# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_dl4
_database_code_depnum_ccdc_archive 'CCDC 1483959'
_audit_update_record             
;
2016-06-07 deposited with the CCDC.
2016-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H26'
_chemical_formula_sum            'C38 H26'
_chemical_formula_weight         482.59

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   15.7112(6)
_cell_length_b                   15.4073(10)
_cell_length_c                   21.2986(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5155.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    5049
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      25.60

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2032
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9590
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26125
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         26.37
_reflns_number_total             5223
_reflns_number_gt                3281
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0401P)²+0.8225P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5223
_refine_ls_number_parameters     447
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0794
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
C1 C 0.25685(10) 0.70619(11) 0.16416(8) 0.0272(4) Uani 1 1 d . . .
C2 C 0.32972(11) 0.71806(12) 0.19945(9) 0.0344(4) Uani 1 1 d . . .
H2 H 0.3853(11) 0.7057(11) 0.1805(7) 0.036(5) Uiso 1 1 d . . .
C3 C 0.32447(12) 0.75198(13) 0.25925(9) 0.0386(5) Uani 1 1 d . . .
H3 H 0.3760(12) 0.7588(13) 0.2842(9) 0.054(6) Uiso 1 1 d . . .
C4 C 0.24632(12) 0.77516(13) 0.28336(8) 0.0365(5) Uani 1 1 d . . .
H4 H 0.2422(11) 0.7975(12) 0.3263(9) 0.046(5) Uiso 1 1 d . . .
C5 C 0.17298(11) 0.76320(11) 0.24824(8) 0.0290(4) Uani 1 1 d . . .
H5 H 0.1191(10) 0.7792(11) 0.2664(7) 0.032(5) Uiso 1 1 d . . .
C6 C 0.17676(9) 0.72705(10) 0.18830(7) 0.0234(4) Uani 1 1 d . . .
C7 C 0.09824(9) 0.71325(10) 0.15020(7) 0.0220(4) Uani 1 1 d . . .
C8 C 0.03941(10) 0.77928(12) 0.14555(7) 0.0249(4) Uani 1 1 d . . .
H8 H 0.0475(10) 0.8330(12) 0.1677(7) 0.028(4) Uiso 1 1 d . . .
C9 C -0.03206(10) 0.77427(11) 0.10527(7) 0.0256(4) Uani 1 1 d . . .
C10 C -0.09042(10) 0.84398(13) 0.09832(9) 0.0331(4) Uani 1 1 d . . .
H10 H -0.0795(10) 0.8969(12) 0.1244(8) 0.040(5) Uiso 1 1 d . . .
C11 C -0.15586(11) 0.83821(15) 0.05645(9) 0.0403(5) Uani 1 1 d . . .
H11 H -0.1941(11) 0.8883(13) 0.0504(8) 0.040(5) Uiso 1 1 d . . .
C12 C -0.16751(11) 0.76311(15) 0.02073(9) 0.0427(5) Uani 1 1 d . . .
H12 H -0.2131(11) 0.7605(12) -0.0099(8) 0.044(5) Uiso 1 1 d . . .
C13 C -0.11337(11) 0.69408(14) 0.02647(9) 0.0365(5) Uani 1 1 d . . .
H13 H -0.1192(11) 0.6414(13) 0.0017(8) 0.045(6) Uiso 1 1 d . . .
C14 C -0.04385(10) 0.69800(12) 0.06907(7) 0.0272(4) Uani 1 1 d . . .
C15 C 0.01503(10) 0.62946(12) 0.07601(8) 0.0268(4) Uani 1 1 d . . .
H15 H 0.0054(9) 0.5751(11) 0.0519(7) 0.029(4) Uiso 1 1 d . . .
C16 C 0.08426(9) 0.63481(10) 0.11536(7) 0.0224(4) Uani 1 1 d . . .
C17 C 0.14569(9) 0.56128(10) 0.11778(7) 0.0229(4) Uani 1 1 d . . .
C18 C 0.18797(11) 0.53950(12) 0.06243(8) 0.0306(4) Uani 1 1 d . . .
H18 H 0.1741(9) 0.5713(11) 0.0224(7) 0.030(4) Uiso 1 1 d . . .
C19 C 0.25178(11) 0.47778(12) 0.06150(9) 0.0366(4) Uani 1 1 d . . .
H19 H 0.2821(11) 0.4661(12) 0.0219(8) 0.047(5) Uiso 1 1 d . . .
C20 C 0.27475(11) 0.43652(13) 0.11637(9) 0.0363(5) Uani 1 1 d . . .
H20 H 0.3201(11) 0.3927(13) 0.1148(8) 0.042(5) Uiso 1 1 d . . .
C21 C 0.23155(10) 0.45536(12) 0.17139(9) 0.0303(4) Uani 1 1 d . . .
H21 H 0.2445(10) 0.4247(12) 0.2092(8) 0.033(5) Uiso 1 1 d . . .
C22 C 0.16602(9) 0.51607(11) 0.17304(7) 0.0228(4) Uani 1 1 d . . .
C23 C 0.11877(9) 0.53093(10) 0.23310(7) 0.0234(4) Uani 1 1 d . . .
C24 C 0.16106(10) 0.56403(11) 0.28407(7) 0.0258(4) Uani 1 1 d . . .
H24 H 0.2208(10) 0.5781(10) 0.2801(7) 0.025(4) Uiso 1 1 d . . .
C25 C 0.11984(10) 0.58356(11) 0.34131(7) 0.0260(4) Uani 1 1 d . . .
C26 C 0.16263(12) 0.62092(12) 0.39311(8) 0.0323(4) Uani 1 1 d . . .
H26 H 0.2239(11) 0.6348(11) 0.3894(7) 0.037(5) Uiso 1 1 d . . .
C27 C 0.11937(12) 0.63921(13) 0.44738(8) 0.0370(5) Uani 1 1 d . . .
H27 H 0.1494(10) 0.6655(12) 0.4827(8) 0.039(5) Uiso 1 1 d . . .
C28 C 0.03236(13) 0.62010(13) 0.45274(9) 0.0399(5) Uani 1 1 d . . .
H28 H 0.0044(11) 0.6308(13) 0.4915(9) 0.051(6) Uiso 1 1 d . . .
C29 C -0.01096(12) 0.58497(13) 0.40360(8) 0.0375(5) Uani 1 1 d . . .
H29 H -0.0711(11) 0.5705(11) 0.4071(7) 0.035(5) Uiso 1 1 d . . .
C30 C 0.03134(10) 0.56658(11) 0.34615(7) 0.0282(4) Uani 1 1 d . . .
C31 C -0.01110(11) 0.53037(12) 0.29391(8) 0.0293(4) Uani 1 1 d . . .
H31 H -0.0702(10) 0.5150(11) 0.2976(7) 0.027(4) Uiso 1 1 d . . .
C32 C 0.02987(9) 0.51156(10) 0.23868(7) 0.0246(4) Uani 1 1 d . . .
C33 C -0.01816(9) 0.46720(11) 0.18767(7) 0.0255(4) Uani 1 1 d . . .
C34 C 0.01345(11) 0.39252(12) 0.15951(8) 0.0319(4) Uani 1 1 d . . .
H34 H 0.0679(11) 0.3722(11) 0.1714(7) 0.036(5) Uiso 1 1 d . . .
C35 C -0.03298(12) 0.34797(13) 0.11504(9) 0.0372(5) Uani 1 1 d . . .
H35 H -0.0098(11) 0.2958(13) 0.0963(8) 0.051(6) Uiso 1 1 d . . .
C36 C -0.11247(12) 0.37785(13) 0.09745(9) 0.0392(5) Uani 1 1 d . . .
H36 H -0.1466(11) 0.3449(13) 0.0667(9) 0.049(5) Uiso 1 1 d . . .
C37 C -0.14476(12) 0.45243(14) 0.12445(9) 0.0413(5) Uani 1 1 d . . .
H37 H -0.2007(12) 0.4740(13) 0.1109(8) 0.051(6) Uiso 1 1 d . . .
C38 C -0.09819(11) 0.49678(13) 0.16928(9) 0.0341(4) Uani 1 1 d . . .
H38 H -0.1220(11) 0.5506(13) 0.1878(8) 0.044(5) Uiso 1 1 d . . .
H1 H 0.2626(9) 0.6841(11) 0.1209(8) 0.031(4) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.382(2) . ?
C1 C6 1.397(2) . ?
C2 C3 1.379(3) . ?
C3 C4 1.378(3) . ?
C4 C5 1.386(2) . ?
C5 C6 1.394(2) . ?
C6 C7 1.492(2) . ?
C7 C8 1.378(2) . ?
C7 C16 1.435(2) . ?
C8 C9 1.415(2) . ?
C9 C14 1.418(2) . ?
C9 C10 1.420(2) . ?
C10 C11 1.364(3) . ?
C11 C12 1.397(3) . ?
C12 C13 1.367(3) . ?
C13 C14 1.421(2) . ?
C14 C15 1.412(2) . ?
C15 C16 1.376(2) . ?
C16 C17 1.489(2) . ?
C17 C18 1.394(2) . ?
C17 C22 1.404(2) . ?
C18 C19 1.382(2) . ?
C19 C20 1.378(3) . ?
C20 C21 1.385(2) . ?
C21 C22 1.391(2) . ?
C22 C23 1.497(2) . ?
C23 C24 1.371(2) . ?
C23 C32 1.433(2) . ?
C24 C25 1.413(2) . ?
C25 C26 1.414(2) . ?
C25 C30 1.419(2) . ?
C26 C27 1.370(2) . ?
C27 C28 1.403(3) . ?
C28 C29 1.361(3) . ?
C29 C30 1.421(2) . ?
C30 C31 1.412(2) . ?
C31 C32 1.372(2) . ?
C32 C33 1.489(2) . ?
C33 C34 1.389(2) . ?
C33 C38 1.394(2) . ?
C34 C35 1.379(2) . ?
C35 C36 1.383(3) . ?
C36 C37 1.381(3) . ?
C37 C38 1.383(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
C2 C1 C6 121.04(16) . . ?
C3 C2 C1 120.20(17) . . ?
C4 C3 C2 119.71(17) . . ?
C3 C4 C5 120.35(17) . . ?
C4 C5 C6 120.79(16) . . ?
C5 C6 C1 117.86(15) . . ?
C5 C6 C7 121.32(14) . . ?
C1 C6 C7 120.79(14) . . ?
C8 C7 C16 118.81(14) . . ?
C8 C7 C6 119.24(15) . . ?
C16 C7 C6 121.86(14) . . ?
C7 C8 C9 122.37(16) . . ?
C8 C9 C14 118.60(15) . . ?
C8 C9 C10 122.30(17) . . ?
C14 C9 C10 119.06(15) . . ?
C11 C10 C9 120.4(2) . . ?
C10 C11 C12 120.59(19) . . ?
C13 C12 C11 120.93(18) . . ?
C12 C13 C14 120.1(2) . . ?
C15 C14 C9 118.52(14) . . ?
C15 C14 C13 122.59(17) . . ?
C9 C14 C13 118.88(16) . . ?
C16 C15 C14 122.49(17) . . ?
C15 C16 C7 119.11(15) . . ?
C15 C16 C17 119.21(15) . . ?
C7 C16 C17 121.57(13) . . ?
C18 C17 C22 118.74(15) . . ?
C18 C17 C16 117.57(14) . . ?
C22 C17 C16 123.61(14) . . ?
C19 C18 C17 121.57(17) . . ?
C20 C19 C18 119.67(17) . . ?
C19 C20 C21 119.50(17) . . ?
C20 C21 C22 121.66(17) . . ?
C21 C22 C17 118.72(15) . . ?
C21 C22 C23 119.43(14) . . ?
C17 C22 C23 121.85(14) . . ?
C24 C23 C32 118.95(14) . . ?
C24 C23 C22 119.57(14) . . ?
C32 C23 C22 121.49(14) . . ?
C23 C24 C25 122.71(15) . . ?
C24 C25 C26 122.81(15) . . ?
C24 C25 C30 118.21(15) . . ?
C26 C25 C30 118.97(15) . . ?
C27 C26 C25 120.39(17) . . ?
C26 C27 C28 120.59(18) . . ?
C29 C28 C27 120.55(18) . . ?
C28 C29 C30 120.51(18) . . ?
C31 C30 C25 118.59(15) . . ?
C31 C30 C29 122.44(16) . . ?
C25 C30 C29 118.96(16) . . ?
C32 C31 C30 122.51(15) . . ?
C31 C32 C23 118.97(15) . . ?
C31 C32 C33 119.01(14) . . ?
C23 C32 C33 121.93(14) . . ?
C34 C33 C38 118.17(16) . . ?
C34 C33 C32 120.94(14) . . ?
C38 C33 C32 120.81(15) . . ?
C35 C34 C33 121.32(17) . . ?
C34 C35 C36 119.89(19) . . ?
C37 C36 C35 119.72(18) . . ?
C36 C37 C38 120.26(18) . . ?
C37 C38 C33 120.64(18) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_dl6
_database_code_depnum_ccdc_archive 'CCDC 1483960'
_audit_update_record             
;
2016-06-07 deposited with the CCDC.
2016-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C70 H46'
_chemical_formula_sum            'C70 H46'
_chemical_formula_weight         887.07

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   22.5254(5)
_cell_length_b                   17.7308(4)
_cell_length_c                   24.2495(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.6360(10)
_cell_angle_gamma                90.00
_cell_volume                     9575.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    7938
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26.96

