#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/25/2212540.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2212540
loop_
_publ_author_name
'Batsanov, Andrei S.'
'Mkhalid, Ibraheem A. I.'
'Marder, Todd B.'
_publ_section_title
;
 4,4'-Di-tert-butyl-2,2'-bipyridine--hexafluorobenzene (1/1)
;
_journal_coeditor_code           FB2037
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1196
_journal_page_last               o1198
_journal_paper_doi               10.1107/S160053680700445X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C18 H24 N2 , C6 F6'
_chemical_formula_moiety         'C18 H24 N2 , C6 F6'
_chemical_formula_sum            'C24 H24 F6 N2'
_chemical_formula_weight         454.45
_chemical_name_systematic
;
4,4'-Di-tert-butyl-2,2'-bipyridine--hexafluorobenzene (1/1)
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.730(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.5150(7)
_cell_length_b                   6.6964(5)
_cell_length_c                   19.2756(18)
_cell_measurement_reflns_used    4097
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.45
_cell_volume                     1072.08(16)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2003)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART 6K CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0474
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            12337
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.204
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    50
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0836P)²+0.0675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1378
_reflns_number_gt                1962
_reflns_number_total             2669
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fb2037.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2212540
_cod_database_fobs_code          2212540
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.6571(2) 0.7500 0.82701(10) 0.0336(4) Uani d S 1
C C2 0.5633(2) 0.7500 0.75872(11) 0.0339(4) Uani d S 1
C C3 0.6353(3) 0.7500 0.70135(10) 0.0336(4) Uani d S 1
C C4 0.7999(3) 0.7500 0.71175(10) 0.0341(4) Uani d S 1
C C5 0.8943(2) 0.7500 0.77986(10) 0.0335(4) Uani d S 1
C C6 0.8220(2) 0.7500 0.83733(10) 0.0331(4) Uani d S 1
F F1 0.58793(15) 0.7500 0.88277(6) 0.0465(3) Uani d S 1
F F2 0.40304(15) 0.7500 0.74889(7) 0.0482(3) Uani d S 1
F F3 0.54412(16) 0.7500 0.63522(6) 0.0459(3) Uani d S 1
F F4 0.86995(17) 0.7500 0.65629(6) 0.0468(3) Uani d S 1
F F5 1.05383(15) 0.7500 0.78996(7) 0.0475(3) Uani d S 1
F F6 0.91353(15) 0.7500 0.90366(6) 0.0446(3) Uani d S 1
N N11 0.32420(17) 0.7500 0.17729(8) 0.0274(3) Uani d S 1
C C12 0.2315(2) 0.7500 0.22505(9) 0.0231(4) Uani d S 1
C C13 0.0633(2) 0.7500 0.20553(9) 0.0250(4) Uani d S 1
H H13 0.0020 0.7500 0.2412 0.030 Uiso d SR 1
C C14 -0.0145(2) 0.7500 0.13405(9) 0.0268(4) Uani d S 1
C C15 0.0835(2) 0.7500 0.08478(9) 0.0302(4) Uani d S 1
H H15 0.0368 0.7500 0.0352 0.036 Uiso d SR 1
C C16 0.2491(2) 0.7500 0.10847(9) 0.0303(4) Uani d S 1
H H16 0.3133 0.7500 0.0739 0.036 Uiso d SR 1
C C17 -0.1979(2) 0.7500 0.10838(9) 0.0326(4) Uani d S 1
C C19 -0.2816(2) 0.7500 0.17042(11) 0.0534(7) Uani d S 1
H H191 -0.3986 0.7500 0.1524 0.054(4) Uiso d SR 1
H H192 -0.2500 0.8687 0.2000 0.054(4) Uiso d R 1
N N21 0.22538(18) 0.7500 0.34977(8) 0.0270(3) Uani d S 1
C C22 0.3176(2) 0.7500 0.30150(8) 0.0223(4) Uani d S 1
C C23 0.4850(2) 0.7500 0.32017(9) 0.0238(4) Uani d S 1
H H23 0.5451 0.7500 0.2841 0.029 Uiso d SR 1
C C24 0.5657(2) 0.7500 0.39175(9) 0.0246(4) Uani d S 1
C C25 0.4695(2) 0.7500 0.44138(9) 0.0298(4) Uani d S 1
H H25 0.5171 0.7500 0.4908 0.036 Uiso d SR 1
C C26 0.3029(2) 0.7500 0.41801(9) 0.0307(4) Uani d S 1
H H26 0.2398 0.7500 0.4530 0.037 Uiso d SR 1
C C27 0.7500(2) 0.7500 0.41172(9) 0.0276(4) Uani d S 1
