412(6) 0.02965(8) 0.0147(2) Uani 1 1 d . . .
C11 C 0.02111(17) 0.55064(6) 0.07743(8) 0.0144(2) Uani 1 1 d . . .
H11 H 0.0359 0.5859 0.1309 0.017 Uiso 1 1 calc R . .
C2 C -0.72582(17) 0.56993(6) 0.44141(8) 0.0158(2) Uani 1 1 d . . .
C12 C 0.16221(16) 0.55330(6) 0.00981(8) 0.0142(2) Uani 1 1 d . . .
C16 C 0.60856(17) 0.69894(7) -0.20057(8) 0.0180(2) Uani 1 1 d . . .
H16A H 0.5036 0.6589 -0.2180 0.022 Uiso 1 1 calc R . .
H16B H 0.5374 0.7481 -0.1916 0.022 Uiso 1 1 calc R . .
C9 C -0.27326(17) 0.50298(6) 0.14627(8) 0.0159(2) Uani 1 1 d . . .
C7 C -0.80879(17) 0.52576(7) 0.36104(8) 0.0178(2) Uani 1 1 d . . .
H7 H -0.9461 0.5084 0.3569 0.021 Uiso 1 1 calc R . .
C19 C 1.04326(18) 0.74140(7) -0.16300(10) 0.0222(2) Uani 1 1 d . . .
H19A H 1.1506 0.7805 -0.1457 0.027 Uiso 1 1 calc R . .
H19B H 1.1112 0.6917 -0.1727 0.027 Uiso 1 1 calc R . .
C14 C 0.61060(17) 0.67514(6) -0.01856(8) 0.0158(2) Uani 1 1 d . . .
H14A H 0.6998 0.6649 0.0437 0.019 Uiso 1 1 calc R . .
H14B H 0.5435 0.7256 -0.0126 0.019 Uiso 1 1 calc R . .
C8 C -0.36881(18) 0.51602(6) 0.21391(8) 0.0169(2) Uani 1 1 d . . .
C4 C -0.40528(18) 0.57437(6) 0.37511(8) 0.0169(2) Uani 1 1 d . . .
H4 H -0.2667 0.5903 0.3806 0.020 Uiso 1 1 calc R . .
C3 C -0.52282(18) 0.59335(7) 0.44934(8) 0.0165(2) Uani 1 1 d . . .
H3 H -0.4650 0.6221 0.5050 0.020 Uiso 1 1 calc R . .
C17 C 0.7389(2) 0.70752(7) -0.28493(9) 0.0214(2) Uani 1 1 d . . .
H17A H 0.6521 0.7256 -0.3447 0.026 Uiso 1 1 calc R . .
H17B H 0.7960 0.6568 -0.2998 0.026 Uiso 1 1 calc R . .
C5 C -0.48746(17) 0.53232(6) 0.29253(8) 0.0152(2) Uani 1 1 d . . .
C20 C 0.91290(17) 0.73383(7) -0.07852(9) 0.0175(2) Uani 1 1 d . . .
H20A H 0.8568 0.7849 -0.0642 0.021 Uiso 1 1 calc R . .
H20B H 0.9996 0.7161 -0.0186 0.021 Uiso 1 1 calc R . .
C6 C -0.69117(18) 0.50724(7) 0.28755(8) 0.0171(2) Uani 1 1 d . . .
H6 H -0.7485 0.4772 0.2330 0.021 Uiso 1 1 calc R . .
C10 C -0.14210(17) 0.49834(6) 0.07045(8) 0.0141(2) Uani 1 1 d . . .
C18 C 0.9136(2) 0.76465(7) -0.25866(9) 0.0223(3) Uani 1 1 d . . .
H18A H 1.0004 0.7664 -0.3127 0.027 Uiso 1 1 calc R . .
H18B H 0.8568 0.8167 -0.2512 0.027 Uiso 1 1 calc R . .
C1 C -0.7784(2) 0.63305(7) 0.59088(9) 0.0225(2) Uani 1 1 d . . .
H1A H -0.6617 0.6070 0.6280 0.034 Uiso 1 1 calc R . .
H1B H -0.8854 0.6409 0.6336 0.034 Uiso 1 1 calc R . .
H1C H -0.7346 0.6830 0.5676 0.034 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C13 1.3371(13) . ?
O2 C14 1.4527(13) . ?
O1 C13 1.2100(13) . ?
O3 C2 1.3638(13) . ?
O3 C1 1.4288(15) . ?
C15 C14 1.5128(15) . ?
C15 C16 1.5306(16) . ?
C15 C20 1.5332(15) . ?
C13 C12 1.4983(15) . ?
C11 C12 1.3915(14) . ?
C11 C10 1.4039(15) . ?
C2 C3 1.3919(16) . ?
C2 C7 1.3964(16) . ?
C12 C10 1.4113(15) 3_565 ?
C16 C17 1.5288(15) . ?
C9 C8 1.2033(15) . ?
C9 C10 1.4323(14) . ?
C7 C6 1.3813(15) . ?
C19 C18 1.5273(19) . ?
C19 C20 1.5286(16) . ?
C8 C5 1.4339(15) . ?
C4 C3 1.3910(15) . ?
C4 C5 1.3977(15) . ?
C17 C18 1.5309(18) . ?
C5 C6 1.4073(16) . ?
C10 C12 1.4113(15) 3_565 ?