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3728
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9594
_exptl_absorpt_correction_T_max  0.9965
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            39013
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         26.37
_reflns_number_total             9682
_reflns_number_gt                5632
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0364P)²+6.0071P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9682
_refine_ls_number_parameters     815
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
C1 C 0.06469(9) 0.09173(13) 0.01756(9) 0.0462(5) Uani 1 1 d . . .
C2 C 0.01025(10) 0.12610(14) -0.00123(11) 0.0595(7) Uani 1 1 d . . .
H2 H -0.0275(11) 0.0938(14) -0.0043(10) 0.080(8) Uiso 1 1 d . . .
C3 C 0.00793(11) 0.20151(15) -0.01391(11) 0.0628(7) Uani 1 1 d . . .
H3 H -0.0303(10) 0.2275(13) -0.0263(9) 0.075(7) Uiso 1 1 d . . .
C4 C 0.05988(10) 0.24337(14) -0.00758(10) 0.0552(6) Uani 1 1 d . . .
H4 H 0.0586(9) 0.2976(13) -0.0144(9) 0.065(7) Uiso 1 1 d . . .
C5 C 0.11454(10) 0.20960(12) 0.01090(9) 0.0445(5) Uani 1 1 d . . .
H5 H 0.1526(9) 0.2418(12) 0.0145(8) 0.055(6) Uiso 1 1 d . . .
C6 C 0.11771(8) 0.13313(11) 0.02369(7) 0.0360(5) Uani 1 1 d . . .
C7 C 0.17740(8) 0.09676(10) 0.03987(7) 0.0338(4) Uani 1 1 d . . .
C8 C 0.22118(9) 0.11029(12) 0.00710(8) 0.0398(5) Uani 1 1 d . . .
H8 H 0.2119(8) 0.1452(11) -0.0258(8) 0.046(5) Uiso 1 1 d . . .
C9 C 0.27792(9) 0.07453(11) 0.01604(8) 0.0378(5) Uani 1 1 d . . .
C10 C 0.32250(10) 0.08682(13) -0.01860(9) 0.0484(5) Uani 1 1 d . . .
H10 H 0.3126(9) 0.1238(12) -0.0506(9) 0.053(6) Uiso 1 1 d . . .
C11 C 0.37586(10) 0.04927(14) -0.00900(10) 0.0530(6) Uani 1 1 d . . .
H11 H 0.4074(9) 0.0588(12) -0.0331(9) 0.060(6) Uiso 1 1 d . . .
C12 C 0.38746(10) -0.00263(14) 0.03477(9) 0.0509(6) Uani 1 1 d . . .
H12 H 0.4264(10) -0.0293(13) 0.0410(9) 0.070(7) Uiso 1 1 d . . .
C13 C 0.34556(9) -0.01599(13) 0.06884(9) 0.0437(5) Uani 1 1 d . . .
H13 H 0.3521(8) -0.0520(11) 0.0994(8) 0.051(6) Uiso 1 1 d . . .
C14 C 0.28974(8) 0.02230(11) 0.06054(7) 0.0344(4) Uani 1 1 d . . .
C15 C 0.24499(8) 0.00995(11) 0.09438(8) 0.0350(4) Uani 1 1 d . . .
H15 H 0.2529(8) -0.0263(11) 0.1263(8) 0.043(5) Uiso 1 1 d . . .
C16 C 0.18977(8) 0.04507(10) 0.08568(7) 0.0321(4) Uani 1 1 d . . .
C17 C 0.14490(8) 0.02290(11) 0.12225(7) 0.0323(4) Uani 1 1 d . . .
C18 C 0.13272(9) -0.05432(12) 0.12422(9) 0.0405(5) Uani 1 1 d . . .
H18 H 0.1537(8) -0.0882(10) 0.1003(7) 0.039(5) Uiso 1 1 d . . .
C19 C 0.09153(10) -0.08295(14) 0.15580(9) 0.0491(6) Uani 1 1 d . . .
H19 H 0.0838(9) -0.1334(13) 0.1546(9) 0.059(7) Uiso 1 1 d . . .
C20 C 0.06173(10) -0.03462(13) 0.18676(9) 0.0488(6) Uani 1 1 d . . .
H20 H 0.0311(9) -0.0550(12) 0.2118(9) 0.067(7) Uiso 1 1 d . . .
C21 C 0.07322(9) 0.04148(13) 0.18566(8) 0.0421(5) Uani 1 1 d . . .
H21 H 0.0519(9) 0.0772(11) 0.2089(8) 0.051(6) Uiso 1 1 d . . .
C22 C 0.11460(8) 0.07219(11) 0.15382(7) 0.0332(4) Uani 1 1 d . . .
C23 C 0.12017(8) 0.15600(11) 0.15400(7) 0.0336(4) Uani 1 1 d . . .
C24 C 0.06759(9) 0.19710(13) 0.14239(8) 0.0428(5) Uani 1 1 d . . .
H24 H 0.0290(9) 0.1695(11) 0.1327(8) 0.046(6) Uiso 1 1 d . . .
C25 C 0.06662(10) 0.27671(13) 0.14168(8) 0.0472(6) Uani 1 1 d . . .
C26 C 0.01201(12) 0.31889(18) 0.13425(10) 0.0656(7) Uani 1 1 d . . .
H26 H -0.0250(10) 0.2867(13) 0.1239(9) 0.065(8) Uiso 1 1 d . . .
C27 C 0.01394(17) 0.39595(19) 0.13705(11) 0.0809(10) Uani 1 1 d . . .
H27 H -0.0237(11) 0.4246(14) 0.1334(10) 0.083(8) Uiso 1 1 d . . .
C28 C 0.06900(17) 0.43468(18) 0.14646(11) 0.0781(9) Uani 1 1 d . . .
H28 H 0.0677(12) 0.4926(18) 0.1465(12) 0.110(10) Uiso 1 1 d . . .
C29 C 0.12158(14) 0.39623(13) 0.15257(9) 0.0587(7) Uani 1 1 d . . .
H29 H 0.1612(11) 0.4240(15) 0.1581(10) 0.087(9) Uiso 1 1 d . . .
C30 C 0.12166(10) 0.31619(12) 0.15113(8) 0.0439(5) Uani 1 1 d . . .
C31 C 0.17486(10) 0.27356(11) 0.16250(8) 0.0376(5) Uani 1 1 d . . .
H31 H 0.2139(9) 0.3018(11) 0.1708(8) 0.046(6) Uiso 1 1 d . . .
C32 C 0.17566(8) 0.19627(10) 0.16633(7) 0.0308(4) Uani 1 1 d . . .
C33 C 0.23546(8) 0.15984(10) 0.18297(7) 0.0303(4) Uani 1 1 d . . .
C34 C 0.28002(9) 0.17860(11) 0.15073(9) 0.0381(5) Uani 1 1 d . . .
H34 H 0.2686(8) 0.2139(12) 0.1182(9) 0.054(6) Uiso 1 1 d . . .
C35 C 0.33707(9) 0.14863(12) 0.16144(10) 0.0439(5) Uani 1 1 d . . .
H35 H 0.3671(9) 0.1616(11) 0.1370(8) 0.054(6) Uiso 1 1 d . . .
C36 C 0.35178(9) 0.09990(12) 0.20561(9) 0.0432(5) Uani 1 1 d . . .
H36 H 0.3928(9) 0.0782(11) 0.2143(8) 0.057(6) Uiso 1 1 d . . .
C37 C 0.30900(8) 0.08225(11) 0.23888(9) 0.0362(5) Uani 1 1 d . . .
H37 H 0.3192(7) 0.0495(10) 0.2726(7) 0.032(5) Uiso 1 1 d . . .
C38 C 0.25019(7) 0.11112(10) 0.22874(7) 0.0292(4) Uani 1 1 d . . .
C39 C 0.20823(7) 0.08344(10) 0.26653(7) 0.0286(4) Uani 1 1 d . . .
C40 C 0.20439(8) 0.00652(11) 0.27256(8) 0.0347(4) Uani 1 1 d . . .
H40 H 0.2281(8) -0.0264(10) 0.2507(7) 0.037(5) Uiso 1 1 d . . .
C41 C 0.16680(8) -0.02831(10) 0.30630(8) 0.0348(4) Uani 1 1 d . . .
C42 C 0.16316(10) -0.10777(12) 0.31162(9) 0.0464(5) Uani 1 1 d . . .
H42 H 0.1894(9) -0.1402(11) 0.2898(8) 0.051(6) Uiso 1 1 d . . .
C43 C 0.12525(11) -0.13906(14) 0.34395(10) 0.0545(6) Uani 1 1 d . . .
H43 H 0.1225(10) -0.1941(13) 0.3478(9) 0.069(7) Uiso 1 1 d . . .
C44 C 0.08936(11) -0.09354(13) 0.37282(10) 0.0537(6) Uani 1 1 d . . .
H44 H 0.0633(10) -0.1159(13) 0.3965(9) 0.066(7) Uiso 1 1 d . . .
C45 C 0.09157(10) -0.01669(13) 0.36860(9) 0.0448(5) Uani 1 1 d . . .
H45 H 0.0667(9) 0.0173(11) 0.3872(8) 0.049(6) Uiso 1 1 d . . .
C46 C 0.13015(8) 0.01776(10) 0.33503(7) 0.0343(4) Uani 1 1 d . . .
C47 C 0.13471(8) 0.09660(11) 0.32911(8) 0.0338(4) Uani 1 1 d . . .
H47 H 0.1121(8) 0.1286(11) 0.3502(8) 0.040(5) Uiso 1 1 d . . .
C48 C 0.17285(7) 0.13049(10) 0.29722(7) 0.0276(4) Uani 1 1 d . . .
C49 C 0.17460(8) 0.21443(10) 0.29676(7) 0.0275(4) Uani 1 1 d . . .
C50 C 0.12031(8) 0.25354(11) 0.28303(7) 0.0324(4) Uani 1 1 d . . .
H50 H 0.0827(8) 0.2230(10) 0.2731(7) 0.037(5) Uiso 1 1 d . . .
C51 C 0.11800(9) 0.33132(11) 0.28198(8) 0.0377(5) Uani 1 1 d . . .
H51 H 0.0798(9) 0.3579(11) 0.2724(8) 0.047(6) Uiso 1 1 d . . .
C52 C 0.17054(9) 0.37242(11) 0.29335(8) 0.0379(5) Uani 1 1 d . . .
H52 H 0.1699(8) 0.4297(12) 0.2918(8) 0.055(6) Uiso 1 1 d . . .
C53 C 0.22453(9) 0.33493(11) 0.30810(8) 0.0351(4) Uani 1 1 d . . .
H53 H 0.2634(8) 0.3650(11) 0.3178(7) 0.043(5) Uiso 1 1 d . . .
C54 C 0.22742(8) 0.25665(10) 0.31214(7) 0.0278(4) Uani 1 1 d . . .
C55 C 0.28587(8) 0.22193(9) 0.33696(7) 0.0288(4) Uani 1 1 d . . .
C56 C 0.33583(8) 0.23191(10) 0.31185(8) 0.0324(4) Uani 1 1 d . . .
H56 H 0.3320(8) 0.2621(10) 0.2757(8) 0.041(5) Uiso 1 1 d . . .
C57 C 0.39242(8) 0.20108(10) 0.33376(7) 0.0321(4) Uani 1 1 d . . .
C58 C 0.44412(9) 0.21140(12) 0.30800(9) 0.0429(5) Uani 1 1 d . . .
H58 H 0.4399(8) 0.2435(12) 0.2733(8) 0.051(6) Uiso 1 1 d . . .
C59 C 0.49733(9) 0.17899(13) 0.32962(10) 0.0496(6) Uani 1 1 d . . .
H59 H 0.5334(10) 0.1870(12) 0.3116(9) 0.064(7) Uiso 1 1 d . . .
C60 C 0.50185(9) 0.13453(12) 0.37793(9) 0.0455(5) Uani 1 1 d . . .
H60 H 0.5408(9) 0.1111(11) 0.3928(8) 0.047(6) Uiso 1 1 d . . .
C61 C 0.45316(9) 0.12456(11) 0.40442(9) 0.0396(5) Uani 1 1 d . . .
H61 H 0.4563(8) 0.0950(10) 0.4389(8) 0.039(5) Uiso 1 1 d . . .
C62 C 0.39699(8) 0.15721(10) 0.38290(7) 0.0316(4) Uani 1 1 d . . .
C63 C 0.34548(8) 0.14846(11) 0.40901(8) 0.0353(4) Uani 1 1 d . . .
H63 H 0.3485(8) 0.1204(11) 0.4444(8) 0.046(6) Uiso 1 1 d . . .
C64 C 0.29096(8) 0.18084(10) 0.38857(7) 0.0310(4) Uani 1 1 d . . .
C65 C 0.24085(8) 0.17556(11) 0.42175(7) 0.0349(4) Uani 1 1 d . . .
C66 C 0.22739(9) 0.10697(13) 0.44488(8) 0.0443(5) Uani 1 1 d . . .
H66 H 0.2502(9) 0.0588(12) 0.4356(8) 0.050(6) Uiso 1 1 d . . .
C67 C 0.18228(10) 0.10250(17) 0.47777(10) 0.0582(7) Uani 1 1 d . . .
H67 H 0.1713(11) 0.0529(14) 0.4916(10) 0.082(8) Uiso 1 1 d . . .
C68 C 0.15047(11) 0.16569(17) 0.48789(10) 0.0654(7) Uani 1 1 d . . .
H68 H 0.1172(11) 0.1642(13) 0.5119(10) 0.083(8) Uiso 1 1 d . . .
C69 C 0.16312(10) 0.23426(16) 0.46532(9) 0.0543(6) Uani 1 1 d . . .
H69 H 0.1395(10) 0.2802(13) 0.4719(9) 0.067(7) Uiso 1 1 d . . .
C70 C 0.20815(9) 0.23934(13) 0.43264(8) 0.0404(5) Uani 1 1 d . . .
H70 H 0.2179(8) 0.2905(12) 0.4182(8) 0.050(6) Uiso 1 1 d . . .
H1 H 0.0662(8) 0.0372(12) 0.0258(8) 0.051(6) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.384(3) . ?
C1 C6 1.391(3) . ?
C2 C3 1.371(3) . ?
C3 C4 1.375(3) . ?
C4 C5 1.382(3) . ?
C5 C6 1.390(3) . ?
C6 C7 1.490(2) . ?
C7 C8 1.377(3) . ?
C7 C16 1.435(2) . ?
C8 C9 1.414(3) . ?
C9 C14 1.416(3) . ?
C9 C10 1.419(3) . ?
C10 C11 1.363(3) . ?
C11 C12 1.399(3) . ?
C12 C13 1.365(3) . ?
C13 C14 1.417(3) . ?
C14 C15 1.409(3) . ?
C15 C16 1.379(2) . ?
C16 C17 1.494(2) . ?
C17 C18 1.398(3) . ?
C17 C22 1.404(3) . ?
C18 C19 1.385(3) . ?
C19 C20 1.378(3) . ?
C20 C21 1.375(3) . ?
C21 C22 1.406(3) . ?
C22 C23 1.491(3) . ?
C23 C24 1.383(3) . ?
C23 C32 1.431(2) . ?
C24 C25 1.412(3) . ?
C25 C30 1.412(3) . ?
C25 C26 1.428(3) . ?
C26 C27 1.368(4) . ?
C27 C28 1.406(4) . ?
C28 C29 1.355(4) . ?
C29 C30 1.420(3) . ?
C30 C31 1.409(3) . ?
C31 C32 1.373(3) . ?
C32 C33 1.494(2) . ?
C33 C34 1.402(2) . ?
C33 C38 1.406(2) . ?
C34 C35 1.379(3) . ?
C35 C36 1.377(3) . ?
C36 C37 1.382(3) . ?
C37 C38 1.407(2) . ?
C38 C39 1.495(2) . ?
C39 C40 1.376(3) . ?
C39 C48 1.436(2) . ?
C40 C41 1.406(3) . ?
C41 C46 1.417(3) . ?
C41 C42 1.418(3) . ?
C42 C43 1.361(3) . ?
C43 C44 1.402(3) . ?
C44 C45 1.368(3) . ?
C45 C46 1.416(3) . ?
C46 C47 1.411(3) . ?
C47 C48 1.377(2) . ?
C48 C49 1.489(2) . ?
C49 C50 1.402(2) . ?
C49 C54 1.408(2) . ?
C50 C51 1.380(3) . ?
C51 C52 1.382(3) . ?
C52 C53 1.385(3) . ?
C53 C54 1.392(2) . ?
C54 C55 1.496(2) . ?
C55 C56 1.369(2) . ?
C55 C64 1.438(2) . ?
C56 C57 1.415(2) . ?
C57 C58 1.414(3) . ?
C57 C62 1.414(2) . ?
C58 C59 1.361(3) . ?
C59 C60 1.403(3) . ?
C60 C61 1.363(3) . ?
C61 C62 1.418(3) . ?
C62 C63 1.411(3) . ?
C63 C64 1.379(2) . ?
C64 C65 1.484(2) . ?
C65 C66 1.392(3) . ?
C65 C70 1.396(3) . ?
C66 C67 1.385(3) . ?
C67 C68 1.372(4) . ?
C68 C69 1.381(3) . ?
C69 C70 1.381(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
C2 C1 C6 120.5(2) . . ?
C3 C2 C1 120.4(2) . . ?
C2 C3 C4 119.9(2) . . ?
C3 C4 C5 120.3(2) . . ?
C4 C5 C6 120.6(2) . . ?
C5 C6 C1 118.45(19) . . ?
C5 C6 C7 119.67(18) . . ?
C1 C6 C7 121.76(18) . . ?
C8 C7 C16 119.02(17) . . ?
C8 C7 C6 117.97(17) . . ?
C16 C7 C6 122.90(16) . . ?
C7 C8 C9 122.86(18) . . ?
C8 C9 C14 118.17(17) . . ?
C8 C9 C10 122.95(19) . . ?
C14 C9 C10 118.85(18) . . ?
C11 C10 C9 120.5(2) . . ?
C10 C11 C12 120.7(2) . . ?
C13 C12 C11 120.4(2) . . ?
C12 C13 C14 120.7(2) . . ?
C15 C14 C9 118.44(17) . . ?
C15 C14 C13 122.68(18) . . ?
C9 C14 C13 118.87(18) . . ?
C16 C15 C14 123.26(18) . . ?
C15 C16 C7 118.22(17) . . ?
C15 C16 C17 117.75(16) . . ?
C7 C16 C17 123.89(16) . . ?
C18 C17 C22 118.47(17) . . ?
C18 C17 C16 115.56(17) . . ?
C22 C17 C16 125.97(17) . . ?
C19 C18 C17 121.9(2) . . ?
C20 C19 C18 119.6(2) . . ?
C21 C20 C19 119.4(2) . . ?
C20 C21 C22 122.2(2) . . ?
C17 C22 C21 118.34(18) . . ?
C17 C22 C23 125.04(16) . . ?
C21 C22 C23 116.53(17) . . ?
C24 C23 C32 118.28(19) . . ?
C24 C23 C22 117.08(18) . . ?
C32 C23 C22 124.62(16) . . ?
C23 C24 C25 122.7(2) . . ?
C24 C25 C30 118.82(19) . . ?
C24 C25 C26 122.5(2) . . ?
C30 C25 C26 118.7(2) . . ?
C27 C26 C25 119.8(3) . . ?
C26 C27 C28 121.1(3) . . ?
C29 C28 C27 120.5(3) . . ?
C28 C29 C30 120.3(3) . . ?
C31 C30 C25 117.77(19) . . ?
C31 C30 C29 122.4(2) . . ?
C25 C30 C29 119.7(2) . . ?
C32 C31 C30 123.4(2) . . ?
C31 C32 C23 118.78(17) . . ?
C31 C32 C33 116.87(17) . . ?
C23 C32 C33 124.35(17) . . ?
C34 C33 C38 118.81(17) . . ?
C34 C33 C32 116.04(17) . . ?
C38 C33 C32 125.12(15) . . ?
C35 C34 C33 121.9(2) . . ?
C36 C35 C34 119.8(2) . . ?
C35 C36 C37 119.24(19) . . ?
C36 C37 C38 122.42(19) . . ?
C33 C38 C37 117.77(17) . . ?
C33 C38 C39 126.13(15) . . ?
C37 C38 C39 116.03(16) . . ?
C40 C39 C48 118.17(17) . . ?
C40 C39 C38 116.51(16) . . ?
C48 C39 C38 125.31(16) . . ?
C39 C40 C41 123.40(18) . . ?
C40 C41 C46 118.65(17) . . ?
C40 C41 C42 122.51(19) . . ?
C46 C41 C42 118.82(19) . . ?
C43 C42 C41 120.5(2) . . ?
C42 C43 C44 120.8(2) . . ?
C45 C44 C43 120.4(2) . . ?
C44 C45 C46 120.3(2) . . ?
C47 C46 C45 123.13(19) . . ?
C47 C46 C41 117.69(17) . . ?
C45 C46 C41 119.18(19) . . ?
C48 C47 C46 123.41(18) . . ?
C47 C48 C39 118.61(17) . . ?
C47 C48 C49 117.38(16) . . ?
C39 C48 C49 124.01(16) . . ?
C50 C49 C54 118.18(17) . . ?
C50 C49 C48 118.24(16) . . ?
C54 C49 C48 123.50(15) . . ?
C51 C50 C49 121.87(18) . . ?
C50 C51 C52 119.63(19) . . ?
C51 C52 C53 119.40(19) . . ?
C52 C53 C54 121.79(19) . . ?
C53 C54 C49 118.86(16) . . ?
C53 C54 C55 117.90(16) . . ?
C49 C54 C55 123.07(16) . . ?
C56 C55 C64 119.29(16) . . ?
C56 C55 C54 120.04(16) . . ?
C64 C55 C54 120.61(15) . . ?
C55 C56 C57 122.50(17) . . ?
C58 C57 C62 118.88(17) . . ?
C58 C57 C56 122.66(18) . . ?
C62 C57 C56 118.46(16) . . ?
C59 C58 C57 120.8(2) . . ?
C58 C59 C60 120.5(2) . . ?
C61 C60 C59 120.2(2) . . ?
C60 C61 C62 120.7(2) . . ?
C63 C62 C57 118.54(16) . . ?
C63 C62 C61 122.57(18) . . ?
C57 C62 C61 118.89(17) . . ?
C64 C63 C62 122.75(18) . . ?
C63 C64 C55 118.31(17) . . ?
C63 C64 C65 119.20(16) . . ?
C55 C64 C65 122.42(15) . . ?
C66 C65 C70 118.60(18) . . ?
C66 C65 C64 120.20(17) . . ?
C70 C65 C64 121.14(17) . . ?
C67 C66 C65 120.3(2) . . ?
C68 C67 C66 120.3(2) . . ?
C67 C68 C69 120.3(2) . . ?
C70 C69 C68 119.9(2) . . ?
C69 C70 C65 120.6(2) . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_dl5
_database_code_depnum_ccdc_archive 'CCDC 1483961'
_audit_update_record             
;
2016-06-07 deposited with the CCDC.
2016-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C54 H36'
_chemical_formula_sum            'C54 H36'
_chemical_formula_weight         684.83

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   16.2638(11)
_cell_length_b                   21.1086(15)
_cell_length_c                   14.1182(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.136(2)
_cell_angle_gamma                90.00
_cell_volume                     4387.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4310
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      27.17

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.037
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    0.059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9769
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19126
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         27.48
_reflns_number_total             5037
_reflns_number_gt                3323
_reflns_threshold_expression     >2sigma(I)

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

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

# SQUEEZE RESULTS 
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 -0.028 469 58 ' '
2 0.500 1.000 0.031 469 58 ' '
_platon_squeeze_details          
;
;


