# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Gautam R. Desiraju'
_publ_contact_author_email       'GAUTAM DESIRAJU@YAHOO.COM'

_publ_section_title              
;
Additive induced polymorphism. The
pentafluorophenol-pentafluoroaniline system.
;
loop_
_publ_author_name
'Gautam Desiraju'
'Dieter Blaser'
'Roland Boese'
'Michael Kirchner'

# Attachment 'pfcoc_133_0m.cif'

data_pfcoc_133_0m
_database_code_depnum_ccdc_archive 'CCDC 678815'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
cocrystal pentafluorophenol * pentafluoroaniline 6:3
;
_chemical_name_common            
'cocrystal pentafluorophenol * pentafluoroaniline 6:3'
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H2 F5 N, 2(C6 H F5 O)'
_chemical_formula_sum            'C18 H4 F15 N O2'
_chemical_formula_weight         551.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Cc

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'

_cell_length_a                   21.1790(5)
_cell_length_b                   17.0734(4)
_cell_length_c                   16.6258(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.6340(10)
_cell_angle_gamma                90.00
_cell_volume                     5464.7(2)
_cell_formula_units_Z            12
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9847
_cell_measurement_theta_min      2.355
_cell_measurement_theta_max      35.728

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.010
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3240
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8506
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_process_details   
;
BRUKER AXS SMART APEX 2 Vers. 2.1-4
R.H. Blessing, Acta Cryst. (1995) A51 33-38
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      140(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  
;
Siemens SMART three axis goniometer with APEX II area detector system
;
_diffrn_measurement_method       
;
Data collection strategy APEX 2 / COSMO

with chi = 0
;

_diffrn_detector_area_resol_mean 512
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            84547
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         36.15
_reflns_number_total             17115
_reflns_number_gt                10484
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER AXS SMART APEX 2 Vers. 2.1-4'
_computing_cell_refinement       'BRUKER AXS SMART APEX 2 Vers. 2.1-4'
_computing_data_reduction        'BRUKER AXS SMART APEX 2 Vers. 2.1-4'
_computing_structure_solution    'BRUKER AXS SHELXTL (c) 2001 / Vers.6.12'
_computing_structure_refinement  'BRUKER AXS SHELXTL (c) 2001 / Vers.6.12'
_computing_molecular_graphics    'BRUKER AXS SHELXTL (c) 2001 / Vers.6.12'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2001 / Vers.6.12'

_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.
Hydrogen treatment:
All hydrogen positions are taken from the fourier map and refined riding
on the respective oxygen or nitrogen atom. Only exception is residue 8,
which was generated on an idealized position on maximum residual electron
density (AFIX 147) and allowed to rotate on the C-O bond while riding the
oxygen atom.
;

_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)+(0.0794P)²+2.6132P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(4)
_refine_ls_number_reflns         17115
_refine_ls_number_parameters     974
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1612
_refine_ls_wR_factor_gt          0.1293
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1_1 O 0.29067(10) -0.08826(14) 0.36189(15) 0.0273(5) Uani 1 1 d . . .
H1_1 H 0.3171 -0.0426 0.4130 0.041 Uiso 1 1 d R . .
F2_1 F 0.22406(12) -0.21365(13) 0.26563(14) 0.0414(5) Uani 1 1 d . . .
F3_1 F 0.08576(12) -0.23260(14) 0.21280(14) 0.0487(6) Uani 1 1 d . . .
F4_1 F 0.01143(9) -0.12389(12) 0.25772(13) 0.0431(5) Uani 1 1 d . . .
F5_1 F 0.07685(9) 0.00536(13) 0.35276(13) 0.0386(5) Uani 1 1 d . . .
F6_1 F 0.21508(10) 0.02550(12) 0.40526(13) 0.0368(5) Uani 1 1 d . . .
C1_1 C 0.22172(14) -0.0950(2) 0.33670(19) 0.0235(7) Uani 1 1 d . . .
C2_1 C 0.18779(17) -0.1596(2) 0.2870(2) 0.0279(7) Uani 1 1 d . . .
C3_1 C 0.11740(17) -0.1691(2) 0.2606(2) 0.0299(7) Uani 1 1 d . . .
C4_1 C 0.07989(15) -0.1142(2) 0.2825(2) 0.0304(7) Uani 1 1 d . . .
C5_1 C 0.11224(14) -0.0494(2) 0.33016(19) 0.0276(7) Uani 1 1 d . . .
