# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

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

data_exp_3540
_database_code_depnum_ccdc_archive 'CCDC 1842300'
_audit_update_record             
;
2018-05-09 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;
_audit_creation_date             2015-10-26
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '5(C6 H2 F4 O2), 2(C12 H8 N)'
_chemical_formula_sum            'C54 H26 F20 N2 O10'
_chemical_formula_weight         1242.77
_chemical_melting_point          431.15
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.0315(17)
_cell_length_b                   7.416(2)
_cell_length_c                   26.164(7)
_cell_angle_alpha                88.67(2)
_cell_angle_beta                 88.29(2)
_cell_angle_gamma                85.06(2)
_cell_volume                     1165.3(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1426
_cell_measurement_temperature    102.2
_cell_measurement_theta_max      29.5838
_cell_measurement_theta_min      2.8709
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.771
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0979
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            8188
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.88
_diffrn_ambient_temperature      102.2
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -22.00   22.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2918  -99.0000  169.0000 44

#__ type_ start__ end____ width___ exp.time_
  2 omega  -32.00   -6.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.2918   99.0000   96.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -16.00   38.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4480  -99.0000  -96.0000 54

#__ type_ start__ end____ width___ exp.time_
  4 omega   28.00   55.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4480  -99.0000  -10.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -46.00  -13.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4480  -37.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
  6 omega   -1.00   88.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4480   37.0000  120.0000 89