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
C13 O2 C14 113.93(8) . . ?
C2 O3 C1 117.08(9) . . ?
C14 C15 C16 111.91(9) . . ?
C14 C15 C20 108.30(9) . . ?
C16 C15 C20 110.90(9) . . ?
O1 C13 O2 123.68(10) . . ?
O1 C13 C12 122.68(10) . . ?
O2 C13 C12 113.62(9) . . ?
C12 C11 C10 123.16(10) . . ?
O3 C2 C3 124.48(10) . . ?
O3 C2 C7 115.32(10) . . ?
C3 C2 C7 120.20(10) . . ?
C11 C12 C10 119.27(10) . 3_565 ?
C11 C12 C13 114.81(9) . . ?
C10 C12 C13 125.90(9) 3_565 . ?
C17 C16 C15 112.01(10) . . ?
C8 C9 C10 170.94(12) . . ?
C6 C7 C2 119.98(10) . . ?
C18 C19 C20 111.22(10) . . ?
O2 C14 C15 109.09(9) . . ?
C9 C8 C5 178.35(13) . . ?
C3 C4 C5 121.18(10) . . ?
C4 C3 C2 119.45(10) . . ?
C16 C17 C18 111.33(10) . . ?
C4 C5 C6 118.36(10) . . ?
C4 C5 C8 121.03(10) . . ?
C6 C5 C8 120.60(10) . . ?
C19 C20 C15 111.55(10) . . ?
C7 C6 C5 120.77(10) . . ?
C11 C10 C12 117.57(9) . 3_565 ?
C11 C10 C9 116.18(9) . . ?
C12 C10 C9 126.25(10) 3_565 . ?
C19 C18 C17 110.87(10) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.051

_database_code_depnum_ccdc_archive 'CCDC 1003638'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_RP100913_0m_a_a

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H20 F10 O6'
_chemical_formula_weight         786.56

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                   6.816(2)
_cell_length_b                   7.448(3)
_cell_length_c                   16.417(6)
_cell_angle_alpha                79.881(7)
_cell_angle_beta                 81.961(7)
_cell_angle_gamma                75.475(7)
_cell_volume                     790.2(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_F_000             398
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.101
_exptl_absorpt_coefficient_mu    0.150
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11514
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.856
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3224
_reflns_number_gt                2558
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.1469P)²+0.3675P] 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         3224
_refine_ls_number_parameters     254
_refine_ls_number_restraints     68
_refine_ls_R_factor_all          0.0908
_refine_ls_R_factor_gt           0.0751
_refine_ls_wR_factor_ref         0.2180
_refine_ls_wR_factor_gt          0.2009
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.3572(2) 0.1242(2) 1.19703(10) 0.0243(4) Uani 1 1 d . U . . .
F002 F 0.1841(3) 0.7812(2) 1.18594(11) 0.0306(5) Uani 1 1 d . U . . .
F003 F 0.2912(3) 0.0843(3) 1.36564(11) 0.0320(5) Uani 1 1 d . U . . .
F004 F 0.1266(3) 0.7395(3) 1.35390(12) 0.0341(5) Uani 1 1 d . U . . .
F005 F 0.1779(3) 0.3913(3) 1.44345(11) 0.0358(5) Uani 1 1 d . U . . .
O006 O 0.1694(3) 0.3763(3) 1.06757(12) 0.0205(5) Uani 1 1 d . U . . .
O007 O 0.2306(3) -0.1539(3) 0.64602(12) 0.0258(5) Uani 1 1 d . U . . .
O008 O 0.4157(3) 0.2407(3) 0.97643(13) 0.0285(5) Uani 1 1 d . U . . .
C009 C 0.2501(4) 0.2531(4) 1.01497(16) 0.0186(6) Uani 1 1 d . U . . .
C00A C 0.0649(4) -0.1133(4) 0.93540(16) 0.0174(5) Uani 1 1 d . U . . .
C00B C 0.1385(4) -0.2180(4) 0.86729(16) 0.0190(6) Uani 1 1 d . U . . .
C00C C 0.1736(4) 0.0149(4) 0.94752(16) 0.0170(5) Uani 1 1 d . U . . .
H00C H 0.2942 0.0247 0.9119 0.020 Uiso 1 1 calc R U . . .
C00D C 0.1120(4) 0.1280(4) 1.00940(16) 0.0166(5) Uani 1 1 d . U . . .
C00E C 0.2707(4) 0.4535(4) 1.18677(16) 0.0173(6) Uani 1 1 d . U . . .
C00F C 0.2932(4) -0.6162(4) 0.76701(18) 0.0223(6) Uani 1 1 d . U . . .
H00F H 0.2825 -0.6690 0.8240 0.027 Uiso 1 1 calc R U . . .
C00G C 0.1989(4) -0.3038(4) 0.80996(17) 0.0214(6) Uani 1 1 d . U . . .
C00H C 0.2971(4) 0.2784(4) 1.23495(17) 0.0193(6) Uani 1 1 d . U . . .
C00I C 0.2572(4) -0.4224(4) 0.74665(18) 0.0213(6) Uani 1 1 d . U . . .
C00J C 0.2119(4) 0.6079(4) 1.22874(18) 0.0216(6) Uani 1 1 d . U . . .
C00K C 0.2075(4) 0.4124(4) 1.36014(17) 0.0233(6) Uani 1 1 d . U . . .
C00L C 0.2652(4) 0.2556(4) 1.32012(18) 0.0226(6) Uani 1 1 d . U . . .
C00M C 0.3065(4) 0.4723(4) 1.09346(17) 0.0214(6) Uani 1 1 d . U . . .
H00A H 0.2767 0.6061 1.0686 0.026 Uiso 1 1 calc R U . . .
H00B H 0.4499 0.4140 1.0758 0.026 Uiso 1 1 calc R U . . .
C00N C 0.3226(4) -0.4634(4) 0.60168(17) 0.0222(6) Uani 1 1 d . U . . .
H00N H 0.3320 -0.4114 0.5445 0.027 Uiso 1 1 calc R U . . .
C00O C 0.1811(4) 0.5886(4) 1.31454(18) 0.0239(6) Uani 1 1 d . U . . .
C00P C 0.2721(4) -0.3461(4) 0.66189(18) 0.0218(6) Uani 1 1 d . U . . .
C00Q C 0.3437(4) -0.7349(4) 0.7080(2) 0.0281(7) Uani 1 1 d . U . . .
H00Q H 0.3671 -0.8668 0.7238 0.034 Uiso 1 1 calc R U . . .
C00R C 0.3596(5) -0.6566(4) 0.62423(19) 0.0268(6) Uani 1 1 d . U . . .
H00R H 0.3960 -0.7360 0.5825 0.032 Uiso 1 1 calc R U . . .
C00S C 0.2314(5) -0.0736(5) 0.56115(19) 0.0306(7) Uani 1 1 d . U . . .
H00D H 0.3693 -0.1080 0.5332 0.046 Uiso 1 1 calc R U . . .
H00E H 0.1874 0.0632 0.5569 0.046 Uiso 1 1 calc R U . . .
H00G H 0.1379 -0.1204 0.5346 0.046 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C00H 1.348(3) . ?
F002 C00J 1.339(3) . ?
F003 C00L 1.344(3) . ?
F004 C00O 1.341(3) . ?
F005 C00K 1.341(3) . ?
O006 C009 1.335(3) . ?
O006 C00M 1.455(3) . ?
O007 C00P 1.373(3) . ?
O007 C00S 1.416(4) . ?
O008 C009 1.205(3) . ?
C009 C00D 1.502(4) . ?
C00A C00C 1.401(4) . ?
C00A C00D 1.419(4) 2_557 ?
C00A C00B 1.436(4) . ?
C00B C00G 1.198(4) . ?
C00C C00D 1.386(4) . ?
C00D C00A 1.419(4) 2_557 ?
C00E C00H 1.385(4) . ?
C00E C00J 1.389(4) . ?
C00E C00M 1.504(4) . ?
C00F C00Q 1.376(4) . ?
C00F C00I 1.390(4) . ?
C00G C00I 1.431(4) . ?
C00H C00L 1.372(4) . ?
C00I C00P 1.407(4) . ?
C00J C00O 1.382(4) . ?
C00K C00O 1.375(4) . ?
C00K C00L 1.385(4) . ?
C00N C00P 1.384(4) . ?
C00N C00R 1.388(4) . ?
C00Q C00R 1.396(4) . ?

