# Supplementary Material (ESI) 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        'ProfD Pierangelo Metrangolo'
_publ_contact_author_email       PIERANGELO.METRANGOLO@POLIMI.IT

_publ_section_title              
;
Site selective supramolecular synthesis of halogen
bonded cocrystals incorporating the photoactive azo group

;
loop_
_publ_author_name
'Pierangelo Metrangolo'
'David Fox'
'Dario Pasini'
'Tullio Pilati'
'Giuseppe Resnati'
'Giancarlo Terraneo'

# Attachment '3a_revised.cif'

data_re110_3a
_database_code_depnum_ccdc_archive 'CCDC 685634'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
trans-4,4'-azobipyridine.
1,1,2,2,3,3,4,4,5,5,6,6-dodecafluoro-1,8-diiodooctane
;
_chemical_name_common            
;trans-4,4'-azobipyridine. 1,1,2,2,3,3,4,4,5,5,6,6-
dodecafluoro-1,8-diiodooctane
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N4, C6 F12 I2'
_chemical_formula_sum            'C16 H8 F12 I2 N4'
_chemical_formula_weight         738.06

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.2392(5)
_cell_length_b                   8.8344(9)
_cell_length_c                   11.5520(13)
_cell_angle_alpha                94.526(8)
_cell_angle_beta                 95.701(7)
_cell_angle_gamma                91.302(8)
_cell_volume                     530.13(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9860
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      29.88

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             346
_exptl_absorpt_coefficient_mu    3.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS,(Bruker, 1997)'
_exptl_absorpt_correction_T_min  0.406236
_exptl_absorpt_correction_T_max  0.548812

_exptl_special_details           
;
Crystal of this material were too large, but by cutting always we obtained
very bad champions. The crystal used for data collection was then reduced
at reasonable dimensions by partial melting in chloroform.
The crystal temperature was controlled by the Bruker KRIOFLEX low temperature
device.
;