C C29 0.8142(2) 0.7500 0.49233(10) 0.0369(5) Uani d S 1
H H291 0.9322 0.7500 0.5034 0.048(4) Uiso d SR 1
H H292 0.7745 0.6315 0.5129 0.048(4) Uiso d R 1
C C18 -0.24974(16) 0.9365(2) 0.06286(8) 0.0419(4) Uani d . 1
H H181 -0.3670 0.9364 0.0459 0.054(3) Uiso d R 1
H H182 -0.1984 0.9360 0.0221 0.054(3) Uiso d R 1
H H183 -0.2168 1.0564 0.0916 0.054(3) Uiso d R 1
C C28 0.81300(15) 0.5629(2) 0.38063(7) 0.0354(3) Uani d . 1
H H281 0.9310 0.5641 0.3921 0.043(2) Uiso d R 1
H H282 0.7737 0.5617 0.3289 0.043(2) Uiso d R 1
H H283 0.7744 0.4433 0.4011 0.043(2) Uiso d R 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
F1 C1 C6 . . 120.10(17)
F1 C1 C2 . . 120.18(19)
C6 C1 C2 . . 119.72(19)
F2 C2 C3 . . 120.51(17)
F2 C2 C1 . . 119.55(18)
C3 C2 C1 . . 119.94(19)
F3 C3 C4 . . 119.93(18)
F3 C3 C2 . . 119.82(19)
C4 C3 C2 . . 120.25(17)
F4 C4 C3 . . 120.39(17)
F4 C4 C5 . . 119.50(19)
C3 C4 C5 . . 120.11(19)
F5 C5 C4 . . 120.11(19)
F5 C5 C6 . . 120.30(17)
C4 C5 C6 . . 119.59(19)
F6 C6 C1 . . 119.87(17)
F6 C6 C5 . . 119.73(18)
C1 C6 C5 . . 120.39(17)
C12 N11 C16 . . 117.11(14)
N11 C12 C13 . . 122.64(15)
N11 C12 C22 . . 116.28(14)
C13 C12 C22 . . 121.08(15)
C14 C13 C12 . . 120.17(16)
C14 C13 H13 . . 119.9
C12 C13 H13 . . 119.9
C13 C14 C15 . . 116.62(16)
C13 C14 C17 . . 123.34(15)
C15 C14 C17 . . 120.05(15)
C16 C15 C14 . . 119.63(16)
C16 C15 H15 . . 120.2
C14 C15 H15 . . 120.2
N11 C16 C15 . . 123.83(16)
N11 C16 H16 . . 118.1
C15 C16 H16 . . 118.1
C19 C17 C14 . . 111.54(15)
C19 C17 C18 . 4_575 108.91(11)
C14 C17 C18 . 4_575 109.22(10)
C19 C17 C18 . . 108.91(11)
C14 C17 C18 . . 109.22(10)
C18 C17 C18 4_575 . 109.00(16)
C17 C19 H191 . . 109.7
C17 C19 H192 . . 109.9
H191 C19 H192 . . 109.5
C26 N21 C22 . . 116.41(15)
N21 C22 C23 . . 122.88(15)
N21 C22 C12 . . 116.63(14)
C23 C22 C12 . . 120.48(15)
C22 C23 C24 . . 120.48(15)
C22 C23 H23 . . 119.8
C24 C23 H23 . . 119.8
C25 C24 C23 . . 116.31(15)
C25 C24 C27 . . 123.63(15)
C23 C24 C27 . . 120.06(15)
C24 C25 C26 . . 119.40(16)
C24 C25 H25 . . 120.3
C26 C25 H25 . . 120.3
N21 C26 C25 . . 124.52(16)
N21 C26 H26 . . 117.7
C25 C26 H26 . . 117.8
C29 C27 C24 . . 111.87(15)
C29 C27 C28 . . 108.61(10)
C24 C27 C28 . . 109.18(9)
C29 C27 C28 . 4_575 108.61(10)
C24 C27 C28 . 4_575 109.18(9)
C28 C27 C28 . 4_575 109.35(16)
C27 C29 H291 . . 110.0
C27 C29 H292 . . 109.5
H291 C29 H292 . . 109.9
C17 C18 H181 . . 109.5
C17 C18 H182 . . 109.4
H181 C18 H182 . . 109.5
C17 C18 H183 . . 109.5
H181 C18 H183 . . 109.5
H182 C18 H183 . . 109.5
C27 C28 H281 . . 109.5
C27 C28 H282 . . 109.5
H281 C28 H282 . . 109.5
C27 C28 H283 . . 109.4
H281 C28 H283 . . 109.5
H282 C28 H283 . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 F1 . 1.334(2)
C1 C6 . 1.374(3)
C1 C2 . 1.381(3)
C2 F2 . 1.336(2)
C2 C3 . 1.377(3)
C3 F3 . 1.338(2)
C3 C4 . 1.371(3)
C4 F4 . 1.334(2)
C4 C5 . 1.380(3)
C5 F5 . 1.329(2)
C5 C6 . 1.381(3)
C6 F6 . 1.343(2)
N11 C12 . 1.338(2)
N11 C16 . 1.340(2)
C12 C13 . 1.399(2)
C12 C22 . 1.494(2)
C13 C14 . 1.391(2)
C13 H13 . 0.9500
C14 C15 . 1.396(2)
C14 C17 . 1.531(2)
C15 C16 . 1.382(3)
C15 H15 . 0.9500
C16 H16 . 0.9500
C17 C19 . 1.521(3)
C17 C18 4_575 1.5343(18)
C17 C18 . 1.5343(18)
C19 H191 . 0.9800
C19 H192 . 0.9800
N21 C26 . 1.335(2)
N21 C22 . 1.343(2)
C22 C23 . 1.391(2)
C23 C24 . 1.399(2)
C23 H23 . 0.9500
C24 C25 . 1.390(2)
C24 C27 . 1.531(2)
C25 C26 . 1.390(3)
C25 H25 . 0.9500
C26 H26 . 0.9500
C27 C29 . 1.529(2)
C27 C28 . 1.5359(17)
C27 C28 4_575 1.5360(17)
C29 H291 . 0.9800
C29 H292 . 0.9800
C18 H181 . 0.9800
C18 H182 . 0.9800
C18 H183 . 0.9800
C28 H281 . 0.9800
C28 H282 . 0.9800
C28 H283 . 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C13 H13 N21 . 0.95 2.50 2.819(2) 99.7
C23 H23 N11 . 0.95 2.46 2.793(2) 100.2
C15 H15 F6 1_454 0.95 2.52 3.472(2) 179.8
C25 H25 F3 . 0.95 2.74 3.649(2) 160.1
C19 H191 N11 1_455 0.98 2.51 3.388(2) 149.0
