# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global

_journal_coden_Cambridge         1350
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Akiko Hori'
'Miki Hasegawa'
'Takeshi Miyamoto'
'Shohei Takatani'

_publ_contact_author_name        'Akiko Hori'
_publ_contact_author_email       HORI@KITASATO-U.AC.JP

_publ_section_title              
;
Luminescence from pi-pi stacked bipyridines through
arene-perfluoroarene interactions
;

data_CCDC699205
_database_code_depnum_ccdc_archive 'CCDC 699205'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

4,4'-bis(pentafluorophenylethnyl)-2,2'-bipyridine

;

_chemical_name_common            
4,4'-bis(pentafluorophenylethnyl)-2,2'-bipyridine

_chemical_melting_point          ?

_chemical_formula_moiety         'C26 H6 F10 N2'

_chemical_formula_sum            'C26 H6 F10 N2'

_chemical_formula_weight         536.33

loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source

C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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                   5.8933(7)

_cell_length_b                   7.9383(9)

_cell_length_c                   11.0988(13)

_cell_angle_alpha                88.1100(10)

_cell_angle_beta                 84.5460(10)

_cell_angle_gamma                89.8360(10)

_cell_volume                     516.60(10)

_cell_formula_units_Z            1

_cell_measurement_temperature    100

_cell_measurement_reflns_used    1383

_cell_measurement_theta_min      2.57

_cell_measurement_theta_max      26.34

_exptl_crystal_description       plate

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.25

_exptl_crystal_size_mid          0.15

_exptl_crystal_size_min          0.06

_exptl_crystal_density_diffrn    1.724

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             266

_exptl_absorpt_coefficient_mu    0.166

_exptl_absorpt_correction_type   empirical

_exptl_absorpt_correction_T_min  0.9597

_exptl_absorpt_correction_T_max  0.9901

_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      100

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'

_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            2730

_diffrn_reflns_av_R_equivalents  0.0220

_diffrn_reflns_av_sigmaI/netI    0.0283

_diffrn_reflns_limit_h_min       -4

_diffrn_reflns_limit_h_max       7

_diffrn_reflns_limit_k_min       -9

_diffrn_reflns_limit_k_max       9

_diffrn_reflns_limit_l_min       -13

_diffrn_reflns_limit_l_max       13

_diffrn_reflns_theta_min         2.57

_diffrn_reflns_theta_max         26.34

_reflns_number_total             2043

_reflns_number_gt                1724

_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'

_computing_cell_refinement       'Bruker SAINT'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;

Refinement of F² against ALL reflections. The weighted R-factor wR and

goodness of fit S are based on F², conventional R-factors R are based

on F, with F set to zero for negative F². The threshold expression of

F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F² are statistically about twice as large as those based on F, and R-

factors based on ALL data will be even larger.

;

_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0546P)²+0.1458P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         2043

_refine_ls_number_parameters     172

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0430

_refine_ls_R_factor_gt           0.0351

_refine_ls_wR_factor_ref         0.1004

_refine_ls_wR_factor_gt          0.0944

_refine_ls_goodness_of_fit_ref   1.067

_refine_ls_restrained_S_all      1.067

_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

N1 N 0.7400(2) 0.62020(16) 0.50391(11) 0.0211(3) Uani 1 1 d . . .
C1 C 0.9303(2) 0.55336(17) 0.54332(12) 0.0173(3) Uani 1 1 d . . .
C2 C 0.9979(2) 0.58045(18) 0.65793(12) 0.0183(3) Uani 1 1 d . . .
H2 H 1.1356 0.5332 0.6819 0.022 Uiso 1 1 calc R . .
C3 C 0.8590(2) 0.67859(18) 0.73692(13) 0.0189(3) Uani 1 1 d . . .
C4 C 0.6584(3) 0.74515(19) 0.69752(13) 0.0226(3) Uani 1 1 d . . .
H4 H 0.5583 0.8106 0.7494 0.027 Uiso 1 1 calc R . .
C5 C 0.6087(3) 0.7132(2) 0.58044(14) 0.0244(3) Uani 1 1 d . . .
H5 H 0.4734 0.7603 0.5534 0.029 Uiso 1 1 calc R . .
C6 C 0.9213(2) 0.71111(18) 0.85595(13) 0.0200(3) Uani 1 1 d . . .
C7 C 0.9704(2) 0.74064(18) 0.95499(13) 0.0197(3) Uani 1 1 d . . .
C8 C 1.0212(2) 0.77842(17) 1.07414(13) 0.0181(3) Uani 1 1 d . . .
C9 C 1.2207(2) 0.72265(18) 1.12107(13) 0.0190(3) Uani 1 1 d . . .
C10 C 1.2664(2) 0.75766(18) 1.23737(13) 0.0195(3) Uani 1 1 d . . .
C11 C 1.1132(2) 0.85065(18) 1.30978(12) 0.0195(3) Uani 1 1 d . . .
C12 C 0.9151(2) 0.90856(18) 1.26626(13) 0.0190(3) Uani 1 1 d . . .
C13 C 0.8713(2) 0.87311(18) 1.14985(13) 0.0180(3) Uani 1 1 d . . .
F1 F 1.37140(15) 0.63267(11) 1.05272(8) 0.0275(2) Uani 1 1 d . . .
F2 F 1.45550(14) 0.69882(11) 1.28156(8) 0.0271(2) Uani 1 1 d . . .
F3 F 1.15702(15) 0.88411(11) 1.42247(7) 0.0264(2) Uani 1 1 d . . .
F4 F 0.76690(15) 0.99980(11) 1.33617(8) 0.0268(2) Uani 1 1 d . . .
F5 F 0.68008(14) 0.93439(11) 1.10830(8) 0.0236(2) 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

N1 C5 1.334(2) . ?
N1 C1 1.3433(19) . ?
C1 C2 1.392(2) . ?
C1 C1 1.489(3) 2_766 ?
C2 C3 1.397(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(2) . ?
C3 C6 1.436(2) . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.194(2) . ?
C7 C8 1.4248(19) . ?
C8 C13 1.396(2) . ?
C8 C9 1.396(2) . ?
C9 F1 1.3334(16) . ?
C9 C10 1.380(2) . ?
C10 F2 1.3367(16) . ?
C10 C11 1.380(2) . ?
C11 F3 1.3362(15) . ?
C11 C12 1.377(2) . ?
C12 F4 1.3395(16) . ?
C12 C13 1.379(2) . ?
C13 F5 1.3419(16) . ?