#__ type_ start__ end____ width___ exp.time_
  7 omega  -48.00   28.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       18.4480  -37.0000  -60.0000 76
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0411314000
_diffrn_orient_matrix_UB_12      0.0637173000
_diffrn_orient_matrix_UB_13      -0.0187675000
_diffrn_orient_matrix_UB_21      0.0845129000
_diffrn_orient_matrix_UB_22      -0.0334965000
_diffrn_orient_matrix_UB_23      -0.0174970000
_diffrn_orient_matrix_UB_31      -0.0709838000
_diffrn_orient_matrix_UB_32      -0.0632927000
_diffrn_orient_matrix_UB_33      -0.0087506000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2810
_reflns_number_total             4578
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         4578
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0209P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.1127
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
F8 F 0.2694(3) 1.5443(2) 0.40666(7) 0.0200(4) Uani 1 1 d . . .
F7 F 0.9302(3) 1.6970(2) 0.47955(7) 0.0205(4) Uani 1 1 d . . .
F5 F 0.1366(3) 1.8970(2) 0.39386(7) 0.0193(4) Uani 1 1 d . . .
O4 O 0.6817(3) 1.4340(2) 0.44836(8) 0.0163(5) Uani 1 1 d . . .
H4A H 0.5826 1.3697 0.4419 0.024 Uiso 1 1 calc R . .
F6 F 0.7979(3) 2.0503(2) 0.46658(6) 0.0193(4) Uani 1 1 d . . .
O2 O 1.0086(3) 1.2756(3) 0.37877(8) 0.0179(5) Uani 1 1 d . . .
H2A H 0.9066 1.3324 0.3944 0.027 Uiso 1 1 calc R . .
O3 O 0.4047(3) 2.1638(2) 0.42515(9) 0.0185(5) Uani 1 1 d . . .
H3A H 0.2859 2.1796 0.4106 0.028 Uiso 1 1 calc R . .
C16 C 0.9520(5) 1.2601(4) 0.32888(12) 0.0154(7) Uani 1 1 d . . .
C19 C 0.4670(5) 1.9833(4) 0.42899(11) 0.0146(7) Uani 1 1 d . . .
C23 C 0.7367(5) 1.7441(4) 0.45732(11) 0.0153(7) Uani 1 1 d . . .
C22 C 0.6056(5) 1.6118(4) 0.44195(11) 0.0133(7) Uani 1 1 d . . .
C20 C 0.3357(5) 1.8498(4) 0.41423(11) 0.0144(7) Uani 1 1 d . . .
F2 F 0.5003(3) 1.3733(2) 0.24322(6) 0.0206(4) Uani 1 1 d . . .
F3 F 0.5939(3) 1.4077(2) 0.34137(6) 0.0200(4) Uani 1 1 d . . .
O1 O 0.8152(4) 1.2116(3) 0.17393(8) 0.0206(5) Uani 1 1 d . . .
H1 H 0.7009 1.2736 0.1667 0.031 Uiso 1 1 calc R . .
F1 F 1.2151(3) 1.0843(2) 0.21192(7) 0.0214(4) Uani 1 1 d . . .
F9 F 0.6961(3) 1.1693(2) 0.06504(7) 0.0257(5) Uani 1 1 d . . .
O5 O 1.1133(4) 1.0383(3) 0.10107(8) 0.0250(6) Uani 1 1 d . . .
H5A H 1.0118 1.0939 0.1172 0.038 Uiso 1 1 calc R . .
F10 F 1.4029(3) 0.8662(2) 0.03413(7) 0.0247(5) Uani 1 1 d . . .
C12 C 0.2696(6) 1.4832(4) 0.12633(12) 0.0187(7) Uani 1 1 d . . .
C7 C -0.0889(5) 1.6552(4) 0.13783(12) 0.0192(7) Uani 1 1 d . . .
H7 H -0.2129 1.7060 0.1208 0.023 Uiso 1 1 calc R . .
C4 C -0.1450(6) 1.7631(4) 0.29758(13) 0.0238(8) Uani 1 1 d . . .
H4 H -0.1619 1.7842 0.3324 0.029 Uiso 1 1 calc R . .
C2 C 0.0810(5) 1.6534(4) 0.22551(12) 0.0190(7) Uani 1 1 d . . .
H2 H 0.2167 1.6027 0.2124 0.023 Uiso 1 1 calc R . .
