# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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_pfn
_database_code_depnum_ccdc_archive 'CCDC 1436913'
_audit_update_record             
;
2015-11-13 deposited with the CCDC.
2016-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 Octafluoronaphthalene 
;
_chemical_name_common            Perfluoronaphthalene
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 F8'
_chemical_formula_sum            'C10 F8'
_chemical_formula_weight         272.10

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'
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   P21/c

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

_cell_length_a                   13.3203(9)
_cell_length_b                   4.8791(3)
_cell_length_c                   19.8516(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.245(6)
_cell_angle_gamma                90.00
_cell_volume                     1269.61(15)
_cell_formula_units_Z            6
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Grey
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.135
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_type   None
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9920
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2470
_reflns_number_gt                1833
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0443P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    .
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0021(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2470
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0663
_refine_ls_wR_factor_gt          0.0637
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_restrained_S_all      0.934
_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 0.30285(6) 0.05566(16) 0.43418(4) 0.0239(2) Uani 1 1 d . . .
F2 F 0.11597(6) 0.03692(17) 0.35785(4) 0.0264(2) Uani 1 1 d . . .
F3 F 0.06103(6) 0.38428(18) 0.25274(4) 0.0283(2) Uani 1 1 d . . .
F4 F 0.19024(6) 0.76512(16) 0.22237(4) 0.0269(2) Uani 1 1 d . . .
F5 F 0.36984(6) 0.98195(16) 0.24637(4) 0.0239(2) Uani 1 1 d . . .
F6 F 0.55706(6) 0.99722(16) 0.32107(4) 0.0257(2) Uani 1 1 d . . .
F7 F 0.61363(6) 0.64463(17) 0.42523(4) 0.0263(2) Uani 1 1 d . . .
F8 F 0.48480(6) 0.26068(16) 0.45541(4) 0.0237(2) Uani 1 1 d . . .
C1 C 0.27876(11) 0.2326(3) 0.38225(7) 0.0181(3) Uani 1 1 d . . .
C2 C 0.18355(11) 0.2222(3) 0.34416(7) 0.0197(3) Uani 1 1 d . . .
C3 C 0.15433(11) 0.4027(3) 0.28962(7) 0.0210(3) Uani 1 1 d . . .
C4 C 0.22170(11) 0.5928(3) 0.27483(7) 0.0194(3) Uani 1 1 d . . .
C10 C 0.32129(11) 0.6110(3) 0.31231(7) 0.0177(3) Uani 1 1 d . . .
C9 C 0.35166(11) 0.4248(3) 0.36796(7) 0.0173(3) Uani 1 1 d . . .
C5 C 0.39423(11) 0.8039(3) 0.29808(7) 0.0183(3) Uani 1 1 d . . .
C6 C 0.48952(11) 0.8129(3) 0.33542(7) 0.0192(3) Uani 1 1 d . . .
C7 C 0.51947(11) 0.6304(3) 0.38967(7) 0.0189(3) Uani 1 1 d . . .
C8 C 0.45207(11) 0.4401(3) 0.40475(7) 0.0183(3) Uani 1 1 d . . .
C11 C 0.87993(11) 0.3032(3) 0.99592(7) 0.0193(3) Uani 1 1 d . . .
C12 C 0.81851(11) 0.4200(3) 0.94168(8) 0.0211(3) Uani 1 1 d . . .
C13 C 0.85593(11) 0.6356(3) 0.90625(7) 0.0211(3) Uani 1 1 d . . .
C14 C 0.98082(11) 0.3905(3) 1.01813(7) 0.0175(3) Uani 1 1 d . . .
C15 C 1.04721(11) 0.2749(3) 1.07460(7) 0.0189(3) Uani 1 1 d . . .
F9 F 0.84097(6) 0.09704(17) 1.02861(4) 0.0253(2) Uani 1 1 d . . .
F10 F 0.72373(6) 0.33341(18) 0.92120(4) 0.0292(2) Uani 1 1 d . . .
F11 F 0.79374(6) 0.74916(17) 0.85354(4) 0.0275(2) Uani 1 1 d . . .