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

C5 N1 C1 117.61(13) . . ?
N1 C1 C2 123.13(13) . . ?
N1 C1 C1 116.17(15) . 2_766 ?
C2 C1 C1 120.69(16) . 2_766 ?
C1 C2 C3 118.58(13) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 118.56(13) . . ?
C4 C3 C6 120.59(13) . . ?
C2 C3 C6 120.85(13) . . ?
C5 C4 C3 118.30(13) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
N1 C5 C4 123.80(14) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C7 C6 C3 178.79(16) . . ?
C6 C7 C8 177.97(16) . . ?
C13 C8 C9 116.82(13) . . ?
C13 C8 C7 121.07(13) . . ?
C9 C8 C7 122.11(13) . . ?
F1 C9 C10 118.79(12) . . ?
F1 C9 C8 119.61(13) . . ?
C10 C9 C8 121.60(13) . . ?
F2 C10 C11 119.59(13) . . ?
F2 C10 C9 120.53(13) . . ?
C11 C10 C9 119.86(13) . . ?
F3 C11 C12 120.00(13) . . ?
F3 C11 C10 119.86(13) . . ?
C12 C11 C10 120.14(13) . . ?
F4 C12 C11 120.22(12) . . ?
F4 C12 C13 120.25(13) . . ?
C11 C12 C13 119.53(13) . . ?
F5 C13 C12 118.51(13) . . ?
F5 C13 C8 119.44(12) . . ?
C12 C13 C8 122.04(13) . . ?

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

C5 N1 C1 C2 -1.7(2) . . . . ?
C5 N1 C1 C1 178.47(15) . . . 2_766 ?
N1 C1 C2 C3 1.5(2) . . . . ?
C1 C1 C2 C3 -178.67(15) 2_766 . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C1 C2 C3 C6 -179.71(13) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C6 C3 C4 C5 178.50(14) . . . . ?
C1 N1 C5 C4 0.4(2) . . . . ?
C3 C4 C5 N1 1.1(2) . . . . ?
C4 C3 C6 C7 -19(8) . . . . ?
C2 C3 C6 C7 160(8) . . . . ?
C3 C6 C7 C8 29(11) . . . . ?
C6 C7 C8 C13 -7(4) . . . . ?
C6 C7 C8 C9 173(4) . . . . ?
C13 C8 C9 F1 -179.50(12) . . . . ?
C7 C8 C9 F1 0.8(2) . . . . ?
C13 C8 C9 C10 0.8(2) . . . . ?
C7 C8 C9 C10 -178.91(13) . . . . ?
F1 C9 C10 F2 -1.6(2) . . . . ?
C8 C9 C10 F2 178.07(12) . . . . ?
F1 C9 C10 C11 179.94(12) . . . . ?
C8 C9 C10 C11 -0.4(2) . . . . ?
F2 C10 C11 F3 1.4(2) . . . . ?
C9 C10 C11 F3 179.80(12) . . . . ?
F2 C10 C11 C12 -178.45(12) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
F3 C11 C12 F4 0.6(2) . . . . ?
C10 C11 C12 F4 -179.56(12) . . . . ?
F3 C11 C12 C13 -179.90(12) . . . . ?
C10 C11 C12 C13 -0.1(2) . . . . ?
F4 C12 C13 F5 1.1(2) . . . . ?
C11 C12 C13 F5 -178.34(12) . . . . ?
F4 C12 C13 C8 -179.95(12) . . . . ?
C11 C12 C13 C8 0.6(2) . . . . ?
C9 C8 C13 F5 178.00(12) . . . . ?
C7 C8 C13 F5 -2.3(2) . . . . ?
C9 C8 C13 C12 -0.9(2) . . . . ?
C7 C8 C13 C12 178.80(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.967

_diffrn_reflns_theta_full        26.34

_diffrn_measured_fraction_theta_full 0.967

_refine_diff_density_max         0.232

_refine_diff_density_min         -0.292

_refine_diff_density_rms         0.070

# Attachment 'B818880G_CCDC699206.cif'

data_CCDC699206
_database_code_depnum_ccdc_archive 'CCDC 699206'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

4,4'-diphenylethnyl-2,2'-bipyridine,
4,4'-bis(pentafluorophenylethnyl)-2,2'-bipyridine, benzene

;

_chemical_name_common            
;
4,4'-diphenylethnyl-2,2'-bipyridine, 4,4'-
bis(pentafluorophenylethnyl)-2,2'-bipyridine, benzene
;

_chemical_melting_point          ?

_chemical_formula_moiety         'C26 H6 F10 N2, C26 H16 N2, 0.5(C6 H6)'

_chemical_formula_sum            'C55 H25 F10 N4'

_chemical_formula_weight         931.79

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'

_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                   7.463(2)

_cell_length_b                   15.200(5)

_cell_length_c                   18.460(6)

_cell_angle_alpha                95.369(4)

_cell_angle_beta                 90.520(4)

_cell_angle_gamma                92.737(4)

_cell_volume                     2082.3(11)

_cell_formula_units_Z            2

_cell_measurement_temperature    100

_cell_measurement_reflns_used    2369

_cell_measurement_theta_min      2.48

_cell_measurement_theta_max      26.31

_exptl_crystal_description       prismatic

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.35

_exptl_crystal_size_mid          0.25

_exptl_crystal_size_min          0.08

_exptl_crystal_density_diffrn    1.486

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             946

_exptl_absorpt_coefficient_mu    0.119

_exptl_absorpt_correction_type   empirical

_exptl_absorpt_correction_T_min  0.9595

_exptl_absorpt_correction_T_max  0.9905

_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      100

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'

_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            11010

_diffrn_reflns_av_R_equivalents  0.0225

_diffrn_reflns_av_sigmaI/netI    0.0589

_diffrn_reflns_limit_h_min       -9

_diffrn_reflns_limit_h_max       8

_diffrn_reflns_limit_k_min       -16

_diffrn_reflns_limit_k_max       18

_diffrn_reflns_limit_l_min       -20

_diffrn_reflns_limit_l_max       23

_diffrn_reflns_theta_min         1.35

_diffrn_reflns_theta_max         26.38

_reflns_number_total             8261

_reflns_number_gt                5067

_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'

_computing_cell_refinement       'Bruker SAINT'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;

Refinement of F² against ALL reflections. The weighted R-factor wR and

goodness of fit S are based on F², conventional R-factors R are based

on F, with F set to zero for negative F². The threshold expression of

F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F² are statistically about twice as large as those based on F, and R-

factors based on ALL data will be even larger.