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
C009 O006 C00M 117.0(2) . . ?
C00P O007 C00S 116.1(2) . . ?
O008 C009 O006 124.5(2) . . ?
O008 C009 C00D 123.0(2) . . ?
O006 C009 C00D 112.5(2) . . ?
C00C C00A C00D 117.5(2) . 2_557 ?
C00C C00A C00B 117.7(2) . . ?
C00D C00A C00B 124.8(2) 2_557 . ?
C00G C00B C00A 179.4(3) . . ?
C00D C00C C00A 122.5(2) . . ?
C00C C00D C00A 119.9(2) . 2_557 ?
C00C C00D C009 115.4(2) . . ?
C00A C00D C009 124.6(2) 2_557 . ?
C00H C00E C00J 116.8(3) . . ?
C00H C00E C00M 120.7(2) . . ?
C00J C00E C00M 122.4(2) . . ?
C00Q C00F C00I 122.7(3) . . ?
C00B C00G C00I 173.0(3) . . ?
F001 C00H C00L 118.5(2) . . ?
F001 C00H C00E 119.0(2) . . ?
C00L C00H C00E 122.5(3) . . ?
C00F C00I C00P 118.0(3) . . ?
C00F C00I C00G 120.9(3) . . ?
C00P C00I C00G 121.1(3) . . ?
F002 C00J C00O 118.3(3) . . ?
F002 C00J C00E 119.9(3) . . ?
C00O C00J C00E 121.8(3) . . ?
F005 C00K C00O 120.3(3) . . ?
F005 C00K C00L 119.7(3) . . ?
C00O C00K C00L 120.0(3) . . ?
F003 C00L C00H 121.5(3) . . ?
F003 C00L C00K 119.3(3) . . ?
C00H C00L C00K 119.3(3) . . ?
O006 C00M C00E 106.3(2) . . ?
C00P C00N C00R 120.5(3) . . ?
F004 C00O C00K 119.6(3) . . ?
F004 C00O C00J 120.9(3) . . ?
C00K C00O C00J 119.6(3) . . ?
O007 C00P C00N 124.9(3) . . ?
O007 C00P C00I 115.1(2) . . ?
C00N C00P C00I 120.0(3) . . ?
C00F C00Q C00R 118.4(3) . . ?
C00N C00R C00Q 120.4(3) . . ?

_refine_diff_density_max         0.555
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.128

_shelxl_version_number           2013-3



_database_code_depnum_ccdc_archive 'CCDC 1003639'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mo_x8_12144_0m

_audit_update_record             
;
2014-03-27 # Formatted by publCIF

;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C40 H20 F10 O6'
_chemical_formula_weight         786.56

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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9613(5)
_cell_length_b                   7.1312(5)
_cell_length_c                   17.3912(13)
_cell_angle_alpha                91.6740(10)
_cell_angle_beta                 90.0290(10)
_cell_angle_gamma                106.6190(10)
_cell_volume                     826.89(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             398
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9720
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_process_details   ?

_exptl_special_details           ?