F12 F 1.01474(6) 0.06855(17) 1.11007(4) 0.0258(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0309(5) 0.0220(4) 0.0193(4) 0.0066(4) 0.0053(4) -0.0026(4)
F2 0.0260(5) 0.0272(5) 0.0277(5) 0.0012(4) 0.0092(4) -0.0064(4)
F3 0.0227(5) 0.0293(5) 0.0309(5) 0.0010(4) -0.0011(4) -0.0008(4)
F4 0.0316(5) 0.0226(5) 0.0240(5) 0.0064(4) -0.0022(4) 0.0018(4)
F5 0.0317(5) 0.0195(4) 0.0210(4) 0.0061(4) 0.0059(4) 0.0001(4)
F6 0.0269(5) 0.0237(5) 0.0283(5) 0.0035(4) 0.0098(4) -0.0055(4)
F7 0.0207(5) 0.0279(5) 0.0299(5) 0.0017(4) 0.0034(4) -0.0009(4)
F8 0.0286(5) 0.0210(4) 0.0208(4) 0.0054(4) 0.0022(4) 0.0020(4)
C1 0.0270(8) 0.0155(7) 0.0135(7) 0.0017(6) 0.0081(6) 0.0022(6)
C2 0.0230(8) 0.0172(7) 0.0216(8) -0.0024(6) 0.0109(7) -0.0027(6)
C3 0.0219(8) 0.0208(8) 0.0203(8) -0.0050(6) 0.0040(7) 0.0019(6)
C4 0.0269(8) 0.0159(7) 0.0155(7) 0.0014(6) 0.0042(6) 0.0039(6)
C10 0.0254(8) 0.0130(7) 0.0162(7) -0.0029(6) 0.0079(6) 0.0024(6)
C9 0.0249(8) 0.0140(7) 0.0143(7) -0.0024(6) 0.0073(6) 0.0023(6)
C5 0.0280(8) 0.0138(7) 0.0146(7) 0.0019(6) 0.0082(6) 0.0037(6)
C6 0.0242(8) 0.0148(7) 0.0214(8) -0.0030(6) 0.0117(6) -0.0025(6)
C7 0.0203(8) 0.0188(7) 0.0178(7) -0.0029(6) 0.0038(6) 0.0035(6)
C8 0.0250(8) 0.0163(7) 0.0141(7) 0.0005(6) 0.0050(6) 0.0050(6)
C11 0.0240(8) 0.0165(7) 0.0195(8) -0.0002(6) 0.0100(7) 0.0003(6)
C12 0.0198(8) 0.0205(7) 0.0235(8) -0.0048(6) 0.0057(6) 0.0001(6)
C13 0.0257(8) 0.0222(8) 0.0154(7) -0.0001(6) 0.0035(6) 0.0074(6)
C14 0.0238(8) 0.0151(7) 0.0156(7) -0.0017(6) 0.0089(6) 0.0020(6)
C15 0.0269(8) 0.0157(7) 0.0166(7) 0.0025(6) 0.0103(6) 0.0023(6)
F9 0.0273(5) 0.0217(4) 0.0289(5) 0.0035(4) 0.0101(4) -0.0042(4)
F10 0.0214(5) 0.0299(5) 0.0348(5) -0.0013(4) 0.0012(4) -0.0023(4)
F11 0.0283(5) 0.0309(5) 0.0219(5) 0.0054(4) 0.0007(4) 0.0072(4)
F12 0.0316(5) 0.0222(4) 0.0252(5) 0.0074(4) 0.0094(4) 0.0015(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.3391(15) . ?
F2 C2 1.3372(15) . ?
F3 C3 1.3285(17) . ?
F4 C4 1.3460(15) . ?
F5 C5 1.3398(15) . ?
F6 C6 1.3383(15) . ?
F7 C7 1.3272(17) . ?
F8 C8 1.3462(15) . ?
C1 C2 1.357(2) . ?
C1 C9 1.4145(19) . ?
C2 C3 1.396(2) . ?
C3 C4 1.359(2) . ?
C4 C10 1.404(2) . ?
C10 C5 1.4167(19) . ?
C10 C9 1.432(2) . ?
C9 C8 1.407(2) . ?
C5 C6 1.352(2) . ?
C6 C7 1.400(2) . ?
C7 C8 1.361(2) . ?
C11 F9 1.3500(15) . ?
C11 C12 1.356(2) . ?
C11 C14 1.404(2) . ?
C12 F10 1.3249(16) . ?
C12 C13 1.405(2) . ?
C13 F11 1.3339(16) . ?
C13 C15 1.351(2) 3_767 ?
C14 C15 1.4155(19) . ?
C14 C14 1.433(3) 3_767 ?
C15 F12 1.3435(15) . ?
C15 C13 1.351(2) 3_767 ?

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
F1 C1 C2 118.49(12) . . ?
F1 C1 C9 120.18(13) . . ?
C2 C1 C9 121.33(13) . . ?
F2 C2 C1 120.54(13) . . ?
F2 C2 C3 118.63(13) . . ?
C1 C2 C3 120.82(13) . . ?
F3 C3 C4 121.08(13) . . ?
F3 C3 C2 119.28(13) . . ?
C4 C3 C2 119.64(14) . . ?
F4 C4 C3 117.84(13) . . ?
F4 C4 C10 120.35(13) . . ?