_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5037
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1701
_refine_ls_wR_factor_gt          0.1543
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.002
_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
C1 C -0.21236(11) 0.10011(9) 0.44358(13) 0.0541(4) Uani 1 1 d . . .
C2 C -0.21377(13) 0.05443(11) 0.37280(17) 0.0702(6) Uani 1 1 d . . .
H2 H -0.2092(15) 0.0655(11) 0.3074(18) 0.085(7) Uiso 1 1 d . . .
C3 C -0.21982(14) -0.00832(12) 0.3930(2) 0.0792(7) Uani 1 1 d . . .
H3 H -0.2203(16) -0.0426(11) 0.339(2) 0.093(7) Uiso 1 1 d . . .
C4 C -0.22526(14) -0.02628(10) 0.4842(2) 0.0797(7) Uani 1 1 d . . .
H4A H -0.2300 -0.0689 0.4975 0.096 Uiso 1 1 calc R . .
C5 C -0.22369(12) 0.01944(8) 0.55650(18) 0.0612(5) Uani 1 1 d . . .
H5 H -0.2222(14) 0.0077(10) 0.6271(17) 0.077(6) Uiso 1 1 d . . .
C6 C -0.21718(9) 0.08340(7) 0.53722(12) 0.0464(4) Uani 1 1 d . . .
C7 C -0.21898(10) 0.13248(7) 0.61194(11) 0.0421(4) Uani 1 1 d . . .
C8 C -0.28292(11) 0.12715(8) 0.65266(13) 0.0504(4) Uani 1 1 d . . .
H8 H -0.3208(11) 0.0896(8) 0.6315(12) 0.047(4) Uiso 1 1 d . . .
C9 C -0.29439(11) 0.17402(9) 0.71743(12) 0.0532(4) Uani 1 1 d . . .
C10 C -0.35665(14) 0.16693(12) 0.76375(17) 0.0712(6) Uani 1 1 d . . .
H10 H -0.3916(13) 0.1251(10) 0.7455(15) 0.072(6) Uiso 1 1 d . . .
C11 C -0.36458(17) 0.21352(15) 0.82628(18) 0.0855(7) Uani 1 1 d . . .
H11 H -0.4048(16) 0.2078(11) 0.8627(18) 0.097(7) Uiso 1 1 d . . .
C12 C -0.31302(17) 0.26908(15) 0.84510(18) 0.0855(7) Uani 1 1 d . . .
H12 H -0.3262(18) 0.2999(13) 0.890(2) 0.120(9) Uiso 1 1 d . . .
C13 C -0.25391(15) 0.27758(12) 0.80131(16) 0.0690(6) Uani 1 1 d . . .
H13 H -0.2188(16) 0.3165(11) 0.8123(18) 0.085(7) Uiso 1 1 d . . .
C14 C -0.24264(11) 0.22988(8) 0.73670(12) 0.0527(4) Uani 1 1 d . . .
C15 C -0.17649(11) 0.23505(8) 0.69629(12) 0.0470(4) Uani 1 1 d . . .
H15 H -0.1364(11) 0.2734(8) 0.7135(13) 0.052(5) Uiso 1 1 d . . .
C16 C -0.16189(10) 0.18751(7) 0.63837(11) 0.0402(3) Uani 1 1 d . . .
C17 C -0.08541(10) 0.19601(7) 0.60686(10) 0.0382(3) Uani 1 1 d . . .
C18 C -0.08783(12) 0.24916(8) 0.54654(13) 0.0501(4) Uani 1 1 d . . .
H18 H -0.1370(12) 0.2801(9) 0.5298(14) 0.059(5) Uiso 1 1 d . . .
C19 C -0.02160(12) 0.25953(8) 0.51142(13) 0.0542(4) Uani 1 1 d . . .
H19 H -0.0258(12) 0.2961(9) 0.4734(14) 0.059(5) Uiso 1 1 d . . .
C20 C 0.04881(11) 0.21675(8) 0.53555(11) 0.0489(4) Uani 1 1 d . . .
H20 H 0.0991(14) 0.2225(10) 0.5103(17) 0.085(6) Uiso 1 1 d . . .
C21 C 0.05303(10) 0.16450(7) 0.59616(11) 0.0406(3) Uani 1 1 d . . .
H21 H 0.1060(11) 0.1345(8) 0.6149(12) 0.048(4) Uiso 1 1 d . . .
C22 C -0.01193(9) 0.15348(6) 0.63443(10) 0.0349(3) Uani 1 1 d . . .
C23 C -0.00247(8) 0.09486(6) 0.69785(9) 0.0323(3) Uani 1 1 d . . .
C24 C 0.00063(9) 0.03769(7) 0.65271(10) 0.0364(3) Uani 1 1 d . . .
H24 H 0.0011(9) 0.0360(7) 0.5828(12) 0.039(4) Uiso 1 1 d . . .
C25 C 0.00221(9) -0.02114(6) 0.70102(10) 0.0356(3) Uani 1 1 d . . .
C26 C 0.00517(10) -0.08007(7) 0.65402(11) 0.0433(4) Uani 1 1 d . . .
H26 H 0.0071(11) -0.0814(8) 0.5868(13) 0.055(5) Uiso 1 1 d . . .
C27 C 0.00311(11) -0.13507(7) 0.70163(12) 0.0488(4) Uani 1 1 d . . .
H27A H 0.0058 -0.1733 0.6704 0.059 Uiso 1 1 calc R . .
H1 H -0.2067(11) 0.1464(9) 0.4317(14) 0.056(5) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.382(3) . ?
C1 C6 1.402(2) . ?
C2 C3 1.367(3) . ?
C3 C4 1.381(3) . ?
C4 C5 1.397(3) . ?
C5 C6 1.390(2) . ?
C6 C7 1.488(2) . ?
C7 C8 1.390(2) . ?
C7 C16 1.434(2) . ?
C8 C9 1.412(2) . ?
C9 C14 1.406(3) . ?
C9 C10 1.428(2) . ?
C10 C11 1.364(3) . ?
C11 C12 1.400(4) . ?
C12 C13 1.358(3) . ?
C13 C14 1.422(3) . ?
C14 C15 1.420(2) . ?
C15 C16 1.377(2) . ?
C16 C17 1.499(2) . ?
C17 C18 1.399(2) . ?
C17 C22 1.411(2) . ?
C18 C19 1.381(2) . ?
C19 C20 1.383(3) . ?
C20 C21 1.380(2) . ?
C21 C22 1.3954(19) . ?
C22 C23 1.4965(18) . ?
C23 C24 1.3755(18) . ?
C23 C23 1.440(2) 2_556 ?
C24 C25 1.4117(19) . ?
C25 C25 1.415(3) 2_556 ?
C25 C26 1.4203(19) . ?
C26 C27 1.349(2) . ?
C27 C27 1.412(3) 2_556 ?

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
C2 C1 C6 121.05(19) . . ?
C3 C2 C1 120.4(2) . . ?
C2 C3 C4 119.9(2) . . ?
C3 C4 C5 120.2(2) . . ?
C4 C5 C6 120.5(2) . . ?
C5 C6 C1 117.93(17) . . ?
C5 C6 C7 120.75(16) . . ?
C1 C6 C7 121.27(15) . . ?
C8 C7 C16 118.24(14) . . ?
C8 C7 C6 118.71(14) . . ?
C16 C7 C6 122.89(13) . . ?
C7 C8 C9 122.60(16) . . ?
C14 C9 C8 118.67(15) . . ?
C14 C9 C10 118.81(17) . . ?
C8 C9 C10 122.52(19) . . ?
C11 C10 C9 120.1(2) . . ?
C10 C11 C12 120.9(2) . . ?
C13 C12 C11 120.5(2) . . ?
C12 C13 C14 120.5(2) . . ?
C9 C14 C15 118.68(15) . . ?
C9 C14 C13 119.22(17) . . ?
C15 C14 C13 121.97(19) . . ?
C16 C15 C14 122.25(16) . . ?
C15 C16 C7 119.27(14) . . ?
C15 C16 C17 117.58(14) . . ?
C7 C16 C17 123.14(13) . . ?
C18 C17 C22 118.67(13) . . ?
C18 C17 C16 117.66(13) . . ?
C22 C17 C16 123.67(12) . . ?
C19 C18 C17 121.41(16) . . ?
C20 C19 C18 119.91(15) . . ?
C19 C20 C21 119.52(15) . . ?
C20 C21 C22 121.80(15) . . ?
C21 C22 C17 118.62(13) . . ?
C21 C22 C23 117.85(12) . . ?
C17 C22 C23 123.43(12) . . ?
C24 C23 C23 118.47(7) . 2_556 ?
C24 C23 C22 117.57(11) . . ?
C23 C23 C22 123.96(7) 2_556 . ?
C23 C24 C25 122.99(12) . . ?
C24 C25 C25 118.30(7) . 2_556 ?
C24 C25 C26 122.82(12) . . ?
C25 C25 C26 118.85(8) 2_556 . ?
C27 C26 C25 120.54(13) . . ?
C26 C27 C27 120.61(9) . 2_556 ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_dl10
_database_code_depnum_ccdc_archive 'CCDC 1483962'
_audit_update_record             
;
2016-06-07 deposited with the CCDC.
2016-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 F2'
_chemical_formula_sum            'C22 H14 F2'
_chemical_formula_weight         316.33

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'

_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                   16.4358(10)
_cell_length_b                   19.7791(12)
_cell_length_c                   10.5249(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.8353(6)
_cell_angle_gamma                90.00
_cell_volume                     3257.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9966
_cell_measurement_theta_min      3.42
_cell_measurement_theta_max      27.00

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9482
_exptl_absorpt_correction_T_max  0.9823
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            50564
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.35
_diffrn_reflns_theta_max         28.29
_reflns_number_total             8057
_reflns_number_gt                5440
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0447P)²+0.6373P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8057
_refine_ls_number_parameters     545
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1156
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.002
_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 0.10170(8) 1.06124(5) 0.37667(12) 0.0934(3) Uani 1 1 d . . .
F2 F 0.24465(7) 1.00491(5) 0.36044(12) 0.0940(3) Uani 1 1 d . . .
C1 C 0.10603(10) 0.63758(9) 0.29571(19) 0.0642(4) Uani 1 1 d . . .
H1 H 0.1108(11) 0.6664(9) 0.2224(19) 0.078(5) Uiso 1 1 d . . .
C2 C 0.12579(12) 0.56972(10) 0.2988(3) 0.0857(6) Uani 1 1 d . . .
H2 H 0.1458(14) 0.5492(11) 0.225(2) 0.109(7) Uiso 1 1 d . . .
C3 C 0.11824(14) 0.53011(12) 0.4007(3) 0.0996(8) Uani 1 1 d . . .
H3 H 0.1287(14) 0.4812(12) 0.402(2) 0.117(8) Uiso 1 1 d . . .
C4 C 0.09109(14) 0.55785(11) 0.5002(3) 0.0905(7) Uani 1 1 d . . .
H4 H 0.0828(13) 0.5331(11) 0.570(2) 0.096(7) Uiso 1 1 d . . .
C5 C 0.07156(11) 0.62637(9) 0.49937(18) 0.0673(4) Uani 1 1 d . . .
H5 H 0.0526(10) 0.6467(8) 0.5683(16) 0.062(5) Uiso 1 1 d . . .
C6 C 0.07904(8) 0.66707(7) 0.39595(14) 0.0524(3) Uani 1 1 d . . .
C7 C 0.06413(8) 0.74139(7) 0.39322(12) 0.0467(3) Uani 1 1 d . . .
C8 C 0.12822(9) 0.78251(7) 0.37866(14) 0.0509(3) Uani 1 1 d . . .
H8 H 0.1808(9) 0.7624(7) 0.3725(14) 0.053(4) Uiso 1 1 d . . .
C9 C 0.12298(8) 0.85362(7) 0.37809(13) 0.0497(3) Uani 1 1 d . . .
C10 C 0.19087(10) 0.89562(8) 0.36868(16) 0.0599(4) Uani 1 1 d . . .
H10 H 0.2418(11) 0.8755(8) 0.3596(17) 0.074(5) Uiso 1 1 d . . .
C11 C 0.18150(11) 0.96328(8) 0.36917(16) 0.0655(4) Uani 1 1 d . . .
C12 C 0.10622(11) 0.99295(8) 0.37724(16) 0.0658(4) Uani 1 1 d . . .
C13 C 0.04025(11) 0.95496(8) 0.38567(16) 0.0627(4) Uani 1 1 d . . .
H13 H -0.0097(11) 0.9753(8) 0.3909(16) 0.067(5) Uiso 1 1 d . . .
C14 C 0.04708(9) 0.88364(7) 0.38845(13) 0.0513(3) Uani 1 1 d . . .
C15 C -0.01836(9) 0.84106(8) 0.40274(14) 0.0541(3) Uani 1 1 d . . .
H15 H -0.0703(10) 0.8620(7) 0.4099(14) 0.057(4) Uiso 1 1 d . . .
C16 C -0.01169(8) 0.77180(7) 0.40726(12) 0.0480(3) Uani 1 1 d . . .
C17 C -0.08344(8) 0.73162(7) 0.42720(13) 0.0502(3) Uani 1 1 d . . .
C18 C -0.11936(11) 0.75144(10) 0.52482(18) 0.0722(5) Uani 1 1 d . . .
H18 H -0.0942(12) 0.7897(9) 0.5798(19) 0.084(6) Uiso 1 1 d . . .
C19 C -0.18723(13) 0.71655(11) 0.5445(2) 0.0854(6) Uani 1 1 d . . .
H19 H -0.2096(13) 0.7312(10) 0.613(2) 0.099(6) Uiso 1 1 d . . .
C20 C -0.22064(12) 0.66146(10) 0.4673(2) 0.0755(5) Uani 1 1 d . . .
H20 H -0.2672(13) 0.6372(9) 0.4797(19) 0.092(6) Uiso 1 1 d . . .
C21 C -0.18605(10) 0.64097(9) 0.36970(17) 0.0628(4) Uani 1 1 d . . .
H21 H -0.2083(11) 0.6025(9) 0.3153(17) 0.072(5) Uiso 1 1 d . . .
C22 C -0.11803(9) 0.67551(8) 0.34999(14) 0.0534(3) Uani 1 1 d . . .
H22 H -0.0926(10) 0.6605(7) 0.2835(16) 0.059(4) Uiso 1 1 d . . .
F3 F 0.76387(7) 0.54110(6) 0.84066(11) 0.0944(3) Uani 1 1 d . . .
F4 F 0.67089(7) 0.47149(5) 0.62966(11) 0.0873(3) Uani 1 1 d . . .
C23 C 0.57905(11) 0.89533(8) 0.64071(16) 0.0607(4) Uani 1 1 d . . .
H23 H 0.6355(11) 0.8836(8) 0.6467(16) 0.069(5) Uiso 1 1 d . . .
C24 C 0.56003(13) 0.96056(9) 0.66962(18) 0.0715(5) Uani 1 1 d . . .
H24 H 0.6053(12) 0.9948(9) 0.6927(18) 0.085(5) Uiso 1 1 d . . .
C25 C 0.47730(13) 0.97784(10) 0.65914(17) 0.0715(5) Uani 1 1 d . . .
H25 H 0.4623(11) 1.0239(9) 0.6741(18) 0.083(5) Uiso 1 1 d . . .
C26 C 0.41344(11) 0.93015(9) 0.61888(16) 0.0651(4) Uani 1 1 d . . .
H26 H 0.3577(11) 0.9407(8) 0.6124(16) 0.072(5) Uiso 1 1 d . . .
C27 C 0.43217(9) 0.86519(8) 0.58960(14) 0.0547(3) Uani 1 1 d . . .
H27 H 0.3879(10) 0.8309(7) 0.5634(15) 0.058(4) Uiso 1 1 d . . .
C28 C 0.51557(8) 0.84651(7) 0.60028(12) 0.0487(3) Uani 1 1 d . . .
C29 C 0.53688(8) 0.77539(7) 0.57657(13) 0.0476(3) Uani 1 1 d . . .
C30 C 0.60103(8) 0.74309(8) 0.67288(14) 0.0522(3) Uani 1 1 d . . .
H30 H 0.6314(9) 0.7682(7) 0.7534(15) 0.057(4) Uiso 1 1 d . . .
C31 C 0.62064(8) 0.67435(7) 0.66303(13) 0.0510(3) Uani 1 1 d . . .
C32 C 0.68645(10) 0.64037(9) 0.76255(16) 0.0612(4) Uani 1 1 d . . .
H32 H 0.7180(11) 0.6657(8) 0.8365(17) 0.069(5) Uiso 1 1 d . . .
C33 C 0.70108(10) 0.57427(9) 0.74756(16) 0.0650(4) Uani 1 1 d . . .
C34 C 0.65288(10) 0.53776(8) 0.63674(17) 0.0622(4) Uani 1 1 d . . .
C35 C 0.58993(10) 0.56773(8) 0.53944(16) 0.0568(4) Uani 1 1 d . . .
H35 H 0.5568(11) 0.5411(8) 0.4609(18) 0.074(5) Uiso 1 1 d . . .
C36 C 0.57201(8) 0.63725(7) 0.55002(13) 0.0496(3) Uani 1 1 d . . .
C37 C 0.50772(9) 0.67138(8) 0.45066(14) 0.0506(3) Uani 1 1 d . . .
H37 H 0.4762(10) 0.6453(7) 0.3708(15) 0.059(4) Uiso 1 1 d . . .
C38 C 0.48969(8) 0.73844(7) 0.46053(12) 0.0469(3) Uani 1 1 d . . .
C39 C 0.42398(8) 0.77094(7) 0.34697(13) 0.0492(3) Uani 1 1 d . . .
C40 C 0.34430(9) 0.74104(9) 0.29187(15) 0.0608(4) Uani 1 1 d . . .
H40 H 0.3311(10) 0.6993(8) 0.3301(16) 0.067(5) Uiso 1 1 d . . .
C41 C 0.28500(10) 0.76967(11) 0.18211(17) 0.0727(5) Uani 1 1 d . . .
H41 H 0.2296(13) 0.7467(9) 0.1468(19) 0.090(6) Uiso 1 1 d . . .
C42 C 0.30384(11) 0.82739(11) 0.12512(17) 0.0740(5) Uani 1 1 d . . .
H42 H 0.2631(12) 0.8477(9) 0.0496(19) 0.083(5) Uiso 1 1 d . . .
C43 C 0.38255(11) 0.85769(10) 0.17811(16) 0.0670(4) Uani 1 1 d . . .
H43 H 0.3972(11) 0.8977(9) 0.1379(18) 0.082(6) Uiso 1 1 d . . .
C44 C 0.44188(10) 0.82970(8) 0.28829(14) 0.0561(3) Uani 1 1 d . . .
H44 H 0.4969(10) 0.8509(7) 0.3251(15) 0.058(4) Uiso 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
F1 C12 1.3525(18) . ?
F2 C11 1.3499(18) . ?
C1 C2 1.379(3) . ?
C1 C6 1.392(2) . ?
C2 C3 1.364(3) . ?
C3 C4 1.372(4) . ?
C4 C5 1.392(3) . ?
C5 C6 1.389(2) . ?
C6 C7 1.4890(19) . ?
C7 C8 1.3760(19) . ?
C7 C16 1.4317(18) . ?
C8 C9 1.409(2) . ?
C9 C10 1.419(2) . ?
C9 C14 1.4156(19) . ?
C10 C11 1.347(2) . ?
C11 C12 1.395(2) . ?
C12 C13 1.344(2) . ?
C13 C14 1.415(2) . ?
C14 C15 1.410(2) . ?
C15 C16 1.374(2) . ?
C16 C17 1.4892(18) . ?
C17 C22 1.390(2) . ?
C17 C18 1.389(2) . ?
C18 C19 1.380(2) . ?
C19 C20 1.370(3) . ?
C20 C21 1.378(2) . ?
C21 C22 1.379(2) . ?
F3 C33 1.3551(17) . ?
F4 C34 1.3509(18) . ?
C23 C24 1.383(2) . ?
C23 C28 1.389(2) . ?
C24 C25 1.373(3) . ?
C25 C26 1.378(3) . ?
C26 C27 1.378(2) . ?
C27 C28 1.3905(19) . ?
C28 C29 1.4891(19) . ?
C29 C30 1.3758(19) . ?
C29 C38 1.4307(18) . ?
C30 C31 1.408(2) . ?
C31 C36 1.4177(19) . ?
C31 C32 1.423(2) . ?
C32 C33 1.347(2) . ?
C33 C34 1.394(2) . ?
C34 C35 1.350(2) . ?
C35 C36 1.418(2) . ?
C36 C37 1.4102(19) . ?
C37 C38 1.370(2) . ?
C38 C39 1.4892(18) . ?
C39 C40 1.391(2) . ?
C39 C44 1.389(2) . ?
C40 C41 1.384(2) . ?
C41 C42 1.369(3) . ?
C42 C43 1.379(3) . ?
C43 C44 1.382(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
C2 C1 C6 121.2(2) . . ?
C3 C2 C1 120.0(2) . . ?
C2 C3 C4 120.0(2) . . ?
C3 C4 C5 120.8(2) . . ?
C6 C5 C4 119.6(2) . . ?
C5 C6 C1 118.45(16) . . ?
C5 C6 C7 122.25(14) . . ?
C1 C6 C7 119.20(14) . . ?
C8 C7 C16 118.91(13) . . ?
C8 C7 C6 117.30(12) . . ?
C16 C7 C6 123.79(12) . . ?
C7 C8 C9 122.86(13) . . ?
C8 C9 C10 122.44(13) . . ?
C8 C9 C14 118.20(12) . . ?
C10 C9 C14 119.36(13) . . ?
C11 C10 C9 119.22(15) . . ?
C10 C11 F2 120.96(16) . . ?
C10 C11 C12 121.51(15) . . ?
F2 C11 C12 117.53(15) . . ?
C13 C12 F1 120.94(16) . . ?
C13 C12 C11 121.13(15) . . ?
F1 C12 C11 117.92(15) . . ?
C12 C13 C14 119.89(16) . . ?
C15 C14 C13 122.65(14) . . ?
C15 C14 C9 118.47(13) . . ?
C13 C14 C9 118.87(14) . . ?
C16 C15 C14 122.96(13) . . ?
C15 C16 C7 118.56(12) . . ?
C15 C16 C17 118.61(12) . . ?
C7 C16 C17 122.83(12) . . ?
C22 C17 C18 117.86(14) . . ?
C22 C17 C16 122.92(12) . . ?
C18 C17 C16 119.20(13) . . ?
C19 C18 C17 121.08(17) . . ?
C20 C19 C18 120.26(17) . . ?
C19 C20 C21 119.62(16) . . ?
C22 C21 C20 120.32(16) . . ?
C21 C22 C17 120.85(14) . . ?
C24 C23 C28 121.11(16) . . ?
C25 C24 C23 119.96(17) . . ?
C24 C25 C26 119.78(17) . . ?
C27 C26 C25 120.38(16) . . ?
C26 C27 C28 120.79(15) . . ?
C27 C28 C23 117.99(14) . . ?
C27 C28 C29 120.93(13) . . ?
C23 C28 C29 120.98(13) . . ?
C30 C29 C38 118.97(13) . . ?
C30 C29 C28 118.80(12) . . ?
C38 C29 C28 122.13(12) . . ?
C29 C30 C31 122.35(13) . . ?
C30 C31 C36 118.58(12) . . ?
C30 C31 C32 122.77(13) . . ?
C36 C31 C32 118.64(14) . . ?
C33 C32 C31 119.66(15) . . ?
F3 C33 C32 120.58(16) . . ?
F3 C33 C34 117.78(15) . . ?
C32 C33 C34 121.64(15) . . ?
C35 C34 F4 120.95(16) . . ?
C35 C34 C33 120.96(15) . . ?
F4 C34 C33 118.09(14) . . ?
C34 C35 C36 119.72(15) . . ?
C37 C36 C31 118.44(13) . . ?
C37 C36 C35 122.18(13) . . ?
C31 C36 C35 119.38(13) . . ?
C38 C37 C36 122.52(13) . . ?
C37 C38 C29 119.08(12) . . ?
C37 C38 C39 118.54(12) . . ?
C29 C38 C39 122.34(12) . . ?
C40 C39 C44 118.08(14) . . ?
C40 C39 C38 120.64(13) . . ?
C44 C39 C38 121.18(12) . . ?
C41 C40 C39 120.42(17) . . ?
C42 C41 C40 120.74(17) . . ?
C41 C42 C43 119.70(16) . . ?
C42 C43 C44 119.91(18) . . ?
C43 C44 C39 121.14(15) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_dl8
_database_code_depnum_ccdc_archive 'CCDC 1483963'
_audit_update_record             
;
2016-06-07 deposited with the CCDC.
2016-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H22 F4'
_chemical_formula_sum            'C38 H22 F4'
_chemical_formula_weight         554.56