;

_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0726P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         8261

_refine_ls_number_parameters     622

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0999

_refine_ls_R_factor_gt           0.0494

_refine_ls_wR_factor_ref         0.1435

_refine_ls_wR_factor_gt          0.1115

_refine_ls_goodness_of_fit_ref   0.989

_refine_ls_restrained_S_all      0.989

_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

N2 N 0.6087(3) 1.07738(13) 0.06877(11) 0.0220(5) Uani 1 1 d . . .
N1 N 0.1141(3) 1.07681(13) 0.06739(11) 0.0221(5) Uani 1 1 d . . .
N3 N -0.1176(3) 0.40296(13) -0.04464(10) 0.0211(5) Uani 1 1 d . . .
N4 N 0.3951(3) 0.40067(13) -0.04593(10) 0.0197(5) Uani 1 1 d . . .
C15 C 0.5119(3) 0.92509(16) 0.07518(13) 0.0208(6) Uani 1 1 d . . .
H15 H 0.4586 0.8719 0.0515 0.025 Uiso 1 1 calc R . .
C14 C 0.5319(3) 0.99997(16) 0.03845(13) 0.0205(5) Uani 1 1 d . . .
C1 C 0.0332(3) 1.00064(16) 0.03824(13) 0.0208(5) Uani 1 1 d . . .
C13 C 0.0582(3) 0.72370(16) 0.33946(13) 0.0223(6) Uani 1 1 d . . .
C22 C 0.4339(3) 0.63343(16) 0.22919(14) 0.0243(6) Uani 1 1 d . . .
H22 H 0.4044 0.6277 0.1788 0.029 Uiso 1 1 calc R . .
C8 C 0.0036(3) 0.71998(16) 0.26674(13) 0.0212(6) Uani 1 1 d . . .
C4 C 0.1590(3) 1.00860(16) 0.17821(14) 0.0238(6) Uani 1 1 d . . .
H4 H 0.2046 1.0138 0.2267 0.029 Uiso 1 1 calc R . .
C5 C 0.1750(3) 1.07906(17) 0.13607(14) 0.0242(6) Uani 1 1 d . . .
H5 H 0.2328 1.1325 0.1572 0.029 Uiso 1 1 calc R . .
C9 C -0.0790(3) 0.64037(16) 0.23704(13) 0.0210(6) Uani 1 1 d . . .
C24 C 0.4507(3) 0.57011(17) 0.34311(14) 0.0267(6) Uani 1 1 d . . .
H24 H 0.4313 0.5208 0.3705 0.032 Uiso 1 1 calc R . .
C26 C 0.5492(3) 0.72120(17) 0.33685(14) 0.0251(6) Uani 1 1 d . . .
H26 H 0.5992 0.7755 0.3598 0.030 Uiso 1 1 calc R . .
C16 C 0.5706(3) 0.92821(16) 0.14740(13) 0.0212(6) Uani 1 1 d . . .
C11 C -0.0545(3) 0.57629(16) 0.34895(13) 0.0215(6) Uani 1 1 d . . .
C18 C 0.6654(3) 1.07897(16) 0.13816(14) 0.0241(6) Uani 1 1 d . . .
H18 H 0.7206 1.1325 0.1604 0.029 Uiso 1 1 calc R . .
C23 C 0.4080(3) 0.56242(16) 0.26939(14) 0.0256(6) Uani 1 1 d . . .
H23 H 0.3604 0.5076 0.2465 0.031 Uiso 1 1 calc R . .
C19 C 0.5484(3) 0.85258(16) 0.18757(14) 0.0229(6) Uani 1 1 d . . .
C7 C 0.0304(3) 0.79346(17) 0.22500(13) 0.0226(6) Uani 1 1 d . . .
C25 C 0.5216(3) 0.64962(17) 0.37677(14) 0.0266(6) Uani 1 1 d . . .
H25 H 0.5511 0.6548 0.4272 0.032 Uiso 1 1 calc R . .
C2 C 0.0117(3) 0.92589(16) 0.07582(13) 0.0216(6) Uani 1 1 d . . .
H2 H -0.0447 0.8730 0.0530 0.026 Uiso 1 1 calc R . .
C12 C 0.0310(3) 0.65337(17) 0.37985(13) 0.0217(6) Uani 1 1 d . . .
C17 C 0.6486(3) 1.00773(16) 0.17923(14) 0.0238(6) Uani 1 1 d . . .
H17 H 0.6896 1.0129 0.2284 0.029 Uiso 1 1 calc R . .
C6 C 0.0512(3) 0.85498(17) 0.18939(13) 0.0237(6) Uani 1 1 d . . .
C3 C 0.0742(3) 0.92956(16) 0.14771(13) 0.0210(6) Uani 1 1 d . . .
C21 C 0.5041(3) 0.71444(16) 0.26284(13) 0.0222(6) Uani 1 1 d . . .
C10 C -0.1072(3) 0.56945(16) 0.27688(13) 0.0213(5) Uani 1 1 d . . .
C20 C 0.5294(3) 0.78946(17) 0.22187(13) 0.0235(6) Uani 1 1 d . . .
C47 C 0.5409(3) 0.27328(16) 0.29548(12) 0.0189(5) Uani 1 1 d . . .
C48 C 0.6176(3) 0.33935(16) 0.34519(13) 0.0215(6) Uani 1 1 d . . .
H48 H 0.6448 0.3966 0.3304 0.026 Uiso 1 1 calc R . .
C49 C 0.6544(3) 0.32221(17) 0.41598(13) 0.0247(6) Uani 1 1 d . . .
H49 H 0.7056 0.3677 0.4497 0.030 Uiso 1 1 calc R . .
C51 C 0.5413(3) 0.17222(17) 0.38851(14) 0.0258(6) Uani 1 1 d . . .
H51 H 0.5154 0.1149 0.4035 0.031 Uiso 1 1 calc R . .
C27 C -0.0318(3) 0.45492(15) 0.00875(13) 0.0194(5) Uani 1 1 d . . .
C50 C 0.6163(3) 0.23849(17) 0.43754(13) 0.0252(6) Uani 1 1 d . . .
H50 H 0.6419 0.2266 0.4861 0.030 Uiso 1 1 calc R . .
C40 C 0.4712(3) 0.45473(15) 0.00861(13) 0.0177(5) Uani 1 1 d . . .
C52 C 0.5037(3) 0.18905(16) 0.31768(13) 0.0214(6) Uani 1 1 d . . .
H52 H 0.4525 0.1433 0.2842 0.026 Uiso 1 1 calc R . .
C41 C 0.4974(3) 0.42867(15) 0.07817(12) 0.0183(5) Uani 1 1 d . . .
H41 H 0.5518 0.4686 0.1155 0.022 Uiso 1 1 calc R . .
C31 C -0.1707(3) 0.32116(16) -0.03035(13) 0.0220(6) Uani 1 1 d . . .
H31 H -0.2300 0.2838 -0.0682 0.026 Uiso 1 1 calc R . .
C43 C 0.3618(3) 0.28696(16) 0.03562(13) 0.0192(5) Uani 1 1 d . . .
H43 H 0.3215 0.2283 0.0432 0.023 Uiso 1 1 calc R . .
C46 C 0.5016(3) 0.29326(16) 0.22265(13) 0.0205(5) Uani 1 1 d . . .
C45 C 0.4720(3) 0.31428(15) 0.16286(13) 0.0197(5) Uani 1 1 d . . .
C29 C -0.0579(3) 0.34175(16) 0.09142(13) 0.0197(5) Uani 1 1 d . . .
C34 C 0.0429(3) 0.27104(16) 0.29414(13) 0.0192(5) Uani 1 1 d . . .
C33 C 0.0021(3) 0.29011(16) 0.22162(13) 0.0214(6) Uani 1 1 d . . .
C44 C 0.3418(3) 0.31895(16) -0.03149(13) 0.0203(5) Uani 1 1 d . . .
H44 H 0.2868 0.2805 -0.0697 0.024 Uiso 1 1 calc R . .
C35 C 0.1284(3) 0.33471(16) 0.34295(13) 0.0215(6) Uani 1 1 d . . .
C36 C 0.1694(3) 0.31937(17) 0.41337(13) 0.0231(6) Uani 1 1 d . . .
C42 C 0.4425(3) 0.34296(15) 0.09193(12) 0.0176(5) Uani 1 1 d . . .
C39 C -0.0012(3) 0.18968(16) 0.32040(13) 0.0204(5) Uani 1 1 d . . .
C30 C -0.1450(3) 0.28735(16) 0.03571(13) 0.0225(6) Uani 1 1 d . . .
H30 H -0.1856 0.2287 0.0429 0.027 Uiso 1 1 calc R . .
C38 C 0.0405(3) 0.17283(16) 0.39011(13) 0.0237(6) Uani 1 1 d . . .
C28 C 0.0002(3) 0.42716(16) 0.07741(13) 0.0213(6) Uani 1 1 d . . .
H28 H 0.0606 0.4658 0.1141 0.026 Uiso 1 1 calc R . .
C32 C -0.0263(3) 0.31227(16) 0.16223(14) 0.0211(6) Uani 1 1 d . . .
C37 C 0.1267(3) 0.23765(17) 0.43669(13) 0.0238(6) Uani 1 1 d . . .
C54 C 0.3232(4) 0.98075(19) 0.47958(18) 0.0414(8) Uani 1 1 d . . .
H54 H 0.2014 0.9675 0.4655 0.050 Uiso 1 1 calc R . .
C55 C 0.3642(4) 1.03637(19) 0.54115(19) 0.0446(8) Uani 1 1 d . . .
H55 H 0.2708 1.0615 0.5696 0.053 Uiso 1 1 calc R . .
C53 C 0.4581(4) 0.94420(19) 0.43829(18) 0.0434(8) Uani 1 1 d . . .
H53 H 0.4296 0.9057 0.3958 0.052 Uiso 1 1 calc R . .
F4 F 0.08652(19) 0.65801(10) 0.44952(7) 0.0324(4) Uani 1 1 d . . .
F6 F 0.17538(19) 0.41394(9) 0.32072(8) 0.0291(4) Uani 1 1 d . . .
F5 F 0.13812(19) 0.79827(10) 0.37141(8) 0.0324(4) Uani 1 1 d . . .
F2 F -0.18709(19) 0.49379(9) 0.24610(8) 0.0304(4) Uani 1 1 d . . .
F9 F -0.0023(2) 0.09379(9) 0.41295(8) 0.0340(4) Uani 1 1 d . . .
F1 F -0.13580(19) 0.63305(9) 0.16794(7) 0.0287(4) Uani 1 1 d . . .
F8 F 0.1697(2) 0.22119(10) 0.50462(7) 0.0343(4) Uani 1 1 d . . .
F7 F 0.25057(19) 0.38343(10) 0.45882(8) 0.0329(4) Uani 1 1 d . . .
F10 F -0.08571(18) 0.12555(9) 0.27646(7) 0.0275(4) Uani 1 1 d . . .
F3 F -0.08714(19) 0.50877(9) 0.38924(8) 0.0317(4) 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