C3 C4 C10 121.81(13) . . ?
C4 C10 C5 123.61(13) . . ?
C4 C10 C9 118.64(13) . . ?
C5 C10 C9 117.75(13) . . ?
C8 C9 C1 123.66(13) . . ?
C8 C9 C10 118.59(13) . . ?
C1 C9 C10 117.75(13) . . ?
F5 C5 C6 118.38(12) . . ?
F5 C5 C10 120.13(13) . . ?
C6 C5 C10 121.50(13) . . ?
F6 C6 C5 120.41(13) . . ?
F6 C6 C7 118.75(13) . . ?
C5 C6 C7 120.85(13) . . ?
F7 C7 C8 121.10(13) . . ?
F7 C7 C6 119.28(13) . . ?
C8 C7 C6 119.61(14) . . ?
F8 C8 C7 117.99(13) . . ?
F8 C8 C9 120.31(13) . . ?
C7 C8 C9 121.69(13) . . ?
F9 C11 C12 117.74(13) . . ?
F9 C11 C14 120.22(12) . . ?
C12 C11 C14 122.04(13) . . ?
F10 C12 C11 121.14(13) . . ?
F10 C12 C13 119.25(13) . . ?
C11 C12 C13 119.62(13) . . ?
F11 C13 C15 121.02(13) . 3_767 ?
F11 C13 C12 118.52(13) . . ?
C15 C13 C12 120.46(13) 3_767 . ?
C11 C14 C15 123.79(12) . . ?
C11 C14 C14 118.39(16) . 3_767 ?
C15 C14 C14 117.82(16) . 3_767 ?
F12 C15 C13 118.35(12) . 3_767 ?
F12 C15 C14 119.97(12) . . ?
C13 C15 C14 121.67(13) 3_767 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 F2 -0.8(2) . . . . ?
C9 C1 C2 F2 179.17(11) . . . . ?
F1 C1 C2 C3 179.73(11) . . . . ?
C9 C1 C2 C3 -0.3(2) . . . . ?
F2 C2 C3 F3 -0.49(19) . . . . ?
C1 C2 C3 F3 179.02(12) . . . . ?
F2 C2 C3 C4 179.92(12) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
F3 C3 C4 F4 1.2(2) . . . . ?
C2 C3 C4 F4 -179.24(12) . . . . ?
F3 C3 C4 C10 -178.56(12) . . . . ?
C2 C3 C4 C10 1.0(2) . . . . ?
F4 C4 C10 C5 -0.5(2) . . . . ?
C3 C4 C10 C5 179.24(13) . . . . ?
F4 C4 C10 C9 179.70(11) . . . . ?
C3 C4 C10 C9 -0.6(2) . . . . ?
F1 C1 C9 C8 1.5(2) . . . . ?
C2 C1 C9 C8 -178.43(13) . . . . ?
F1 C1 C9 C10 -179.30(11) . . . . ?
C2 C1 C9 C10 0.8(2) . . . . ?
C4 C10 C9 C8 178.92(12) . . . . ?
C5 C10 C9 C8 -0.90(19) . . . . ?
C4 C10 C9 C1 -0.32(19) . . . . ?
C5 C10 C9 C1 179.86(11) . . . . ?
C4 C10 C5 F5 -0.1(2) . . . . ?
C9 C10 C5 F5 179.70(11) . . . . ?
C4 C10 C5 C6 -179.67(13) . . . . ?
C9 C10 C5 C6 0.1(2) . . . . ?
F5 C5 C6 F6 0.5(2) . . . . ?
C10 C5 C6 F6 -179.90(11) . . . . ?
F5 C5 C6 C7 -179.49(11) . . . . ?
C10 C5 C6 C7 0.1(2) . . . . ?
F6 C6 C7 F7 -0.09(19) . . . . ?
C5 C6 C7 F7 179.92(12) . . . . ?
F6 C6 C7 C8 -179.54(12) . . . . ?
C5 C6 C7 C8 0.5(2) . . . . ?
F7 C7 C8 F8 -2.1(2) . . . . ?
C6 C7 C8 F8 177.29(11) . . . . ?
F7 C7 C8 C9 179.28(12) . . . . ?
C6 C7 C8 C9 -1.3(2) . . . . ?
C1 C9 C8 F8 2.1(2) . . . . ?
C10 C9 C8 F8 -177.05(11) . . . . ?
C1 C9 C8 C7 -179.31(13) . . . . ?
C10 C9 C8 C7 1.5(2) . . . . ?
F9 C11 C12 F10 -0.4(2) . . . . ?
C14 C11 C12 F10 179.49(12) . . . . ?
F9 C11 C12 C13 179.90(12) . . . . ?