C6_1 C 0.18381(14) -0.0389(2) 0.35729(18) 0.0231(6) Uani 1 1 d . . .
F1_2 F 0.28576(11) 0.25557(14) 0.36123(15) 0.0424(5) Uani 1 1 d . . .
F2_2 F 0.22964(11) 0.12450(13) 0.26565(14) 0.0376(5) Uani 1 1 d . . .
F3_2 F 0.09341(12) 0.09327(14) 0.20836(14) 0.0433(5) Uani 1 1 d . . .
N4_2 N 0.00675(14) 0.1908(2) 0.25136(19) 0.0433(8) Uani 1 1 d . . .
H1_2 H -0.0250 0.2266 0.2350 0.065 Uiso 1 1 d R . .
H2_2 H -0.0056 0.1523 0.2071 0.065 Uiso 1 1 d R . .
F5_2 F 0.06469(12) 0.32573(16) 0.34213(17) 0.0521(7) Uani 1 1 d . . .
F6_2 F 0.20241(13) 0.35695(14) 0.39810(15) 0.0424(6) Uani 1 1 d . . .
C1_2 C 0.21832(16) 0.2408(2) 0.3334(2) 0.0257(7) Uani 1 1 d . . .
C2_2 C 0.18916(15) 0.17414(19) 0.2842(2) 0.0259(7) Uani 1 1 d . . .
C3_2 C 0.11927(17) 0.1589(2) 0.2559(2) 0.0288(7) Uani 1 1 d . . .
C4_2 C 0.07556(17) 0.2088(2) 0.2742(2) 0.0339(8) Uani 1 1 d . . .
C5_2 C 0.10477(18) 0.2753(2) 0.3221(2) 0.0333(8) Uani 1 1 d . . .
C6_2 C 0.17535(17) 0.2922(2) 0.3514(2) 0.0299(7) Uani 1 1 d . . .
O1_3 O 0.29098(11) 0.58251(15) 0.36095(16) 0.0327(5) Uani 1 1 d . . .
H1_3 H 0.3007 0.6228 0.3983 0.049 Uiso 1 1 d R . .
F2_3 F 0.22519(12) 0.45638(13) 0.26496(15) 0.0430(5) Uani 1 1 d . . .
F3_3 F 0.08803(13) 0.43490(15) 0.21217(15) 0.0511(6) Uani 1 1 d . . .
F4_3 F 0.01122(10) 0.53977(15) 0.25760(14) 0.0514(6) Uani 1 1 d . . .
F5_3 F 0.07511(11) 0.66925(14) 0.35477(14) 0.0468(6) Uani 1 1 d . . .
F6_3 F 0.21264(10) 0.69182(12) 0.40576(13) 0.0353(4) Uani 1 1 d . . .
C1_3 C 0.22200(15) 0.5743(2) 0.3364(2) 0.0256(6) Uani 1 1 d . . .
C2_3 C 0.18836(17) 0.5091(2) 0.2867(2) 0.0284(7) Uani 1 1 d . . .
C3_3 C 0.11806(18) 0.4976(2) 0.2603(2) 0.0352(8) Uani 1 1 d . . .
C4_3 C 0.07972(15) 0.5518(2) 0.2825(2) 0.0351(8) Uani 1 1 d . . .
C5_3 C 0.11120(16) 0.6163(2) 0.3311(2) 0.0312(7) Uani 1 1 d . . .
C6_3 C 0.18200(16) 0.6282(2) 0.3576(2) 0.0264(7) Uani 1 1 d . . .
O1_4 O 0.37030(11) 0.03082(14) 0.48252(13) 0.0293(5) Uani 1 1 d . . .
H1_4 H 0.3722 0.0274 0.5330 0.044 Uiso 1 1 d R . .
F2_4 F 0.44492(9) 0.14051(12) 0.61369(12) 0.0321(4) Uani 1 1 d . . .
F3_4 F 0.50125(10) 0.26765(13) 0.57087(14) 0.0375(5) Uani 1 1 d . . .
F4_4 F 0.48863(11) 0.28828(13) 0.40162(15) 0.0433(5) Uani 1 1 d . . .
F5_4 F 0.41761(10) 0.17970(13) 0.27618(12) 0.0364(5) Uani 1 1 d . . .
F6_4 F 0.36179(9) 0.05235(12) 0.31944(12) 0.0314(4) Uani 1 1 d . . .