N2 C18 1.343(3) . ?
N2 C14 1.354(3) . ?
N1 C5 1.340(3) . ?
N1 C1 1.344(3) . ?
N3 C31 1.337(3) . ?
N3 C27 1.342(3) . ?
N4 C44 1.338(3) . ?
N4 C40 1.342(3) . ?
C15 C14 1.381(3) . ?
C15 C16 1.396(3) . ?
C15 H15 0.9500 . ?
C14 C14 1.493(5) 2_675 ?
C1 C2 1.389(3) . ?
C1 C1 1.490(5) 2_575 ?
C13 F5 1.339(3) . ?
C13 C12 1.368(3) . ?
C13 C8 1.395(3) . ?
C22 C23 1.373(3) . ?
C22 C21 1.402(3) . ?
C22 H22 0.9500 . ?
C8 C9 1.394(3) . ?
C8 C7 1.423(3) . ?
C4 C5 1.383(3) . ?
C4 C3 1.399(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C9 F1 1.334(3) . ?
C9 C10 1.370(3) . ?
C24 C25 1.385(3) . ?
C24 C23 1.388(3) . ?
C24 H24 0.9500 . ?
C26 C25 1.379(3) . ?
C26 C21 1.397(3) . ?
C26 H26 0.9500 . ?
C16 C17 1.392(3) . ?
C16 C19 1.429(4) . ?
C11 F3 1.337(3) . ?
C11 C10 1.377(3) . ?
C11 C12 1.379(3) . ?
C18 C17 1.380(3) . ?
C18 H18 0.9500 . ?
C23 H23 0.9500 . ?
C19 C20 1.202(3) . ?
C7 C6 1.197(3) . ?
C25 H25 0.9500 . ?
C2 C3 1.398(3) . ?
C2 H2 0.9500 . ?
C12 F4 1.342(3) . ?
C17 H17 0.9500 . ?
C6 C3 1.433(3) . ?
C21 C20 1.432(4) . ?
C10 F2 1.344(3) . ?
C47 C48 1.393(3) . ?
C47 C52 1.397(3) . ?
C47 C46 1.437(3) . ?
C48 C49 1.384(3) . ?
C48 H48 0.9500 . ?
C49 C50 1.386(3) . ?
C49 H49 0.9500 . ?
C51 C50 1.383(3) . ?
C51 C52 1.384(3) . ?
C51 H51 0.9500 . ?
C27 C28 1.395(3) . ?
C27 C27 1.494(5) 2_565 ?
C50 H50 0.9500 . ?
C40 C41 1.394(3) . ?
C40 C40 1.486(5) 2_665 ?
C52 H52 0.9500 . ?
C41 C42 1.394(3) . ?
C41 H41 0.9500 . ?
C31 C30 1.382(3) . ?
C31 H31 0.9500 . ?
C43 C44 1.382(3) . ?
C43 C42 1.394(3) . ?
C43 H43 0.9500 . ?
C46 C45 1.199(3) . ?
C45 C42 1.437(3) . ?
C29 C30 1.393(3) . ?
C29 C28 1.397(3) . ?
C29 C32 1.442(3) . ?
C34 C35 1.387(3) . ?
C34 C39 1.396(3) . ?
C34 C33 1.429(3) . ?
C33 C32 1.197(3) . ?
C44 H44 0.9500 . ?
C35 F6 1.340(3) . ?
C35 C36 1.376(3) . ?
C36 F7 1.342(3) . ?
C36 C37 1.376(4) . ?
C39 F10 1.338(3) . ?
C39 C38 1.371(3) . ?
C30 H30 0.9500 . ?
C38 F9 1.336(3) . ?
C38 C37 1.377(3) . ?
C28 H28 0.9500 . ?
C37 F8 1.341(3) . ?
C54 C55 1.375(4) . ?
C54 C53 1.375(4) . ?
C54 H54 0.9500 . ?
C55 C53 1.386(4) 2_676 ?
C55 H55 0.9500 . ?
C53 C55 1.386(4) 2_676 ?
C53 H53 0.9500 . ?