C14 C11 C12 C13 -0.2(2) . . . . ?
F10 C12 C13 F11 1.1(2) . . . . ?
C11 C12 C13 F11 -179.27(12) . . . . ?
F10 C12 C13 C15 -178.98(12) . . . 3_767 ?
C11 C12 C13 C15 0.7(2) . . . 3_767 ?
F9 C11 C14 C15 -0.3(2) . . . . ?
C12 C11 C14 C15 179.74(13) . . . . ?
F9 C11 C14 C14 179.86(13) . . . 3_767 ?
C12 C11 C14 C14 -0.1(2) . . . 3_767 ?
C11 C14 C15 F12 0.4(2) . . . . ?
C14 C14 C15 F12 -179.83(14) 3_767 . . . ?
C11 C14 C15 C13 179.49(13) . . . 3_767 ?
C14 C14 C15 C13 -0.7(2) 3_767 . . 3_767 ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.042
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_pcln
_database_code_depnum_ccdc_archive 'CCDC 1436914'
_audit_update_record             
;
2015-11-13 deposited with the CCDC.
2016-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 Octachloronaphthalene 
;
_chemical_name_common            Perchloronaphthalene
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 Cl8'
_chemical_formula_sum            'C10 Cl8'
_chemical_formula_weight         403.70

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'
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   P21/n

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

_cell_length_a                   9.7244(12)
_cell_length_b                   7.1739(8)
_cell_length_c                   18.2816(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.317(9)
_cell_angle_gamma                90.00
_cell_volume                     1262.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.125
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    1.756
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_T_max  0.839
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9328
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2235
_reflns_number_gt                1717
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    .
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00330(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2214
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0197
_refine_ls_wR_factor_ref         0.0257
_refine_ls_wR_factor_gt          0.0252
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.14367(5) 0.68422(6) 0.12517(2) 0.02121(13) Uani 1 1 d . . .
Cl7 Cl 0.05114(5) 0.61872(6) 0.42301(3) 0.02388(13) Uani 1 1 d . . .
Cl4 Cl 0.70130(5) 0.50083(7) 0.32391(3) 0.02287(12) Uani 1 1 d . . .
Cl5 Cl 0.59258(5) 0.75575(6) 0.43403(2) 0.02255(12) Uani 1 1 d . . .
Cl8 Cl 0.01356(5) 0.57155(6) 0.25713(3) 0.02094(12) Uani 1 1 d . . .
Cl2 Cl 0.40725(5) 0.62082(7) 0.05883(2) 0.02437(13) Uani 1 1 d . . .
Cl6 Cl 0.33303(5) 0.73611(6) 0.50985(2) 0.02464(13) Uani 1 1 d . . .
Cl3 Cl 0.68023(5) 0.50685(6) 0.15577(3) 0.02400(13) Uani 1 1 d . . .
C1 C 0.29316(18) 0.6319(2) 0.18448(9) 0.0130(4) Uani 1 1 d . . .
C2 C 0.4121(2) 0.6078(2) 0.15324(9) 0.0156(4) Uani 1 1 d . . .
C3 C 0.53927(19) 0.5694(2) 0.19730(10) 0.0154(4) Uani 1 1 d . . .
C4 C 0.54919(18) 0.5769(2) 0.27306(9) 0.0138(4) Uani 1 1 d . . .
C10 C 0.43102(18) 0.6269(2) 0.30730(9) 0.0120(4) Uani 1 1 d . . .
C9 C 0.29738(18) 0.6270(2) 0.26335(9) 0.0121(4) Uani 1 1 d . . .
C5 C 0.43990(19) 0.6763(2) 0.38411(9) 0.0137(4) Uani 1 1 d . . .
C6 C 0.32359(19) 0.6807(2) 0.41800(9) 0.0149(4) Uani 1 1 d . . .
C7 C 0.19260(19) 0.6406(2) 0.37708(10) 0.0152(4) Uani 1 1 d . . .