C1_4 C 0.40150(13) 0.09437(18) 0.46694(17) 0.0206(6) Uani 1 1 d . . .
C2_4 C 0.43811(14) 0.1506(2) 0.53007(18) 0.0242(6) Uani 1 1 d . . .
C3_4 C 0.46760(15) 0.2144(2) 0.5098(2) 0.0260(6) Uani 1 1 d . . .
C4_4 C 0.46067(15) 0.2247(2) 0.4234(2) 0.0286(7) Uani 1 1 d . . .
C5_4 C 0.42494(15) 0.1705(2) 0.35993(19) 0.0267(7) Uani 1 1 d . . .
C6_4 C 0.39646(14) 0.1056(2) 0.38178(18) 0.0223(6) Uani 1 1 d . . .
F1_5 F 0.38020(13) 0.37303(15) 0.48337(17) 0.0495(6) Uani 1 1 d . . .
F2_5 F 0.45136(11) 0.47983(13) 0.61186(13) 0.0413(6) Uani 1 1 d . . .
F3_5 F 0.50629(11) 0.60822(13) 0.57077(14) 0.0379(5) Uani 1 1 d . . .
O4_5 O 0.49731(13) 0.62995(16) 0.40544(17) 0.0372(6) Uani 1 1 d . . .
H1_5 H 0.4972 0.6366 0.3607 0.056 Uiso 1 1 d R . .
F5_5 F 0.42486(11) 0.52165(14) 0.27518(13) 0.0390(5) Uani 1 1 d . . .
F6_5 F 0.36773(11) 0.39387(14) 0.31602(14) 0.0416(6) Uani 1 1 d . . .
C1_5 C 0.40867(17) 0.4347(2) 0.4648(2) 0.0325(8) Uani 1 1 d . . .
C2_5 C 0.44456(16) 0.4903(2) 0.5283(2) 0.0303(8) Uani 1 1 d . . .
C3_5 C 0.47295(15) 0.5548(2) 0.5079(2) 0.0310(8) Uani 1 1 d . . .
C4_5 C 0.46832(16) 0.5676(2) 0.4219(2) 0.0310(7) Uani 1 1 d . . .
C5_5 C 0.43187(16) 0.5113(2) 0.3586(2) 0.0304(7) Uani 1 1 d . . .
C6_5 C 0.40345(15) 0.4465(2) 0.3801(2) 0.0299(8) Uani 1 1 d . . .
O1_6 O 0.36999(10) 0.69694(14) 0.47983(14) 0.0283(5) Uani 1 1 d . . .
H1_6 H 0.3719 0.6994 0.5344 0.043 Uiso 1 1 d R . .
F2_6 F 0.44517(9) 0.80530(13) 0.61321(12) 0.0331(4) Uani 1 1 d . . .
F3_6 F 0.50201(10) 0.93329(13) 0.57398(15) 0.0387(5) Uani 1 1 d . . .
F4_6 F 0.49001(11) 0.95655(13) 0.40508(15) 0.0418(5) Uani 1 1 d . . .
F5_6 F 0.41828(10) 0.85091(13) 0.27667(13) 0.0364(5) Uani 1 1 d . . .
F6_6 F 0.36211(10) 0.72241(13) 0.31685(12) 0.0331(4) Uani 1 1 d . . .
C1_6 C 0.40152(13) 0.76200(19) 0.46535(18) 0.0221(6) Uani 1 1 d . . .
C2_6 C 0.43837(13) 0.8163(2) 0.52940(18) 0.0241(6) Uani 1 1 d . . .
C3_6 C 0.46801(15) 0.8814(2) 0.5108(2) 0.0289(7) Uani 1 1 d . . .
C4_6 C 0.46180(15) 0.8935(2) 0.4249(2) 0.0287(7) Uani 1 1 d . . .
C5_6 C 0.42551(15) 0.8394(2) 0.3603(2) 0.0268(7) Uani 1 1 d . . .
C6_6 C 0.39643(14) 0.7748(2) 0.38000(19) 0.0227(6) Uani 1 1 d . . .
N1_7 N 0.36415(12) -0.01515(17) 0.63848(16) 0.0293(5) Uani 1 1 d . . .
H1_7 H 0.3760 0.0183 0.6777 0.044 Uiso 1 1 d R . .
H2_7 H 0.3864 -0.0595 0.6519 0.044 Uiso 1 1 d R . .
F2_7 F 0.30619(10) -0.15392(12) 0.54891(13) 0.0364(5) Uani 1 1 d . . .