_diffrn_ambient_temperature      190(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5012
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.17
_diffrn_reflns_theta_max         30.51
_reflns_number_total             5012
_reflns_number_gt                4159
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0632P)²+0.3944P] 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         5012
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.28686(16) -0.11366(17) 0.07177(6) 0.0373(3) Uani 1 1 d . . .
C2 C 0.38562(17) -0.36800(17) 0.00904(7) 0.0222(2) Uani 1 1 d . . .
C3 C 0.34935(18) -0.50417(18) -0.05183(7) 0.0234(2) Uani 1 1 d . . .
H3 H 0.2447 -0.5068 -0.0873 0.028 Uiso 1 1 calc R . .
F5 F 0.24313(19) 0.37378(15) 0.16000(6) 0.0515(3) Uani 1 1 d . . .
C12 C 0.58505(19) -0.23307(19) 0.12932(7) 0.0262(2) Uani 1 1 d . . .
F1 F 0.05227(18) -0.30532(14) 0.19650(6) 0.0490(3) Uani 1 1 d . . .
C1 C 0.53918(17) -0.36222(18) 0.06306(7) 0.0223(2) Uani 1 1 d . . .
C13 C 0.6225(2) -0.1307(2) 0.18665(8) 0.0290(3) Uani 1 1 d . . .
F4 F 0.2662(2) 0.43941(17) 0.31311(7) 0.0595(3) Uani 1 1 d . . .
C6 C 0.15070(19) 0.0320(2) 0.17383(7) 0.0268(2) Uani 1 1 d . . .
C4 C 0.2470(2) -0.2414(2) 0.01317(7) 0.0269(3) Uani 1 1 d . . .
F3 F 0.18436(19) 0.1330(2) 0.40926(6) 0.0597(3) Uani 1 1 d . . .
C5 C 0.1411(2) -0.0081(2) 0.08847(8) 0.0322(3) Uani 1 1 d . . .
H5A H 0.0050 -0.0881 0.0726 0.039 Uiso 1 1 calc R . .
H5B H 0.1742 0.1161 0.0607 0.039 Uiso 1 1 calc R . .
C14 C 0.65537(19) 0.0056(2) 0.25082(8) 0.0286(3) Uani 1 1 d . . .
O1 O 0.1134(2) -0.2552(2) -0.03205(8) 0.0612(5) Uani 1 1 d . . .
F2 F 0.0771(2) -0.23846(19) 0.35027(7) 0.0664(4) Uani 1 1 d . . .
C11 C 0.2022(2) 0.2198(2) 0.20557(8) 0.0319(3) Uani 1 1 d . . .
C7 C 0.1086(2) -0.1200(2) 0.22435(8) 0.0323(3) Uani 1 1 d . . .
O3 O 0.7290(3) 0.4273(2) 0.42681(8) 0.0606(4) Uani 1 1 d . . .
C9 C 0.1733(2) 0.1014(3) 0.33272(8) 0.0390(3) Uani 1 1 d . . .
C15 C 0.6444(2) -0.0534(2) 0.32637(9) 0.0376(3) Uani 1 1 d . . .
H15 H 0.6190 -0.1882 0.3369 0.045 Uiso 1 1 calc R . .
C10 C 0.2135(2) 0.2555(2) 0.28439(9) 0.0370(3) Uani 1 1 d . . .
C17 C 0.7062(2) 0.2808(2) 0.37194(9) 0.0402(3) Uani 1 1 d . . .
C8 C 0.1198(3) -0.0883(3) 0.30290(9) 0.0390(3) Uani 1 1 d . . .
C19 C 0.6948(2) 0.2057(2) 0.23686(9) 0.0360(3) Uani 1 1 d . . .
H19 H 0.7045 0.2481 0.1854 0.043 Uiso 1 1 calc R . .
C18 C 0.7197(3) 0.3421(2) 0.29678(10) 0.0414(4) Uani 1 1 d . . .
H18 H 0.7459 0.4771 0.2865 0.050 Uiso 1 1 calc R . .
C16 C 0.6706(3) 0.0848(3) 0.38732(9) 0.0427(4) Uani 1 1 d . . .
H16 H 0.6638 0.0439 0.4390 0.051 Uiso 1 1 calc R . .
C20 C 0.7222(6) 0.3736(5) 0.50482(13) 0.1032(12) Uani 1 1 d . . .
H20A H 0.5881 0.2891 0.5163 0.155 Uiso 1 1 calc R . .
H20B H 0.7524 0.4916 0.5382 0.155 Uiso 1 1 calc R . .
H20C H 0.8215 0.3028 0.5138 0.155 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C4 1.3212(15) . ?
O2 C5 1.4508(15) . ?
C2 C3 1.3881(16) . ?
C2 C1 1.4137(16) . ?
C2 C4 1.4987(16) . ?
C3 C1 1.4001(16) 2_645 ?
F5 C11 1.3367(18) . ?
C12 C13 1.2011(18) . ?
C12 C1 1.4309(16) . ?
F1 C7 1.3421(17) . ?
C1 C3 1.4001(16) 2_645 ?
C13 C14 1.4326(17) . ?
F4 C10 1.3382(17) . ?
C6 C7 1.381(2) . ?
C6 C11 1.3821(19) . ?
C6 C5 1.5014(18) . ?
C4 O1 1.1984(17) . ?
F3 C9 1.3421(17) . ?
C14 C15 1.387(2) . ?
C14 C19 1.403(2) . ?
F2 C8 1.3353(19) . ?
C11 C10 1.385(2) . ?
C7 C8 1.377(2) . ?
O3 C17 1.3690(18) . ?
O3 C20 1.418(3) . ?
C9 C10 1.368(3) . ?
C9 C8 1.381(2) . ?
C15 C16 1.401(2) . ?
C17 C16 1.382(3) . ?
C17 C18 1.385(2) . ?
C19 C18 1.380(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
C4 O2 C5 117.15(10) . . ?
C3 C2 C1 119.82(10) . . ?
C3 C2 C4 115.11(10) . . ?
C1 C2 C4 125.02(10) . . ?
C2 C3 C1 122.64(10) . 2_645 ?
C13 C12 C1 177.52(15) . . ?
C3 C1 C2 117.53(10) 2_645 . ?
C3 C1 C12 117.83(10) 2_645 . ?
C2 C1 C12 124.62(10) . . ?
C12 C13 C14 173.33(14) . . ?
C7 C6 C11 116.96(13) . . ?
C7 C6 C5 120.74(12) . . ?
C11 C6 C5 122.30(13) . . ?
O1 C4 O2 123.54(12) . . ?
O1 C4 C2 123.28(12) . . ?
O2 C4 C2 113.18(10) . . ?
O2 C5 C6 106.34(10) . . ?
C15 C14 C19 118.69(13) . . ?
C15 C14 C13 122.42(14) . . ?
C19 C14 C13 118.87(13) . . ?
F5 C11 C6 120.12(13) . . ?
F5 C11 C10 117.98(13) . . ?
C6 C11 C10 121.89(14) . . ?
F1 C7 C8 118.43(14) . . ?
F1 C7 C6 119.33(13) . . ?
C8 C7 C6 122.23(14) . . ?
C17 O3 C20 117.21(18) . . ?
F3 C9 C10 120.41(15) . . ?
F3 C9 C8 119.53(16) . . ?
C10 C9 C8 120.06(14) . . ?
C14 C15 C16 120.39(15) . . ?
F4 C10 C9 120.18(14) . . ?
F4 C10 C11 120.27(16) . . ?
C9 C10 C11 119.54(14) . . ?
O3 C17 C16 124.65(16) . . ?
O3 C17 C18 114.83(16) . . ?
C16 C17 C18 120.52(14) . . ?
F2 C8 C7 120.80(15) . . ?
F2 C8 C9 119.89(15) . . ?
C7 C8 C9 119.31(15) . . ?
C18 C19 C14 121.05(15) . . ?
C19 C18 C17 119.62(16) . . ?
C17 C16 C15 119.73(15) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.051