C11 C -0.1748(5) 1.5754(4) 0.02969(12) 0.0195(7) Uani 1 1 d . . .
H11 H -0.2945 1.6255 0.0494 0.023 Uiso 1 1 calc R . .
C6 C -0.2951(5) 1.7741(4) 0.21330(13) 0.0217(8) Uani 1 1 d . . .
H6 H -0.4128 1.8063 0.1918 0.026 Uiso 1 1 calc R . .
C5 C -0.3203(6) 1.8065(4) 0.26544(13) 0.0252(8) Uani 1 1 d . . .
H5 H -0.4556 1.8574 0.2787 0.030 Uiso 1 1 calc R . .
C10 C 0.2015(5) 1.4521(4) 0.02163(12) 0.0189(7) Uani 1 1 d . . .
H10 H 0.3384 1.4182 0.0360 0.023 Uiso 1 1 calc R . .
C3 C 0.0562(6) 1.6879(4) 0.27742(12) 0.0205(8) Uani 1 1 d . . .
H3 H 0.1754 1.6602 0.2988 0.025 Uiso 1 1 calc R . .
C21 C 0.4058(5) 1.6692(4) 0.42088(11) 0.0142(7) Uani 1 1 d . . .
C15 C 1.1043(5) 1.1801(4) 0.29453(12) 0.0145(7) Uani 1 1 d . . .
C24 C 0.6668(5) 1.9263(4) 0.45021(11) 0.0140(7) Uani 1 1 d . . .
C8 C 0.0601(5) 1.5612(4) 0.10745(12) 0.0177(7) Uani 1 1 d . . .
C9 C 0.0281(5) 1.5295(4) 0.05243(12) 0.0160(7) Uani 1 1 d . . .
F4 F 1.3064(3) 1.1143(2) 0.31147(7) 0.0201(4) Uani 1 1 d . . .
C1 C -0.0951(5) 1.6940(4) 0.19295(12) 0.0171(7) Uani 1 1 d . . .
C18 C 0.7023(5) 1.3082(4) 0.25896(12) 0.0168(7) Uani 1 1 d . . .
N1 N 0.4417(5) 1.4178(4) 0.13835(10) 0.0264(7) Uani 1 1 d . . .
C13 C 0.8555(5) 1.2289(4) 0.22466(12) 0.0168(7) Uani 1 1 d . . .
C14 C 1.0580(5) 1.1646(4) 0.24346(12) 0.0168(7) Uani 1 1 d . . .
C27 C 1.2022(5) 0.9345(4) 0.01758(13) 0.0166(7) Uani 1 1 d . . .
C17 C 0.7488(5) 1.3248(4) 0.30974(12) 0.0150(7) Uani 1 1 d . . .
C26 C 0.8496(5) 1.0844(4) 0.03296(13) 0.0181(7) Uani 1 1 d . . .
C25 C 1.0519(5) 1.0204(4) 0.05185(12) 0.0179(7) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F8 C21 1.356(3) . ?
F7 C23 1.335(3) . ?
F5 C20 1.344(3) . ?
O4 H4A 0.8200 . ?
O4 C22 1.367(3) . ?
F6 C24 1.349(3) . ?
O2 H2A 0.8200 . ?
O2 C16 1.369(4) . ?
O3 H3A 0.8200 . ?
O3 C19 1.361(3) . ?
C16 C15 1.373(4) . ?
C16 C17 1.381(4) . ?
C19 C20 1.389(4) . ?
C19 C24 1.371(4) . ?
C23 C22 1.386(4) . ?
C23 C24 1.390(4) . ?
C22 C21 1.370(4) . ?
C20 C21 1.378(4) . ?
F2 C18 1.344(3) . ?
F3 C17 1.347(3) . ?
O1 H1 0.8200 . ?
O1 C13 1.367(4) . ?
F1 C14 1.346(3) . ?
F9 C26 1.354(3) . ?
O5 H5A 0.8200 . ?
O5 C25 1.363(4) . ?
F10 C27 1.351(4) . ?
C12 C8 1.440(5) . ?
C12 N1 1.157(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.342(4) . ?
C7 C1 1.476(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(5) . ?
C4 C3 1.386(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(4) . ?
C2 C1 1.390(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.379(4) 2_585 ?
C11 C9 1.389(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.392(4) . ?
C6 C1 1.394(4) . ?
C5 H5 0.9300 . ?
C10 C11 1.379(4) 2_585 ?
C10 H10 0.9300 . ?
C10 C9 1.393(4) . ?
C3 H3 0.9300 . ?
C15 F4 1.357(3) . ?
C15 C14 1.382(4) . ?
C8 C9 1.485(4) . ?
C18 C13 1.374(4) . ?
C18 C17 1.377(4) . ?
C13 C14 1.374(4) . ?
C27 C26 1.381(4) 2_775 ?
C27 C25 1.382(4) . ?
C26 C27 1.381(4) 2_775 ?
C26 C25 1.373(5) . ?