F3_7 F 0.17032(10) -0.18729(12) 0.49268(13) 0.0348(4) Uani 1 1 d . . .
F4_7 F 0.08427(9) -0.08743(13) 0.52613(14) 0.0351(5) Uani 1 1 d . . .
F5_7 F 0.13719(10) 0.04593(13) 0.62035(14) 0.0378(5) Uani 1 1 d . . .
F6_7 F 0.27409(10) 0.07948(12) 0.67673(13) 0.0339(4) Uani 1 1 d . . .
C1_7 C 0.29385(14) -0.0363(2) 0.61391(17) 0.0233(6) Uani 1 1 d . . .
C2_7 C 0.26534(15) -0.1034(2) 0.56795(19) 0.0248(6) Uani 1 1 d . . .
C3_7 C 0.19590(16) -0.12206(19) 0.5387(2) 0.0247(6) Uani 1 1 d . . .
C4_7 C 0.15205(15) -0.0708(2) 0.5560(2) 0.0264(7) Uani 1 1 d . . .
C5_7 C 0.17888(15) -0.0032(2) 0.6025(2) 0.0257(6) Uani 1 1 d . . .
C6_7 C 0.24905(15) 0.0140(2) 0.63164(19) 0.0239(6) Uani 1 1 d . . .
O1_8 O 0.35922(12) 0.2982(2) 0.62914(19) 0.0548(9) Uani 1 1 d . . .
H1_8 H 0.3810 0.2569 0.6518 0.082 Uiso 1 1 calc R . .
F2_8 F 0.29546(12) 0.16771(15) 0.53720(16) 0.0511(7) Uani 1 1 d . . .
F3_8 F 0.15797(13) 0.14420(14) 0.48575(15) 0.0450(6) Uani 1 1 d . . .
F4_8 F 0.08074(10) 0.25315(14) 0.52800(15) 0.0427(6) Uani 1 1 d . . .
F5_8 F 0.14319(13) 0.38169(14) 0.62052(15) 0.0447(6) Uani 1 1 d . . .
F6_8 F 0.28166(14) 0.40583(14) 0.67215(16) 0.0538(7) Uani 1 1 d . . .
C1_8 C 0.29086(18) 0.2869(3) 0.6059(2) 0.0376(9) Uani 1 1 d . . .
C2_8 C 0.25873(18) 0.2212(2) 0.5589(2) 0.0346(8) Uani 1 1 d . . .
C3_8 C 0.18859(16) 0.2082(2) 0.5328(2) 0.0263(7) Uani 1 1 d . . .
C4_8 C 0.14916(16) 0.2632(2) 0.5537(2) 0.0254(7) Uani 1 1 d . . .
C5_8 C 0.18075(17) 0.3290(2) 0.6004(2) 0.0298(7) Uani 1 1 d . . .
C6_8 C 0.25171(18) 0.3411(2) 0.6271(2) 0.0321(8) Uani 1 1 d . . .
N1_9 N 0.36525(12) 0.65241(18) 0.63639(17) 0.0326(6) Uani 1 1 d . . .
H1_9 H 0.3755 0.6875 0.6764 0.049 Uiso 1 1 d R . .
H2_9 H 0.3894 0.6063 0.6480 0.049 Uiso 1 1 d R . .
F2_9 F 0.30830(10) 0.51286(13) 0.54798(14) 0.0394(5) Uani 1 1 d . . .
F3_9 F 0.17234(10) 0.47785(12) 0.49209(13) 0.0353(5) Uani 1 1 d . . .
F4_9 F 0.08591(9) 0.57725(13) 0.52715(14) 0.0377(5) Uani 1 1 d . . .
F5_9 F 0.13806(10) 0.71096(14) 0.61960(14) 0.0387(5) Uani 1 1 d . . .
F6_9 F 0.27467(10) 0.74651(12) 0.67526(13) 0.0352(4) Uani 1 1 d . . .
C1_9 C 0.29501(15) 0.6307(2) 0.61277(18) 0.0242(6) Uani 1 1 d . . .
C2_9 C 0.26732(15) 0.5625(2) 0.5672(2) 0.0270(6) Uani 1 1 d . . .
C3_9 C 0.19767(16) 0.5436(2) 0.53867(19) 0.0260(6) Uani 1 1 d . . .
C4_9 C 0.15378(15) 0.5942(2) 0.5560(2) 0.0267(7) Uani 1 1 d . . .