_database_code_depnum_ccdc_archive 'CCDC 1003640'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_rp_a

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H16 F10 O4'
_chemical_formula_weight         726.51

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

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

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

_cell_length_a                   6.8870(7)
_cell_length_b                   31.518(3)
_cell_length_c                   7.1384(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.6540(19)
_cell_angle_gamma                90
_cell_volume                     1476.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_F_000             732
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.715
_exptl_crystal_size_mid          0.274
_exptl_crystal_size_min          0.222
_exptl_absorpt_coefficient_mu    0.148
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22257
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.064
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3013
_reflns_number_gt                2814
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0215P)²+1.8345P] 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         3013
_refine_ls_number_parameters     235
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1014
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_restrained_S_all      1.186
_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
F001 F 0.1889(2) 0.72496(4) 0.61723(18) 0.0272(3) Uani 1 1 d . U . . .
F002 F 0.2435(2) 0.58674(4) 0.86664(17) 0.0265(3) Uani 1 1 d . U . . .
F003 F 0.05512(19) 0.60942(4) 0.18309(16) 0.0249(3) Uani 1 1 d . U . . .
F004 F 0.0800(2) 0.69402(4) 0.24510(18) 0.0299(3) Uani 1 1 d . U . . .
F005 F 0.2705(2) 0.67090(4) 0.92753(17) 0.0282(3) Uani 1 1 d . U . . .
O006 O 0.2896(2) 0.53926(4) 0.3824(2) 0.0202(3) Uani 1 1 d . U . . .
O007 O 0.1114(3) 0.48207(5) 0.2453(2) 0.0326(4) Uani 1 1 d . U . . .
C008 C 0.4607(3) 0.46548(6) -0.1334(3) 0.0137(4) Uani 1 1 d . U . . .
C009 C 0.2473(3) 0.50683(6) 0.2580(3) 0.0160(4) Uani 1 1 d . U . . .
C00A C 0.1116(3) 0.62411(6) 0.3683(3) 0.0172(4) Uani 1 1 d . U . . .
C00B C 0.3860(3) 0.50469(6) 0.1316(3) 0.0139(4) Uani 1 1 d . U . . .
C00C C 0.3496(3) 0.47131(6) -0.0008(3) 0.0143(4) Uani 1 1 d . U . . .
H00C H 0.2450 0.4516 -0.0015 0.017 Uiso 1 1 calc R U . . .
C00D C 0.1781(3) 0.68311(6) 0.5875(3) 0.0190(4) Uani 1 1 d . U . . .
C00E C 0.4153(3) 0.42876(6) -0.2578(3) 0.0159(4) Uani 1 1 d . U . . .
C00F C 0.2056(3) 0.61243(6) 0.7103(3) 0.0171(4) Uani 1 1 d . U . . .
C00G C 0.2184(3) 0.65561(6) 0.7441(3) 0.0187(4) Uani 1 1 d . U . . .
C00H C 0.3432(3) 0.36086(6) -0.4824(3) 0.0173(4) Uani 1 1 d . U . . .
C00I C 0.1236(3) 0.66718(6) 0.3975(3) 0.0196(4) Uani 1 1 d . U . . .
C00J C 0.1535(3) 0.59548(6) 0.5230(3) 0.0153(4) Uani 1 1 d . U . . .
C00K C 0.3781(3) 0.39699(6) -0.3537(3) 0.0173(4) Uani 1 1 d . U . . .
C00L C 0.1419(3) 0.54858(6) 0.4853(3) 0.0174(4) Uani 1 1 d . U . . .
H00A H 0.1753 0.5327 0.6108 0.021 Uiso 1 1 calc R U . . .
H00B H 0.0032 0.5405 0.4038 0.021 Uiso 1 1 calc R U . . .
C00M C 0.2940(3) 0.36745(6) -0.6850(3) 0.0202(4) Uani 1 1 d . U . . .
H00M H 0.2823 0.3955 -0.7360 0.024 Uiso 1 1 calc R U . . .
C00N C 0.3600(3) 0.31947(6) -0.4087(3) 0.0208(4) Uani 1 1 d . U . . .
H00N H 0.3938 0.3147 -0.2711 0.025 Uiso 1 1 calc R U . . .
C00O C 0.3273(3) 0.28532(7) -0.5373(3) 0.0253(4) Uani 1 1 d . U . . .
H00O H 0.3386 0.2572 -0.4877 0.030 Uiso 1 1 calc R U . . .
C00P C 0.2622(3) 0.33301(7) -0.8114(3) 0.0252(4) Uani 1 1 d . U . . .
H00P H 0.2294 0.3375 -0.9491 0.030 Uiso 1 1 calc R U . . .
C00Q C 0.2782(3) 0.29222(7) -0.7379(3) 0.0256(5) Uani 1 1 d . U . . .
H00Q H 0.2555 0.2687 -0.8253 0.031 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C00D 1.334(2) . ?
F002 C00F 1.339(2) . ?
F003 C00A 1.342(2) . ?
F004 C00I 1.338(2) . ?
F005 C00G 1.338(2) . ?
O006 C009 1.328(2) . ?
O006 C00L 1.453(2) . ?
O007 C009 1.201(2) . ?
C008 C00C 1.398(3) . ?
C008 C00B 1.411(3) 3_665 ?
C008 C00E 1.434(3) . ?
C009 C00B 1.501(3) . ?
C00A C00I 1.372(3) . ?
C00A C00J 1.387(3) . ?
C00B C00C 1.385(3) . ?
C00B C008 1.411(3) 3_665 ?
C00D C00G 1.374(3) . ?
C00D C00I 1.387(3) . ?
C00E C00K 1.196(3) . ?
C00F C00G 1.380(3) . ?
C00F C00J 1.382(3) . ?
C00H C00M 1.397(3) . ?
C00H C00N 1.398(3) . ?
C00H C00K 1.437(3) . ?
C00J C00L 1.500(3) . ?
C00M C00P 1.386(3) . ?
C00N C00O 1.388(3) . ?
C00O C00Q 1.385(3) . ?
C00P C00Q 1.380(3) . ?