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   15.7303(14)
_cell_length_b                   15.2924(17)
_cell_length_c                   23.248(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5592.4(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3104
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      20.31

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2288
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9634
_exptl_absorpt_correction_T_max  0.9953
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19580
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         23.26
_reflns_number_total             4016
_reflns_number_gt                2253
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0385P)²+1.6277P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4016
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 0.19367(10) 0.89203(11) 0.04598(9) 0.0803(6) Uani 1 1 d . . .
F2 F 0.21226(11) 0.74974(13) -0.01694(9) 0.0976(7) Uani 1 1 d . . .
F3 F 0.03467(17) 0.59710(17) 0.46942(10) 0.1347(10) Uani 1 1 d . . .
F4 F -0.12929(16) 0.63611(16) 0.46742(9) 0.1204(8) Uani 1 1 d . . .
C1 C -0.25513(17) 0.68825(17) 0.17963(13) 0.0502(8) Uani 1 1 d . . .
H1A H -0.2666 0.6663 0.1431 0.060 Uiso 1 1 calc R . .
C2 C -0.3211(2) 0.7011(2) 0.21796(17) 0.0679(10) Uani 1 1 d . . .
H2A H -0.3764 0.6868 0.2074 0.081 Uiso 1 1 calc R . .
C3 C -0.3052(3) 0.7349(2) 0.27175(18) 0.0806(11) Uani 1 1 d . . .
H3A H -0.3495 0.7425 0.2977 0.097 Uiso 1 1 calc R . .
C4 C -0.2243(3) 0.7574(2) 0.28696(15) 0.0744(10) Uani 1 1 d . . .
H4A H -0.2141 0.7822 0.3228 0.089 Uiso 1 1 calc R . .
C5 C -0.1574(2) 0.74367(17) 0.24939(14) 0.0572(8) Uani 1 1 d . . .
H5A H -0.1025 0.7584 0.2605 0.069 Uiso 1 1 calc R . .
C6 C -0.17161(17) 0.70774(16) 0.19492(12) 0.0415(7) Uani 1 1 d . . .
C7 C -0.09984(15) 0.69538(15) 0.15419(11) 0.0377(7) Uani 1 1 d . . .
C8 C -0.04084(16) 0.76144(16) 0.14789(12) 0.0423(7) Uani 1 1 d . . .
H8A H -0.0450 0.8103 0.1715 0.051 Uiso 1 1 calc R . .
C9 C 0.02547(15) 0.75806(16) 0.10725(12) 0.0403(7) Uani 1 1 d . . .
C10 C 0.08192(17) 0.82932(18) 0.09851(13) 0.0482(8) Uani 1 1 d . . .
H10A H 0.0775 0.8795 0.1209 0.058 Uiso 1 1 calc R . .
C11 C 0.14156(18) 0.8235(2) 0.05768(15) 0.0540(8) Uani 1 1 d . . .
C12 C 0.15084(18) 0.7490(2) 0.02399(15) 0.0634(9) Uani 1 1 d . . .
C13 C 0.09895(18) 0.67916(19) 0.03069(14) 0.0600(9) Uani 1 1 d . . .
H13A H 0.1061 0.6295 0.0081 0.072 Uiso 1 1 calc R . .
C14 C 0.03370(16) 0.68255(17) 0.07258(12) 0.0431(7) Uani 1 1 d . . .
C15 C -0.02573(17) 0.61462(16) 0.08023(12) 0.0450(7) Uani 1 1 d . . .
H15A H -0.0205 0.5646 0.0577 0.054 Uiso 1 1 calc R . .
C16 C -0.09093(15) 0.61871(15) 0.11935(11) 0.0365(7) Uani 1 1 d . . .
C17 C -0.15245(15) 0.54441(16) 0.12118(12) 0.0384(7) Uani 1 1 d . . .
C18 C -0.19934(17) 0.52735(18) 0.07174(13) 0.0511(8) Uani 1 1 d . . .
H18A H -0.1904 0.5614 0.0392 0.061 Uiso 1 1 calc R . .
C19 C -0.25850(18) 0.4615(2) 0.06981(15) 0.0632(9) Uani 1 1 d . . .
H19A H -0.2891 0.4510 0.0363 0.076 Uiso 1 1 calc R . .
C20 C -0.27208(19) 0.4112(2) 0.11784(17) 0.0658(10) Uani 1 1 d . . .
H20A H -0.3124 0.3667 0.1170 0.079 Uiso 1 1 calc R . .
C21 C -0.22637(17) 0.42635(18) 0.16722(15) 0.0552(9) Uani 1 1 d . . .
H21A H -0.2367 0.3924 0.1997 0.066 Uiso 1 1 calc R . .
C22 C -0.16472(15) 0.49188(16) 0.16945(13) 0.0408(7) Uani 1 1 d . . .
C23 C -0.11299(16) 0.50270(16) 0.22271(13) 0.0421(7) Uani 1 1 d . . .
C24 C -0.15027(18) 0.53306(17) 0.27204(14) 0.0500(8) Uani 1 1 d . . .
H24A H -0.2086 0.5432 0.2719 0.060 Uiso 1 1 calc R . .
C25 C -0.1046(2) 0.54968(18) 0.32282(14) 0.0539(8) Uani 1 1 d . . .
C26 C -0.1431(2) 0.5848(2) 0.37270(16) 0.0697(10) Uani 1 1 d . . .
H26A H -0.2010 0.5970 0.3733 0.084 Uiso 1 1 calc R . .
C27 C -0.0945(3) 0.6004(2) 0.41945(17) 0.0822(12) Uani 1 1 d . . .
C28 C -0.0079(3) 0.5806(3) 0.42013(19) 0.0857(12) Uani 1 1 d . . .
C29 C 0.0313(3) 0.5486(2) 0.37372(17) 0.0774(11) Uani 1 1 d . . .
H29A H 0.0893 0.5370 0.3748 0.093 Uiso 1 1 calc R . .
C30 C -0.0159(2) 0.53244(18) 0.32273(14) 0.0536(8) Uani 1 1 d . . .
C31 C 0.02141(19) 0.49816(18) 0.27255(15) 0.0555(8) Uani 1 1 d . . .
H31A H 0.0792 0.4854 0.2729 0.067 Uiso 1 1 calc R . .
C32 C -0.02355(17) 0.48293(17) 0.22352(14) 0.0461(8) Uani 1 1 d . . .
C33 C 0.01966(18) 0.44338(18) 0.17324(13) 0.0494(8) Uani 1 1 d . . .
C34 C 0.09528(19) 0.4787(2) 0.15282(16) 0.0667(10) Uani 1 1 d . . .
H34A H 0.1177 0.5283 0.1703 0.080 Uiso 1 1 calc R . .
C35 C 0.1374(2) 0.4414(2) 0.10703(18) 0.0832(12) Uani 1 1 d . . .
H35A H 0.1882 0.4656 0.0941 0.100 Uiso 1 1 calc R . .
C36 C 0.1049(2) 0.3688(2) 0.08047(17) 0.0821(11) Uani 1 1 d . . .
H36A H 0.1334 0.3439 0.0495 0.098 Uiso 1 1 calc R . .
C37 C 0.0303(2) 0.3328(2) 0.09952(16) 0.0753(11) Uani 1 1 d . . .
H37A H 0.0079 0.2838 0.0814 0.090 Uiso 1 1 calc R . .
C38 C -0.01166(19) 0.36995(19) 0.14609(15) 0.0618(9) Uani 1 1 d . . .
H38A H -0.0619 0.3448 0.1592 0.074 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 C11 1.358(3) . ?
F2 C12 1.356(3) . ?
F3 C28 1.351(4) . ?
F4 C27 1.357(4) . ?
C1 C2 1.382(4) . ?
C1 C6 1.393(4) . ?
C2 C3 1.377(4) . ?
C3 C4 1.365(4) . ?
C4 C5 1.383(4) . ?
C5 C6 1.398(4) . ?
C6 C7 1.486(4) . ?
C7 C8 1.380(3) . ?
C7 C16 1.432(3) . ?
C8 C9 1.408(4) . ?
C9 C14 1.414(3) . ?
C9 C10 1.420(3) . ?
C10 C11 1.338(4) . ?
C11 C12 1.391(4) . ?
C12 C13 1.353(4) . ?
C13 C14 1.416(4) . ?
C14 C15 1.409(3) . ?
C15 C16 1.372(3) . ?
C16 C17 1.493(3) . ?
C17 C18 1.390(4) . ?
C17 C22 1.393(3) . ?
C18 C19 1.372(4) . ?
C19 C20 1.373(4) . ?
C20 C21 1.374(4) . ?
C21 C22 1.395(4) . ?
C22 C23 1.491(4) . ?
C23 C24 1.369(4) . ?
C23 C32 1.439(4) . ?
C24 C25 1.405(4) . ?
C25 C26 1.414(4) . ?
C25 C30 1.419(4) . ?
C26 C27 1.350(5) . ?
C27 C28 1.396(5) . ?
C28 C29 1.335(5) . ?
C29 C30 1.421(4) . ?
C30 C31 1.408(4) . ?
C31 C32 1.361(4) . ?
C32 C33 1.481(4) . ?
C33 C38 1.379(4) . ?
C33 C34 1.390(4) . ?
C34 C35 1.378(4) . ?
C35 C36 1.370(5) . ?
C36 C37 1.368(4) . ?
C37 C38 1.389(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
C2 C1 C6 120.9(3) . . ?
C3 C2 C1 120.2(3) . . ?
C4 C3 C2 120.0(3) . . ?
C3 C4 C5 120.5(3) . . ?
C4 C5 C6 120.7(3) . . ?
C1 C6 C5 117.8(3) . . ?
C1 C6 C7 121.8(3) . . ?
C5 C6 C7 120.4(3) . . ?
C8 C7 C16 118.3(2) . . ?
C8 C7 C6 119.1(2) . . ?
C16 C7 C6 122.6(2) . . ?
C7 C8 C9 122.9(2) . . ?
C8 C9 C14 118.7(2) . . ?
C8 C9 C10 122.1(3) . . ?
C14 C9 C10 119.2(3) . . ?
C11 C10 C9 119.3(3) . . ?
C10 C11 F1 121.0(3) . . ?
C10 C11 C12 121.9(3) . . ?
F1 C11 C12 117.1(3) . . ?
C13 C12 F2 121.1(3) . . ?
C13 C12 C11 121.2(3) . . ?
F2 C12 C11 117.6(3) . . ?
C12 C13 C14 119.2(3) . . ?
C15 C14 C9 118.0(2) . . ?
C15 C14 C13 122.7(3) . . ?
C9 C14 C13 119.2(2) . . ?
C16 C15 C14 123.1(2) . . ?
C15 C16 C7 119.0(2) . . ?
C15 C16 C17 117.9(2) . . ?
C7 C16 C17 122.9(2) . . ?
C18 C17 C22 118.9(2) . . ?
C18 C17 C16 117.6(2) . . ?
C22 C17 C16 123.5(2) . . ?
C19 C18 C17 121.6(3) . . ?
C18 C19 C20 119.4(3) . . ?
C19 C20 C21 120.2(3) . . ?
C20 C21 C22 121.0(3) . . ?
C17 C22 C21 118.7(3) . . ?
C17 C22 C23 122.0(2) . . ?
C21 C22 C23 119.3(3) . . ?
C24 C23 C32 118.6(3) . . ?
C24 C23 C22 120.0(2) . . ?
C32 C23 C22 121.4(3) . . ?
C23 C24 C25 123.1(3) . . ?
C24 C25 C26 122.6(3) . . ?
C24 C25 C30 117.9(3) . . ?
C26 C25 C30 119.5(3) . . ?
C27 C26 C25 119.0(4) . . ?
C26 C27 F4 120.3(4) . . ?
C26 C27 C28 121.6(4) . . ?
F4 C27 C28 118.1(4) . . ?
C29 C28 F3 121.7(4) . . ?
C29 C28 C27 121.4(4) . . ?
F3 C28 C27 117.0(4) . . ?
C28 C29 C30 119.8(4) . . ?
C31 C30 C25 118.7(3) . . ?
C31 C30 C29 122.6(3) . . ?
C25 C30 C29 118.7(3) . . ?
C32 C31 C30 122.7(3) . . ?
C31 C32 C23 118.9(3) . . ?
C31 C32 C33 119.5(3) . . ?
C23 C32 C33 121.6(3) . . ?
C38 C33 C34 117.8(3) . . ?
C38 C33 C32 122.0(3) . . ?
C34 C33 C32 120.2(3) . . ?
C35 C34 C33 120.9(3) . . ?
C36 C35 C34 120.3(3) . . ?
C37 C36 C35 120.0(3) . . ?
C36 C37 C38 119.7(3) . . ?
C33 C38 C37 121.3(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        23.26
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_dl7
_database_code_depnum_ccdc_archive 'CCDC 1483964'
_audit_update_record             
;
2016-06-07 deposited with the CCDC.
2016-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C54 H30 F6'
_chemical_formula_sum            'C54 H30 F6'
_chemical_formula_weight         792.78

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Iba2

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

_cell_length_a                   21.8211(7)
_cell_length_b                   19.2793(6)
_cell_length_c                   19.7602(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     8313.0(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2990
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      21.90

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3264
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9687
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12234
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         23.81
_reflns_number_total             3273
_reflns_number_gt                2312
_reflns_threshold_expression     >2sigma(I)

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

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

# SQUEEZE RESULTS 
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.312 199 48 ' '
2 0.000 0.000 0.348 15 0 ' '
3 0.500 0.000 0.812 199 48 ' '
4 0.000 0.000 0.848 15 0 ' '
5 1.000 0.500 0.312 199 48 ' '
6 0.000 0.500 0.812 199 48 ' '
7 0.500 0.500 0.348 15 0 ' '
8 0.500 0.500 0.848 15 0 ' '
_platon_squeeze_details          
;
;