C5_9 C 0.17961(16) 0.6620(2) 0.6019(2) 0.0271(7) Uani 1 1 d . . .
C6_9 C 0.24995(15) 0.6795(2) 0.63070(19) 0.0246(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
O1_1 C1_1 1.346(3) . ?
O1_1 H1_1 1.1162 . ?
F2_1 C2_1 1.340(4) . ?
F3_1 C3_1 1.346(4) . ?
F4_1 C4_1 1.342(3) . ?
F5_1 C5_1 1.346(4) . ?
F6_1 C6_1 1.358(4) . ?
C1_1 C6_1 1.381(4) . ?
C1_1 C2_1 1.387(5) . ?
C2_1 C3_1 1.377(4) . ?
C3_1 C4_1 1.373(5) . ?
C4_1 C5_1 1.367(5) . ?
C5_1 C6_1 1.401(4) . ?
F1_2 C1_2 1.329(4) . ?
F2_2 C2_2 1.330(4) . ?
F3_2 C3_2 1.349(4) . ?
N4_2 C4_2 1.379(4) . ?
N4_2 H1_2 0.8635 . ?
N4_2 H2_2 0.9399 . ?
F5_2 C5_2 1.345(4) . ?
F6_2 C6_2 1.335(4) . ?
C1_2 C6_2 1.384(4) . ?
C1_2 C2_2 1.387(5) . ?
C2_2 C3_2 1.378(4) . ?
C3_2 C4_2 1.382(5) . ?
C4_2 C5_2 1.377(6) . ?
C5_2 C6_2 1.396(5) . ?
O1_3 C1_3 1.351(4) . ?
O1_3 H1_3 0.8920 . ?
F2_3 C2_3 1.335(4) . ?
F3_3 C3_3 1.330(4) . ?
F4_3 C4_3 1.348(3) . ?
F5_3 C5_3 1.345(4) . ?
F6_3 C6_3 1.345(4) . ?
C1_3 C6_3 1.391(5) . ?
C1_3 C2_3 1.393(5) . ?
C2_3 C3_3 1.380(5) . ?
C3_3 C4_3 1.378(5) . ?
C4_3 C5_3 1.364(5) . ?
C5_3 C6_3 1.390(4) . ?
O1_4 C1_4 1.350(3) . ?
O1_4 H1_4 0.8260 . ?
F2_4 C2_4 1.348(3) . ?
F3_4 C3_4 1.327(4) . ?
F4_4 C4_4 1.356(4) . ?
F5_4 C5_4 1.344(3) . ?
F6_4 C6_4 1.343(3) . ?
C1_4 C6_4 1.388(4) . ?
C1_4 C2_4 1.395(4) . ?
C2_4 C3_4 1.365(4) . ?
C3_4 C4_4 1.393(4) . ?
C4_4 C5_4 1.370(5) . ?
C5_4 C6_4 1.382(4) . ?
F1_5 C1_5 1.312(4) . ?
F2_5 C2_5 1.348(4) . ?
F3_5 C3_5 1.345(4) . ?
O4_5 C4_5 1.313(5) . ?
O4_5 H1_5 0.7512 . ?
F5_5 C5_5 1.343(4) . ?
F6_5 C6_5 1.358(4) . ?
C1_5 C6_5 1.380(5) . ?
C1_5 C2_5 1.388(5) . ?
C2_5 C3_5 1.363(5) . ?
C3_5 C4_5 1.409(5) . ?
C4_5 C5_5 1.396(5) . ?
C5_5 C6_5 1.376(5) . ?
O1_6 C1_6 1.368(4) . ?
O1_6 H1_6 0.8915 . ?
F2_6 C2_6 1.353(3) . ?
F3_6 C3_6 1.333(4) . ?
F4_6 C4_6 1.338(4) . ?
F5_6 C5_6 1.348(3) . ?
F6_6 C6_6 1.340(3) . ?
C1_6 C2_6 1.382(4) . ?
C1_6 C6_6 1.395(4) . ?
C2_6 C3_6 1.373(5) . ?
C3_6 C4_6 1.395(4) . ?
C4_6 C5_6 1.381(5) . ?
C5_6 C6_6 1.368(4) . ?
N1_7 C1_7 1.417(3) . ?
N1_7 H1_7 0.8235 . ?
N1_7 H2_7 0.8702 . ?
F2_7 C2_7 1.349(3) . ?
F3_7 C3_7 1.332(4) . ?
F4_7 C4_7 1.339(3) . ?