_diffrn_ambient_temperature      153(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 CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            12026
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         29.99
_reflns_number_total             3089
_reflns_number_gt                2970
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
;
M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo,
G. Polidori, R. Spagna (2003).
SIR2002: the program. J. Appl. Cryst. 36,1103
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
ORTEP-III (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
and Mercury 1.4.2, CCDC
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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     
'w=1/[σ²(Fo²)+(0.0541P)²+0.3679P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3089
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0813
_refine_ls_wR_factor_gt          0.0807
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_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
I1 I 0.41055(3) 0.502189(16) 0.241119(13) 0.02030(7) Uani 1 1 d . . .
F1 F 0.7450(4) 0.3917(2) 0.06798(18) 0.0337(4) Uani 1 1 d . . .
F2 F 0.7999(4) 0.2755(2) 0.22715(18) 0.0351(5) Uani 1 1 d . . .
F3 F 0.3399(4) 0.1315(2) 0.17921(16) 0.0273(4) Uani 1 1 d . . .
F4 F 0.2590(4) 0.2517(2) 0.02275(16) 0.0284(4) Uani 1 1 d . . .
F5 F 0.6534(4) 0.1359(2) -0.07387(16) 0.0303(4) Uani 1 1 d . . .
F6 F 0.7945(3) 0.0320(2) 0.08406(16) 0.0275(4) Uani 1 1 d . . .
N1 N -0.4467(5) 0.9493(3) 0.5270(2) 0.0203(4) Uani 1 1 d . . .
N2 N 0.1191(5) 0.7121(3) 0.3602(2) 0.0245(5) Uani 1 1 d . . .
C1 C -0.2590(5) 0.8717(3) 0.4645(2) 0.0184(5) Uani 1 1 d . . .
C2 C -0.2164(6) 0.8913(3) 0.3500(2) 0.0237(5) Uani 1 1 d . . .
C3 C -0.0267(6) 0.8087(3) 0.3017(3) 0.0261(6) Uani 1 1 d . . .
C4 C 0.0752(6) 0.6941(3) 0.4699(3) 0.0252(5) Uani 1 1 d . . .
C5 C -0.1119(6) 0.7704(3) 0.5257(2) 0.0230(5) Uani 1 1 d . . .
C6 C 0.6199(5) 0.3315(3) 0.1506(2) 0.0210(5) Uani 1 1 d . . .
C7 C 0.4467(5) 0.1970(3) 0.0937(2) 0.0173(4) Uani 1 1 d . . .
C8 C 0.5825(5) 0.0730(3) 0.0205(2) 0.0170(4) Uani 1 1 d . . .
H2 H -0.313(8) 0.962(4) 0.307(3) 0.025(9) Uiso 1 1 d . . .
H3 H 0.013(8) 0.826(5) 0.223(4) 0.029(10) Uiso 1 1 d . . .
H4 H 0.188(8) 0.636(5) 0.510(3) 0.030(10) Uiso 1 1 d . . .
H5 H -0.135(8) 0.760(5) 0.604(4) 0.030(10) Uiso 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
I1 0.02134(11) 0.01583(10) 0.02306(11) -0.00463(6) 0.00377(7) 0.00107(6)
F1 0.0353(10) 0.0272(9) 0.0403(10) -0.0068(8) 0.0217(8) -0.0077(8)
F2 0.0278(9) 0.0355(10) 0.0366(10) -0.0126(8) -0.0142(8) 0.0125(8)
F3 0.0318(9) 0.0225(8) 0.0296(9) -0.0034(7) 0.0184(7) -0.0008(7)
F4 0.0240(9) 0.0260(8) 0.0317(9) -0.0069(7) -0.0092(7) 0.0115(7)
F5 0.0473(11) 0.0203(8) 0.0257(8) -0.0012(6) 0.0193(8) -0.0049(7)
F6 0.0171(8) 0.0270(8) 0.0355(9) -0.0096(7) -0.0041(7) 0.0077(6)
N1 0.0227(11) 0.0188(10) 0.0198(10) -0.0014(8) 0.0059(8) 0.0040(8)
N2 0.0242(12) 0.0204(10) 0.0284(12) -0.0039(9) 0.0054(9) 0.0023(9)
C1 0.0193(12) 0.0153(10) 0.0205(11) -0.0035(8) 0.0045(9) 0.0003(9)
C2 0.0279(14) 0.0240(13) 0.0200(12) 0.0014(10) 0.0057(10) 0.0071(11)
C3 0.0297(15) 0.0263(13) 0.0229(12) -0.0030(10) 0.0082(11) 0.0044(11)
C4 0.0236(13) 0.0198(12) 0.0322(14) -0.0001(10) 0.0031(11) 0.0062(10)
C5 0.0247(13) 0.0223(12) 0.0224(12) 0.0014(10) 0.0044(10) 0.0033(10)
C6 0.0176(12) 0.0202(12) 0.0240(12) -0.0040(9) 0.0014(9) 0.0014(9)
C7 0.0155(11) 0.0178(10) 0.0183(10) -0.0016(8) 0.0019(8) 0.0032(8)
C8 0.0163(11) 0.0175(11) 0.0176(10) -0.0014(8) 0.0047(8) 0.0030(9)

_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
I1 C6 2.151(3) . ?
F1 C6 1.345(3) . ?
F2 C6 1.357(3) . ?
F3 C7 1.345(3) . ?
F4 C7 1.340(3) . ?
F5 C8 1.342(3) . ?
F6 C8 1.343(3) . ?
N1 N1 1.243(5) 2_476 ?
N1 C1 1.432(3) . ?
N2 C4 1.331(4) . ?
N2 C3 1.336(4) . ?
C1 C5 1.385(4) . ?
C1 C2 1.387(4) . ?
C2 C3 1.382(4) . ?
C2 H2 0.95(4) . ?
C3 H3 0.98(4) . ?
C4 C5 1.385(4) . ?
C4 H4 0.91(4) . ?
C5 H5 0.94(4) . ?
C6 C7 1.541(4) . ?
C7 C8 1.559(3) . ?
C8 C8 1.551(5) 2_655 ?