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

C18 N2 C14 116.5(2) . . ?
C5 N1 C1 117.2(2) . . ?
C31 N3 C27 117.4(2) . . ?
C44 N4 C40 117.5(2) . . ?
C14 C15 C16 119.4(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
N2 C14 C15 123.2(2) . . ?
N2 C14 C14 115.6(3) . 2_675 ?
C15 C14 C14 121.2(3) . 2_675 ?
N1 C1 C2 123.1(2) . . ?
N1 C1 C1 116.4(3) . 2_575 ?
C2 C1 C1 120.6(3) . 2_575 ?
F5 C13 C12 118.5(2) . . ?
F5 C13 C8 119.5(2) . . ?
C12 C13 C8 122.0(2) . . ?
C23 C22 C21 119.8(2) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C9 C8 C13 116.4(2) . . ?
C9 C8 C7 121.7(2) . . ?
C13 C8 C7 121.9(2) . . ?
C5 C4 C3 118.4(2) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N1 C5 C4 124.2(2) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
F1 C9 C10 118.5(2) . . ?
F1 C9 C8 119.2(2) . . ?
C10 C9 C8 122.2(2) . . ?
C25 C24 C23 120.1(2) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C25 C26 C21 120.5(2) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
C17 C16 C15 117.8(2) . . ?
C17 C16 C19 121.3(2) . . ?
C15 C16 C19 120.9(2) . . ?
F3 C11 C10 120.3(2) . . ?
F3 C11 C12 119.9(2) . . ?
C10 C11 C12 119.9(2) . . ?
N2 C18 C17 124.1(2) . . ?
N2 C18 H18 117.9 . . ?
C17 C18 H18 117.9 . . ?
C22 C23 C24 120.6(2) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C20 C19 C16 179.4(3) . . ?
C6 C7 C8 179.2(3) . . ?
C26 C25 C24 119.8(2) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C1 C2 C3 119.1(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
F4 C12 C13 121.0(2) . . ?
F4 C12 C11 119.1(2) . . ?
C13 C12 C11 119.9(2) . . ?
C18 C17 C16 118.9(2) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C7 C6 C3 179.0(3) . . ?
C2 C3 C4 118.0(2) . . ?
C2 C3 C6 121.2(2) . . ?
C4 C3 C6 120.7(2) . . ?
C26 C21 C22 119.3(2) . . ?
C26 C21 C20 120.3(2) . . ?
C22 C21 C20 120.4(2) . . ?
F2 C10 C9 120.3(2) . . ?
F2 C10 C11 120.1(2) . . ?
C9 C10 C11 119.6(2) . . ?
C19 C20 C21 179.2(3) . . ?
C48 C47 C52 119.2(2) . . ?
C48 C47 C46 119.4(2) . . ?
C52 C47 C46 121.5(2) . . ?
C49 C48 C47 120.5(2) . . ?
C49 C48 H48 119.7 . . ?
C47 C48 H48 119.7 . . ?
C48 C49 C50 119.8(2) . . ?
C48 C49 H49 120.1 . . ?
C50 C49 H49 120.1 . . ?
C50 C51 C52 120.3(2) . . ?
C50 C51 H51 119.9 . . ?
C52 C51 H51 119.9 . . ?
N3 C27 C28 122.6(2) . . ?
N3 C27 C27 116.8(3) . 2_565 ?
C28 C27 C27 120.6(3) . 2_565 ?
C51 C50 C49 120.1(2) . . ?
C51 C50 H50 119.9 . . ?
C49 C50 H50 119.9 . . ?
N4 C40 C41 122.7(2) . . ?
N4 C40 C40 116.6(3) . 2_665 ?
C41 C40 C40 120.6(3) . 2_665 ?
C51 C52 C47 120.0(2) . . ?
C51 C52 H52 120.0 . . ?
C47 C52 H52 120.0 . . ?
C40 C41 C42 118.8(2) . . ?
C40 C41 H41 120.6 . . ?
C42 C41 H41 120.6 . . ?
N3 C31 C30 124.4(2) . . ?
N3 C31 H31 117.8 . . ?
C30 C31 H31 117.8 . . ?
C44 C43 C42 118.3(2) . . ?
C44 C43 H43 120.9 . . ?
C42 C43 H43 120.9 . . ?
C45 C46 C47 176.7(3) . . ?
C46 C45 C42 177.3(3) . . ?
C30 C29 C28 118.4(2) . . ?
C30 C29 C32 122.0(2) . . ?
C28 C29 C32 119.7(2) . . ?
C35 C34 C39 116.3(2) . . ?
C35 C34 C33 120.6(2) . . ?
C39 C34 C33 123.2(2) . . ?
C32 C33 C34 175.1(3) . . ?
N4 C44 C43 124.0(2) . . ?
N4 C44 H44 118.0 . . ?
C43 C44 H44 118.0 . . ?
F6 C35 C36 118.5(2) . . ?
F6 C35 C34 119.0(2) . . ?
C36 C35 C34 122.5(2) . . ?
F7 C36 C35 120.3(2) . . ?
F7 C36 C37 120.3(2) . . ?
C35 C36 C37 119.4(2) . . ?
C43 C42 C41 118.6(2) . . ?
C43 C42 C45 121.8(2) . . ?
C41 C42 C45 119.6(2) . . ?
F10 C39 C38 118.5(2) . . ?
F10 C39 C34 119.4(2) . . ?
C38 C39 C34 122.1(2) . . ?
C31 C30 C29 118.1(2) . . ?
C31 C30 H30 120.9 . . ?
C29 C30 H30 120.9 . . ?
F9 C38 C39 120.2(2) . . ?
F9 C38 C37 119.9(2) . . ?
C39 C38 C37 119.8(2) . . ?
C27 C28 C29 119.1(2) . . ?
C27 C28 H28 120.5 . . ?
C29 C28 H28 120.5 . . ?
C33 C32 C29 178.1(3) . . ?
F8 C37 C36 120.0(2) . . ?
F8 C37 C38 120.1(2) . . ?
C36 C37 C38 119.9(2) . . ?
C55 C54 C53 120.1(3) . . ?
C55 C54 H54 119.9 . . ?
C53 C54 H54 119.9 . . ?
C54 C55 C53 120.0(3) . 2_676 ?
C54 C55 H55 120.0 . . ?
C53 C55 H55 120.0 2_676 . ?
C54 C53 C55 119.9(3) . 2_676 ?
C54 C53 H53 120.1 . . ?
C55 C53 H53 120.1 2_676 . ?