_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)+(0.0400P)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    riding
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00084(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_number_reflns         3273
_refine_ls_number_parameters     542
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0743
_refine_ls_wR_factor_gt          0.0670
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_restrained_S_all      0.982
_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
F1 F -0.41546(13) 0.45462(13) 0.73814(14) 0.1127(9) Uani 1 1 d . . .
F2 F -0.29607(13) 0.45404(11) 0.71033(12) 0.0984(8) Uani 1 1 d . . .
F3 F -0.43331(13) 0.24962(17) 1.32113(14) 0.1295(10) Uani 1 1 d . . .
F4 F -0.41667(12) 0.38477(16) 1.31178(13) 0.1140(9) Uani 1 1 d . . .
F5 F 0.05718(10) 0.04614(10) 0.97578(13) 0.0900(7) Uani 1 1 d . . .
F6 F 0.07206(11) 0.04067(11) 1.10837(15) 0.1045(8) Uani 1 1 d . . .
C1 C -0.42041(15) 0.20052(18) 1.0325(2) 0.0612(10) Uani 1 1 d . . .
H1A H -0.4295 0.2475 1.0354 0.073 Uiso 1 1 calc R . .
C2 C -0.45001(16) 0.1546(2) 1.0752(2) 0.0731(11) Uani 1 1 d . . .
H2A H -0.4783 0.1709 1.1066 0.088 Uiso 1 1 calc R . .
C3 C -0.43759(17) 0.08469(19) 1.0710(2) 0.0812(12) Uani 1 1 d . . .
H3A H -0.4577 0.0533 1.0990 0.097 Uiso 1 1 calc R . .
C4 C -0.3946(2) 0.06196(18) 1.0244(3) 0.0861(13) Uani 1 1 d . . .
H4A H -0.3855 0.0149 1.0214 0.103 Uiso 1 1 calc R . .
C5 C -0.36525(17) 0.10810(16) 0.9826(2) 0.0647(10) Uani 1 1 d . . .
H5A H -0.3365 0.0919 0.9516 0.078 Uiso 1 1 calc R . .
C6 C -0.37778(13) 0.17852(15) 0.98580(17) 0.0488(9) Uani 1 1 d . . .
C7 C -0.34918(14) 0.22817(15) 0.93819(17) 0.0461(8) Uani 1 1 d . . .
C8 C -0.38642(16) 0.27315(16) 0.90269(19) 0.0566(10) Uani 1 1 d . . .
H8A H -0.4282 0.2727 0.9119 0.068 Uiso 1 1 calc R . .
C9 C -0.36478(17) 0.31942(16) 0.85370(18) 0.0532(9) Uani 1 1 d . . .
C10 C -0.40373(18) 0.36522(19) 0.8179(2) 0.0699(11) Uani 1 1 d . . .
H10A H -0.4457 0.3653 0.8261 0.084 Uiso 1 1 calc R . .
C11 C -0.3794(2) 0.4086(2) 0.7718(2) 0.0775(13) Uani 1 1 d . . .
C12 C -0.3175(2) 0.4087(2) 0.75765(19) 0.0731(12) Uani 1 1 d . . .
C13 C -0.27855(19) 0.36524(18) 0.78929(19) 0.0655(10) Uani 1 1 d . . .
H13A H -0.2371 0.3654 0.7783 0.079 Uiso 1 1 calc R . .
C14 C -0.30127(17) 0.31929(16) 0.83941(17) 0.0511(9) Uani 1 1 d . . .
C15 C -0.26303(16) 0.27336(16) 0.87557(17) 0.0529(9) Uani 1 1 d . . .
H15A H -0.2214 0.2725 0.8656 0.063 Uiso 1 1 calc R . .
C16 C -0.28492(14) 0.22990(15) 0.92485(17) 0.0451(8) Uani 1 1 d . . .
C17 C -0.24140(13) 0.18352(15) 0.96162(18) 0.0461(8) Uani 1 1 d . . .
C18 C -0.20835(15) 0.13417(16) 0.9244(2) 0.0578(9) Uani 1 1 d . . .
H18A H -0.2106 0.1350 0.8774 0.069 Uiso 1 1 calc R . .
C19 C -0.17276(15) 0.08475(17) 0.9551(2) 0.0641(11) Uani 1 1 d . . .
H19A H -0.1518 0.0522 0.9292 0.077 Uiso 1 1 calc R . .
C20 C -0.16824(15) 0.08369(17) 1.0241(3) 0.0636(11) Uani 1 1 d . . .
H20A H -0.1454 0.0493 1.0454 0.076 Uiso 1 1 calc R . .
C21 C -0.19774(15) 0.13377(16) 1.0623(2) 0.0579(10) Uani 1 1 d . . .
H21A H -0.1935 0.1334 1.1091 0.070 Uiso 1 1 calc R . .
C22 C -0.23397(13) 0.18508(15) 1.03177(19) 0.0470(8) Uani 1 1 d . . .
C23 C -0.26332(13) 0.23676(15) 1.07753(17) 0.0460(8) Uani 1 1 d . . .
C24 C -0.29951(15) 0.21131(17) 1.12971(18) 0.0551(9) Uani 1 1 d . . .
H24A H -0.3041 0.1635 1.1339 0.066 Uiso 1 1 calc R . .
C25 C -0.32967(16) 0.2545(2) 1.17660(19) 0.0599(10) Uani 1 1 d . . .
C26 C -0.36849(18) 0.2283(2) 1.2284(2) 0.0757(11) Uani 1 1 d . . .
H26A H -0.3749 0.1808 1.2326 0.091 Uiso 1 1 calc R . .
C27 C -0.39561(19) 0.2725(3) 1.2709(2) 0.0843(13) Uani 1 1 d . . .
C28 C -0.38612(19) 0.3438(3) 1.2665(2) 0.0789(12) Uani 1 1 d . . .
C29 C -0.35116(17) 0.3708(2) 1.2184(2) 0.0686(11) Uani 1 1 d . . .
H29A H -0.3461 0.4186 1.2155 0.082 Uiso 1 1 calc R . .
C30 C -0.32140(15) 0.32657(19) 1.17142(19) 0.0557(9) Uani 1 1 d . . .
C31 C -0.28504(15) 0.35248(17) 1.11852(19) 0.0531(9) Uani 1 1 d . . .
H31A H -0.2806 0.4003 1.1145 0.064 Uiso 1 1 calc R . .
C32 C -0.25542(13) 0.31028(15) 1.07204(17) 0.0447(8) Uani 1 1 d . . .
C33 C -0.21919(15) 0.34625(14) 1.01856(16) 0.0466(8) Uani 1 1 d . . .
C34 C -0.24863(15) 0.39901(15) 0.98299(19) 0.0559(9) Uani 1 1 d . . .
H34A H -0.2892 0.4090 0.9934 0.067 Uiso 1 1 calc R . .
C35 C -0.22021(19) 0.43685(16) 0.9331(2) 0.0622(10) Uani 1 1 d . . .
H35A H -0.2414 0.4714 0.9101 0.075 Uiso 1 1 calc R . .
C36 C -0.15998(18) 0.42293(16) 0.91754(19) 0.0616(10) Uani 1 1 d . . .
H36A H -0.1401 0.4478 0.8838 0.074 Uiso 1 1 calc R . .
C37 C -0.12951(16) 0.37167(16) 0.95258(18) 0.0559(9) Uani 1 1 d . . .
H37A H -0.0891 0.3619 0.9412 0.067 Uiso 1 1 calc R . .
C38 C -0.15721(14) 0.33382(14) 1.00456(17) 0.0453(8) Uani 1 1 d . . .
C39 C -0.11756(13) 0.28144(15) 1.03953(17) 0.0435(8) Uani 1 1 d . . .
C40 C -0.08690(14) 0.23406(15) 1.00040(19) 0.0497(8) Uani 1 1 d . . .
H40A H -0.0927 0.2353 0.9538 0.060 Uiso 1 1 calc R . .
C41 C -0.04708(14) 0.18358(16) 1.02720(18) 0.0481(9) Uani 1 1 d . . .
C42 C -0.01503(15) 0.13607(15) 0.9853(2) 0.0579(9) Uani 1 1 d . . .
H42A H -0.0212 0.1362 0.9387 0.069 Uiso 1 1 calc R . .
C43 C 0.02434(16) 0.09092(17) 1.0135(2) 0.0637(10) Uani 1 1 d . . .
C44 C 0.03265(17) 0.08894(17) 1.0832(3) 0.0710(11) Uani 1 1 d . . .
C45 C 0.00246(16) 0.13128(16) 1.1255(2) 0.0640(10) Uani 1 1 d . . .
H45A H 0.0082 0.1281 1.1720 0.077 Uiso 1 1 calc R . .
C46 C -0.03869(14) 0.18147(15) 1.09765(19) 0.0495(9) Uani 1 1 d . . .
C47 C -0.07002(15) 0.23056(17) 1.13800(19) 0.0535(9) Uani 1 1 d . . .
H47A H -0.0650 0.2289 1.1847 0.064 Uiso 1 1 calc R . .
C48 C -0.10770(13) 0.28073(15) 1.11097(18) 0.0457(8) Uani 1 1 d . . .
C49 C -0.13339(14) 0.33466(17) 1.15672(17) 0.0502(9) Uani 1 1 d . . .
C50 C -0.15968(15) 0.3165(2) 1.2179(2) 0.0629(10) Uani 1 1 d . . .
H50A H -0.1625 0.2699 1.2298 0.075 Uiso 1 1 calc R . .
C51 C -0.18171(19) 0.3662(3) 1.2613(2) 0.0814(12) Uani 1 1 d . . .
H51A H -0.1987 0.3529 1.3025 0.098 Uiso 1 1 calc R . .
C52 C -0.17903(19) 0.4346(2) 1.2449(2) 0.0805(12) Uani 1 1 d . . .
H52A H -0.1952 0.4677 1.2741 0.097 Uiso 1 1 calc R . .
C53 C -0.15204(19) 0.45467(19) 1.1846(2) 0.0730(11) Uani 1 1 d . . .
H53A H -0.1492 0.5014 1.1734 0.088 Uiso 1 1 calc R . .
C54 C -0.12948(16) 0.40499(17) 1.14115(19) 0.0596(10) Uani 1 1 d . . .
H54A H -0.1113 0.4186 1.1007 0.072 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 C11 1.360(4) . ?
F2 C12 1.363(4) . ?
F3 C27 1.362(5) . ?
F4 C28 1.367(5) . ?
F5 C43 1.347(4) . ?
F6 C44 1.361(4) . ?
C1 C2 1.383(5) . ?
C1 C6 1.377(4) . ?
C2 C3 1.377(5) . ?
C3 C4 1.386(5) . ?
C4 C5 1.372(5) . ?
C5 C6 1.386(4) . ?
C6 C7 1.480(4) . ?
C7 C8 1.380(4) . ?
C7 C16 1.427(4) . ?
C8 C9 1.399(5) . ?
C9 C14 1.414(5) . ?
C9 C10 1.416(5) . ?
C10 C11 1.346(6) . ?
C11 C12 1.379(6) . ?
C12 C13 1.347(5) . ?
C13 C14 1.418(5) . ?
C14 C15 1.411(4) . ?
C15 C16 1.370(4) . ?
C16 C17 1.493(4) . ?
C17 C22 1.396(5) . ?
C17 C18 1.402(4) . ?
C18 C19 1.371(5) . ?
C19 C20 1.367(5) . ?
C20 C21 1.384(5) . ?
C21 C22 1.402(4) . ?
C22 C23 1.490(5) . ?
C23 C24 1.389(4) . ?
C23 C32 1.432(4) . ?
C24 C25 1.409(5) . ?
C25 C30 1.405(5) . ?
C25 C26 1.421(5) . ?
C26 C27 1.335(6) . ?
C27 C28 1.394(6) . ?
C28 C29 1.324(5) . ?
C29 C30 1.419(5) . ?
C30 C31 1.404(5) . ?
C31 C32 1.387(4) . ?
C32 C33 1.491(4) . ?
C33 C34 1.393(4) . ?
C33 C38 1.401(4) . ?
C34 C35 1.374(5) . ?
C35 C36 1.376(5) . ?
C36 C37 1.378(5) . ?
C37 C38 1.397(4) . ?
C38 C39 1.499(4) . ?
C39 C40 1.371(4) . ?
C39 C48 1.428(4) . ?
C40 C41 1.408(4) . ?
C41 C46 1.405(5) . ?
C41 C42 1.419(5) . ?
C42 C43 1.344(5) . ?
C43 C44 1.390(6) . ?
C44 C45 1.341(5) . ?
C45 C46 1.430(4) . ?
C46 C47 1.414(5) . ?
C47 C48 1.377(4) . ?
C48 C49 1.487(5) . ?
C49 C50 1.383(5) . ?
C49 C54 1.393(4) . ?
C50 C51 1.373(5) . ?
C51 C52 1.359(6) . ?
C52 C53 1.385(6) . ?
C53 C54 1.377(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
C2 C1 C6 121.8(3) . . ?
C1 C2 C3 119.9(4) . . ?
C2 C3 C4 118.8(3) . . ?
C5 C4 C3 120.7(3) . . ?
C4 C5 C6 121.0(3) . . ?
C1 C6 C5 117.8(3) . . ?
C1 C6 C7 120.8(3) . . ?
C5 C6 C7 121.4(3) . . ?
C8 C7 C16 118.0(3) . . ?
C8 C7 C6 118.8(3) . . ?
C16 C7 C6 123.1(3) . . ?
C7 C8 C9 123.6(3) . . ?
C8 C9 C14 117.9(3) . . ?
C8 C9 C10 122.8(3) . . ?
C14 C9 C10 119.3(3) . . ?
C11 C10 C9 119.3(4) . . ?
C10 C11 F1 120.5(5) . . ?
C10 C11 C12 121.6(4) . . ?
F1 C11 C12 117.8(4) . . ?
C13 C12 F2 120.1(4) . . ?
C13 C12 C11 121.5(4) . . ?
F2 C12 C11 118.4(4) . . ?
C12 C13 C14 119.5(4) . . ?
C9 C14 C15 118.6(3) . . ?
C9 C14 C13 118.7(3) . . ?
C15 C14 C13 122.6(3) . . ?
C16 C15 C14 122.5(3) . . ?
C15 C16 C7 119.2(3) . . ?
C15 C16 C17 119.4(3) . . ?
C7 C16 C17 121.4(3) . . ?
C22 C17 C18 118.4(3) . . ?
C22 C17 C16 123.0(3) . . ?
C18 C17 C16 118.6(3) . . ?
C19 C18 C17 122.0(4) . . ?
C18 C19 C20 119.6(4) . . ?
C19 C20 C21 120.0(3) . . ?
C20 C21 C22 121.4(4) . . ?
C17 C22 C21 118.5(3) . . ?
C17 C22 C23 124.5(3) . . ?
C21 C22 C23 117.0(3) . . ?
C24 C23 C32 118.3(3) . . ?
C24 C23 C22 117.3(3) . . ?
C32 C23 C22 124.3(3) . . ?
C23 C24 C25 123.1(3) . . ?
C24 C25 C30 118.4(3) . . ?
C24 C25 C26 122.8(4) . . ?
C30 C25 C26 118.7(4) . . ?
C27 C26 C25 119.4(4) . . ?
C26 C27 F3 121.3(5) . . ?
C26 C27 C28 121.6(4) . . ?
F3 C27 C28 117.0(4) . . ?
C29 C28 F4 121.6(5) . . ?
C29 C28 C27 121.2(4) . . ?
F4 C28 C27 117.2(4) . . ?
C28 C29 C30 119.8(4) . . ?
C31 C30 C25 118.6(3) . . ?
C31 C30 C29 122.2(3) . . ?
C25 C30 C29 119.2(4) . . ?
C32 C31 C30 123.2(3) . . ?
C31 C32 C23 118.3(3) . . ?
C31 C32 C33 116.3(3) . . ?
C23 C32 C33 125.3(3) . . ?
C34 C33 C38 118.1(3) . . ?
C34 C33 C32 116.9(3) . . ?
C38 C33 C32 124.9(3) . . ?
C35 C34 C33 122.8(3) . . ?
C36 C35 C34 119.2(3) . . ?
C35 C36 C37 119.2(3) . . ?
C36 C37 C38 122.4(3) . . ?
C37 C38 C33 118.2(3) . . ?
C37 C38 C39 116.2(3) . . ?
C33 C38 C39 125.6(3) . . ?
C40 C39 C48 118.5(3) . . ?
C40 C39 C38 118.1(3) . . ?
C48 C39 C38 123.3(3) . . ?
C39 C40 C41 123.3(3) . . ?
C46 C41 C40 118.2(3) . . ?
C46 C41 C42 119.7(3) . . ?
C40 C41 C42 122.0(3) . . ?
C43 C42 C41 119.4(4) . . ?
C42 C43 F5 121.7(4) . . ?
C42 C43 C44 120.8(4) . . ?
F5 C43 C44 117.5(4) . . ?
C45 C44 F6 120.0(4) . . ?
C45 C44 C43 122.4(3) . . ?
F6 C44 C43 117.6(4) . . ?
C44 C45 C46 118.8(4) . . ?
C41 C46 C47 118.5(3) . . ?
C41 C46 C45 118.9(3) . . ?
C47 C46 C45 122.7(3) . . ?
C48 C47 C46 122.7(3) . . ?
C47 C48 C39 118.7(3) . . ?
C47 C48 C49 118.7(3) . . ?
C39 C48 C49 122.5(3) . . ?
C50 C49 C54 117.7(3) . . ?
C50 C49 C48 120.7(3) . . ?
C54 C49 C48 121.5(3) . . ?
C51 C50 C49 121.0(4) . . ?
C52 C51 C50 120.8(4) . . ?
C51 C52 C53 119.6(4) . . ?
C54 C53 C52 119.6(4) . . ?
C53 C54 C49 121.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        23.81
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.029
####################################################################### 
# 
# 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_dl9
_database_code_depnum_ccdc_archive 'CCDC 1483965'
_audit_update_record             
;
2016-06-07 deposited with the CCDC.
2016-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C64 H34 F8'
_chemical_formula_sum            'C64 H34 F8'
_chemical_formula_weight         954.91

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'

_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                   11.1751(4)
_cell_length_b                   12.6389(5)
_cell_length_c                   19.1180(7)
_cell_angle_alpha                83.981(2)
_cell_angle_beta                 85.728(2)
_cell_angle_gamma                64.491(2)
_cell_volume                     2422.29(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4708
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      23.70

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             980
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9810
_exptl_absorpt_correction_T_max  0.9976
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker X8 APEX II diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23933
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0521
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.79
_diffrn_reflns_theta_max         23.26
_reflns_number_total             6818
_reflns_number_gt                3692
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
 C59 > C64 ring is disordered ( two positions).
 Disordered solvent was SQEEZEd
;

# SQUEEZE RESULTS 
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.400 0.138 0.662 105 36 ' '
2 0.600 -0.138 0.338 105 36 ' '
3 0.500 0.000 1.000 17 4 ' '
_platon_squeeze_details          
;
;

_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)+(0.1269P)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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6818
_refine_ls_number_parameters     692
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0613
_refine_ls_wR_factor_ref         0.2147
_refine_ls_wR_factor_gt          0.1925
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.084
_refine_ls_shift/su_mean         0.004