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
N1 N1 C1 113.3(3) 2_476 . ?
C4 N2 C3 117.7(2) . . ?
C5 C1 C2 119.1(2) . . ?
C5 C1 N1 115.9(2) . . ?
C2 C1 N1 125.0(2) . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2 121(2) . . ?
C1 C2 H2 121(2) . . ?
N2 C3 C2 123.3(3) . . ?
N2 C3 H3 117(2) . . ?
C2 C3 H3 119(2) . . ?
N2 C4 C5 123.4(3) . . ?
N2 C4 H4 116(3) . . ?
C5 C4 H4 120(3) . . ?
C4 C5 C1 118.2(3) . . ?
C4 C5 H5 122(3) . . ?
C1 C5 H5 119(3) . . ?
F1 C6 F2 107.1(2) . . ?
F1 C6 C7 109.0(2) . . ?
F2 C6 C7 107.7(2) . . ?
F1 C6 I1 110.78(18) . . ?
F2 C6 I1 109.33(18) . . ?
C7 C6 I1 112.75(17) . . ?
F4 C7 F3 108.4(2) . . ?
F4 C7 C6 108.4(2) . . ?
F3 C7 C6 107.8(2) . . ?
F4 C7 C8 107.6(2) . . ?
F3 C7 C8 108.8(2) . . ?
C6 C7 C8 115.7(2) . . ?
F5 C8 F6 108.5(2) . . ?
F5 C8 C8 108.7(3) . 2_655 ?
F6 C8 C8 107.8(3) . 2_655 ?
F5 C8 C7 107.5(2) . . ?
F6 C8 C7 108.9(2) . . ?
C8 C8 C7 115.3(3) 2_655 . ?

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
N1 N1 C1 C5 172.4(3) 2_476 . . . ?
N1 N1 C1 C2 -7.5(5) 2_476 . . . ?
C5 C1 C2 C3 -0.3(4) . . . . ?
N1 C1 C2 C3 179.6(3) . . . . ?
C4 N2 C3 C2 0.9(5) . . . . ?
C1 C2 C3 N2 -0.6(5) . . . . ?
C3 N2 C4 C5 -0.2(5) . . . . ?
N2 C4 C5 C1 -0.7(5) . . . . ?
C2 C1 C5 C4 0.9(4) . . . . ?
N1 C1 C5 C4 -179.0(3) . . . . ?
F1 C6 C7 F4 -67.6(3) . . . . ?
F2 C6 C7 F4 176.5(2) . . . . ?
I1 C6 C7 F4 55.8(2) . . . . ?
F1 C6 C7 F3 175.2(2) . . . . ?
F2 C6 C7 F3 59.3(3) . . . . ?
I1 C6 C7 F3 -61.4(2) . . . . ?
F1 C6 C7 C8 53.2(3) . . . . ?
F2 C6 C7 C8 -62.6(3) . . . . ?
I1 C6 C7 C8 176.67(16) . . . . ?
F4 C7 C8 F5 53.7(3) . . . . ?
F3 C7 C8 F5 170.9(2) . . . . ?
C6 C7 C8 F5 -67.6(3) . . . . ?
F4 C7 C8 F6 171.0(2) . . . . ?
F3 C7 C8 F6 -71.7(3) . . . . ?
C6 C7 C8 F6 49.7(3) . . . . ?
F4 C7 C8 C8 -67.7(3) . . . 2_655 ?
F3 C7 C8 C8 49.6(3) . . . 2_655 ?
C6 C7 C8 C8 171.0(3) . . . 2_655 ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        29.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.759
_refine_diff_density_min         -2.784
_refine_diff_density_rms         0.183

# Attachment '3b_revised.cif'

data_re101_3b
_database_code_depnum_ccdc_archive 'CCDC 685635'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
trans-4,4'-azobipyridine
1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-hexadecafluoro-1,8-diiodooctane
;
_chemical_name_common            
;
trans-4,4'-azobipyridine 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-
hexadecafluoro-1,8-diiodooctane
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 F16 I2, C10 H8 N4'
_chemical_formula_sum            'C18 H8 F16 I2 N4'
_chemical_formula_weight         838.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.2482(7)
_cell_length_b                   8.6925(14)
_cell_length_c                   13.289(2)
_cell_angle_alpha                84.316(7)
_cell_angle_beta                 86.245(7)
_cell_angle_gamma                88.241(8)
_cell_volume                     601.79(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    6523
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      29.43