C8 C 0.17866(18) 0.6213(2) 0.30154(9) 0.0136(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0207(3) 0.0254(3) 0.0157(3) 0.0003(2) -0.0037(2) 0.0031(2)
Cl7 0.0206(3) 0.0283(3) 0.0257(3) -0.0007(2) 0.0135(2) -0.0003(2)
Cl4 0.0131(3) 0.0324(3) 0.0227(3) 0.0015(2) 0.0013(2) 0.0040(2)
Cl5 0.0184(3) 0.0302(3) 0.0177(3) -0.0038(2) -0.0020(2) -0.0049(2)
Cl8 0.0119(3) 0.0256(3) 0.0250(3) -0.0031(2) 0.0016(2) -0.0019(2)
Cl2 0.0330(3) 0.0288(3) 0.0122(3) -0.0003(2) 0.0065(2) 0.0007(3)
Cl6 0.0299(3) 0.0326(3) 0.0119(3) -0.0026(2) 0.0051(2) 0.0021(3)
Cl3 0.0184(3) 0.0312(3) 0.0247(3) -0.0058(2) 0.0109(2) -0.0007(2)
C1 0.0128(11) 0.0098(10) 0.0150(11) -0.0019(8) -0.0030(9) -0.0001(8)
C2 0.0253(12) 0.0108(10) 0.0109(10) -0.0012(8) 0.0034(9) -0.0017(9)
C3 0.0157(11) 0.0115(10) 0.0207(11) -0.0019(8) 0.0082(9) -0.0019(9)
C4 0.0115(11) 0.0107(10) 0.0188(11) 0.0009(8) 0.0007(9) -0.0010(8)
C10 0.0144(11) 0.0083(9) 0.0136(11) 0.0023(8) 0.0030(9) -0.0011(8)
C9 0.0151(11) 0.0055(9) 0.0161(11) -0.0013(8) 0.0037(9) -0.0004(9)
C5 0.0138(11) 0.0108(10) 0.0157(11) 0.0021(8) -0.0008(9) -0.0016(8)
C6 0.0223(12) 0.0109(10) 0.0115(10) 0.0007(8) 0.0025(9) 0.0008(9)
C7 0.0166(11) 0.0101(10) 0.0209(11) 0.0005(8) 0.0092(9) 0.0013(9)
C8 0.0119(11) 0.0097(9) 0.0185(11) -0.0015(8) -0.0004(9) -0.0002(8)

_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 1.7244(17) . ?
Cl7 C7 1.7194(17) . ?
Cl4 C4 1.7183(18) . ?
Cl5 C5 1.7234(18) . ?
Cl8 C8 1.7284(18) . ?
Cl2 C2 1.7223(17) . ?
Cl6 C6 1.7150(17) . ?
Cl3 C3 1.7197(17) . ?
C1 C2 1.373(2) . ?
C1 C9 1.437(2) . ?
C2 C3 1.402(2) . ?
C3 C4 1.375(2) . ?
C4 C10 1.431(2) . ?
C10 C9 1.426(2) . ?
C10 C5 1.439(2) . ?
C9 C8 1.434(2) . ?
C5 C6 1.366(2) . ?
C6 C7 1.410(2) . ?
C7 C8 1.375(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 C9 120.71(16) . . ?
C2 C1 Cl1 116.76(14) . . ?
C9 C1 Cl1 122.37(14) . . ?
C1 C2 C3 120.79(16) . . ?
C1 C2 Cl2 120.47(15) . . ?
C3 C2 Cl2 118.73(14) . . ?
C4 C3 C2 119.90(16) . . ?
C4 C3 Cl3 120.69(14) . . ?
C2 C3 Cl3 119.38(13) . . ?
C3 C4 C10 120.43(16) . . ?
C3 C4 Cl4 117.51(14) . . ?
C10 C4 Cl4 121.71(13) . . ?
C9 C10 C4 118.53(15) . . ?
C9 C10 C5 118.10(16) . . ?
C4 C10 C5 123.36(17) . . ?
C10 C9 C8 117.26(15) . . ?
C10 C9 C1 117.19(15) . . ?
C8 C9 C1 125.55(17) . . ?
C6 C5 C10 120.77(17) . . ?
C6 C5 Cl5 117.28(14) . . ?
C10 C5 Cl5 121.59(14) . . ?
C5 C6 C7 119.87(16) . . ?
C5 C6 Cl6 121.25(15) . . ?
C7 C6 Cl6 118.88(14) . . ?
C8 C7 C6 120.23(16) . . ?
C8 C7 Cl7 120.78(15) . . ?
C6 C7 Cl7 118.98(14) . . ?
C7 C8 C9 121.13(17) . . ?
C7 C8 Cl8 116.26(14) . . ?
C9 C8 Cl8 122.40(13) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.052
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_pbrn
_database_code_depnum_ccdc_archive 'CCDC 1436915'
_audit_update_record             
;
2015-11-13 deposited with the CCDC.
2016-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 Octabromonaphthalene 
;
_chemical_name_common            Perbromonaphthalene
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 Br8'
_chemical_formula_sum            'C10 Br8'
_chemical_formula_weight         759.38

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   11.3832(4)
_cell_length_b                   7.8114(3)
_cell_length_c                   16.5506(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1471.66(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    3.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    21.775
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.008
_exptl_absorpt_correction_T_max  0.113
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10395
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1297
_reflns_number_gt                1135
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0126P)²+0.8689P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    .