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 1.1208(3) 0.0080(2) 0.72319(16) 0.1022(10) Uani 1 1 d . . .
F2 F 1.0707(3) 0.0170(2) 0.86119(16) 0.1078(10) Uani 1 1 d . . .
F3 F 0.2524(3) 0.9181(2) 0.43908(11) 0.0791(8) Uani 1 1 d . . .
F4 F 0.2704(2) 0.7087(2) 0.41465(11) 0.0741(7) Uani 1 1 d . . .
F5 F 0.8271(3) -0.0558(2) 0.78428(14) 0.0903(9) Uani 1 1 d . . .
F6 F 0.7431(3) -0.0510(2) 0.91813(14) 0.0933(9) Uani 1 1 d . . .
F7 F -0.0396(3) 0.8749(2) 0.49334(12) 0.0775(8) Uani 1 1 d . . .
F8 F -0.0334(2) 0.6709(2) 0.46727(11) 0.0750(8) Uani 1 1 d . . .
C1 C 0.7296(4) 0.7382(4) 0.6840(2) 0.0616(12) Uani 1 1 d D . .
H1A H 0.7530 0.7394 0.7294 0.074 Uiso 1 1 calc R . .
C2 C 0.7015(5) 0.8360(5) 0.6365(3) 0.0874(17) Uani 1 1 d D . .
H2A H 0.7072 0.9021 0.6502 0.105 Uiso 1 1 calc R . .
C3 C 0.6651(5) 0.8356(5) 0.5688(3) 0.0912(19) Uani 1 1 d D . .
H3A H 0.6432 0.9021 0.5375 0.109 Uiso 1 1 calc R . .
C4 C 0.6615(4) 0.7369(5) 0.5487(3) 0.0830(17) Uani 1 1 d D . .
H4A H 0.6398 0.7356 0.5028 0.100 Uiso 1 1 calc R . .
C5 C 0.6898(4) 0.6383(4) 0.5954(2) 0.0628(12) Uani 1 1 d D . .
H5A H 0.6865 0.5718 0.5807 0.075 Uiso 1 1 calc R . .
C6 C 0.7231(3) 0.6382(3) 0.6639(2) 0.0454(10) Uani 1 1 d . . .
C7 C 0.7607(3) 0.5305(3) 0.71235(18) 0.0406(9) Uani 1 1 d . . .
C8 C 0.8452(3) 0.4249(3) 0.6870(2) 0.0463(10) Uani 1 1 d . . .
H8A H 0.8667 0.4234 0.6390 0.056 Uiso 1 1 calc R . .
C9 C 0.9007(3) 0.3191(3) 0.72981(19) 0.0441(9) Uani 1 1 d . . .
C10 C 0.9869(4) 0.2106(4) 0.7035(2) 0.0593(11) Uani 1 1 d . . .
H10A H 1.0070 0.2061 0.6555 0.071 Uiso 1 1 calc R . .
C11 C 1.0391(4) 0.1149(4) 0.7477(3) 0.0684(13) Uani 1 1 d . . .
C12 C 1.0118(4) 0.1184(4) 0.8196(3) 0.0665(12) Uani 1 1 d . . .
C13 C 0.9297(4) 0.2186(4) 0.8474(2) 0.0600(12) Uani 1 1 d . . .
H13A H 0.9119 0.2194 0.8957 0.072 Uiso 1 1 calc R . .
C14 C 0.8700(3) 0.3232(3) 0.8030(2) 0.0470(10) Uani 1 1 d . . .
C15 C 0.7787(3) 0.4302(3) 0.82840(19) 0.0456(10) Uani 1 1 d . . .
H15A H 0.7563 0.4323 0.8762 0.055 Uiso 1 1 calc R . .
C16 C 0.7211(3) 0.5318(3) 0.78508(18) 0.0402(9) Uani 1 1 d . . .
C17 C 0.6214(3) 0.6391(3) 0.81751(18) 0.0422(9) Uani 1 1 d . . .
C18 C 0.6584(4) 0.6744(4) 0.8755(2) 0.0548(11) Uani 1 1 d . . .
H18A H 0.7428 0.6296 0.8926 0.066 Uiso 1 1 calc R . .
C19 C 0.5758(4) 0.7727(4) 0.9086(2) 0.0623(12) Uani 1 1 d . . .
H19A H 0.6043 0.7940 0.9471 0.075 Uiso 1 1 calc R . .
C20 C 0.4500(4) 0.8395(4) 0.8840(2) 0.0575(11) Uani 1 1 d . . .
H20A H 0.3932 0.9069 0.9054 0.069 Uiso 1 1 calc R . .
C21 C 0.4089(4) 0.8056(3) 0.82746(19) 0.0478(10) Uani 1 1 d . . .
H21A H 0.3233 0.8504 0.8118 0.057 Uiso 1 1 calc R . .
C22 C 0.4921(3) 0.7055(3) 0.79268(17) 0.0376(9) Uani 1 1 d . . .
C23 C 0.4414(3) 0.6825(3) 0.72872(17) 0.0363(9) Uani 1 1 d . . .
C24 C 0.3962(3) 0.7735(3) 0.67687(18) 0.0398(9) Uani 1 1 d . . .
H24A H 0.3904 0.8465 0.6859 0.048 Uiso 1 1 calc R . .
C25 C 0.3584(3) 0.7607(3) 0.61087(17) 0.0382(9) Uani 1 1 d . . .
C26 C 0.3170(4) 0.8537(3) 0.55614(19) 0.0499(10) Uani 1 1 d . . .
H26A H 0.3086 0.9281 0.5638 0.060 Uiso 1 1 calc R . .
C27 C 0.2903(4) 0.8312(4) 0.4926(2) 0.0524(11) Uani 1 1 d . . .
C28 C 0.3012(4) 0.7223(4) 0.47970(18) 0.0489(10) Uani 1 1 d . . .
C29 C 0.3384(3) 0.6318(3) 0.52945(18) 0.0445(10) Uani 1 1 d . . .
H29A H 0.3446 0.5591 0.5196 0.053 Uiso 1 1 calc R . .
C30 C 0.3682(3) 0.6483(3) 0.59705(17) 0.0380(9) Uani 1 1 d . . .
C31 C 0.4054(3) 0.5593(3) 0.65196(17) 0.0362(9) Uani 1 1 d . . .
H31A H 0.4073 0.4872 0.6440 0.043 Uiso 1 1 calc R . .
C32 C 0.4393(3) 0.5727(3) 0.71707(17) 0.0336(8) Uani 1 1 d . . .
C33 C 0.4772(3) 0.4679(3) 0.76981(17) 0.0345(8) Uani 1 1 d . . .
C34 C 0.5667(3) 0.3620(3) 0.74712(18) 0.0400(9) Uani 1 1 d . . .
H34A H 0.6010 0.3609 0.7012 0.048 Uiso 1 1 calc R . .
C35 C 0.6091(3) 0.2557(3) 0.78907(18) 0.0388(9) Uani 1 1 d . . .
C36 C 0.7008(4) 0.1478(3) 0.7636(2) 0.0513(10) Uani 1 1 d . . .
H36A H 0.7328 0.1452 0.7172 0.062 Uiso 1 1 calc R . .
C37 C 0.7408(4) 0.0497(4) 0.8069(2) 0.0598(11) Uani 1 1 d . . .
C38 C 0.6959(4) 0.0512(4) 0.8773(2) 0.0609(12) Uani 1 1 d . . .
C39 C 0.6088(4) 0.1519(4) 0.9037(2) 0.0557(11) Uani 1 1 d . . .
H39A H 0.5798 0.1517 0.9505 0.067 Uiso 1 1 calc R . .
C40 C 0.5614(3) 0.2587(3) 0.85952(18) 0.0419(9) Uani 1 1 d . . .
C41 C 0.4696(4) 0.3667(3) 0.88258(18) 0.0429(9) Uani 1 1 d . . .
H41A H 0.4375 0.3682 0.9289 0.051 Uiso 1 1 calc R . .
C42 C 0.4244(3) 0.4702(3) 0.84079(17) 0.0352(9) Uani 1 1 d . . .
C43 C 0.3214(3) 0.5773(3) 0.87279(16) 0.0360(9) Uani 1 1 d . . .
C44 C 0.3547(4) 0.6049(3) 0.93522(18) 0.0462(10) Uani 1 1 d . . .
H44A H 0.4391 0.5600 0.9524 0.055 Uiso 1 1 calc R . .
C45 C 0.2663(4) 0.6968(4) 0.97222(19) 0.0530(11) Uani 1 1 d . . .
H45A H 0.2901 0.7118 1.0144 0.064 Uiso 1 1 calc R . .
C46 C 0.1428(4) 0.7659(4) 0.9463(2) 0.0565(11) Uani 1 1 d . . .
H46A H 0.0829 0.8290 0.9702 0.068 Uiso 1 1 calc R . .
C47 C 0.1090(4) 0.7408(3) 0.88485(19) 0.0517(10) Uani 1 1 d . . .
H47A H 0.0254 0.7883 0.8676 0.062 Uiso 1 1 calc R . .
C48 C 0.1948(3) 0.6469(3) 0.84704(17) 0.0404(9) Uani 1 1 d . . .
C49 C 0.1476(3) 0.6285(3) 0.78061(17) 0.0380(9) Uani 1 1 d . . .
C50 C 0.1070(3) 0.7200(3) 0.72894(17) 0.0407(9) Uani 1 1 d . . .
H50A H 0.1056 0.7912 0.7384 0.049 Uiso 1 1 calc R . .
C51 C 0.0673(3) 0.7109(3) 0.66242(18) 0.0379(9) Uani 1 1 d . . .
C52 C 0.0288(3) 0.8047(4) 0.6092(2) 0.0482(10) Uani 1 1 d . . .
H52A H 0.0258 0.8770 0.6177 0.058 Uiso 1 1 calc R . .
C53 C -0.0030(4) 0.7884(4) 0.5469(2) 0.0492(10) Uani 1 1 d . . .
C54 C 0.0013(4) 0.6804(4) 0.53266(19) 0.0514(11) Uani 1 1 d . . .
C55 C 0.0368(4) 0.5883(4) 0.5817(2) 0.0524(11) Uani 1 1 d . . .
H55A H 0.0388 0.5172 0.5714 0.063 Uiso 1 1 calc R . .
C56 C 0.0711(3) 0.6015(3) 0.64897(18) 0.0417(9) Uani 1 1 d . . .
C57 C 0.1068(3) 0.5103(3) 0.7038(2) 0.0462(10) Uani 1 1 d . . .
H57A H 0.1070 0.4392 0.6952 0.055 Uiso 1 1 calc R . .
C58 C 0.1409(3) 0.5217(3) 0.76841(19) 0.0414(9) Uani 1 1 d . A .
C59 C 0.1605(4) 0.4273(4) 0.8252(2) 0.0557(11) Uani 1 1 d U . .
C60 C 0.089(3) 0.461(2) 0.8897(14) 0.100(8) Uani 0.51(4) 1 d PDU A 1
H60A H 0.0413 0.5413 0.8956 0.120 Uiso 0.51(4) 1 calc PR A 1
C61 C 0.086(3) 0.381(2) 0.9445(14) 0.100(8) Uani 0.51(4) 1 d PDU A 1
H61A H 0.0283 0.4042 0.9835 0.120 Uiso 0.51(4) 1 calc PR A 1
C62 C 0.173(3) 0.262(2) 0.9384(14) 0.078(6) Uani 0.51(4) 1 d PDU A 1
H62A H 0.1862 0.2086 0.9776 0.094 Uiso 0.51(4) 1 calc PR A 1
C63 C 0.240(2) 0.2232(14) 0.8769(10) 0.065(5) Uani 0.51(4) 1 d PDU A 1
H63A H 0.2871 0.1429 0.8727 0.078 Uiso 0.51(4) 1 calc PR A 1
C64 C 0.237(2) 0.3076(14) 0.8169(10) 0.049(4) Uani 0.51(4) 1 d PRDU A 1
H64A H 0.2870 0.2814 0.7742 0.059 Uiso 0.51(4) 1 d PR A 1
C60' C 0.108(2) 0.4406(18) 0.8916(11) 0.066(6) Uani 0.49(4) 1 d PD A 2
H60B H 0.0529 0.5155 0.9050 0.079 Uiso 0.49(4) 1 calc PR A 2
C61' C 0.135(3) 0.343(3) 0.9402(11) 0.082(8) Uani 0.49(4) 1 d PD A 2
H61B H 0.1028 0.3533 0.9864 0.098 Uiso 0.49(4) 1 calc PR A 2
C62' C 0.213(4) 0.230(2) 0.9183(14) 0.093(10) Uani 0.49(4) 1 d PD A 2
H62B H 0.2254 0.1641 0.9484 0.111 Uiso 0.49(4) 1 calc PR A 2
C63' C 0.271(3) 0.219(2) 0.8521(16) 0.081(6) Uani 0.49(4) 1 d PD A 2
H63B H 0.3280 0.1447 0.8381 0.098 Uiso 0.49(4) 1 calc PR A 2
C64' C 0.245(3) 0.319(3) 0.8054(13) 0.105(10) Uani 0.49(4) 1 d PD A 2
H64B H 0.2855 0.3113 0.7608 0.127 Uiso 0.49(4) 1 calc PR A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C11 1.373(5) . ?
F2 C12 1.359(5) . ?
F3 C27 1.365(4) . ?
F4 C28 1.362(4) . ?
F5 C37 1.359(4) . ?
F6 C38 1.349(4) . ?
F7 C53 1.362(4) . ?
F8 C54 1.367(4) . ?
C1 C2 1.386(6) . ?
C1 C6 1.390(5) . ?
C2 C3 1.387(7) . ?
C3 C4 1.361(7) . ?
C4 C5 1.385(6) . ?
C5 C6 1.388(5) . ?
C6 C7 1.479(5) . ?
C7 C8 1.375(5) . ?
C7 C16 1.427(5) . ?
C8 C9 1.405(5) . ?
C9 C10 1.413(5) . ?
C9 C14 1.417(5) . ?
C10 C11 1.329(6) . ?
C11 C12 1.387(6) . ?
C12 C13 1.341(6) . ?
C13 C14 1.415(5) . ?
C14 C15 1.407(5) . ?
C15 C16 1.376(5) . ?
C16 C17 1.495(5) . ?
C17 C18 1.389(5) . ?
C17 C22 1.412(5) . ?
C18 C19 1.374(5) . ?
C19 C20 1.380(6) . ?
C20 C21 1.379(5) . ?
C21 C22 1.407(5) . ?
C22 C23 1.490(5) . ?
C23 C24 1.377(4) . ?
C23 C32 1.438(5) . ?
C24 C25 1.406(5) . ?
C25 C26 1.427(5) . ?
C25 C30 1.429(5) . ?
C26 C27 1.358(5) . ?
C27 C28 1.376(6) . ?
C28 C29 1.344(5) . ?
C29 C30 1.416(5) . ?
C30 C31 1.398(5) . ?
C31 C32 1.376(4) . ?
C32 C33 1.501(4) . ?
C33 C34 1.372(5) . ?
C33 C42 1.437(4) . ?
C34 C35 1.398(5) . ?
C35 C40 1.409(5) . ?
C35 C36 1.418(5) . ?
C36 C37 1.336(5) . ?
C37 C38 1.400(6) . ?
C38 C39 1.347(5) . ?
C39 C40 1.423(5) . ?
C40 C41 1.401(5) . ?
C41 C42 1.370(5) . ?
C42 C43 1.503(5) . ?
C43 C44 1.397(5) . ?
C43 C48 1.400(5) . ?
C44 C45 1.380(5) . ?
C45 C46 1.373(5) . ?
C46 C47 1.367(5) . ?
C47 C48 1.395(5) . ?
C48 C49 1.487(5) . ?
C49 C50 1.376(4) . ?
C49 C58 1.428(5) . ?
C50 C51 1.409(5) . ?
C51 C52 1.414(5) . ?
C51 C56 1.415(5) . ?
C52 C53 1.329(5) . ?
C53 C54 1.400(6) . ?
C54 C55 1.349(5) . ?
C55 C56 1.416(5) . ?
C56 C57 1.414(5) . ?
C57 C58 1.359(5) . ?
C58 C59 1.480(5) . ?
C59 C60' 1.35(2) . ?
C59 C64 1.400(17) . ?
C59 C64' 1.36(3) . ?
C59 C60 1.42(3) . ?
C60 C61 1.393(15) . ?
C61 C62 1.405(15) . ?
C62 C63 1.361(15) . ?
C63 C64 1.4751 . ?
C60' C61' 1.395(13) . ?
C61' C62' 1.405(14) . ?
C62' C63' 1.371(13) . ?
C63' C64' 1.402(13) . ?