F5_7 C5_7 1.339(3) . ?
F6_7 C6_7 1.327(4) . ?
C1_7 C2_7 1.370(4) . ?
C1_7 C6_7 1.399(4) . ?
C2_7 C3_7 1.380(4) . ?
C3_7 C4_7 1.390(4) . ?
C4_7 C5_7 1.373(5) . ?
C5_7 C6_7 1.389(4) . ?
O1_8 C1_8 1.348(4) . ?
O1_8 H1_8 0.8400 . ?
F2_8 C2_8 1.343(4) . ?
F3_8 C3_8 1.343(4) . ?
F4_8 C4_8 1.340(4) . ?
F5_8 C5_8 1.332(4) . ?
F6_8 C6_8 1.338(4) . ?
C1_8 C2_8 1.374(6) . ?
C1_8 C6_8 1.382(5) . ?
C2_8 C3_8 1.381(5) . ?
C3_8 C4_8 1.393(4) . ?
C4_8 C5_8 1.371(5) . ?
C5_8 C6_8 1.394(5) . ?
N1_9 C1_9 1.420(4) . ?
N1_9 H1_9 0.8528 . ?
N1_9 H2_9 0.9152 . ?
F2_9 C2_9 1.344(4) . ?
F3_9 C3_9 1.342(4) . ?
F4_9 C4_9 1.344(3) . ?
F5_9 C5_9 1.333(3) . ?
F6_9 C6_9 1.345(4) . ?
C1_9 C2_9 1.380(5) . ?
C1_9 C6_9 1.389(4) . ?
C2_9 C3_9 1.386(4) . ?
C3_9 C4_9 1.385(4) . ?
C4_9 C5_9 1.368(5) . ?
C5_9 C6_9 1.394(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
C1_1 O1_1 H1_1 115.5 . . ?
O1_1 C1_1 C6_1 122.1(3) . . ?
O1_1 C1_1 C2_1 118.6(3) . . ?
C6_1 C1_1 C2_1 119.3(3) . . ?
F2_1 C2_1 C3_1 119.9(3) . . ?
F2_1 C2_1 C1_1 119.6(3) . . ?
C3_1 C2_1 C1_1 120.5(3) . . ?
F3_1 C3_1 C4_1 120.4(3) . . ?
F3_1 C3_1 C2_1 119.3(3) . . ?
C4_1 C3_1 C2_1 120.3(3) . . ?
F4_1 C4_1 C5_1 119.6(3) . . ?
F4_1 C4_1 C3_1 120.3(3) . . ?
C5_1 C4_1 C3_1 120.1(3) . . ?
F5_1 C5_1 C4_1 121.4(3) . . ?
F5_1 C5_1 C6_1 118.4(3) . . ?
C4_1 C5_1 C6_1 120.2(3) . . ?
F6_1 C6_1 C1_1 121.0(3) . . ?
F6_1 C6_1 C5_1 119.3(3) . . ?
C1_1 C6_1 C5_1 119.6(3) . . ?
C4_2 N4_2 H1_2 121.5 . . ?
C4_2 N4_2 H2_2 106.7 . . ?
H1_2 N4_2 H2_2 108.8 . . ?
F1_2 C1_2 C6_2 120.8(3) . . ?
F1_2 C1_2 C2_2 120.7(3) . . ?
C6_2 C1_2 C2_2 118.4(3) . . ?
F2_2 C2_2 C3_2 120.3(3) . . ?
F2_2 C2_2 C1_2 119.2(3) . . ?
C3_2 C2_2 C1_2 120.5(3) . . ?
F3_2 C3_2 C2_2 118.2(3) . . ?
F3_2 C3_2 C4_2 119.7(3) . . ?
C2_2 C3_2 C4_2 122.1(3) . . ?
N4_2 C4_2 C5_2 120.8(3) . . ?
N4_2 C4_2 C3_2 122.0(4) . . ?
C5_2 C4_2 C3_2 117.1(3) . . ?
F5_2 C5_2 C4_2 119.6(3) . . ?
F5_2 C5_2 C6_2 118.5(4) . . ?
C4_2 C5_2 C6_2 122.0(3) . . ?
F6_2 C6_2 C1_2 119.3(3) . . ?
F6_2 C6_2 C5_2 120.8(3) . . ?
C1_2 C6_2 C5_2 119.9(3) . . ?
C1_3 O1_3 H1_3 101.3 . . ?
O1_3 C1_3 C6_3 123.5(3) . . ?
