# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_r150114c1
_database_code_depnum_ccdc_archive 'CCDC 1049144'
_audit_update_record             
;
2015-03-24 deposited with the CCDC.
2015-04-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H24 F4 N2 O8'
_chemical_formula_weight         640.53

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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)/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                   22.639(5)
_cell_length_b                   5.0207(10)
_cell_length_c                   11.438(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.54(3)
_cell_angle_gamma                90.00
_cell_volume                     1297.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3240
_cell_measurement_theta_min      1.8025
_cell_measurement_theta_max      28.0510

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_T_max  0.9838
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9216
_diffrn_reflns_av_R_equivalents  0.1034
_diffrn_reflns_av_sigmaI/netI    0.1176
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2266
_reflns_number_gt                1722
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_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)+(0.0604P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.031(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2266
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.1617
_refine_ls_wR_factor_gt          0.1470
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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
F1 F 0.46216(7) -0.4727(4) 0.70886(15) 0.0478(6) Uani 1 1 d . . .
F2 F 0.47055(8) -0.2396(4) 0.55387(18) 0.0575(7) Uani 1 1 d . . .
F3 F 0.41281(7) -0.5782(4) 0.54855(14) 0.0387(5) Uani 1 1 d . . .
F4 F 0.25733(6) 0.5032(3) 0.81891(13) 0.0278(5) Uani 1 1 d . . .
O1 O 0.16255(7) 0.1759(4) 0.96772(14) 0.0254(5) Uani 1 1 d . . .
C1 C 0.43156(12) -0.3703(6) 0.6150(3) 0.0319(7) Uani 1 1 d . . .
C2 C 0.38177(11) -0.1939(5) 0.6477(2) 0.0257(7) Uani 1 1 d . . .
C3 C 0.33253(12) -0.1641(5) 0.5691(2) 0.0275(7) Uani 1 1 d . . .
H3 H 0.3301 -0.2603 0.4974 0.033 Uiso 1 1 calc R . .
C4 C 0.28740(11) 0.0051(5) 0.5959(2) 0.0267(7) Uani 1 1 d . . .
H4 H 0.2538 0.0246 0.5426 0.032 Uiso 1 1 calc R . .
C5 C 0.29067(11) 0.1481(5) 0.7007(2) 0.0219(6) Uani 1 1 d . . .
C6 C 0.34050(11) 0.1191(6) 0.7784(2) 0.0260(7) Uani 1 1 d . . .
H6 H 0.3434 0.2179 0.8494 0.031 Uiso 1 1 calc R . .
C7 C 0.38571(11) -0.0543(6) 0.7519(2) 0.0280(7) Uani 1 1 d . . .
H7 H 0.4192 -0.0765 0.8053 0.034 Uiso 1 1 calc R . .
C8 C 0.23961(11) 0.3277(5) 0.7266(2) 0.0228(7) Uani 1 1 d . . .
H8 H 0.2282 0.4348 0.6550 0.027 Uiso 1 1 calc R . .
C9 C 0.18508(11) 0.1739(5) 0.7632(2) 0.0228(7) Uani 1 1 d . . .
H9 H 0.1722 0.0432 0.7008 0.027 Uiso 1 1 calc R . .
C10 C 0.13415(11) 0.3582(5) 0.7874(2) 0.0210(6) Uani 1 1 d . . .
C11 C 0.10037(11) 0.5293(5) 0.7150(2) 0.0249(7) Uani 1 1 d . . .
H11 H 0.1057 0.5363 0.6334 0.030 Uiso 1 1 calc R . .
C12 C 0.05847(12) 0.6907(5) 0.7647(2) 0.0279(7) Uani 1 1 d . . .
H12 H 0.0350 0.8088 0.7164 0.033 Uiso 1 1 calc R . .
C13 C 0.05072(12) 0.6801(5) 0.8843(2) 0.0283(7) Uani 1 1 d . . .
H13 H 0.0223 0.7929 0.9168 0.034 Uiso 1 1 calc R . .
C14 C 0.08402(11) 0.5067(5) 0.9573(2) 0.0254(7) Uani 1 1 d . . .
H14 H 0.0785 0.4971 1.0388 0.030 Uiso 1 1 calc R . .
C15 C 0.12550(11) 0.3489(5) 0.9063(2) 0.0214(6) Uani 1 1 d . . .
C16 C 0.19519(11) 0.0287(6) 0.8821(2) 0.0249(7) Uani 1 1 d . . .
H16A H 0.1806 -0.1569 0.8756 0.030 Uiso 1 1 calc R . .
H16B H 0.2379 0.0247 0.9065 0.030 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
F1 C1 1.343(3) . ?
F2 C1 1.333(3) . ?
F3 C1 1.344(3) . ?
F4 C8 1.414(3) . ?
O1 C15 1.371(3) . ?
O1 C16 1.463(3) . ?