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale red'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             394
_exptl_absorpt_coefficient_mu    2.754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS,(Bruker, 1997)'
_exptl_absorpt_correction_T_min  0.67612
_exptl_absorpt_correction_T_max  0.818731

_exptl_special_details           
;
The crystal temperature was controlled by the Bruker KRIOFLEX low temperature
device.
;

_diffrn_ambient_temperature      153(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 CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            12848
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         30.00
_reflns_number_total             3491
_reflns_number_gt                3219
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
;
M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo,
G. Polidori, R. Spagna (2003).
SIR2002: the program. J. Appl. Cryst. 36,1103
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
ORTEP-III (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
and Mercury 1.4.2, CCDC
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0398P)²+0.2274P] 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         3491
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0642
_refine_ls_wR_factor_gt          0.0628
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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
I I 0.07045(3) 0.559270(16) 0.274102(11) 0.02192(6) Uani 1 1 d . . .
F1 F -0.2842(3) 0.48764(19) 0.12690(13) 0.0356(4) Uani 1 1 d . . .
F2 F -0.3059(3) 0.3253(2) 0.26248(13) 0.0361(4) Uani 1 1 d . . .
F3 F 0.2046(3) 0.36934(18) 0.07989(12) 0.0314(3) Uani 1 1 d . . .
F4 F 0.1549(3) 0.20173(17) 0.21245(12) 0.0292(3) Uani 1 1 d . . .
F5 F -0.2040(3) 0.26828(18) -0.00121(12) 0.0326(3) Uani 1 1 d . . .
F6 F -0.3007(3) 0.11529(19) 0.13436(12) 0.0332(4) Uani 1 1 d . . .
F7 F 0.2699(3) 0.1137(2) -0.01560(16) 0.0473(5) Uani 1 1 d . . .
F8 F 0.1432(5) -0.0420(2) 0.11444(14) 0.0516(6) Uani 1 1 d . . .
N1 N 0.9487(4) 0.9423(2) 0.52342(15) 0.0217(4) Uani 1 1 d . . .
C1 C 0.7556(4) 0.8799(3) 0.46840(17) 0.0205(4) Uani 1 1 d . . .
C2 C 0.6114(5) 0.7646(3) 0.52176(18) 0.0236(4) Uani 1 1 d . . .
C3 C 0.4198(5) 0.7014(3) 0.4735(2) 0.0266(5) Uani 1 1 d . . .
N2 N 0.3699(4) 0.7452(2) 0.37761(17) 0.0256(4) Uani 1 1 d . . .
C4 C 0.5135(5) 0.8558(3) 0.32688(19) 0.0276(5) Uani 1 1 d . . .
C5 C 0.7075(5) 0.9264(3) 0.36891(19) 0.0254(5) Uani 1 1 d . . .
C6 C -0.1432(4) 0.4058(3) 0.19511(17) 0.0220(4) Uani 1 1 d . . .
C7 C 0.0315(4) 0.2899(3) 0.14080(16) 0.0192(4) Uani 1 1 d . . .
C8 C -0.1065(4) 0.1821(3) 0.07647(16) 0.0190(4) Uani 1 1 d . . .
C9 C 0.0653(4) 0.0514(3) 0.03500(18) 0.0220(4) Uani 1 1 d . . .
H2 H 0.637(6) 0.728(4) 0.591(3) 0.034(8) Uiso 1 1 d . . .
H3 H 0.321(7) 0.627(4) 0.508(3) 0.033(8) Uiso 1 1 d . . .
H4 H 0.474(7) 0.883(4) 0.259(3) 0.037(9) Uiso 1 1 d . . .
H5 H 0.789(6) 0.997(3) 0.331(2) 0.021(7) Uiso 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