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
C22 O4 H4A 109.5 . . ?
C16 O2 H2A 109.5 . . ?
C19 O3 H3A 109.5 . . ?
O2 C16 C15 119.7(3) . . ?
O2 C16 C17 123.9(3) . . ?
C15 C16 C17 116.4(3) . . ?
O3 C19 C20 123.8(3) . . ?
O3 C19 C24 119.3(3) . . ?
C24 C19 C20 116.8(3) . . ?
F7 C23 C22 120.0(3) . . ?
F7 C23 C24 119.6(2) . . ?
C22 C23 C24 120.3(3) . . ?
O4 C22 C23 118.8(3) . . ?
O4 C22 C21 124.0(3) . . ?
C21 C22 C23 117.1(3) . . ?
F5 C20 C19 119.7(3) . . ?
F5 C20 C21 119.6(2) . . ?
C21 C20 C19 120.8(3) . . ?
C13 O1 H1 109.5 . . ?
C25 O5 H5A 109.5 . . ?
N1 C12 C8 175.7(3) . . ?
C8 C7 H7 113.6 . . ?
C8 C7 C1 132.8(3) . . ?
C1 C7 H7 113.6 . . ?
C5 C4 H4 120.3 . . ?
C5 C4 C3 119.4(3) . . ?
C3 C4 H4 120.3 . . ?
C3 C2 H2 119.7 . . ?
C3 C2 C1 120.6(3) . . ?
C1 C2 H2 119.7 . . ?
C10 C11 H11 119.5 2_585 . ?
C10 C11 C9 121.0(3) 2_585 . ?
C9 C11 H11 119.5 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C1 120.7(3) . . ?
C1 C6 H6 119.7 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C11 C10 H10 119.2 2_585 . ?
C11 C10 C9 121.5(3) 2_585 . ?
C9 C10 H10 119.2 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
F8 C21 C22 119.1(3) . . ?
F8 C21 C20 118.4(3) . . ?
C22 C21 C20 122.5(3) . . ?
C16 C15 C14 122.2(3) . . ?
F4 C15 C16 118.7(3) . . ?
F4 C15 C14 119.2(3) . . ?
F6 C24 C19 119.3(3) . . ?
F6 C24 C23 118.3(3) . . ?
C19 C24 C23 122.4(3) . . ?
C12 C8 C9 114.2(3) . . ?
C7 C8 C12 121.6(3) . . ?
C7 C8 C9 124.3(3) . . ?
C11 C9 C10 117.5(3) . . ?
C11 C9 C8 121.6(3) . . ?
C10 C9 C8 121.0(3) . . ?
C2 C1 C7 124.8(3) . . ?
C2 C1 C6 118.6(3) . . ?
C6 C1 C7 116.7(3) . . ?
F2 C18 C13 120.0(3) . . ?
F2 C18 C17 118.0(3) . . ?
C13 C18 C17 122.0(3) . . ?
O1 C13 C18 123.4(3) . . ?
O1 C13 C14 119.7(3) . . ?
C14 C13 C18 116.8(3) . . ?
F1 C14 C15 119.0(3) . . ?
F1 C14 C13 119.8(3) . . ?
C13 C14 C15 121.2(3) . . ?
F10 C27 C26 119.5(3) . 2_775 ?
F10 C27 C25 119.2(3) . . ?
C26 C27 C25 121.4(3) 2_775 . ?
F3 C17 C16 119.2(3) . . ?
F3 C17 C18 119.4(3) . . ?
C18 C17 C16 121.4(3) . . ?
F9 C26 C27 119.1(3) . 2_775 ?
F9 C26 C25 118.8(3) . . ?
C25 C26 C27 122.2(3) . 2_775 ?
O5 C25 C27 118.9(3) . . ?
O5 C25 C26 124.6(3) . . ?
C26 C25 C27 116.5(3) . . ?