O1_3 C1_3 C2_3 118.9(3) . . ?
C6_3 C1_3 C2_3 117.7(3) . . ?
F2_3 C2_3 C3_3 119.6(3) . . ?
F2_3 C2_3 C1_3 119.2(3) . . ?
C3_3 C2_3 C1_3 121.3(3) . . ?
F3_3 C3_3 C4_3 120.9(3) . . ?
F3_3 C3_3 C2_3 119.2(4) . . ?
C4_3 C3_3 C2_3 119.9(3) . . ?
F4_3 C4_3 C5_3 120.2(3) . . ?
F4_3 C4_3 C3_3 119.6(3) . . ?
C5_3 C4_3 C3_3 120.2(3) . . ?
F5_3 C5_3 C4_3 121.3(3) . . ?
F5_3 C5_3 C6_3 118.6(3) . . ?
C4_3 C5_3 C6_3 120.1(3) . . ?
F6_3 C6_3 C5_3 119.7(3) . . ?
F6_3 C6_3 C1_3 119.4(3) . . ?
C5_3 C6_3 C1_3 120.9(3) . . ?
C1_4 O1_4 H1_4 115.5 . . ?
O1_4 C1_4 C6_4 118.1(3) . . ?
O1_4 C1_4 C2_4 124.9(2) . . ?
C6_4 C1_4 C2_4 117.1(3) . . ?
F2_4 C2_4 C3_4 119.5(3) . . ?
F2_4 C2_4 C1_4 118.4(3) . . ?
C3_4 C2_4 C1_4 122.1(3) . . ?
F3_4 C3_4 C2_4 120.9(3) . . ?
F3_4 C3_4 C4_4 119.6(3) . . ?
C2_4 C3_4 C4_4 119.5(3) . . ?
F4_4 C4_4 C5_4 119.8(3) . . ?
F4_4 C4_4 C3_4 120.5(3) . . ?
C5_4 C4_4 C3_4 119.7(3) . . ?
F5_4 C5_4 C4_4 120.5(3) . . ?
F5_4 C5_4 C6_4 119.4(3) . . ?
C4_4 C5_4 C6_4 120.1(3) . . ?
F6_4 C6_4 C5_4 119.9(3) . . ?
F6_4 C6_4 C1_4 118.6(3) . . ?
C5_4 C6_4 C1_4 121.5(3) . . ?
C4_5 O4_5 H1_5 121.3 . . ?
F1_5 C1_5 C6_5 120.6(3) . . ?
F1_5 C1_5 C2_5 122.0(3) . . ?
C6_5 C1_5 C2_5 117.5(3) . . ?
F2_5 C2_5 C3_5 119.7(3) . . ?
F2_5 C2_5 C1_5 118.8(3) . . ?
C3_5 C2_5 C1_5 121.5(3) . . ?
F3_5 C3_5 C2_5 119.8(3) . . ?
F3_5 C3_5 C4_5 118.4(3) . . ?
C2_5 C3_5 C4_5 121.8(3) . . ?
O4_5 C4_5 C5_5 124.1(3) . . ?
O4_5 C4_5 C3_5 119.8(3) . . ?
C5_5 C4_5 C3_5 116.1(3) . . ?
F5_5 C5_5 C6_5 120.1(3) . . ?
F5_5 C5_5 C4_5 118.4(3) . . ?
C6_5 C5_5 C4_5 121.5(3) . . ?
F6_5 C6_5 C5_5 119.3(3) . . ?
F6_5 C6_5 C1_5 119.0(3) . . ?
C5_5 C6_5 C1_5 121.7(3) . . ?
C1_6 O1_6 H1_6 108.7 . . ?
O1_6 C1_6 C2_6 124.7(3) . . ?
O1_6 C1_6 C6_6 118.1(3) . . ?
C2_6 C1_6 C6_6 117.2(3) . . ?
F2_6 C2_6 C3_6 118.8(3) . . ?
F2_6 C2_6 C1_6 119.0(3) . . ?
C3_6 C2_6 C1_6 122.3(3) . . ?
F3_6 C3_6 C2_6 120.6(3) . . ?
F3_6 C3_6 C4_6 119.9(3) . . ?
C2_6 C3_6 C4_6 119.5(3) . . ?
F4_6 C4_6 C5_6 120.5(3) . . ?
F4_6 C4_6 C3_6 120.7(3) . . ?
C5_6 C4_6 C3_6 118.8(3) . . ?