I 0.02315(8) 0.01957(8) 0.02442(9) -0.00768(5) -0.00324(5) -0.00142(5)
F1 0.0344(8) 0.0347(8) 0.0412(9) -0.0143(7) -0.0185(7) 0.0111(7)
F2 0.0335(8) 0.0392(9) 0.0367(9) -0.0166(7) 0.0156(7) -0.0167(7)
F3 0.0299(8) 0.0312(8) 0.0342(8) -0.0130(6) 0.0115(6) -0.0157(6)
F4 0.0334(8) 0.0261(7) 0.0309(7) -0.0086(6) -0.0176(6) 0.0042(6)
F5 0.0444(9) 0.0277(7) 0.0281(7) -0.0072(6) -0.0184(7) 0.0095(7)
F6 0.0274(7) 0.0390(9) 0.0352(8) -0.0161(7) 0.0091(6) -0.0179(6)
F7 0.0265(8) 0.0483(10) 0.0721(13) -0.0383(10) 0.0179(8) -0.0182(7)
F8 0.0872(15) 0.0335(9) 0.0400(10) -0.0155(8) -0.0412(10) 0.0233(10)
N1 0.0239(9) 0.0204(9) 0.0217(9) -0.0040(7) -0.0044(7) -0.0008(7)
C1 0.0215(10) 0.0189(10) 0.0220(10) -0.0063(8) -0.0035(8) 0.0022(8)
C2 0.0248(11) 0.0226(11) 0.0233(11) -0.0006(8) -0.0036(8) -0.0004(8)
C3 0.0256(11) 0.0202(11) 0.0343(13) -0.0028(9) -0.0015(9) -0.0039(9)
N2 0.0239(9) 0.0244(10) 0.0308(10) -0.0105(8) -0.0058(8) -0.0024(8)
C4 0.0323(13) 0.0276(12) 0.0244(11) -0.0052(9) -0.0086(9) -0.0033(10)
C5 0.0314(12) 0.0218(11) 0.0233(11) -0.0016(9) -0.0034(9) -0.0065(9)
C6 0.0193(10) 0.0267(11) 0.0209(10) -0.0061(8) -0.0017(8) -0.0021(8)
C7 0.0178(9) 0.0206(10) 0.0197(9) -0.0041(8) -0.0009(7) -0.0044(8)
C8 0.0187(9) 0.0209(10) 0.0182(9) -0.0038(8) -0.0030(7) -0.0040(8)
C9 0.0202(10) 0.0229(10) 0.0249(11) -0.0071(8) -0.0073(8) -0.0023(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
I C6 2.159(2) . ?
F1 C6 1.343(3) . ?
F2 C6 1.354(3) . ?
F3 C7 1.337(2) . ?
F4 C7 1.349(3) . ?
F5 C8 1.335(3) . ?
F6 C8 1.346(3) . ?
F7 C9 1.329(3) . ?
F8 C9 1.344(3) . ?
N1 N1 1.245(4) 2_776 ?
N1 C1 1.437(3) . ?
C1 C5 1.381(3) . ?
C1 C2 1.384(3) . ?
C2 C3 1.383(3) . ?
C2 H2 0.97(3) . ?
C3 N2 1.333(3) . ?
C3 H3 0.91(3) . ?
N2 C4 1.340(3) . ?
C4 C5 1.380(3) . ?
C4 H4 0.95(4) . ?
C5 H5 0.86(3) . ?
C6 C7 1.542(3) . ?
C7 C8 1.554(3) . ?
C8 C9 1.550(3) . ?
C9 C9 1.555(4) 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
N1 N1 C1 113.0(2) 2_776 . ?
C5 C1 C2 119.4(2) . . ?
C5 C1 N1 125.0(2) . . ?
C2 C1 N1 115.6(2) . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2 119(2) . . ?
C1 C2 H2 123(2) . . ?
N2 C3 C2 123.0(2) . . ?
N2 C3 H3 117(2) . . ?
C2 C3 H3 120(2) . . ?
C3 N2 C4 117.7(2) . . ?
N2 C4 C5 123.4(2) . . ?
N2 C4 H4 115(2) . . ?
C5 C4 H4 121(2) . . ?
C4 C5 C1 118.0(2) . . ?
C4 C5 H5 117(2) . . ?
C1 C5 H5 125(2) . . ?
F1 C6 F2 107.51(19) . . ?
F1 C6 C7 109.12(18) . . ?
F2 C6 C7 108.54(19) . . ?
F1 C6 I 110.20(16) . . ?
F2 C6 I 109.11(15) . . ?
C7 C6 I 112.23(14) . . ?
F3 C7 F4 108.44(18) . . ?
F3 C7 C6 108.48(18) . . ?
F4 C7 C6 107.45(18) . . ?
F3 C7 C8 108.23(17) . . ?
F4 C7 C8 108.65(18) . . ?
C6 C7 C8 115.40(18) . . ?
F5 C8 F6 108.24(19) . . ?
F5 C8 C9 108.97(18) . . ?
F6 C8 C9 107.75(18) . . ?
F5 C8 C7 108.51(18) . . ?
F6 C8 C7 108.54(17) . . ?
C9 C8 C7 114.67(18) . . ?
F7 C9 F8 108.4(2) . . ?
F7 C9 C8 108.91(19) . . ?
F8 C9 C8 108.04(19) . . ?
F7 C9 C9 108.6(2) . 2 ?
F8 C9 C9 107.3(2) . 2 ?
C8 C9 C9 115.3(2) . 2 ?