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
F7 C23 C22 O4 -2.2(4) . . . . ?
F7 C23 C22 C21 178.0(3) . . . . ?
F7 C23 C24 F6 -0.5(4) . . . . ?
F7 C23 C24 C19 -178.1(3) . . . . ?
F5 C20 C21 F8 -0.3(4) . . . . ?
F5 C20 C21 C22 -179.2(3) . . . . ?
O4 C22 C21 F8 2.1(4) . . . . ?
O4 C22 C21 C20 -179.0(3) . . . . ?
O2 C16 C15 F4 1.6(4) . . . . ?
O2 C16 C15 C14 -178.5(2) . . . . ?
O2 C16 C17 F3 -0.4(4) . . . . ?
O2 C16 C17 C18 178.8(2) . . . . ?
O3 C19 C20 F5 1.4(4) . . . . ?
O3 C19 C20 C21 -177.7(3) . . . . ?
O3 C19 C24 F6 -0.3(4) . . . . ?
O3 C19 C24 C23 177.2(3) . . . . ?
C16 C15 C14 F1 -179.9(2) . . . . ?
C16 C15 C14 C13 -0.1(4) . . . . ?
C19 C20 C21 F8 178.8(2) . . . . ?
C19 C20 C21 C22 -0.1(5) . . . . ?
C23 C22 C21 F8 -178.1(2) . . . . ?
C23 C22 C21 C20 0.8(4) . . . . ?
C22 C23 C24 F6 178.8(2) . . . . ?
C22 C23 C24 C19 1.3(4) . . . . ?
C20 C19 C24 F6 -178.1(2) . . . . ?
C20 C19 C24 C23 -0.5(4) . . . . ?
F2 C18 C13 O1 0.2(4) . . . . ?
F2 C18 C13 C14 -179.7(2) . . . . ?
F2 C18 C17 C16 179.5(2) . . . . ?
F2 C18 C17 F3 -1.2(4) . . . . ?
O1 C13 C14 F1 -0.3(4) . . . . ?
O1 C13 C14 C15 179.9(2) . . . . ?
F9 C26 C25 O5 -1.1(4) . . . . ?
F9 C26 C25 C27 179.8(2) . . . . ?
F10 C27 C25 O5 1.8(4) . . . . ?
F10 C27 C25 C26 -179.0(2) . . . . ?
C12 C8 C9 C11 171.8(3) . . . . ?
C12 C8 C9 C10 -8.1(4) . . . . ?
C7 C8 C9 C11 -8.9(4) . . . . ?
C7 C8 C9 C10 171.2(3) . . . . ?
C11 C10 C9 C11 1.1(5) 2_585 . . . ?
C11 C10 C9 C8 -179.0(2) 2_585 . . . ?
C5 C4 C3 C2 -1.0(4) . . . . ?
C5 C6 C1 C7 176.4(2) . . . . ?
C5 C6 C1 C2 -2.4(4) . . . . ?
C10 C11 C9 C10 -1.1(5) 2_585 . . . ?
C10 C11 C9 C8 179.0(2) 2_585 . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C3 C2 C1 C7 -177.1(3) . . . . ?
C3 C2 C1 C6 1.6(4) . . . . ?
C15 C16 C17 F3 -178.8(2) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C24 C19 C20 F5 179.1(3) . . . . ?
C24 C19 C20 C21 0.0(4) . . . . ?
C24 C23 C22 O4 178.4(3) . . . . ?
C24 C23 C22 C21 -1.4(4) . . . . ?
C8 C7 C1 C2 8.5(5) . . . . ?
C8 C7 C1 C6 -170.2(3) . . . . ?
F4 C15 C14 F1 0.1(4) . . . . ?
F4 C15 C14 C13 179.9(2) . . . . ?
C1 C7 C8 C12 -4.3(5) . . . . ?
C1 C7 C8 C9 176.4(3) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C1 C6 C5 C4 1.5(4) . . . . ?
C18 C13 C14 F1 179.6(2) . . . . ?
C18 C13 C14 C15 -0.2(4) . . . . ?
N1 C12 C8 C7 -173(4) . . . . ?
N1 C12 C8 C9 7(4) . . . . ?
C13 C18 C17 C16 -0.8(4) . . . . ?
C13 C18 C17 F3 178.4(2) . . . . ?
C27 C26 C25 O5 178.7(3) 2_775 . . . ?
C27 C26 C25 C27 -0.4(5) 2_775 . . . ?
C17 C16 C15 F4 180.0(2) . . . . ?
C17 C16 C15 C14 -0.1(4) . . . . ?
C17 C18 C13 O1 -179.5(2) . . . . ?
C17 C18 C13 C14 0.6(4) . . . . ?
C26 C27 C25 O5 -178.8(2) 2_775 . . . ?
C26 C27 C25 C26 0.4(5) 2_775 . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3 and CH3OH'
_chemical_properties_physical    Light-sensitive
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1842301'
_audit_update_record             
;
2018-05-09 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          530.15
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H20 F8 N2 O6'
_chemical_formula_weight         752.56