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
C2 C1 C6 120.4(5) . . ?
C1 C2 C3 120.3(5) . . ?
C4 C3 C2 119.4(5) . . ?
C3 C4 C5 121.0(5) . . ?
C4 C5 C6 120.4(5) . . ?
C5 C6 C1 118.5(4) . . ?
C5 C6 C7 120.2(4) . . ?
C1 C6 C7 121.1(4) . . ?
C8 C7 C16 118.4(3) . . ?
C8 C7 C6 118.1(3) . . ?
C16 C7 C6 123.3(3) . . ?
C7 C8 C9 123.3(3) . . ?
C8 C9 C10 123.2(4) . . ?
C8 C9 C14 117.8(3) . . ?
C10 C9 C14 119.1(4) . . ?
C11 C10 C9 119.7(4) . . ?
C10 C11 F1 120.7(4) . . ?
C10 C11 C12 121.8(4) . . ?
F1 C11 C12 117.5(4) . . ?
C13 C12 F2 120.8(4) . . ?
C13 C12 C11 121.1(4) . . ?
F2 C12 C11 118.0(4) . . ?
C12 C13 C14 119.8(4) . . ?
C15 C14 C13 122.7(4) . . ?
C15 C14 C9 118.7(3) . . ?
C13 C14 C9 118.6(4) . . ?
C16 C15 C14 122.5(3) . . ?
C15 C16 C7 118.9(3) . . ?
C15 C16 C17 117.7(3) . . ?
C7 C16 C17 123.4(3) . . ?
C18 C17 C22 118.5(3) . . ?
C18 C17 C16 117.9(3) . . ?
C22 C17 C16 123.6(3) . . ?
C19 C18 C17 123.0(4) . . ?
C18 C19 C20 119.0(4) . . ?
C21 C20 C19 119.7(4) . . ?
C20 C21 C22 122.2(4) . . ?
C21 C22 C17 117.7(3) . . ?
C21 C22 C23 117.7(3) . . ?
C17 C22 C23 124.4(3) . . ?
C24 C23 C32 118.5(3) . . ?
C24 C23 C22 116.5(3) . . ?
C32 C23 C22 124.9(3) . . ?
C23 C24 C25 122.8(3) . . ?
C24 C25 C26 122.7(3) . . ?
C24 C25 C30 118.5(3) . . ?
C26 C25 C30 118.8(3) . . ?
C27 C26 C25 118.6(4) . . ?
C26 C27 F3 119.8(4) . . ?
C26 C27 C28 122.2(4) . . ?
F3 C27 C28 118.1(4) . . ?
C29 C28 F4 120.3(4) . . ?
C29 C28 C27 121.8(4) . . ?
F4 C28 C27 117.9(3) . . ?
C28 C29 C30 119.4(4) . . ?
C31 C30 C29 122.9(3) . . ?
C31 C30 C25 117.9(3) . . ?
C29 C30 C25 119.3(3) . . ?
C32 C31 C30 123.5(3) . . ?
C31 C32 C23 118.5(3) . . ?
C31 C32 C33 116.4(3) . . ?
C23 C32 C33 125.1(3) . . ?
C34 C33 C42 118.4(3) . . ?
C34 C33 C32 116.7(3) . . ?
C42 C33 C32 124.9(3) . . ?
C33 C34 C35 123.7(3) . . ?
C34 C35 C40 117.9(3) . . ?
C34 C35 C36 122.1(3) . . ?
C40 C35 C36 119.9(3) . . ?
C37 C36 C35 119.3(4) . . ?
C36 C37 F5 121.1(4) . . ?
C36 C37 C38 121.6(4) . . ?
F5 C37 C38 117.3(4) . . ?
C39 C38 F6 121.0(4) . . ?
C39 C38 C37 121.0(4) . . ?
F6 C38 C37 118.0(4) . . ?
C38 C39 C40 119.8(4) . . ?
C41 C40 C35 118.3(3) . . ?
C41 C40 C39 123.3(3) . . ?
C35 C40 C39 118.4(3) . . ?
C42 C41 C40 123.8(3) . . ?
C41 C42 C33 117.8(3) . . ?
C41 C42 C43 117.1(3) . . ?
C33 C42 C43 125.1(3) . . ?
C44 C43 C48 118.3(3) . . ?
C44 C43 C42 116.1(3) . . ?
C48 C43 C42 125.5(3) . . ?
C45 C44 C43 122.0(4) . . ?
C46 C45 C44 119.5(4) . . ?
C47 C46 C45 119.2(4) . . ?
C46 C47 C48 122.8(4) . . ?
C47 C48 C43 118.2(3) . . ?
C47 C48 C49 118.0(3) . . ?
C43 C48 C49 123.8(3) . . ?
C50 C49 C58 118.8(3) . . ?
C50 C49 C48 118.0(3) . . ?
C58 C49 C48 123.2(3) . . ?
C49 C50 C51 123.1(3) . . ?
C50 C51 C52 122.5(4) . . ?
C50 C51 C56 117.6(3) . . ?
C52 C51 C56 119.9(3) . . ?
C53 C52 C51 119.1(4) . . ?
C52 C53 F7 122.0(4) . . ?
C52 C53 C54 121.6(4) . . ?
F7 C53 C54 116.4(4) . . ?
C55 C54 F8 120.5(4) . . ?
C55 C54 C53 121.6(4) . . ?
F8 C54 C53 117.9(4) . . ?
C54 C55 C56 118.9(4) . . ?
C57 C56 C51 118.6(3) . . ?
C57 C56 C55 122.6(4) . . ?
C51 C56 C55 118.8(3) . . ?
C58 C57 C56 123.1(4) . . ?
C57 C58 C49 118.6(3) . . ?
C57 C58 C59 119.3(4) . . ?
C49 C58 C59 122.0(3) . . ?
C60' C59 C64 109.4(10) . . ?
C60' C59 C58 126.8(9) . . ?
C64 C59 C58 123.8(9) . . ?
C60' C59 C64' 120.5(13) . . ?
C64 C59 C64' 11.6(12) . . ?
C58 C59 C64' 112.7(11) . . ?
C60' C59 C60 10.4(18) . . ?
C64 C59 C60 119.1(12) . . ?
C58 C59 C60 116.9(11) . . ?
C64' C59 C60 130.4(13) . . ?
C61 C60 C59 122.9(17) . . ?
C60 C61 C62 117.1(18) . . ?
C63 C62 C61 122.0(15) . . ?
C62 C63 C64 120.4(12) . . ?
C59 C64 C63 117.5(8) . . ?
C59 C60' C61' 120.8(15) . . ?
C60' C61' C62' 119.0(14) . . ?
C63' C62' C61' 119.3(13) . . ?
C62' C63' C64' 119.8(16) . . ?
C63' C64' C59 120.3(18) . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        23.26
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_dl28_a
_database_code_depnum_ccdc_archive 'CCDC 1483966'
_audit_update_record             
;
2016-06-07 deposited with the CCDC.
2016-07-08 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          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H14 Cl2'
_chemical_formula_weight         349.23

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           103
_space_group_name_H-M_alt        'P 4 c c'
_space_group_name_Hall           'P 4 -2c'

_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'
'-y, x, z'
'y, -x, z'
'x, -y, z+1/2'
'-x, y, z+1/2'
'-y, -x, z+1/2'
'y, x, z+1/2'

_cell_length_a                   22.2731(11)
_cell_length_b                   22.2731(11)
_cell_length_c                   7.1270(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3535.6(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4179
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      24.14

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.366
_shelx_estimated_absorpt_T_min   0.898
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6886
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20144
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.045
_diffrn_reflns_theta_max         28.702
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_point_group_measured_fraction_full 0.955
_reflns_number_total             4239
_reflns_number_gt                2902
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_max     0.839
_reflns_Friedel_fraction_full    0.903

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-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)+(0.0680P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 921 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.01(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4239
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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
Cl1 Cl 0.46798(4) 0.64097(6) 0.6852(2) 0.1078(5) Uani 1 1 d . . . . .
Cl2 Cl 0.47222(3) 0.78010(5) 0.58941(19) 0.0967(4) Uani 1 1 d . . . . .
C1 C 0.40324(12) 0.67917(18) 0.6234(5) 0.0699(10) Uani 1 1 d . . . . .
C2 C 0.35025(14) 0.64878(16) 0.6181(5) 0.0636(9) Uani 1 1 d . . . . .
H2 H 0.3495 0.6073 0.6427 0.076 Uiso 1 1 calc R U . . .
C3 C 0.29645(11) 0.67937(14) 0.5757(5) 0.0523(7) Uani 1 1 d . . . . .
C4 C 0.24065(12) 0.65032(13) 0.5790(5) 0.0494(7) Uani 1 1 d . . . . .
H4 H 0.2394 0.6090 0.6054 0.059 Uiso 1 1 calc R U . . .
C5 C 0.18777(11) 0.67989(11) 0.5452(4) 0.0446(7) Uani 1 1 d . . . . .
C6 C 0.18944(11) 0.74179(12) 0.4921(4) 0.0440(6) Uani 1 1 d . . . . .
C7 C 0.24383(12) 0.77087(12) 0.4902(4) 0.0488(7) Uani 1 1 d . . . . .
H7 H 0.2451 0.8118 0.4579 0.059 Uiso 1 1 calc R U . . .
C8 C 0.29783(11) 0.74113(14) 0.5352(4) 0.0527(7) Uani 1 1 d . . . . .
C9 C 0.35382(13) 0.77136(16) 0.5397(5) 0.0606(9) Uani 1 1 d . . . . .
H9 H 0.3557 0.8126 0.5120 0.073 Uiso 1 1 calc R U . . .
C10 C 0.40494(12) 0.74084(18) 0.5840(6) 0.0668(9) Uani 1 1 d . . . . .
C11 C 0.13049(11) 0.64672(11) 0.5813(4) 0.0448(6) Uani 1 1 d . . . . .
C12 C 0.12186(13) 0.58960(12) 0.5091(5) 0.0531(7) Uani 1 1 d . . . . .
H12 H 0.1503 0.5733 0.4259 0.064 Uiso 1 1 calc R U . . .
C13 C 0.07180(13) 0.55640(12) 0.5584(5) 0.0607(9) Uani 1 1 d . . . . .
H13 H 0.0664 0.5176 0.5090 0.073 Uiso 1 1 calc R U . . .
C14 C 0.02971(13) 0.57995(12) 0.6797(6) 0.0613(9) Uani 1 1 d . . . . .
H14 H -0.0041 0.5572 0.7140 0.074 Uiso 1 1 calc R U . . .
C15 C 0.03751(13) 0.63699(12) 0.7502(5) 0.0572(8) Uani 1 1 d . . . . .
H15 H 0.0088 0.6534 0.8321 0.069 Uiso 1 1 calc R U . . .
C16 C 0.08749(11) 0.67010(12) 0.7009(5) 0.0500(7) Uani 1 1 d . . . . .
H16 H 0.0924 0.7091 0.7492 0.060 Uiso 1 1 calc R U . . .
C17 C 0.13472(12) 0.77524(12) 0.4335(4) 0.0449(7) Uani 1 1 d . . . . .
C18 C 0.09410(11) 0.75085(13) 0.3053(5) 0.0504(7) Uani 1 1 d . . . . .
H18 H 0.1000 0.7116 0.2602 0.061 Uiso 1 1 calc R U . . .
C19 C 0.04518(13) 0.78384(13) 0.2438(5) 0.0583(8) Uani 1 1 d . . . . .
H19 H 0.0187 0.7672 0.1552 0.070 Uiso 1 1 calc R U . . .
C20 C 0.03523(13) 0.84063(15) 0.3115(6) 0.0628(9) Uani 1 1 d . . . . .
H20 H 0.0015 0.8625 0.2719 0.075 Uiso 1 1 calc R U . . .
C21 C 0.07519(13) 0.86548(13) 0.4384(5) 0.0592(8) Uani 1 1 d . . . . .
H21 H 0.0687 0.9046 0.4839 0.071 Uiso 1 1 calc R U . . .
C22 C 0.12442(12) 0.83316(13) 0.4983(5) 0.0512(7) Uani 1 1 d . . . . .
H22 H 0.1513 0.8505 0.5841 0.061 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
Cl1 C1 1.731(3) . ?
Cl2 C10 1.735(3) . ?
C1 C2 1.361(5) . ?
C1 C10 1.403(5) . ?
C2 C3 1.411(4) . ?
C2 H2 0.9400 . ?
C3 C4 1.401(4) . ?
C3 C8 1.406(4) . ?
C4 C5 1.371(4) . ?
C4 H4 0.9400 . ?
C5 C6 1.430(4) . ?
C5 C11 1.496(3) . ?
C6 C7 1.374(3) . ?
C6 C17 1.488(4) . ?
C7 C8 1.410(4) . ?
C7 H7 0.9400 . ?
C8 C9 1.418(4) . ?
C9 C10 1.363(4) . ?
C9 H9 0.9400 . ?
C11 C16 1.384(4) . ?
C11 C12 1.386(4) . ?
C12 C13 1.383(4) . ?
C12 H12 0.9400 . ?
C13 C14 1.379(4) . ?
C13 H13 0.9400 . ?
C14 C15 1.377(4) . ?
C14 H14 0.9400 . ?
C15 C16 1.381(4) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C17 C22 1.389(4) . ?
C17 C18 1.396(4) . ?
C18 C19 1.385(4) . ?
C18 H18 0.9400 . ?
C19 C20 1.372(4) . ?
C19 H19 0.9400 . ?
C20 C21 1.384(5) . ?
C20 H20 0.9400 . ?
C21 C22 1.380(4) . ?
C21 H21 0.9400 . ?
C22 H22 0.9400 . ?

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
C2 C1 C10 120.3(3) . . ?
C2 C1 Cl1 119.0(3) . . ?
C10 C1 Cl1 120.6(2) . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C8 118.3(2) . . ?
C4 C3 C2 121.8(3) . . ?
C8 C3 C2 119.8(3) . . ?
C5 C4 C3 122.5(3) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 119.2(2) . . ?
C4 C5 C11 117.7(2) . . ?
C6 C5 C11 122.9(2) . . ?
C7 C6 C5 118.7(2) . . ?
C7 C6 C17 118.9(2) . . ?
C5 C6 C17 122.4(2) . . ?
C6 C7 C8 121.9(3) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C3 C8 C7 119.2(2) . . ?
C3 C8 C9 118.6(3) . . ?
C7 C8 C9 122.2(3) . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C1 120.8(3) . . ?
C9 C10 Cl2 118.4(3) . . ?
C1 C10 Cl2 120.8(2) . . ?
C16 C11 C12 118.6(2) . . ?
C16 C11 C5 120.7(2) . . ?
C12 C11 C5 120.5(2) . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.6(3) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 120.9(3) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C22 C17 C18 118.2(3) . . ?
C22 C17 C6 120.4(3) . . ?
C18 C17 C6 121.3(3) . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 119.7(3) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C22 C21 C20 120.3(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C17 120.9(3) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.034



####################################################################### 
# 
# 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_dl26
_database_code_depnum_ccdc_archive 'CCDC 1483967'
_audit_update_record             
;
2016-06-07 deposited with the CCDC.
2016-07-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38.50 H22.50 Cl5.50'
_chemical_formula_weight         680.04

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   20.7464(8)
_cell_length_b                   13.0281(5)
_cell_length_c                   24.8595(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.709(2)
_cell_angle_gamma                90.00
_cell_volume                     6400.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    9926
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      24.98