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

C18 N2 C14 C15 -0.4(3) . . . . ?
C18 N2 C14 C14 179.4(2) . . . 2_675 ?
C16 C15 C14 N2 0.9(4) . . . . ?
C16 C15 C14 C14 -179.0(3) . . . 2_675 ?
C5 N1 C1 C2 -0.3(4) . . . . ?
C5 N1 C1 C1 -179.8(3) . . . 2_575 ?
F5 C13 C8 C9 -179.9(2) . . . . ?
C12 C13 C8 C9 -0.5(4) . . . . ?
F5 C13 C8 C7 0.0(4) . . . . ?
C12 C13 C8 C7 179.4(2) . . . . ?
C1 N1 C5 C4 -0.2(4) . . . . ?
C3 C4 C5 N1 0.0(4) . . . . ?
C13 C8 C9 F1 179.3(2) . . . . ?
C7 C8 C9 F1 -0.6(4) . . . . ?
C13 C8 C9 C10 0.6(4) . . . . ?
C7 C8 C9 C10 -179.3(2) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C14 C15 C16 C19 178.6(2) . . . . ?
C14 N2 C18 C17 -0.5(4) . . . . ?
C21 C22 C23 C24 0.0(4) . . . . ?
C25 C24 C23 C22 -0.6(4) . . . . ?
C17 C16 C19 C20 34(29) . . . . ?
C15 C16 C19 C20 -144(28) . . . . ?
C9 C8 C7 C6 30(24) . . . . ?
C13 C8 C7 C6 -150(23) . . . . ?
C21 C26 C25 C24 0.8(4) . . . . ?
C23 C24 C25 C26 0.2(4) . . . . ?
N1 C1 C2 C3 1.0(4) . . . . ?
C1 C1 C2 C3 -179.5(3) 2_575 . . . ?
F5 C13 C12 F4 -1.4(4) . . . . ?
C8 C13 C12 F4 179.2(2) . . . . ?
F5 C13 C12 C11 178.6(2) . . . . ?
C8 C13 C12 C11 -0.8(4) . . . . ?
F3 C11 C12 F4 2.6(3) . . . . ?
C10 C11 C12 F4 -178.0(2) . . . . ?
F3 C11 C12 C13 -177.4(2) . . . . ?
C10 C11 C12 C13 2.0(4) . . . . ?
N2 C18 C17 C16 1.0(4) . . . . ?
C15 C16 C17 C18 -0.5(4) . . . . ?
C19 C16 C17 C18 -179.4(2) . . . . ?
C8 C7 C6 C3 92(29) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C1 C2 C3 C6 178.4(2) . . . . ?
C5 C4 C3 C2 0.7(3) . . . . ?
C5 C4 C3 C6 -178.9(2) . . . . ?
C7 C6 C3 C2 -120(16) . . . . ?
C7 C6 C3 C4 59(16) . . . . ?
C25 C26 C21 C22 -1.3(4) . . . . ?
C25 C26 C21 C20 178.7(2) . . . . ?
C23 C22 C21 C26 0.9(4) . . . . ?
C23 C22 C21 C20 -179.1(2) . . . . ?
F1 C9 C10 F2 1.4(3) . . . . ?
C8 C9 C10 F2 -179.9(2) . . . . ?
F1 C9 C10 C11 -178.1(2) . . . . ?
C8 C9 C10 C11 0.6(4) . . . . ?
F3 C11 C10 F2 -2.0(4) . . . . ?
C12 C11 C10 F2 178.6(2) . . . . ?
F3 C11 C10 C9 177.5(2) . . . . ?
C12 C11 C10 C9 -1.9(4) . . . . ?
C16 C19 C20 C21 70(38) . . . . ?
C26 C21 C20 C19 -100(19) . . . . ?
C22 C21 C20 C19 80(19) . . . . ?
C52 C47 C48 C49 -0.8(4) . . . . ?
C46 C47 C48 C49 179.0(2) . . . . ?
C47 C48 C49 C50 0.6(4) . . . . ?
C31 N3 C27 C28 -1.1(3) . . . . ?
C31 N3 C27 C27 178.1(2) . . . 2_565 ?
C52 C51 C50 C49 0.0(4) . . . . ?
C48 C49 C50 C51 -0.2(4) . . . . ?
C44 N4 C40 C41 0.7(3) . . . . ?
C44 N4 C40 C40 -179.8(2) . . . 2_665 ?
C50 C51 C52 C47 -0.2(4) . . . . ?
C48 C47 C52 C51 0.6(4) . . . . ?
C46 C47 C52 C51 -179.2(2) . . . . ?
N4 C40 C41 C42 0.0(4) . . . . ?
C40 C40 C41 C42 -179.6(3) 2_665 . . . ?
C27 N3 C31 C30 0.9(4) . . . . ?
C48 C47 C46 C45 -1(5) . . . . ?
C52 C47 C46 C45 179(100) . . . . ?
C47 C46 C45 C42 20(9) . . . . ?
C35 C34 C33 C32 0(3) . . . . ?
C39 C34 C33 C32 180(100) . . . . ?
C40 N4 C44 C43 -0.6(4) . . . . ?
C42 C43 C44 N4 0.0(4) . . . . ?
C39 C34 C35 F6 179.5(2) . . . . ?
C33 C34 C35 F6 -1.2(4) . . . . ?
C39 C34 C35 C36 0.3(4) . . . . ?
C33 C34 C35 C36 179.6(2) . . . . ?
F6 C35 C36 F7 1.6(4) . . . . ?
C34 C35 C36 F7 -179.3(2) . . . . ?
F6 C35 C36 C37 -178.2(2) . . . . ?
C34 C35 C36 C37 0.9(4) . . . . ?
C44 C43 C42 C41 0.7(3) . . . . ?
C44 C43 C42 C45 -178.6(2) . . . . ?
C40 C41 C42 C43 -0.6(3) . . . . ?
C40 C41 C42 C45 178.6(2) . . . . ?
C46 C45 C42 C43 163(6) . . . . ?
C46 C45 C42 C41 -16(6) . . . . ?
C35 C34 C39 F10 179.3(2) . . . . ?
C33 C34 C39 F10 0.0(4) . . . . ?
C35 C34 C39 C38 -1.1(4) . . . . ?
C33 C34 C39 C38 179.6(2) . . . . ?
N3 C31 C30 C29 -0.1(4) . . . . ?
C28 C29 C30 C31 -0.6(3) . . . . ?
C32 C29 C30 C31 179.6(2) . . . . ?
F10 C39 C38 F9 0.3(3) . . . . ?
C34 C39 C38 F9 -179.3(2) . . . . ?
F10 C39 C38 C37 -179.7(2) . . . . ?
C34 C39 C38 C37 0.7(4) . . . . ?
N3 C27 C28 C29 0.5(4) . . . . ?
C27 C27 C28 C29 -178.7(3) 2_565 . . . ?
C30 C29 C28 C27 0.4(3) . . . . ?
C32 C29 C28 C27 -179.8(2) . . . . ?
C34 C33 C32 C29 -1(11) . . . . ?
C30 C29 C32 C33 -178(100) . . . . ?
C28 C29 C32 C33 2(9) . . . . ?
F7 C36 C37 F8 -1.4(4) . . . . ?
C35 C36 C37 F8 178.4(2) . . . . ?
F7 C36 C37 C38 178.8(2) . . . . ?
C35 C36 C37 C38 -1.3(4) . . . . ?
F9 C38 C37 F8 0.8(4) . . . . ?
C39 C38 C37 F8 -179.2(2) . . . . ?
F9 C38 C37 C36 -179.4(2) . . . . ?
C39 C38 C37 C36 0.6(4) . . . . ?
C53 C54 C55 C53 0.1(5) . . . 2_676 ?
C55 C54 C53 C55 -0.1(5) . . . 2_676 ?