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'
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'

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

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

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

_cell_length_a                   9.3317(16)
_cell_length_b                   9.3436(16)
_cell_length_c                   10.5310(18)
_cell_angle_alpha                63.940(3)
_cell_angle_beta                 77.306(3)
_cell_angle_gamma                80.095(3)
_cell_volume                     801.7(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1133
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      24.47

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_F_000             382
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_process_details   SADABS

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4307
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.182
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2952
_reflns_number_gt                1918
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0654P)²+0.1632P] 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         2952
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1379
_refine_ls_wR_factor_gt          0.1137
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
C1 C 0.2030(3) 0.9186(3) 0.4844(3) 0.0506(6) Uani 1 1 d . . . . .
C2 C 0.3618(2) 0.8603(3) 0.4652(3) 0.0438(6) Uani 1 1 d . . . . .
C3 C 0.4176(3) 0.7054(3) 0.5414(3) 0.0467(6) Uani 1 1 d . . . . .
C4 C 0.5657(3) 0.6561(3) 0.5244(3) 0.0482(6) Uani 1 1 d . . . . .
C5 C 0.6675(2) 0.7606(3) 0.4269(3) 0.0452(6) Uani 1 1 d . . . . .
C6 C 0.6130(2) 0.9147(3) 0.3505(3) 0.0456(6) Uani 1 1 d . . . . .
C7 C 0.4659(3) 0.9641(3) 0.3689(3) 0.0456(6) Uani 1 1 d . . . . .
C8 C -0.2858(3) 0.5098(3) 0.9097(3) 0.0596(7) Uani 1 1 d . . . . .
H8 H -0.3798 0.5621 0.9014 0.072 Uiso 1 1 calc R U . . .
C9 C -0.2571(3) 0.3912(3) 1.0394(3) 0.0599(8) Uani 1 1 d . . . . .
H9 H -0.3313 0.3656 1.1190 0.072 Uiso 1 1 calc R U . . .
C10 C -0.1186(3) 0.3098(3) 1.0521(3) 0.0526(7) Uani 1 1 d . . . . .
H10 H -0.0998 0.2303 1.1402 0.063 Uiso 1 1 calc R U . . .
C11 C -0.0074(2) 0.3471(3) 0.9330(3) 0.0434(6) Uani 1 1 d . . . . .
C12 C -0.0380(3) 0.4699(3) 0.8050(3) 0.0540(7) Uani 1 1 d . . . . .
H12 H 0.0360 0.4986 0.7253 0.065 Uiso 1 1 calc R U . . .
C13 C -0.1764(3) 0.5508(3) 0.7933(3) 0.0594(7) Uani 1 1 d . . . . .
H13 H -0.1951 0.6329 0.7063 0.071 Uiso 1 1 calc R U . . .
C14 C 0.1421(2) 0.2675(3) 0.9358(3) 0.0465(6) Uani 1 1 d . . . . .
H14 H 0.2137 0.3279 0.8645 0.056 Uiso 1 1 calc R U . . .
C15 C 0.1932(2) 0.1220(3) 1.0241(2) 0.0413(6) Uani 1 1 d . . . . .
C16 C 0.0946(2) 0.0119(3) 1.1348(3) 0.0451(6) Uani 1 1 d . . . . .
C17 C 0.3508(2) 0.0599(3) 1.0123(2) 0.0388(5) Uani 1 1 d . . . . .
C18 C 0.3919(2) -0.1029(3) 1.0733(3) 0.0468(6) Uani 1 1 d . . . . .
H18 H 0.3195 -0.1737 1.1244 0.056 Uiso 1 1 calc R U . . .
C19 C 0.4627(2) 0.1624(3) 0.9399(3) 0.0476(6) Uani 1 1 d . . . . .
H19 H 0.4388 0.2723 0.9000 0.057 Uiso 1 1 calc R U . . .
