#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:56:56 +0100 (jue 24 de mar de 2016) $
#$Revision: 179605 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/69/4506958.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4506958
loop_
_publ_author_name
'Sun, Haoran'
'Tottempudi, Usha K.'
'Mottishaw, Jeffery D.'
'Basa, Prem N.'
'Putta, Anjaneyulu'
'Sykes, Andrew G.'
_publ_section_title
;
 Strengthening π--π Interactions While Suppressing
 Csp2--H···π (T-Shaped) Interactions via
 Perfluoroalkylation: A Crystallographic and Computational Study That
 Supports the Beneficial Formation of 1-D π--π Stacked Aromatic
 Materials
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5655
_journal_paper_doi               10.1021/cg301151u
_journal_volume                  12
_journal_year                    2012
_chemical_formula_moiety         'C18 H6 F18 N2'
_chemical_formula_sum            'C18 H6 F18 N2'
_chemical_formula_weight         592.25
_chemical_name_common            4,4'-di-perfluorobutyl-2,2'-bipyridine
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.068(3)
_cell_angle_beta                 85.602(3)
_cell_angle_gamma                88.840(3)
_cell_formula_units_Z            1
_cell_length_a                   5.0202(15)
_cell_length_b                   5.2709(16)
_cell_length_c                   18.535(6)
_cell_measurement_reflns_used    4197
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.39
_cell_measurement_theta_min      2.21
_cell_volume                     487.2(3)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'Bruker APEXII (Bruker, 2006)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'Ortep3 for Windows (Farrugia, 1997)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR 97'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4427
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  0.9762
_exptl_absorpt_correction_T_min  0.9310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.019
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             290.0
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1691
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0347
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0383P)²+0.3814P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0896
_reflns_number_gt                1591
_reflns_number_total             1716
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301151u_si_002.cif
_cod_data_source_block           11077
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        487.1(3)
_cod_database_code               4506958
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
F1 F 0.1919(2) 0.4960(2) 0.79066(6) 0.0210(3) Uani 1 1 d .
F2 F 0.6143(2) 0.3862(2) 0.77740(6) 0.0217(3) Uani 1 1 d .
F3 F 0.5074(2) -0.0068(2) 0.70551(6) 0.0224(3) Uani 1 1 d .
F4 F 0.0781(2) 0.0288(2) 0.73309(6) 0.0227(3) Uani 1 1 d .
F5 F 0.1491(3) -0.0004(3) 0.58280(7) 0.0318(3) Uani 1 1 d .
F6 F 0.0337(2) 0.4510(2) 0.65233(6) 0.0264(3) Uani 1 1 d .
F7 F 0.5559(3) 0.1280(3) 0.56311(6) 0.0316(3) Uani 1 1 d .
F8 F 0.4623(2) 0.5207(2) 0.64242(6) 0.0252(3) Uani 1 1 d .
F9 F 0.2344(3) 0.3608(3) 0.52235(6) 0.0323(3) Uani 1 1 d .
N1 N 0.2760(3) -0.2147(3) 0.98124(8) 0.0179(4) Uani 1 1 d .
C1 C 0.3332(4) 0.1169(4) 0.85596(10) 0.0170(4) Uani 1 1 d .
C2 C 0.4743(4) -0.2442(4) 0.93021(10) 0.0183(4) Uani 1 1 d .
H1 H 0.5954 -0.3832 0.9376 0.022 Uiso 1 1 calc R
C3 C 0.5137(4) -0.0831(4) 0.86688(10) 0.0177(4) Uani 1 1 d .
H2 H 0.6593 -0.1091 0.8323 0.021 Uiso 1 1 calc R
C4 C 0.1070(4) -0.0166(4) 0.97063(10) 0.0167(4) Uani 1 1 d .
C5 C 0.1266(4) 0.1518(4) 0.90802(10) 0.0174(4) Uani 1 1 d .
H3 H 0.0008 0.2873 0.9014 0.021 Uiso 1 1 calc R
C6 C 0.3621(4) 0.2935(4) 0.78708(10) 0.0179(4) Uani 1 1 d .
C7 C 0.3064(4) 0.1600(4) 0.71824(10) 0.0177(4) Uani 1 1 d .
C8 C 0.2755(4) 0.3397(4) 0.64800(10) 0.0198(4) Uani 1 1 d .