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2776
_exptl_absorpt_coefficient_mu    0.523
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8936
_exptl_absorpt_correction_T_max  0.9399
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            55922
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         25.02
_reflns_number_total             11299
_reflns_number_gt                6818
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0793P)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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         11299
_refine_ls_number_parameters     793
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1550
_refine_ls_wR_factor_gt          0.1286
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
Cl1 Cl 0.28103(5) 0.08556(9) 0.27443(5) 0.0771(3) Uani 1 1 d . . .
Cl2 Cl 0.29565(5) -0.10100(7) 0.19721(5) 0.0766(3) Uani 1 1 d . . .
Cl3 Cl 0.59299(6) 0.82721(6) 0.13168(5) 0.0843(4) Uani 1 1 d . . .
Cl4 Cl 0.43461(6) 0.82611(6) 0.07549(4) 0.0687(3) Uani 1 1 d . . .
Cl5 Cl 0.22072(5) 0.05033(8) 0.40874(4) 0.0727(3) Uani 1 1 d . . .
Cl6 Cl 0.20713(5) -0.13199(7) 0.32255(5) 0.0677(3) Uani 1 1 d . . .
Cl7 Cl -0.04576(6) 0.82487(6) 0.11013(5) 0.0695(3) Uani 1 1 d . . .
Cl8 Cl 0.10689(6) 0.81029(6) 0.11472(4) 0.0677(3) Uani 1 1 d . . .
C1 C 0.56298(17) 0.4394(2) 0.22722(14) 0.0466(8) Uani 1 1 d . . .
H1A H 0.5161 0.4510 0.2167 0.056 Uiso 1 1 calc R . .
C2 C 0.6072(2) 0.5214(3) 0.24312(15) 0.0564(10) Uani 1 1 d . . .
H2A H 0.5901 0.5883 0.2430 0.068 Uiso 1 1 calc R . .
C3 C 0.6754(2) 0.5056(3) 0.25901(16) 0.0631(10) Uani 1 1 d . . .
H3A H 0.7051 0.5617 0.2699 0.076 Uiso 1 1 calc R . .
C4 C 0.70125(18) 0.4072(3) 0.25921(16) 0.0597(10) Uani 1 1 d . . .
H4A H 0.7483 0.3965 0.2705 0.072 Uiso 1 1 calc R . .
C5 C 0.65728(17) 0.3243(3) 0.24258(14) 0.0488(8) Uani 1 1 d . . .
H5A H 0.6747 0.2578 0.2421 0.059 Uiso 1 1 calc R . .
C6 C 0.58737(15) 0.3396(2) 0.22664(13) 0.0383(7) Uani 1 1 d . . .
C7 C 0.53897(15) 0.2526(2) 0.21165(13) 0.0367(7) Uani 1 1 d . . .
C8 C 0.48859(16) 0.2483(2) 0.23656(13) 0.0418(8) Uani 1 1 d . . .
H8A H 0.4847 0.3024 0.2604 0.050 Uiso 1 1 calc R . .
C9 C 0.44231(15) 0.1663(2) 0.22797(13) 0.0391(7) Uani 1 1 d . . .
C10 C 0.39013(16) 0.1637(2) 0.25305(14) 0.0480(8) Uani 1 1 d . . .
H10A H 0.3858 0.2181 0.2766 0.058 Uiso 1 1 calc R . .
C11 C 0.34550(16) 0.0834(3) 0.24387(15) 0.0512(9) Uani 1 1 d . . .
C12 C 0.35200(16) 0.0016(2) 0.20898(15) 0.0494(9) Uani 1 1 d . . .
C13 C 0.40173(16) 0.0020(2) 0.18346(14) 0.0462(8) Uani 1 1 d . . .
H13A H 0.4050 -0.0528 0.1599 0.055 Uiso 1 1 calc R . .
C14 C 0.44847(15) 0.0844(2) 0.19224(13) 0.0399(8) Uani 1 1 d . . .
C15 C 0.49970(15) 0.0897(2) 0.16628(13) 0.0372(7) Uani 1 1 d . . .
H15A H 0.5042 0.0354 0.1428 0.045 Uiso 1 1 calc R . .
C16 C 0.54359(14) 0.1715(2) 0.17394(13) 0.0336(7) Uani 1 1 d . . .
C17 C 0.59397(14) 0.1707(2) 0.14211(12) 0.0341(7) Uani 1 1 d . . .
C18 C 0.63768(15) 0.0861(2) 0.14898(14) 0.0415(8) Uani 1 1 d . . .
H18A H 0.6350 0.0336 0.1741 0.050 Uiso 1 1 calc R . .
C19 C 0.68432(17) 0.0779(2) 0.12002(15) 0.0498(9) Uani 1 1 d . . .
H19A H 0.7125 0.0199 0.1251 0.060 Uiso 1 1 calc R . .
C20 C 0.68974(16) 0.1543(3) 0.08367(15) 0.0501(9) Uani 1 1 d . . .
H20A H 0.7220 0.1495 0.0642 0.060 Uiso 1 1 calc R . .
C21 C 0.64725(15) 0.2385(2) 0.07586(14) 0.0441(8) Uani 1 1 d . . .
H21A H 0.6515 0.2911 0.0512 0.053 Uiso 1 1 calc R . .
C22 C 0.59834(15) 0.2475(2) 0.10359(13) 0.0357(7) Uani 1 1 d . . .
C23 C 0.55534(15) 0.3421(2) 0.09200(13) 0.0352(7) Uani 1 1 d . . .
C24 C 0.58843(16) 0.4348(2) 0.10315(14) 0.0420(8) Uani 1 1 d . . .
H24A H 0.6360 0.4352 0.1164 0.050 Uiso 1 1 calc R . .
C25 C 0.55343(16) 0.5296(2) 0.09540(14) 0.0432(8) Uani 1 1 d . . .
C26 C 0.58742(19) 0.6244(2) 0.11182(15) 0.0524(9) Uani 1 1 d . . .
H26A H 0.6349 0.6259 0.1258 0.063 Uiso 1 1 calc R . .
C27 C 0.5514(2) 0.7133(2) 0.10744(15) 0.0550(10) Uani 1 1 d . . .
C28 C 0.4804(2) 0.7119(2) 0.08362(15) 0.0535(9) Uani 1 1 d . . .
C29 C 0.44661(18) 0.6225(2) 0.06735(14) 0.0473(8) Uani 1 1 d . . .
H29A H 0.3993 0.6232 0.0516 0.057 Uiso 1 1 calc R . .
C30 C 0.48195(16) 0.5279(2) 0.07386(13) 0.0412(8) Uani 1 1 d . . .
C31 C 0.44846(16) 0.4327(2) 0.06207(13) 0.0414(8) Uani 1 1 d . . .
H31A H 0.4010 0.4317 0.0476 0.050 Uiso 1 1 calc R . .
C32 C 0.48327(15) 0.3410(2) 0.07114(13) 0.0384(7) Uani 1 1 d . . .
C33 C 0.44283(15) 0.2438(2) 0.05736(13) 0.0383(8) Uani 1 1 d . . .
C34 C 0.38683(16) 0.2301(2) 0.07643(14) 0.0453(8) Uani 1 1 d . . .
H34A H 0.3755 0.2814 0.0986 0.054 Uiso 1 1 calc R . .
C35 C 0.34757(17) 0.1424(3) 0.06329(16) 0.0560(10) Uani 1 1 d . . .
H35A H 0.3105 0.1336 0.0771 0.067 Uiso 1 1 calc R . .
C36 C 0.36296(19) 0.0681(3) 0.02995(18) 0.0611(11) Uani 1 1 d . . .
H36A H 0.3358 0.0090 0.0206 0.073 Uiso 1 1 calc R . .
C37 C 0.41766(19) 0.0793(2) 0.01018(16) 0.0567(10) Uani 1 1 d . . .
H37A H 0.4280 0.0283 -0.0127 0.068 Uiso 1 1 calc R . .
C38 C 0.45781(16) 0.1674(2) 0.02437(14) 0.0447(8) Uani 1 1 d . . .
H38A H 0.4956 0.1749 0.0113 0.054 Uiso 1 1 calc R . .
C39 C -0.14035(17) 0.2949(2) 0.17866(15) 0.0490(9) Uani 1 1 d . . .
H39A H -0.1534 0.2263 0.1697 0.059 Uiso 1 1 calc R . .
C40 C -0.18968(18) 0.3693(3) 0.17366(16) 0.0585(10) Uani 1 1 d . . .
H40A H -0.2357 0.3510 0.1615 0.070 Uiso 1 1 calc R . .
C41 C -0.1712(2) 0.4697(3) 0.18646(16) 0.0612(10) Uani 1 1 d . . .
H41A H -0.2045 0.5201 0.1834 0.073 Uiso 1 1 calc R . .
C42 C -0.1040(2) 0.4966(2) 0.20374(15) 0.0548(9) Uani 1 1 d . . .
H42A H -0.0915 0.5655 0.2120 0.066 Uiso 1 1 calc R . .
C43 C -0.05468(18) 0.4226(2) 0.20903(14) 0.0487(9) Uani 1 1 d . . .
H43A H -0.0088 0.4416 0.2211 0.058 Uiso 1 1 calc R . .
C44 C -0.07234(16) 0.3200(2) 0.19668(13) 0.0400(8) Uani 1 1 d . . .
C45 C -0.01892(15) 0.2400(2) 0.20526(13) 0.0388(8) Uani 1 1 d . . .
C46 C 0.02964(16) 0.2346(2) 0.25708(14) 0.0434(8) Uani 1 1 d . . .
H46A H 0.0318 0.2873 0.2834 0.052 Uiso 1 1 calc R . .
C47 C 0.07656(16) 0.1524(2) 0.27227(14) 0.0416(8) Uani 1 1 d . . .
C48 C 0.12441(16) 0.1440(3) 0.32609(15) 0.0483(8) Uani 1 1 d . . .
H48A H 0.1294 0.1984 0.3519 0.058 Uiso 1 1 calc R . .
C49 C 0.16353(16) 0.0590(3) 0.34157(15) 0.0501(9) Uani 1 1 d . . .
C50 C 0.15805(17) -0.0225(2) 0.30231(16) 0.0491(9) Uani 1 1 d . . .
C51 C 0.11517(16) -0.0143(2) 0.24898(15) 0.0447(8) Uani 1 1 d . . .
H51A H 0.1136 -0.0670 0.2228 0.054 Uiso 1 1 calc R . .
C52 C 0.07247(15) 0.0729(2) 0.23220(14) 0.0409(8) Uani 1 1 d . . .
C53 C 0.02516(15) 0.0826(2) 0.17872(14) 0.0384(7) Uani 1 1 d . . .
H53A H 0.0241 0.0318 0.1516 0.046 Uiso 1 1 calc R . .
C54 C -0.01991(15) 0.1627(2) 0.16393(13) 0.0355(7) Uani 1 1 d . . .
C55 C -0.07137(15) 0.1638(2) 0.10696(13) 0.0370(7) Uani 1 1 d . . .
C56 C -0.11530(15) 0.0804(2) 0.09250(14) 0.0427(8) Uani 1 1 d . . .
H56A H -0.1100 0.0254 0.1179 0.051 Uiso 1 1 calc R . .
C57 C -0.16649(16) 0.0767(2) 0.04166(16) 0.0491(9) Uani 1 1 d . . .
H57A H -0.1945 0.0185 0.0321 0.059 Uiso 1 1 calc R . .
C58 C -0.17625(16) 0.1582(3) 0.00517(15) 0.0498(9) Uani 1 1 d . . .
H58A H -0.2123 0.1575 -0.0287 0.060 Uiso 1 1 calc R . .
C59 C -0.13276(16) 0.2419(2) 0.01832(14) 0.0455(8) Uani 1 1 d . . .
H59A H -0.1395 0.2973 -0.0070 0.055 Uiso 1 1 calc R . .
C60 C -0.07937(15) 0.2452(2) 0.06839(14) 0.0376(7) Uani 1 1 d . . .
C61 C -0.03336(15) 0.3372(2) 0.07788(13) 0.0375(7) Uani 1 1 d . . .
C62 C -0.06171(16) 0.4324(2) 0.07924(14) 0.0447(8) Uani 1 1 d . . .
H62A H -0.1082 0.4368 0.0749 0.054 Uiso 1 1 calc R . .
C63 C -0.02294(16) 0.5240(2) 0.08698(14) 0.0421(8) Uani 1 1 d . . .
C64 C -0.05039(18) 0.6214(2) 0.09285(15) 0.0511(9) Uani 1 1 d . . .
H64A H -0.0962 0.6268 0.0908 0.061 Uiso 1 1 calc R . .
C65 C -0.01132(19) 0.7070(2) 0.10133(14) 0.0499(9) Uani 1 1 d . . .
C66 C 0.05725(19) 0.7006(2) 0.10336(14) 0.0490(9) Uani 1 1 d . . .
C67 C 0.08532(18) 0.6083(2) 0.09860(14) 0.0500(9) Uani 1 1 d . . .
H67A H 0.1311 0.6048 0.1002 0.060 Uiso 1 1 calc R . .
C68 C 0.04631(17) 0.5167(2) 0.09124(14) 0.0437(8) Uani 1 1 d . . .
C69 C 0.07462(17) 0.4192(2) 0.08958(14) 0.0450(8) Uani 1 1 d . . .
H69A H 0.1207 0.4143 0.0923 0.054 Uiso 1 1 calc R . .
C70 C 0.03689(16) 0.3301(2) 0.08401(14) 0.0410(8) Uani 1 1 d . . .
C71 C 0.07294(15) 0.2318(2) 0.08348(14) 0.0386(7) Uani 1 1 d . . .
C72 C 0.13435(16) 0.2136(2) 0.12510(15) 0.0477(8) Uani 1 1 d . . .
H72A H 0.1510 0.2619 0.1541 0.057 Uiso 1 1 calc R . .
C73 C 0.17097(18) 0.1256(2) 0.12424(16) 0.0538(9) Uani 1 1 d . . .
H73A H 0.2123 0.1145 0.1525 0.065 Uiso 1 1 calc R . .
C74 C 0.14739(18) 0.0541(2) 0.08226(17) 0.0550(10) Uani 1 1 d . . .
H74A H 0.1727 -0.0055 0.0817 0.066 Uiso 1 1 calc R . .
C75 C 0.08649(18) 0.0699(2) 0.04080(16) 0.0520(9) Uani 1 1 d . . .
H75A H 0.0702 0.0207 0.0122 0.062 Uiso 1 1 calc R . .
C76 C 0.04934(16) 0.1583(2) 0.04143(14) 0.0447(8) Uani 1 1 d . . .
H76A H 0.0079 0.1686 0.0132 0.054 Uiso 1 1 calc R . .
C77 C 0.7435(2) 0.6999(4) 0.0424(2) 0.0990(16) Uani 1 1 d . . .
H77A H 0.6979 0.7278 0.0234 0.119 Uiso 1 1 calc R . .
Cl9 Cl 0.73699(8) 0.56533(11) 0.04969(6) 0.1140(5) Uani 1 1 d . . .
Cl10 Cl 0.77404(8) 0.75528(11) 0.10899(7) 0.1169(5) Uani 1 1 d . . .
Cl11 Cl 0.79585(7) 0.72506(13) 0.00020(6) 0.1238(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.728(3) . ?
Cl2 C12 1.741(3) . ?
Cl3 C27 1.730(3) . ?
Cl4 C28 1.744(3) . ?
Cl5 C49 1.733(4) . ?
Cl6 C50 1.736(3) . ?
Cl7 C65 1.735(3) . ?
Cl8 C66 1.734(3) . ?
C1 C2 1.386(4) . ?
C1 C6 1.397(4) . ?
C2 C3 1.364(5) . ?
C3 C4 1.390(5) . ?
C4 C5 1.392(5) . ?
C5 C6 1.397(4) . ?
C6 C7 1.485(4) . ?
C7 C8 1.368(4) . ?
C7 C16 1.435(4) . ?
C8 C9 1.408(4) . ?
C9 C10 1.404(4) . ?
C9 C14 1.419(4) . ?
C10 C11 1.370(4) . ?
C11 C12 1.406(5) . ?
C12 C13 1.366(5) . ?
C13 C14 1.419(4) . ?
C14 C15 1.403(4) . ?
C15 C16 1.376(4) . ?
C16 C17 1.490(4) . ?
C17 C18 1.404(4) . ?
C17 C22 1.407(4) . ?
C18 C19 1.375(4) . ?
C19 C20 1.372(5) . ?
C20 C21 1.384(4) . ?
C21 C22 1.394(4) . ?
C22 C23 1.497(4) . ?
C23 C24 1.375(4) . ?
C23 C32 1.426(4) . ?
C24 C25 1.416(4) . ?
C25 C30 1.415(4) . ?
C25 C26 1.419(4) . ?
C26 C27 1.365(4) . ?
C27 C28 1.410(5) . ?
C28 C29 1.357(4) . ?
C29 C30 1.417(4) . ?
C30 C31 1.408(4) . ?
C31 C32 1.379(4) . ?
C32 C33 1.500(4) . ?
C33 C38 1.383(4) . ?
C33 C34 1.393(4) . ?
C34 C35 1.384(4) . ?
C35 C36 1.374(5) . ?
C36 C37 1.375(5) . ?
C37 C38 1.399(4) . ?
C39 C44 1.383(4) . ?
C39 C40 1.387(4) . ?
C40 C41 1.374(5) . ?
C41 C42 1.373(5) . ?
C42 C43 1.383(4) . ?
C43 C44 1.395(4) . ?
C44 C45 1.488(4) . ?
C45 C46 1.375(4) . ?
C45 C54 1.435(4) . ?
C46 C47 1.419(4) . ?
C47 C48 1.407(4) . ?
C47 C52 1.421(4) . ?
C48 C49 1.358(4) . ?
C49 C50 1.423(5) . ?
C50 C51 1.358(5) . ?
C51 C52 1.424(4) . ?
C52 C53 1.397(4) . ?
C53 C54 1.375(4) . ?
C54 C55 1.492(4) . ?
C55 C56 1.393(4) . ?
C55 C60 1.405(4) . ?
C56 C57 1.383(5) . ?
C57 C58 1.372(5) . ?
C58 C59 1.389(4) . ?
C59 C60 1.393(4) . ?
C60 C61 1.505(4) . ?
C61 C62 1.378(4) . ?
C61 C70 1.422(4) . ?
C62 C63 1.419(4) . ?
C63 C68 1.411(4) . ?
C63 C64 1.417(4) . ?
C64 C65 1.357(4) . ?
C65 C66 1.410(5) . ?
C66 C67 1.357(4) . ?
C67 C68 1.422(4) . ?
C68 C69 1.406(4) . ?
C69 C70 1.382(4) . ?
C70 C71 1.486(4) . ?
C71 C76 1.392(4) . ?
C71 C72 1.396(4) . ?
C72 C73 1.379(4) . ?
C73 C74 1.373(5) . ?
C74 C75 1.381(5) . ?
C75 C76 1.389(4) . ?
C77 Cl10 1.739(5) . ?
C77 Cl11 1.755(5) . ?
C77 Cl9 1.772(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
C2 C1 C6 120.7(3) . . ?
C3 C2 C1 120.3(3) . . ?
C2 C3 C4 120.3(3) . . ?
C3 C4 C5 119.8(3) . . ?
C4 C5 C6 120.3(3) . . ?
C1 C6 C5 118.5(3) . . ?
C1 C6 C7 119.6(3) . . ?
C5 C6 C7 121.8(3) . . ?
C8 C7 C16 118.5(3) . . ?
C8 C7 C6 118.0(3) . . ?
C16 C7 C6 123.5(3) . . ?
C7 C8 C9 122.8(3) . . ?
C10 C9 C8 122.2(3) . . ?
C10 C9 C14 119.2(3) . . ?
C8 C9 C14 118.6(3) . . ?
C11 C10 C9 121.2(3) . . ?
C10 C11 C12 119.7(3) . . ?
C10 C11 Cl1 119.3(3) . . ?
C12 C11 Cl1 121.1(3) . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 Cl2 119.2(3) . . ?
C11 C12 Cl2 120.0(3) . . ?
C12 C13 C14 120.6(3) . . ?
C15 C14 C13 123.0(3) . . ?
C15 C14 C9 118.4(3) . . ?
C13 C14 C9 118.6(3) . . ?
C16 C15 C14 122.4(3) . . ?
C15 C16 C7 119.2(3) . . ?
C15 C16 C17 117.5(3) . . ?
C7 C16 C17 123.3(2) . . ?
C18 C17 C22 117.9(3) . . ?
C18 C17 C16 118.2(3) . . ?
C22 C17 C16 123.8(2) . . ?
C19 C18 C17 121.9(3) . . ?
C20 C19 C18 120.0(3) . . ?
C19 C20 C21 119.4(3) . . ?
C20 C21 C22 121.7(3) . . ?
C21 C22 C17 118.9(3) . . ?
C21 C22 C23 117.0(3) . . ?
C17 C22 C23 124.0(3) . . ?
C24 C23 C32 119.1(3) . . ?
C24 C23 C22 116.9(3) . . ?
C32 C23 C22 124.0(2) . . ?
C23 C24 C25 122.3(3) . . ?
C30 C25 C24 118.3(3) . . ?
C30 C25 C26 119.6(3) . . ?
C24 C25 C26 122.1(3) . . ?
C27 C26 C25 120.3(3) . . ?
C26 C27 C28 119.9(3) . . ?
C26 C27 Cl3 119.8(3) . . ?
C28 C27 Cl3 120.3(3) . . ?
C29 C28 C27 121.1(3) . . ?
C29 C28 Cl4 118.9(3) . . ?
C27 C28 Cl4 120.0(3) . . ?
C28 C29 C30 120.6(3) . . ?
C31 C30 C25 119.1(3) . . ?
C31 C30 C29 122.4(3) . . ?
C25 C30 C29 118.5(3) . . ?
C32 C31 C30 121.9(3) . . ?
C31 C32 C23 119.3(3) . . ?
C31 C32 C33 117.7(3) . . ?
C23 C32 C33 122.9(2) . . ?
C38 C33 C34 118.1(3) . . ?
C38 C33 C32 122.1(3) . . ?
C34 C33 C32 119.8(3) . . ?
C35 C34 C33 121.1(3) . . ?
C36 C35 C34 119.8(3) . . ?
C35 C36 C37 120.6(3) . . ?
C36 C37 C38 119.3(3) . . ?
C33 C38 C37 121.0(3) . . ?
C44 C39 C40 121.1(3) . . ?
C41 C40 C39 119.9(3) . . ?
C42 C41 C40 120.1(3) . . ?
C41 C42 C43 120.2(3) . . ?
C42 C43 C44 120.7(3) . . ?
C39 C44 C43 118.1(3) . . ?
C39 C44 C45 121.5(3) . . ?
C43 C44 C45 120.3(3) . . ?
C46 C45 C54 118.8(3) . . ?
C46 C45 C44 118.2(3) . . ?
C54 C45 C44 122.8(3) . . ?
C45 C46 C47 122.4(3) . . ?
C48 C47 C46 122.7(3) . . ?
C48 C47 C52 119.0(3) . . ?
C46 C47 C52 118.3(3) . . ?
C49 C48 C47 121.4(3) . . ?
C48 C49 C50 119.9(3) . . ?
C48 C49 Cl5 120.1(3) . . ?
C50 C49 Cl5 120.1(3) . . ?
C51 C50 C49 120.2(3) . . ?
C51 C50 Cl6 120.0(3) . . ?
C49 C50 Cl6 119.8(3) . . ?
C50 C51 C52 120.9(3) . . ?
C53 C52 C47 118.5(3) . . ?
C53 C52 C51 123.0(3) . . ?
C47 C52 C51 118.5(3) . . ?
C54 C53 C52 123.1(3) . . ?
C53 C54 C45 118.8(3) . . ?
C53 C54 C55 119.6(3) . . ?
C45 C54 C55 121.5(3) . . ?
C56 C55 C60 118.7(3) . . ?
C56 C55 C54 117.4(3) . . ?
C60 C55 C54 123.9(3) . . ?
C57 C56 C55 121.6(3) . . ?
C58 C57 C56 119.7(3) . . ?
C57 C58 C59 119.8(3) . . ?
C58 C59 C60 121.2(3) . . ?
C59 C60 C55 118.9(3) . . ?
C59 C60 C61 117.3(3) . . ?
C55 C60 C61 123.8(3) . . ?
C62 C61 C70 119.1(3) . . ?
C62 C61 C60 117.8(3) . . ?
C70 C61 C60 123.1(2) . . ?
C61 C62 C63 122.1(3) . . ?
C68 C63 C64 119.0(3) . . ?
C68 C63 C62 118.4(3) . . ?
C64 C63 C62 122.6(3) . . ?
C65 C64 C63 120.8(3) . . ?
C64 C65 C66 120.3(3) . . ?
C64 C65 Cl7 119.8(3) . . ?
C66 C65 Cl7 119.9(2) . . ?
C67 C66 C65 120.3(3) . . ?
C67 C66 Cl8 119.7(3) . . ?
C65 C66 Cl8 120.0(2) . . ?
C66 C67 C68 120.8(3) . . ?
C69 C68 C63 118.9(3) . . ?
C69 C68 C67 122.4(3) . . ?
C63 C68 C67 118.7(3) . . ?
C70 C69 C68 122.2(3) . . ?
C69 C70 C61 119.2(3) . . ?
C69 C70 C71 117.0(3) . . ?
C61 C70 C71 123.8(3) . . ?
C76 C71 C72 118.3(3) . . ?
C76 C71 C70 122.5(3) . . ?
C72 C71 C70 119.2(3) . . ?
C73 C72 C71 120.8(3) . . ?
C74 C73 C72 120.3(3) . . ?
C73 C74 C75 120.0(3) . . ?
C74 C75 C76 120.0(3) . . ?
C75 C76 C71 120.6(3) . . ?
Cl10 C77 Cl11 112.3(3) . . ?
Cl10 C77 Cl9 109.3(2) . . ?
Cl11 C77 Cl9 109.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.057