_diffrn_measured_fraction_theta_max 0.968

_diffrn_reflns_theta_full        26.38

_diffrn_measured_fraction_theta_full 0.968

_refine_diff_density_max         0.323

_refine_diff_density_min         -0.237

_refine_diff_density_rms         0.066

# Attachment 'B818880G_CCDC699207.cif'

data_CCDC699207
_database_code_depnum_ccdc_archive 'CCDC 699207'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

4,4'-diphenylethnyl-2,2'-bipyridine, hexafluorobenzene

;

_chemical_formula_moiety         'C26 H16 N2, C6 F6'

_chemical_formula_sum            'C32 H16 F6 N2'

_chemical_formula_weight         542.47

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'

_symmetry_cell_setting           Monoclinic

_symmetry_space_group_name_H-M   P2(1)/c

loop_

_symmetry_equiv_pos_as_xyz

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

_cell_length_a                   10.7927(12)

_cell_length_b                   11.3308(13)

_cell_length_c                   10.4449(12)

_cell_angle_alpha                90.00

_cell_angle_beta                 107.4640(10)

_cell_angle_gamma                90.00

_cell_volume                     1218.4(2)

_cell_formula_units_Z            2

_cell_measurement_temperature    100

_cell_measurement_reflns_used    2497

_cell_measurement_theta_min      2.72

_cell_measurement_theta_max      27.51

_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.35

_exptl_crystal_size_mid          0.25

_exptl_crystal_size_min          0.08

_exptl_crystal_density_diffrn    1.479

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             552

_exptl_absorpt_coefficient_mu    0.119

_exptl_absorpt_correction_type   empirical

_exptl_absorpt_correction_T_min  0.9595

_exptl_absorpt_correction_T_max  0.9905

_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      100

_diffrn_radiation_wavelength     0.71073

_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker APEX-II CCD'

_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            6635

_diffrn_reflns_av_R_equivalents  0.0227

_diffrn_reflns_av_sigmaI/netI    0.0266

_diffrn_reflns_limit_h_min       -12

_diffrn_reflns_limit_h_max       14

_diffrn_reflns_limit_k_min       -14

_diffrn_reflns_limit_k_max       6

_diffrn_reflns_limit_l_min       -13

_diffrn_reflns_limit_l_max       13

_diffrn_reflns_theta_min         1.98

_diffrn_reflns_theta_max         27.94

_reflns_number_total             2778

_reflns_number_gt                2185

_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'

_computing_cell_refinement       'Bruker SAINT'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;

Refinement of F² against ALL reflections. The weighted R-factor wR and

goodness of fit S are based on F², conventional R-factors R are based

on F, with F set to zero for negative F². The threshold expression of

F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F² are statistically about twice as large as those based on F, and R-

factors based on ALL data will be even larger.

;

_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full

_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0551P)²+0.3980P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         2778