C9 C 0.3054(4) 0.2012(4) 0.57745(11) 0.0241(5) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0269(6) 0.0179(6) 0.0180(6) 0.0003(4) -0.0027(5) 0.0028(5)
F2 0.0216(6) 0.0249(6) 0.0187(6) 0.0008(5) -0.0032(4) -0.0058(5)
F3 0.0279(6) 0.0225(6) 0.0173(6) -0.0026(5) -0.0055(5) 0.0064(5)
F4 0.0257(6) 0.0242(6) 0.0182(6) 0.0027(5) -0.0054(5) -0.0076(5)
F5 0.0423(8) 0.0325(7) 0.0220(6) -0.0030(5) -0.0092(5) -0.0085(6)
F6 0.0255(7) 0.0313(7) 0.0214(6) 0.0039(5) -0.0040(5) 0.0084(5)
F7 0.0306(7) 0.0453(8) 0.0190(6) -0.0052(5) -0.0019(5) 0.0081(6)
F8 0.0322(7) 0.0235(6) 0.0193(6) 0.0041(5) -0.0037(5) -0.0063(5)
F9 0.0424(8) 0.0379(8) 0.0160(6) 0.0060(5) -0.0089(5) 0.0033(6)
N1 0.0209(9) 0.0177(8) 0.0155(8) -0.0002(6) -0.0053(6) 0.0008(7)
C1 0.0192(10) 0.0183(10) 0.0142(9) -0.0013(7) -0.0063(7) -0.0029(8)
C2 0.0195(10) 0.0182(10) 0.0175(9) -0.0012(7) -0.0058(7) 0.0031(8)
C3 0.0191(10) 0.0196(10) 0.0150(9) -0.0026(7) -0.0030(7) -0.0014(8)
C4 0.0188(10) 0.0182(10) 0.0137(9) -0.0016(7) -0.0054(8) -0.0027(7)
C5 0.0190(10) 0.0171(10) 0.0167(9) -0.0014(7) -0.0057(7) 0.0008(8)
C6 0.0174(10) 0.0189(10) 0.0172(9) -0.0005(8) -0.0023(7) -0.0004(8)
C7 0.0184(10) 0.0181(10) 0.0162(9) 0.0013(8) -0.0029(7) 0.0000(8)
C8 0.0210(10) 0.0205(11) 0.0176(10) 0.0026(8) -0.0033(8) -0.0001(8)
C9 0.0289(12) 0.0277(12) 0.0158(10) 0.0023(8) -0.0059(8) 0.0006(9)
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'
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_3
C2 N1 C4 117.68(17) .
C5 C1 C3 119.56(18) .
C5 C1 C6 120.49(18) .
C3 C1 C6 119.94(17) .
N1 C2 C3 123.78(18) .
N1 C2 H1 118.1 .
C3 C2 H1 118.1 .
C1 C3 C2 117.74(18) .
C1 C3 H2 121.1 .
C2 C3 H2 121.1 .
N1 C4 C5 122.68(17) .
N1 C4 C4 116.6(2) 2_557
C5 C4 C4 120.7(2) 2_557
C1 C5 C4 118.52(18) .
C1 C5 H3 120.7 .
C4 C5 H3 120.7 .
F1 C6 F2 107.32(15) .
F1 C6 C1 111.26(15) .
F2 C6 C1 109.87(15) .
F1 C6 C7 107.36(15) .
F2 C6 C7 107.98(15) .
C1 C6 C7 112.85(16) .
F3 C7 F4 108.40(15) .
F3 C7 C6 107.94(15) .
F4 C7 C6 107.82(15) .
F3 C7 C8 108.90(15) .
F4 C7 C8 107.86(15) .
C6 C7 C8 115.73(16) .
F6 C8 F8 108.94(16) .
F6 C8 C9 108.13(16) .
F8 C8 C9 107.57(16) .
F6 C8 C7 108.91(15) .
F8 C8 C7 109.54(15) .
C9 C8 C7 113.66(17) .
F7 C9 F5 109.25(18) .
F7 C9 F9 108.33(17) .
F5 C9 F9 108.56(17) .
F7 C9 C8 110.88(16) .
F5 C9 C8 110.83(17) .
F9 C9 C8 108.93(17) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C6 1.356(2) .
F2 C6 1.360(2) .
F3 C7 1.345(2) .
F4 C7 1.348(2) .
F5 C9 1.326(3) .
F6 C8 1.337(2) .
F7 C9 1.322(3) .
F8 C8 1.343(2) .
F9 C9 1.332(2) .
N1 C2 1.336(3) .
N1 C4 1.343(3) .
C1 C5 1.382(3) .
C1 C3 1.388(3) .
C1 C6 1.513(3) .
C2 C3 1.392(3) .
C2 H1 0.9500 .
C3 H2 0.9500 .
C4 C5 1.398(3) .
C4 C4 1.488(4) 2_557
C5 H3 0.9500 .
C6 C7 1.555(3) .
C7 C8 1.559(3) .
C8 C9 1.548(3) .