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00072(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1297
_refine_ls_number_parameters     83
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0148
_refine_ls_R_factor_gt           0.0109
_refine_ls_wR_factor_ref         0.0227
_refine_ls_wR_factor_gt          0.0223
_refine_ls_goodness_of_fit_ref   0.864
_refine_ls_restrained_S_all      0.864
_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
Br3 Br 0.86894(2) 0.11950(3) 0.683303(15) 0.01768(7) Uani 1 1 d . . .
Br4 Br 0.63569(2) 0.05419(3) 0.573000(14) 0.01841(7) Uani 1 1 d . . .
Br2 Br 0.84157(2) 0.28246(3) 0.864694(15) 0.01850(7) Uani 1 1 d . . .
Br1 Br 0.58245(2) 0.32197(3) 0.945062(14) 0.01697(7) Uani 1 1 d . . .
C2 C 0.70612(19) 0.2248(3) 0.80506(14) 0.0121(5) Uani 1 1 d . . .
C4 C 0.62067(19) 0.1575(3) 0.67556(13) 0.0111(5) Uani 1 1 d . . .
C3 C 0.7180(2) 0.1704(3) 0.72359(13) 0.0122(5) Uani 1 1 d . . .
C1 C 0.5970(2) 0.2315(3) 0.83960(13) 0.0112(5) Uani 1 1 d . . .
C10 C 0.5062(2) 0.1944(2) 0.70716(13) 0.0105(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br3 0.01023(12) 0.02157(13) 0.02124(14) 0.00272(10) 0.00336(10) 0.00252(9)
Br4 0.01943(14) 0.02518(14) 0.01060(13) -0.00356(10) 0.00286(10) 0.00291(10)
Br2 0.01243(13) 0.02152(13) 0.02154(14) -0.00185(10) -0.00763(10) 0.00032(10)
Br1 0.02014(14) 0.02123(13) 0.00953(12) -0.00300(9) -0.00265(10) -0.00065(10)
C2 0.0117(12) 0.0097(11) 0.0150(12) 0.0027(10) -0.0058(10) -0.0005(9)
C4 0.0136(12) 0.0116(11) 0.0081(11) 0.0012(9) 0.0032(10) -0.0008(9)
C3 0.0112(12) 0.0101(11) 0.0153(13) 0.0023(10) 0.0030(10) 0.0017(9)
C1 0.0158(13) 0.0102(11) 0.0075(11) 0.0003(9) -0.0013(9) 0.0003(9)
C10 0.0147(12) 0.0078(11) 0.0090(11) -0.0013(9) -0.0007(10) -0.0030(10)

_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
Br3 C3 1.885(2) . ?
Br4 C4 1.887(2) . ?
Br2 C2 1.885(2) . ?
Br1 C1 1.890(2) . ?
C2 C1 1.368(3) . ?
C2 C3 1.420(3) . ?
C4 C3 1.368(3) . ?
C4 C10 1.433(3) . ?
C1 C10 1.436(3) 3_656 ?
C10 C10 1.425(4) 3_656 ?
C10 C1 1.436(3) 3_656 ?

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
C1 C2 C3 119.6(2) . . ?
C1 C2 Br2 120.97(17) . . ?
C3 C2 Br2 119.37(17) . . ?
C3 C4 C10 120.7(2) . . ?
C3 C4 Br4 118.73(17) . . ?
C10 C4 Br4 119.77(16) . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 Br3 121.16(17) . . ?
C2 C3 Br3 119.08(16) . . ?
C2 C1 C10 120.6(2) . 3_656 ?
C2 C1 Br1 118.65(17) . . ?
C10 C1 Br1 120.09(16) 3_656 . ?
C10 C10 C4 117.0(3) 3_656 . ?
C10 C10 C1 117.1(3) 3_656 3_656 ?
C4 C10 C1 126.0(2) . 3_656 ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.070
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
####################################################################### 
# 
# 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_pca-13
_database_code_depnum_ccdc_archive 'CCDC 1436916'
_audit_update_record             
;
2015-11-13 deposited with the CCDC.
2016-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 Decachloroanthracene
;
_chemical_name_common            Perchloroanthracene
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 Cl10'
_chemical_formula_sum            'C14 Cl10'
_chemical_formula_weight         522.64

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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                   7.1558(5)
_cell_length_b                   9.5084(6)
_cell_length_c                   12.4684(8)
_cell_angle_alpha                75.854(5)
_cell_angle_beta                 82.701(6)
_cell_angle_gamma                87.954(5)
_cell_volume                     815.95(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.127
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_absorpt_coefficient_mu    1.701
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_T_max  0.844
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
(compiled May  6 2009,17:20:42)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12603
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2872
_reflns_number_gt                2234
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0369P)²+0.0047P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    .