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
C009 O006 C00L 116.66(14) . . ?
C00C C008 C00B 117.89(17) . 3_665 ?
C00C C008 C00E 117.64(16) . . ?
C00B C008 C00E 124.43(17) 3_665 . ?
O007 C009 O006 123.96(17) . . ?
O007 C009 C00B 123.30(17) . . ?
O006 C009 C00B 112.73(16) . . ?
F003 C00A C00I 118.50(17) . . ?
F003 C00A C00J 119.22(17) . . ?
C00I C00A C00J 122.28(17) . . ?
C00C C00B C008 119.50(17) . 3_665 ?
C00C C00B C009 115.33(16) . . ?
C008 C00B C009 125.12(16) 3_665 . ?
C00B C00C C008 122.61(17) . . ?
F001 C00D C00G 120.41(17) . . ?
F001 C00D C00I 119.92(18) . . ?
C00G C00D C00I 119.66(18) . . ?
C00K C00E C008 176.9(2) . . ?
F002 C00F C00G 117.69(17) . . ?
F002 C00F C00J 120.02(17) . . ?
C00G C00F C00J 122.28(18) . . ?
F005 C00G C00D 119.79(17) . . ?
F005 C00G C00F 120.65(18) . . ?
C00D C00G C00F 119.55(17) . . ?
C00M C00H C00N 119.63(18) . . ?
C00M C00H C00K 119.01(18) . . ?
C00N C00H C00K 121.36(18) . . ?
F004 C00I C00A 120.90(17) . . ?
F004 C00I C00D 119.56(17) . . ?
C00A C00I C00D 119.53(18) . . ?
C00F C00J C00A 116.69(17) . . ?
C00F C00J C00L 122.57(17) . . ?
C00A C00J C00L 120.74(17) . . ?
C00E C00K C00H 174.1(2) . . ?
O006 C00L C00J 106.40(14) . . ?
C00P C00M C00H 119.89(19) . . ?
C00O C00N C00H 119.77(19) . . ?
C00Q C00O C00N 120.1(2) . . ?
C00Q C00P C00M 120.2(2) . . ?
C00P C00Q C00O 120.38(19) . . ?

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-3



_database_code_depnum_ccdc_archive 'CCDC 1003641'
#######################################################################
#
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#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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data_RP-3-30-14_a

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H16 F10 O6'
_chemical_formula_weight         758.51