F5_6 C5_6 C6_6 119.7(3) . . ?
F5_6 C5_6 C4_6 119.5(3) . . ?
C6_6 C5_6 C4_6 120.8(3) . . ?
F6_6 C6_6 C5_6 120.1(3) . . ?
F6_6 C6_6 C1_6 118.6(3) . . ?
C5_6 C6_6 C1_6 121.3(3) . . ?
C1_7 N1_7 H1_7 110.1 . . ?
C1_7 N1_7 H2_7 104.2 . . ?
H1_7 N1_7 H2_7 116.5 . . ?
C2_7 C1_7 C6_7 116.8(3) . . ?
C2_7 C1_7 N1_7 122.7(3) . . ?
C6_7 C1_7 N1_7 120.4(3) . . ?
F2_7 C2_7 C1_7 119.3(3) . . ?
F2_7 C2_7 C3_7 117.6(3) . . ?
C1_7 C2_7 C3_7 123.1(3) . . ?
F3_7 C3_7 C2_7 120.9(3) . . ?
F3_7 C3_7 C4_7 119.9(3) . . ?
C2_7 C3_7 C4_7 119.2(3) . . ?
F4_7 C4_7 C5_7 121.0(3) . . ?
F4_7 C4_7 C3_7 119.7(3) . . ?
C5_7 C4_7 C3_7 119.3(3) . . ?
F5_7 C5_7 C4_7 119.7(3) . . ?
F5_7 C5_7 C6_7 119.9(3) . . ?
C4_7 C5_7 C6_7 120.4(3) . . ?
F6_7 C6_7 C5_7 119.6(3) . . ?
F6_7 C6_7 C1_7 119.3(3) . . ?
C5_7 C6_7 C1_7 121.1(3) . . ?
C1_8 O1_8 H1_8 109.5 . . ?
O1_8 C1_8 C2_8 119.8(4) . . ?
O1_8 C1_8 C6_8 121.2(4) . . ?
C2_8 C1_8 C6_8 118.9(3) . . ?
F2_8 C2_8 C1_8 120.2(3) . . ?
F2_8 C2_8 C3_8 118.3(4) . . ?
C1_8 C2_8 C3_8 121.5(3) . . ?
F3_8 C3_8 C2_8 120.6(3) . . ?
F3_8 C3_8 C4_8 120.0(3) . . ?
C2_8 C3_8 C4_8 119.4(3) . . ?
F4_8 C4_8 C5_8 119.5(3) . . ?
F4_8 C4_8 C3_8 121.0(3) . . ?
C5_8 C4_8 C3_8 119.5(3) . . ?
F5_8 C5_8 C4_8 119.6(3) . . ?
F5_8 C5_8 C6_8 119.9(3) . . ?
C4_8 C5_8 C6_8 120.5(3) . . ?
F6_8 C6_8 C1_8 120.1(3) . . ?
F6_8 C6_8 C5_8 119.8(3) . . ?
C1_8 C6_8 C5_8 120.1(3) . . ?
C1_9 N1_9 H1_9 107.2 . . ?
C1_9 N1_9 H2_9 105.3 . . ?
H1_9 N1_9 H2_9 120.1 . . ?
C2_9 C1_9 C6_9 116.8(3) . . ?
C2_9 C1_9 N1_9 121.9(3) . . ?
C6_9 C1_9 N1_9 121.3(3) . . ?
F2_9 C2_9 C1_9 119.6(3) . . ?
F2_9 C2_9 C3_9 118.1(3) . . ?
C1_9 C2_9 C3_9 122.2(3) . . ?
F3_9 C3_9 C4_9 120.0(3) . . ?
F3_9 C3_9 C2_9 120.4(3) . . ?
C4_9 C3_9 C2_9 119.6(3) . . ?
F4_9 C4_9 C5_9 120.1(3) . . ?
F4_9 C4_9 C3_9 120.1(3) . . ?
C5_9 C4_9 C3_9 119.8(3) . . ?
F5_9 C5_9 C4_9 120.4(3) . . ?
F5_9 C5_9 C6_9 120.0(3) . . ?
C4_9 C5_9 C6_9 119.6(3) . . ?
F6_9 C6_9 C1_9 118.9(3) . . ?
F6_9 C6_9 C5_9 119.1(3) . . ?
C1_9 C6_9 C5_9 122.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.804
_diffrn_reflns_theta_full        36.15
_diffrn_measured_fraction_theta_full 0.804
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.056