F1 F 0.32916(16) 0.59414(18) 0.63908(16) 0.0657(5) Uani 1 1 d . . . . .
F2 F 0.61131(16) 0.50427(17) 0.60390(17) 0.0654(5) Uani 1 1 d . . . . .
F3 F 0.70795(15) 1.02104(17) 0.25567(16) 0.0645(5) Uani 1 1 d . . . . .
F4 F 0.42696(15) 1.11741(18) 0.28879(16) 0.0627(4) Uani 1 1 d . . . . .
N1 N 0.0211(2) -0.0813(3) 1.2230(3) 0.0626(7) Uani 1 1 d . . . . .
O1 O 0.11359(19) 0.8085(2) 0.5521(3) 0.0783(7) Uani 1 1 d . . . . .
H1 H 0.0301 0.8491 0.5670 0.117 Uiso 1 1 calc R U . . .
O2 O 0.1634(2) 1.0601(3) 0.4376(3) 0.0770(7) Uani 1 1 d . . . . .
O3 O 0.81051(17) 0.7065(2) 0.4128(2) 0.0593(5) Uani 1 1 d . . . . .
H3 H 0.8592 0.7797 0.3531 0.089 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
C1 O2 1.211(3) . ?
C1 O1 1.285(3) . ?
C1 C2 1.491(3) . ?
C2 C3 1.383(3) . ?
C2 C7 1.393(3) . ?
C3 F1 1.343(3) . ?
C3 C4 1.378(3) . ?
C4 F2 1.342(3) . ?
C4 C5 1.385(3) . ?
C5 O3 1.343(3) . ?
C5 C6 1.375(3) . ?
C6 F3 1.346(2) . ?
C6 C7 1.371(3) . ?
C7 F4 1.338(3) . ?
C8 C13 1.365(4) . ?
C8 C9 1.376(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.384(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.393(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(3) . ?
C11 C14 1.464(3) . ?
C12 C13 1.380(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.342(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.437(3) . ?
C15 C17 1.485(3) . ?
C16 N1 1.143(3) . ?
C17 C18 1.387(3) . ?
C17 C19 1.393(3) . ?
C18 C19 1.377(3) 2_657 ?
C18 H18 0.9300 . ?
C19 C18 1.377(3) 2_657 ?
C19 H19 0.9300 . ?
O1 H1 0.8200 . ?
O3 H3 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 123.5(2) . . ?
O2 C1 C2 121.4(2) . . ?
O1 C1 C2 115.1(2) . . ?
C3 C2 C7 115.3(2) . . ?
C3 C2 C1 124.1(2) . . ?
C7 C2 C1 120.6(2) . . ?
F1 C3 C4 115.9(2) . . ?
F1 C3 C2 121.3(2) . . ?
C4 C3 C2 122.8(2) . . ?
F2 C4 C3 119.1(2) . . ?
F2 C4 C5 119.8(2) . . ?
C3 C4 C5 121.1(2) . . ?
O3 C5 C6 124.5(2) . . ?
O3 C5 C4 119.0(2) . . ?
C6 C5 C4 116.5(2) . . ?
F3 C6 C7 119.0(2) . . ?
F3 C6 C5 118.7(2) . . ?
C7 C6 C5 122.3(2) . . ?
F4 C7 C6 116.6(2) . . ?
F4 C7 C2 121.5(2) . . ?
C6 C7 C2 121.9(2) . . ?
C13 C8 C9 120.1(2) . . ?
C13 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 118.4(2) . . ?
C12 C11 C14 117.7(2) . . ?
C10 C11 C14 123.9(2) . . ?
C13 C12 C11 121.3(2) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C8 C13 C12 119.8(2) . . ?
C8 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C11 130.8(2) . . ?
C15 C14 H14 114.6 . . ?
C11 C14 H14 114.6 . . ?
C14 C15 C16 121.0(2) . . ?
C14 C15 C17 123.8(2) . . ?
C16 C15 C17 115.21(19) . . ?
N1 C16 C15 176.9(2) . . ?
C18 C17 C19 117.6(2) . . ?
C18 C17 C15 121.0(2) . . ?
C19 C17 C15 121.5(2) . . ?
C19 C18 C17 121.6(2) 2_657 . ?
C19 C18 H18 119.2 2_657 . ?
C17 C18 H18 119.2 . . ?
C18 C19 C17 120.8(2) 2_657 . ?
C18 C19 H19 119.6 2_657 . ?
C17 C19 H19 119.6 . . ?
C1 O1 H1 109.5 . . ?
C5 O3 H3 109.5 . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.046



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3 and CH3OH'
_chemical_properties_physical    Light-sensitive
_exptl_crystal_preparation       Luminescent