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
N1 N1 C1 C5 8.4(4) 2_776 . . . ?
N1 N1 C1 C2 -171.8(2) 2_776 . . . ?
C5 C1 C2 C3 -1.1(4) . . . . ?
N1 C1 C2 C3 179.1(2) . . . . ?
C1 C2 C3 N2 0.8(4) . . . . ?
C2 C3 N2 C4 -0.1(4) . . . . ?
C3 N2 C4 C5 -0.4(4) . . . . ?
N2 C4 C5 C1 0.1(4) . . . . ?
C2 C1 C5 C4 0.7(4) . . . . ?
N1 C1 C5 C4 -179.5(2) . . . . ?
F1 C6 C7 F3 67.8(2) . . . . ?
F2 C6 C7 F3 -175.37(18) . . . . ?
I C6 C7 F3 -54.7(2) . . . . ?
F1 C6 C7 F4 -175.20(18) . . . . ?
F2 C6 C7 F4 -58.3(2) . . . . ?
I C6 C7 F4 62.35(19) . . . . ?
F1 C6 C7 C8 -53.8(3) . . . . ?
F2 C6 C7 C8 63.0(2) . . . . ?
I C6 C7 C8 -176.29(14) . . . . ?
F3 C7 C8 F5 -55.5(2) . . . . ?
F4 C7 C8 F5 -173.07(18) . . . . ?
C6 C7 C8 F5 66.2(2) . . . . ?
F3 C7 C8 F6 -172.92(18) . . . . ?
F4 C7 C8 F6 69.5(2) . . . . ?
C6 C7 C8 F6 -51.2(2) . . . . ?
F3 C7 C8 C9 66.6(2) . . . . ?
F4 C7 C8 C9 -51.0(2) . . . . ?
C6 C7 C8 C9 -171.70(19) . . . . ?
F5 C8 C9 F7 67.9(2) . . . . ?
F6 C8 C9 F7 -174.93(19) . . . . ?
C7 C8 C9 F7 -54.0(3) . . . . ?
F5 C8 C9 F8 -174.60(19) . . . . ?
F6 C8 C9 F8 -57.4(2) . . . . ?
C7 C8 C9 F8 63.6(2) . . . . ?
F5 C8 C9 C9 -54.6(3) . . . 2 ?
F6 C8 C9 C9 62.7(3) . . . 2 ?
C7 C8 C9 C9 -176.4(2) . . . 2 ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.203
_refine_diff_density_min         -0.923
_refine_diff_density_rms         0.115