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                   8.2523(6)
_cell_length_b                   12.5862(10)
_cell_length_c                   15.2850(12)
_cell_angle_alpha                73.9040(17)
_cell_angle_beta                 86.2990(18)
_cell_angle_gamma                83.5410(18)
_cell_volume                     1514.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_F_000             764
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.279
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.153
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30543
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.804
_diffrn_reflns_theta_max         29.127
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8146
_reflns_number_gt                6336
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0526P)²+0.5269P] 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         8146
_refine_ls_number_parameters     489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0933
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
F001 F 0.90320(10) -0.19867(7) 0.51684(6) 0.02140(18) Uani 1 1 d . . . . .
F002 F 0.73791(10) 0.87757(7) 0.16401(5) 0.02061(17) Uani 1 1 d . . . . .
F003 F 1.10049(10) -0.04126(7) 0.72774(6) 0.02325(18) Uani 1 1 d . . . . .
F004 F 0.62715(10) 0.12646(7) 0.56707(6) 0.02309(18) Uani 1 1 d . . . . .
F005 F 1.12437(10) -0.20243(7) 0.64078(6) 0.02531(19) Uani 1 1 d . . . . .
F006 F 0.38860(10) 0.59684(7) 0.19490(6) 0.02413(19) Uani 1 1 d . . . . .
F007 F 0.75893(10) 0.82432(7) 0.34585(6) 0.02459(19) Uani 1 1 d . . . . .
F008 F 0.65931(10) -0.03324(7) 0.47720(6) 0.02368(19) Uani 1 1 d . . . . .
F009 F 0.59697(11) 0.65692(8) 0.45346(6) 0.0276(2) Uani 1 1 d . . . . .
F00A F 0.41374(11) 0.54189(7) 0.37784(6) 0.0277(2) Uani 1 1 d . . . . .
O00B O 0.86523(12) 0.23924(7) 0.62969(6) 0.01630(19) Uani 1 1 d . . . . .
O00C O 0.37348(11) 0.81600(8) 0.04698(6) 0.0172(2) Uani 1 1 d . . . . .
O00D O 0.95234(13) 0.31086(8) 0.73502(6) 0.0205(2) Uani 1 1 d . . . . .
O00E O 0.41346(11) 0.96383(8) 0.09384(7) 0.0183(2) Uani 1 1 d . . . . .
O00F O -0.49810(12) 0.94422(8) -0.22885(7) 0.0230(2) Uani 1 1 d . . . . .
H00F H -0.4505 0.9529 -0.1847 0.034 Uiso 1 1 calc R U . . .
O00G O 0.93125(14) 0.65301(8) 0.10394(7) 0.0255(2) Uani 1 1 d . . . . .
H00G H 0.9525 0.6426 0.1589 0.038 Uiso 1 1 calc R U . . .
C00H C -0.20607(15) 0.83593(10) -0.14965(8) 0.0141(2) Uani 1 1 d . . . . .
C00I C 0.89722(16) 0.49475(10) 0.32757(9) 0.0141(2) Uani 1 1 d . . . . .
C00J C -0.08038(15) 0.94402(10) -0.05028(8) 0.0129(2) Uani 1 1 d . . . . .
C00K C 0.86161(16) 0.04664(10) 0.65059(9) 0.0147(2) Uani 1 1 d . . . . .
C00L C 0.96409(15) 0.41301(10) 0.57651(8) 0.0124(2) Uani 1 1 d . . . . .
C00M C -0.15305(15) 0.88586(11) -0.10323(8) 0.0141(2) Uani 1 1 d . . . . .
C00N C 0.92802(15) 0.31847(10) 0.65645(9) 0.0132(2) Uani 1 1 d . . . . .
C00O C 0.15730(15) 0.95861(10) 0.03049(8) 0.0134(2) Uani 1 1 d . . . . .
C00P C 0.91525(15) 0.41535(10) 0.49071(8) 0.0130(2) Uani 1 1 d . . . . .
H00P H 0.8567 0.3572 0.4845 0.016 Uiso 1 1 calc R U . . .
C00Q C 0.94947(15) 0.50054(10) 0.41310(8) 0.0121(2) Uani 1 1 d . . . . .
C00R C 0.55795(15) 0.74078(10) 0.17414(9) 0.0141(2) Uani 1 1 d . . . . .
C00S C 0.89019(16) -0.11945(10) 0.56003(9) 0.0153(2) Uani 1 1 d . . . . .
C00T C 1.00243(16) -0.12043(11) 0.62297(9) 0.0167(3) Uani 1 1 d . . . . .
C00U C 0.32617(15) 0.91579(11) 0.06071(8) 0.0140(2) Uani 1 1 d . . . . .
C00V C -0.42910(16) 0.85125(11) -0.25008(9) 0.0156(2) Uani 1 1 d . . . . .
C00W C 0.65342(15) 0.79627(11) 0.21489(9) 0.0150(2) Uani 1 1 d . . . . .
C00X C 0.07670(16) 0.90409(11) -0.01846(8) 0.0145(2) Uani 1 1 d . . . . .
H00X H 0.1290 0.8383 -0.0307 0.017 Uiso 1 1 calc R U . . .
C00Y C 0.75105(16) 0.04584(11) 0.58625(9) 0.0155(2) Uani 1 1 d . . . . .
C00Z C 0.76426(16) -0.03508(11) 0.54033(9) 0.0157(2) Uani 1 1 d . . . . .
C010 C 0.85319(16) 0.48218(10) 0.25833(9) 0.0151(2) Uani 1 1 d . . . . .
C011 C -0.28458(15) 0.79191(10) -0.21040(8) 0.0135(2) Uani 1 1 d . . . . .
C012 C 0.81297(16) 0.48000(11) 0.16937(9) 0.0158(3) Uani 1 1 d . . . . .
C013 C -0.21991(16) 0.69662(11) -0.23614(9) 0.0165(3) Uani 1 1 d . . . . .
H013 H -0.1231 0.6557 -0.2095 0.020 Uiso 1 1 calc R U . . .
C014 C 0.98826(16) -0.03757(11) 0.66716(9) 0.0158(3) Uani 1 1 d . . . . .
C015 C 0.47869(16) 0.65492(11) 0.23109(9) 0.0162(3) Uani 1 1 d . . . . .
C016 C 0.49046(16) 0.62614(11) 0.32445(9) 0.0185(3) Uani 1 1 d . . . . .
C017 C 0.66591(16) 0.76964(11) 0.30844(9) 0.0169(3) Uani 1 1 d . . . . .
C018 C 0.58377(17) 0.68447(11) 0.36319(9) 0.0184(3) Uani 1 1 d . . . . .
C019 C -0.29538(18) 0.66155(12) -0.29984(9) 0.0194(3) Uani 1 1 d . . . . .
H019 H -0.2513 0.5966 -0.3165 0.023 Uiso 1 1 calc R U . . .
C01A C -0.50277(17) 0.81602(12) -0.31500(9) 0.0194(3) Uani 1 1 d . . . . .
H01A H -0.5990 0.8566 -0.3426 0.023 Uiso 1 1 calc R U . . .
C01B C 0.85564(17) 0.56671(11) 0.09487(9) 0.0171(3) Uani 1 1 d . . . . .
C01C C 0.84262(18) 0.13629(10) 0.69900(9) 0.0173(3) Uani 1 1 d . . . . .
H01B H 0.7328 0.1401 0.7287 0.021 Uiso 1 1 calc R U . . .
H01C H 0.9254 0.1217 0.7461 0.021 Uiso 1 1 calc R U . . .
C01D C 0.53982(16) 0.77115(11) 0.07271(9) 0.0171(3) Uani 1 1 d . . . . .