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2872
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0678
_refine_ls_wR_factor_gt          0.0660
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.28545(12) 0.40453(9) 0.47374(6) 0.0279(2) Uani 1 1 d . . .
Cl5 Cl 0.07146(11) 0.01558(8) 0.12321(6) 0.02153(18) Uani 1 1 d . . .
Cl6 Cl 0.34772(11) 0.13222(8) -0.08045(6) 0.02188(18) Uani 1 1 d . . .
Cl7 Cl 0.39990(11) 0.42680(8) -0.24594(6) 0.02337(19) Uani 1 1 d . . .
Cl4 Cl 0.25797(11) -0.16342(8) 0.31415(6) 0.02135(18) Uani 1 1 d . . .
Cl3 Cl 0.25667(10) -0.17151(8) 0.55886(6) 0.02246(19) Uani 1 1 d . . .
Cl9 Cl 0.22054(11) 0.71074(8) 0.07060(6) 0.02473(19) Uani 1 1 d . . .
Cl8 Cl 0.29968(11) 0.71052(8) -0.17243(6) 0.02220(18) Uani 1 1 d . . .
Cl2 Cl 0.26722(11) 0.11019(9) 0.63863(6) 0.02434(19) Uani 1 1 d . . .
Cl10 Cl 0.05429(11) 0.53025(8) 0.28895(6) 0.0274(2) Uani 1 1 d . . .
C1 C 0.2347(4) 0.2540(3) 0.4276(2) 0.0159(6) Uani 1 1 d . . .
C2 C 0.2409(4) 0.1220(3) 0.5009(2) 0.0170(7) Uani 1 1 d . . .
C3 C 0.2357(4) -0.0076(3) 0.4646(2) 0.0159(6) Uani 1 1 d . . .
C4 C 0.2262(4) -0.0032(3) 0.3547(2) 0.0142(6) Uani 1 1 d . . .
C12 C 0.2098(4) 0.1332(3) 0.2753(2) 0.0110(6) Uani 1 1 d . . .
C11 C 0.2107(4) 0.2648(3) 0.3128(2) 0.0124(6) Uani 1 1 d . . .
C10 C 0.1891(4) 0.1461(3) 0.1618(2) 0.0132(6) Uani 1 1 d . . .
C14 C 0.2297(4) 0.2785(3) 0.0820(2) 0.0110(6) Uani 1 1 d . . .
C13 C 0.2138(4) 0.4102(3) 0.1199(2) 0.0125(6) Uani 1 1 d . . .
C9 C 0.1756(4) 0.3971(3) 0.2366(2) 0.0133(6) Uani 1 1 d . . .
C5 C 0.2848(4) 0.2859(3) -0.0341(2) 0.0141(6) Uani 1 1 d . . .
C6 C 0.3104(4) 0.4172(3) -0.1095(2) 0.0149(6) Uani 1 1 d . . .
C7 C 0.2759(4) 0.5476(3) -0.0741(2) 0.0155(6) Uani 1 1 d . . .
C8 C 0.2318(4) 0.5449(3) 0.0372(2) 0.0136(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0400(5) 0.0303(4) 0.0169(4) -0.0119(3) -0.0021(3) -0.0081(4)
Cl5 0.0285(4) 0.0198(4) 0.0180(4) -0.0056(3) -0.0057(3) -0.0046(3)
Cl6 0.0285(4) 0.0221(4) 0.0163(4) -0.0093(3) 0.0013(3) 0.0000(3)
Cl7 0.0259(4) 0.0316(4) 0.0104(4) -0.0026(3) 0.0011(3) -0.0003(3)
Cl4 0.0291(4) 0.0159(4) 0.0192(4) -0.0033(3) -0.0061(3) 0.0031(3)
Cl3 0.0217(4) 0.0257(4) 0.0148(4) 0.0054(3) -0.0032(3) 0.0004(3)
Cl9 0.0316(5) 0.0180(4) 0.0254(4) -0.0054(3) -0.0068(3) 0.0007(3)
Cl8 0.0239(4) 0.0198(4) 0.0173(4) 0.0060(3) -0.0020(3) 0.0002(3)
Cl2 0.0250(4) 0.0393(5) 0.0089(3) -0.0047(3) -0.0037(3) -0.0040(3)
Cl10 0.0321(5) 0.0269(4) 0.0252(4) -0.0121(3) -0.0020(4) 0.0075(3)
C1 0.0135(16) 0.0228(17) 0.0133(15) -0.0086(13) 0.0008(12) -0.0034(12)
C2 0.0123(15) 0.0299(18) 0.0069(14) -0.0013(13) 0.0005(12) -0.0038(13)