C1 C2 1.499(4) . ?
C2 C7 1.381(4) . ?
C2 C3 1.396(4) . ?
C3 C4 1.378(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(3) . ?
C5 C8 1.510(3) . ?
C6 C7 1.391(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.536(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.517(3) . ?
C9 C16 1.548(3) . ?
C9 H9 1.0000 . ?
C10 C15 1.386(3) . ?
C10 C11 1.389(3) . ?
C11 C12 1.395(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O1 C16 107.18(18) . . ?
F2 C1 F1 106.4(2) . . ?
F2 C1 F3 106.4(2) . . ?
F1 C1 F3 106.5(2) . . ?
F2 C1 C2 111.9(2) . . ?
F1 C1 C2 112.7(2) . . ?
F3 C1 C2 112.6(2) . . ?
C7 C2 C3 120.5(2) . . ?
C7 C2 C1 120.4(2) . . ?
C3 C2 C1 119.0(2) . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 119.3(2) . . ?
C4 C5 C8 118.4(2) . . ?
C6 C5 C8 122.3(2) . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C2 C7 C6 119.8(2) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
F4 C8 C5 109.46(19) . . ?
F4 C8 C9 107.75(19) . . ?
C5 C8 C9 113.0(2) . . ?
F4 C8 H8 108.8 . . ?
C5 C8 H8 108.8 . . ?
C9 C8 H8 108.8 . . ?
C10 C9 C8 112.1(2) . . ?
C10 C9 C16 101.53(19) . . ?
C8 C9 C16 113.5(2) . . ?
C10 C9 H9 109.8 . . ?
C8 C9 H9 109.8 . . ?
C16 C9 H9 109.8 . . ?
C15 C10 C11 120.0(2) . . ?
C15 C10 C9 108.3(2) . . ?
C11 C10 C9 131.7(2) . . ?
C10 C11 C12 118.7(2) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 121.1(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 117.4(3) . . ?
C15 C14 H14 121.3 . . ?
C13 C14 H14 121.3 . . ?
O1 C15 C14 123.8(2) . . ?
O1 C15 C10 113.9(2) . . ?
C14 C15 C10 122.3(2) . . ?
O1 C16 C9 107.3(2) . . ?
O1 C16 H16A 110.3 . . ?
C9 C16 H16A 110.3 . . ?
O1 C16 H16B 110.3 . . ?
C9 C16 H16B 110.3 . . ?
H16A C16 H16B 108.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F2 C1 C2 C7 -90.4(3) . . . . ?
F1 C1 C2 C7 29.4(4) . . . . ?
F3 C1 C2 C7 149.9(3) . . . . ?
F2 C1 C2 C3 87.0(3) . . . . ?
F1 C1 C2 C3 -153.2(3) . . . . ?
F3 C1 C2 C3 -32.7(4) . . . . ?
C7 C2 C3 C4 -0.2(4) . . . . ?
C1 C2 C3 C4 -177.6(2) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C3 C4 C5 C8 -179.1(2) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
C8 C5 C6 C7 178.3(2) . . . . ?
C3 C2 C7 C6 -0.5(4) . . . . ?
C1 C2 C7 C6 176.8(2) . . . . ?
C5 C6 C7 C2 1.2(4) . . . . ?
C4 C5 C8 F4 -165.0(2) . . . . ?
C6 C5 C8 F4 15.6(3) . . . . ?
C4 C5 C8 C9 74.9(3) . . . . ?
C6 C5 C8 C9 -104.5(3) . . . . ?
F4 C8 C9 C10 59.5(3) . . . . ?
C5 C8 C9 C10 -179.4(2) . . . . ?
F4 C8 C9 C16 -54.8(3) . . . . ?
C5 C8 C9 C16 66.3(3) . . . . ?
C8 C9 C10 C15 -112.1(2) . . . . ?
C16 C9 C10 C15 9.3(3) . . . . ?
C8 C9 C10 C11 64.2(3) . . . . ?
C16 C9 C10 C11 -174.3(3) . . . . ?
C15 C10 C11 C12 0.5(4) . . . . ?
C9 C10 C11 C12 -175.5(2) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C12 C13 C14 C15 0.9(4) . . . . ?
C16 O1 C15 C14 174.5(2) . . . . ?
C16 O1 C15 C10 -7.1(3) . . . . ?
C13 C14 C15 O1 177.9(2) . . . . ?
C13 C14 C15 C10 -0.4(4) . . . . ?
C11 C10 C15 O1 -178.7(2) . . . . ?
C9 C10 C15 O1 -1.9(3) . . . . ?
C11 C10 C15 C14 -0.3(4) . . . . ?
C9 C10 C15 C14 176.5(2) . . . . ?
C15 O1 C16 C9 12.9(3) . . . . ?
C10 C9 C16 O1 -13.3(2) . . . . ?
C8 C9 C16 O1 107.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.071