H01D H 0.6158 0.8270 0.0428 0.020 Uiso 1 1 calc R U . . .
H01E H 0.5699 0.7043 0.0508 0.020 Uiso 1 1 calc R U . . .
C01E C -0.43649(17) 0.72217(12) -0.33947(9) 0.0208(3) Uani 1 1 d . . . . .
H01F H -0.4877 0.6987 -0.3839 0.025 Uiso 1 1 calc R U . . .
C01F C 0.73424(18) 0.39357(13) 0.15438(10) 0.0235(3) Uani 1 1 d . . . . .
H01G H 0.7062 0.3339 0.2045 0.028 Uiso 1 1 calc R U . . .
C01G C 0.73858(19) 0.48226(13) -0.00618(10) 0.0254(3) Uani 1 1 d . . . . .
H01H H 0.7119 0.4836 -0.0660 0.030 Uiso 1 1 calc R U . . .
C01H C 0.81778(19) 0.56710(12) 0.00715(9) 0.0227(3) Uani 1 1 d . . . . .
H01I H 0.8466 0.6259 -0.0435 0.027 Uiso 1 1 calc R U . . .
C01I C 0.6975(2) 0.39490(14) 0.06720(11) 0.0272(3) Uani 1 1 d . . . . .
H01J H 0.6442 0.3363 0.0574 0.033 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C00S 1.3317(14) . ?
F002 C00W 1.3368(15) . ?
F003 C014 1.3396(15) . ?
F004 C00Y 1.3422(15) . ?
F005 C00T 1.3408(15) . ?
F006 C015 1.3388(15) . ?
F007 C017 1.3355(15) . ?
F008 C00Z 1.3314(15) . ?
F009 C018 1.3348(15) . ?
F00A C016 1.3401(16) . ?
O00B C00N 1.3417(15) . ?
O00B C01C 1.4505(15) . ?
O00C C00U 1.3414(15) . ?
O00C C01D 1.4593(15) . ?
O00D C00N 1.2062(16) . ?
O00E C00U 1.2065(15) . ?
O00F C00V 1.3548(16) . ?
O00G C01B 1.3548(17) . ?
C00H C00M 1.1997(18) . ?
C00H C011 1.4257(17) . ?
C00I C010 1.1968(18) . ?
C00I C00Q 1.4258(17) . ?
C00J C00X 1.4031(17) . ?
C00J C00O 1.4149(17) 2_575 ?
C00J C00M 1.4283(17) . ?
C00K C014 1.3842(19) . ?
C00K C00Y 1.3867(18) . ?
C00K C01C 1.5012(18) . ?
C00L C00P 1.3884(17) . ?
C00L C00Q 1.4153(17) 2_766 ?
C00L C00N 1.4913(17) . ?
C00O C00X 1.3874(17) . ?
C00O C00J 1.4149(17) 2_575 ?
C00O C00U 1.4906(17) . ?
C00P C00Q 1.3986(17) . ?
C00Q C00L 1.4153(17) 2_766 ?
C00R C015 1.3846(19) . ?
C00R C00W 1.3874(18) . ?
C00R C01D 1.5035(18) . ?
C00S C00T 1.3745(19) . ?
C00S C00Z 1.3832(18) . ?
C00T C014 1.3821(19) . ?
C00V C01A 1.3904(18) . ?
C00V C011 1.4106(18) . ?
C00W C017 1.3832(18) . ?
C00Y C00Z 1.3796(18) . ?
C010 C012 1.4286(17) . ?
C011 C013 1.4030(18) . ?
C012 C01B 1.3990(19) . ?
C012 C01F 1.4052(19) . ?
C013 C019 1.3817(18) . ?
C015 C016 1.3785(19) . ?
C016 C018 1.382(2) . ?
C017 C018 1.379(2) . ?
C019 C01E 1.393(2) . ?
C01A C01E 1.381(2) . ?
C01B C01H 1.3947(18) . ?
C01F C01I 1.381(2) . ?
C01G C01H 1.380(2) . ?
C01G C01I 1.390(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
C00N O00B C01C 116.74(10) . . ?
C00U O00C C01D 115.11(10) . . ?
C00M C00H C011 171.23(13) . . ?
C010 C00I C00Q 175.49(13) . . ?
C00X C00J C00O 118.54(11) . 2_575 ?
C00X C00J C00M 118.24(11) . . ?
C00O C00J C00M 123.19(11) 2_575 . ?
C014 C00K C00Y 117.20(12) . . ?
C014 C00K C01C 122.35(12) . . ?
C00Y C00K C01C 120.45(12) . . ?
C00P C00L C00Q 119.57(11) . 2_766 ?
C00P C00L C00N 119.78(11) . . ?
C00Q C00L C00N 120.63(11) 2_766 . ?
C00H C00M C00J 176.54(14) . . ?
O00D C00N O00B 123.08(12) . . ?
O00D C00N C00L 126.19(12) . . ?
O00B C00N C00L 110.72(10) . . ?
C00X C00O C00J 120.01(11) . 2_575 ?
C00X C00O C00U 119.97(11) . . ?
C00J C00O C00U 120.01(11) 2_575 . ?
C00L C00P C00Q 122.15(11) . . ?
C00P C00Q C00L 118.28(11) . 2_766 ?
C00P C00Q C00I 118.16(11) . . ?
C00L C00Q C00I 123.55(11) 2_766 . ?
C015 C00R C00W 117.10(12) . . ?
C015 C00R C01D 120.64(12) . . ?
C00W C00R C01D 122.26(12) . . ?
F001 C00S C00T 120.31(12) . . ?
F001 C00S C00Z 119.65(12) . . ?
C00T C00S C00Z 120.03(12) . . ?
F005 C00T C00S 119.24(12) . . ?
F005 C00T C014 120.88(12) . . ?
C00S C00T C014 119.88(12) . . ?
O00E C00U O00C 122.44(11) . . ?
O00E C00U C00O 125.01(12) . . ?
O00C C00U C00O 112.55(10) . . ?
O00F C00V C01A 118.00(12) . . ?
O00F C00V C011 122.23(11) . . ?
C01A C00V C011 119.75(12) . . ?
F002 C00W C017 117.73(11) . . ?
F002 C00W C00R 120.44(12) . . ?
C017 C00W C00R 121.82(12) . . ?
C00O C00X C00J 121.44(11) . . ?
F004 C00Y C00Z 118.37(12) . . ?
F004 C00Y C00K 119.43(11) . . ?
C00Z C00Y C00K 122.20(12) . . ?
F008 C00Z C00Y 121.49(12) . . ?
F008 C00Z C00S 119.42(12) . . ?
C00Y C00Z C00S 119.09(12) . . ?
C00I C010 C012 172.02(14) . . ?
C013 C011 C00V 118.96(11) . . ?
C013 C011 C00H 123.08(12) . . ?
C00V C011 C00H 117.86(11) . . ?
C01B C012 C01F 119.27(12) . . ?
C01B C012 C010 118.40(12) . . ?
C01F C012 C010 122.33(12) . . ?
C019 C013 C011 120.77(12) . . ?
F003 C014 C00T 118.04(12) . . ?
F003 C014 C00K 120.39(12) . . ?
C00T C014 C00K 121.56(12) . . ?
F006 C015 C016 118.48(12) . . ?
F006 C015 C00R 119.39(12) . . ?
C016 C015 C00R 122.13(12) . . ?
F00A C016 C015 120.83(12) . . ?
F00A C016 C018 119.73(12) . . ?
C015 C016 C018 119.44(12) . . ?
F007 C017 C018 119.92(12) . . ?
F007 C017 C00W 120.57(12) . . ?
C018 C017 C00W 119.50(12) . . ?
F009 C018 C017 120.01(12) . . ?
F009 C018 C016 120.00(13) . . ?
C017 C018 C016 119.98(12) . . ?
C013 C019 C01E 119.52(13) . . ?
C01E C01A C00V 120.22(13) . . ?
O00G C01B C01H 117.54(13) . . ?
O00G C01B C012 122.67(12) . . ?
C01H C01B C012 119.78(13) . . ?
O00B C01C C00K 106.10(10) . . ?
O00C C01D C00R 111.93(10) . . ?
C01A C01E C019 120.76(12) . . ?
C01I C01F C012 120.39(14) . . ?
C01H C01G C01I 120.59(13) . . ?
C01G C01H C01B 120.15(14) . . ?
C01F C01I C01G 119.81(14) . . ?

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-4



_database_code_depnum_ccdc_archive 'CCDC 1003642'