_refine_ls_number_parameters     181

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0513

_refine_ls_R_factor_gt           0.0367

_refine_ls_wR_factor_ref         0.1155

_refine_ls_wR_factor_gt          0.0965

_refine_ls_goodness_of_fit_ref   1.092

_refine_ls_restrained_S_all      1.092

_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

N1 N 0.53983(12) 0.15366(11) 0.03398(12) 0.0207(3) Uani 1 1 d . . .
C1 C 0.52761(13) 0.03873(12) 0.05933(13) 0.0171(3) Uani 1 1 d . . .
C2 C 0.56307(13) -0.00792(12) 0.18872(13) 0.0175(3) Uani 1 1 d . . .
H2 H 0.5524 -0.0897 0.2024 0.021 Uiso 1 1 calc R . .
C3 C 0.61437(13) 0.06688(13) 0.29785(14) 0.0174(3) Uani 1 1 d . . .
C4 C 0.62615(14) 0.18694(13) 0.27231(14) 0.0204(3) Uani 1 1 d . . .
H4 H 0.6596 0.2412 0.3437 0.024 Uiso 1 1 calc R . .
C5 C 0.58758(15) 0.22452(13) 0.13991(15) 0.0223(3) Uani 1 1 d . . .
H5 H 0.5956 0.3062 0.1232 0.027 Uiso 1 1 calc R . .
C6 C 0.65329(14) 0.02209(12) 0.43273(14) 0.0182(3) Uani 1 1 d . . .
C7 C 0.68662(14) -0.01398(12) 0.54583(14) 0.0184(3) Uani 1 1 d . . .
C8 C 0.72465(13) -0.05209(13) 0.68326(14) 0.0174(3) Uani 1 1 d . . .
C9 C 0.69476(14) -0.16581(13) 0.71751(15) 0.0211(3) Uani 1 1 d . . .
H9 H 0.6512 -0.2199 0.6493 0.025 Uiso 1 1 calc R . .
C10 C 0.72908(15) -0.19916(14) 0.85141(15) 0.0247(3) Uani 1 1 d . . .
H10 H 0.7088 -0.2763 0.8747 0.030 Uiso 1 1 calc R . .
C11 C 0.79286(15) -0.12057(15) 0.95162(15) 0.0255(3) Uani 1 1 d . . .
H11 H 0.8155 -0.1439 1.0431 0.031 Uiso 1 1 calc R . .
C12 C 0.82343(15) -0.00827(14) 0.91832(15) 0.0240(3) Uani 1 1 d . . .
H12 H 0.8674 0.0452 0.9870 0.029 Uiso 1 1 calc R . .
C13 C 0.79009(14) 0.02640(13) 0.78513(14) 0.0198(3) Uani 1 1 d . . .
H13 H 0.8115 0.1034 0.7627 0.024 Uiso 1 1 calc R . .
C14 C 0.95659(15) 0.46388(16) 0.86809(15) 0.0266(4) Uani 1 1 d . . .
C15 C 0.97032(15) 0.38282(15) 0.96984(16) 0.0269(4) Uani 1 1 d . . .
C16 C 1.01398(15) 0.41915(15) 1.10205(16) 0.0269(4) Uani 1 1 d . . .
F1 F 0.91364(10) 0.42879(10) 0.73991(9) 0.0396(3) Uani 1 1 d . . .
F2 F 0.93963(10) 0.26980(9) 0.94048(11) 0.0401(3) Uani 1 1 d . . .
F3 F 1.02636(10) 0.34059(10) 1.20070(10) 0.0379(3) 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

N1 C5 1.3387(18) . ?
N1 C1 1.3432(18) . ?
C1 C2 1.3935(19) . ?
C1 C1 1.489(3) 3_655 ?
C2 C3 1.3948(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.399(2) . ?
C3 C6 1.4364(19) . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.199(2) . ?
C7 C8 1.4359(19) . ?
C8 C9 1.401(2) . ?
C8 C13 1.404(2) . ?
C9 C10 1.388(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 F1 1.3390(17) . ?
C14 C16 1.377(2) 3_767 ?
C14 C15 1.379(2) . ?
C15 F2 1.335(2) . ?
C15 C16 1.381(2) . ?
C16 F3 1.3376(18) . ?
C16 C14 1.377(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

C5 N1 C1 117.05(12) . . ?
N1 C1 C2 122.97(13) . . ?
N1 C1 C1 116.47(15) . 3_655 ?
C2 C1 C1 120.55(16) . 3_655 ?
C1 C2 C3 119.23(13) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C2 C3 C4 118.12(13) . . ?
C2 C3 C6 120.96(13) . . ?
C4 C3 C6 120.92(13) . . ?
C5 C4 C3 118.13(13) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
N1 C5 C4 124.49(13) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
C7 C6 C3 179.17(16) . . ?
C6 C7 C8 177.35(15) . . ?
C9 C8 C13 119.43(13) . . ?
C9 C8 C7 120.89(13) . . ?
C13 C8 C7 119.67(13) . . ?
C10 C9 C8 119.72(14) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 120.46(14) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C12 C11 C10 120.08(14) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.21(14) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.10(14) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
F1 C14 C16 119.96(15) . 3_767 ?
F1 C14 C15 119.86(16) . . ?
C16 C14 C15 120.18(14) 3_767 . ?
F2 C15 C14 120.01(15) . . ?
F2 C15 C16 120.14(15) . . ?
C14 C15 C16 119.84(16) . . ?
F3 C16 C14 120.22(14) . 3_767 ?
F3 C16 C15 119.80(16) . . ?
C14 C16 C15 119.98(15) 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

C5 N1 C1 C2 -0.5(2) . . . . ?
C5 N1 C1 C1 179.05(15) . . . 3_655 ?
N1 C1 C2 C3 -0.3(2) . . . . ?
C1 C1 C2 C3 -179.92(15) 3_655 . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
C1 C2 C3 C6 -179.39(13) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
C6 C3 C4 C5 179.64(13) . . . . ?
C1 N1 C5 C4 0.8(2) . . . . ?
C3 C4 C5 N1 -0.2(2) . . . . ?
C2 C3 C6 C7 165(100) . . . . ?
C4 C3 C6 C7 -16(12) . . . . ?
C3 C6 C7 C8 49(13) . . . . ?
C6 C7 C8 C9 136(3) . . . . ?
C6 C7 C8 C13 -43(3) . . . . ?
C13 C8 C9 C10 0.5(2) . . . . ?
C7 C8 C9 C10 -178.00(14) . . . . ?
C8 C9 C10 C11 0.0(2) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C11 C12 C13 C8 0.3(2) . . . . ?
C9 C8 C13 C12 -0.7(2) . . . . ?
C7 C8 C13 C12 177.90(13) . . . . ?
F1 C14 C15 F2 -0.6(2) . . . . ?
C16 C14 C15 F2 178.89(14) 3_767 . . . ?
F1 C14 C15 C16 -179.66(13) . . . . ?
C16 C14 C15 C16 -0.1(3) 3_767 . . . ?
F2 C15 C16 F3 0.5(2) . . . . ?
C14 C15 C16 F3 179.51(13) . . . . ?
F2 C15 C16 C14 -178.88(14) . . . 3_767 ?
C14 C15 C16 C14 0.1(3) . . . 3_767 ?

_diffrn_measured_fraction_theta_max 0.949

_diffrn_reflns_theta_full        27.94

_diffrn_measured_fraction_theta_full 0.949

_refine_diff_density_max         0.304

_refine_diff_density_min         -0.226

_refine_diff_density_rms         0.049

_chemical_name_common            
"4,4'-diphenylethnyl-2,2'-bipyridine, hexafluorobenzene"