C3 0.0099(15) 0.0222(17) 0.0122(15) 0.0023(12) -0.0011(12) -0.0004(12)
C4 0.0112(15) 0.0145(15) 0.0167(15) -0.0037(12) -0.0007(12) -0.0025(11)
C12 0.0060(14) 0.0163(15) 0.0098(14) -0.0022(11) 0.0004(11) -0.0007(11)
C11 0.0082(14) 0.0188(15) 0.0103(14) -0.0044(12) 0.0009(11) -0.0034(11)
C10 0.0115(15) 0.0137(15) 0.0161(15) -0.0064(12) -0.0027(12) -0.0011(11)
C14 0.0075(14) 0.0150(15) 0.0109(14) -0.0027(11) -0.0034(11) 0.0005(11)
C13 0.0076(14) 0.0154(15) 0.0150(14) -0.0042(12) -0.0025(11) -0.0016(11)
C9 0.0100(15) 0.0162(15) 0.0159(15) -0.0078(12) -0.0016(12) -0.0005(12)
C5 0.0100(15) 0.0196(16) 0.0159(15) -0.0093(12) -0.0032(12) -0.0003(12)
C6 0.0112(15) 0.0244(17) 0.0082(14) -0.0022(12) -0.0014(11) -0.0011(12)
C7 0.0120(15) 0.0169(16) 0.0149(15) 0.0030(12) -0.0048(12) -0.0009(12)
C8 0.0113(15) 0.0140(15) 0.0168(15) -0.0045(12) -0.0050(12) 0.0026(11)

_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 1.733(3) . ?
Cl5 C10 1.717(3) . ?
Cl6 C5 1.724(3) . ?
Cl7 C6 1.721(3) . ?
Cl4 C4 1.718(3) . ?
Cl3 C3 1.722(3) . ?
Cl9 C8 1.723(3) . ?
Cl8 C7 1.723(3) . ?
Cl2 C2 1.727(3) . ?
Cl10 C9 1.722(3) . ?
C1 C2 1.364(4) . ?
C1 C11 1.442(4) . ?
C2 C3 1.416(4) . ?
C3 C4 1.371(4) . ?
C4 C12 1.437(4) . ?
C12 C10 1.417(4) . ?
C12 C11 1.439(4) . ?
C11 C9 1.415(4) . ?
C10 C14 1.414(4) . ?
C14 C5 1.435(4) . ?
C14 C13 1.440(4) . ?
C13 C9 1.421(4) . ?
C13 C8 1.433(4) . ?
C5 C6 1.369(4) . ?
C6 C7 1.419(4) . ?
C7 C8 1.377(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 C11 120.7(3) . . ?
C2 C1 Cl1 117.2(2) . . ?
C11 C1 Cl1 121.7(2) . . ?
C1 C2 C3 120.8(2) . . ?
C1 C2 Cl2 120.3(2) . . ?
C3 C2 Cl2 118.8(2) . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 Cl3 120.1(2) . . ?
C2 C3 Cl3 119.0(2) . . ?
C3 C4 C12 120.5(3) . . ?
C3 C4 Cl4 117.5(2) . . ?
C12 C4 Cl4 121.7(2) . . ?
C10 C12 C4 123.7(2) . . ?
C10 C12 C11 117.6(2) . . ?
C4 C12 C11 118.7(2) . . ?
C9 C11 C12 118.0(2) . . ?
C9 C11 C1 123.5(3) . . ?
C12 C11 C1 118.4(2) . . ?
C14 C10 C12 120.5(2) . . ?
C14 C10 Cl5 117.9(2) . . ?
C12 C10 Cl5 120.4(2) . . ?
C10 C14 C5 122.7(2) . . ?
C10 C14 C13 117.9(2) . . ?
C5 C14 C13 119.3(2) . . ?
C9 C13 C8 124.8(2) . . ?
C9 C13 C14 117.5(2) . . ?
C8 C13 C14 117.7(2) . . ?
C11 C9 C13 120.5(2) . . ?
C11 C9 Cl10 117.6(2) . . ?
C13 C9 Cl10 121.2(2) . . ?
C6 C5 C14 120.7(3) . . ?
C6 C5 Cl6 117.6(2) . . ?
C14 C5 Cl6 121.3(2) . . ?
C5 C6 C7 120.1(2) . . ?
C5 C6 Cl7 120.8(2) . . ?
C7 C6 Cl7 119.0(2) . . ?
C8 C7 C6 120.9(2) . . ?
C8 C7 Cl8 120.4(2) . . ?
C6 C7 Cl8 118.7(2) . . ?
C7 C8 C13 120.9(3) . . ?
C7 C8 Cl9 116.2(2) . . ?
C13 C8 Cl9 122.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.072
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: toluene'
