#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/74/2227411.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_2227411
loop_
_publ_author_name
'Ma, Yajun'
'Liu, Buming'
'Xue, Chenghu'
_publ_section_title
;
 4-Phenyl-2,6-bis(4-tolyl)pyridine
;
_journal_coeditor_code           FB2207
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2322
_journal_paper_doi               10.1107/S1600536810031764
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C25 H21 N'
_chemical_formula_moiety         'C25 H21 N'
_chemical_formula_sum            'C25 H21 N'
_chemical_formula_weight         335.43
_chemical_name_systematic
;
4-Phenyl-2,6-bis(4-tolyl)pyridine
;
_space_group_IT_number           54
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2a 2ac'
_symmetry_space_group_name_H-M   'P c c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.234(3)
_cell_length_b                   12.0489(15)
_cell_length_c                   7.3601(10)
_cell_measurement_reflns_used    1019
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.32
_cell_measurement_theta_min      2.56
_cell_volume                     1883.1(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type
;
Bruker SMART APEX area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω 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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       2
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6295
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_correction_T_min  0.9839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.115
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    41
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0580
_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)+(0.0910P)²+0.1078P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1513
_refine_ls_wR_factor_ref         0.1785
_reflns_number_gt                1130
_reflns_number_total             1833
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fb2207.cif
_cod_data_source_block           I
_cod_database_code               2227411
_cod_database_fobs_code          2227411
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z'
'x+1/2, -y, -z+1/2'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'-x-1/2, y, z-1/2'
'x, -y, z-1/2'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.0000 0.63606(17) 0.2500 0.0650(6) Uani d S 1 . .
C C1 0.28100(10) 0.8434(2) 0.3583(5) 0.1274(12) Uani d . 1 . .
H H1A 0.3171 0.7958 0.3474 0.191 Uiso calc R 1 . .
H H1B 0.2811 0.8780 0.4758 0.191 Uiso calc R 1 . .
H H1C 0.2826 0.8994 0.2657 0.191 Uiso calc R 1 . .
C C2 0.22150(10) 0.7754(2) 0.3362(4) 0.0965(8) Uani d . 1 . .
C C3 0.16260(9) 0.81731(18) 0.3759(4) 0.0895(8) Uani d . 1 . .
H H3 0.1591 0.8899 0.4179 0.107 Uiso calc R 1 . .
C C4 0.10883(9) 0.75416(17) 0.3549(3) 0.0778(6) Uani d . 1 . .
H H4 0.0699 0.7847 0.3836 0.093 Uiso calc R 1 . .
C C5 0.11203(8) 0.64629(16) 0.2921(3) 0.0686(6) Uani d . 1 . .
C C6 0.17095(9) 0.6050(2) 0.2485(4) 0.0993(9) Uani d . 1 . .
H H6 0.1747 0.5331 0.2036 0.119 Uiso calc R 1 . .
C C7 0.22435(10) 0.6695(2) 0.2710(5) 0.1153(11) Uani d . 1 . .
H H7 0.2634 0.6397 0.2407 0.138 Uiso calc R 1 . .
C C8 0.05366(8) 0.57880(17) 0.2701(2) 0.0637(5) Uani d . 1 . .
C C9 0.05510(8) 0.46379(17) 0.2715(2) 0.0670(6) Uani d . 1 . .
H H9 0.0932 0.4270 0.2870 0.080 Uiso calc R 1 . .
C C10 0.0000 0.4032(2) 0.2500 0.0640(7) Uani d S 1 . .
C C11 0.0000 0.2803(2) 0.2500 0.0657(7) Uani d S 1 . .
C C12 0.04268(9) 0.22100(17) 0.3546(3) 0.0748(6) Uani d . 1 . .
H H12 0.0718 0.2590 0.4257 0.090 Uiso calc R 1 . .
C C13 0.04258(10) 0.10657(18) 0.3546(3) 0.0882(7) Uani d . 1 . .
H H13 0.0715 0.0682 0.4257 0.106 Uiso calc R 1 . .
C C14 0.0000 0.0489(3) 0.2500 0.0930(10) Uani d S 1 . .
H H14 0.0000 -0.0283 0.2500 0.112 Uiso calc SR 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'
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
_geom_angle_publ_flag
C8 N1 C8 . 4 118.0(2) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C7 C2 C3 . . 117.2(2) ?
C7 C2 C1 . . 120.4(2) ?
C3 C2 C1 . . 122.3(2) ?
C2 C3 C4 . . 121.6(2) ?
C2 C3 H3 . . 119.2 ?
C4 C3 H3 . . 119.2 ?
C3 C4 C5 . . 121.02(19) ?
C3 C4 H4 . . 119.5 ?
C5 C4 H4 . . 119.5 ?
C4 C5 C6 . . 117.42(19) ?
C4 C5 C8 . . 120.58(17) ?
C6 C5 C8 . . 122.0(2) ?
C5 C6 C7 . . 120.7(2) ?
C5 C6 H6 . . 119.6 ?
C7 C6 H6 . . 119.6 ?
C2 C7 C6 . . 122.0(2) ?
C2 C7 H7 . . 119.0 ?
C6 C7 H7 . . 119.0 ?
N1 C8 C9 . . 122.30(17) ?
N1 C8 C5 . . 115.96(18) ?
C9 C8 C5 . . 121.73(16) ?
C8 C9 C10 . . 120.43(18) ?
C8 C9 H9 . . 119.8 ?
C10 C9 H9 . . 119.8 ?
C9 C10 C9 . 4 116.5(2) ?
C9 C10 C11 . . 121.74(12) ?
C9 C10 C11 4 . 121.74(12) ?
C12 C11 C12 . 4 118.0(3) ?
C12 C11 C10 . . 121.01(13) ?
C12 C11 C10 4 . 121.01(13) ?
C13 C12 C11 . . 120.9(2) ?
C13 C12 H12 . . 119.5 ?
C11 C12 H12 . . 119.5 ?
C14 C13 C12 . . 120.4(2) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C13 . 4 119.3(3) ?
C13 C14 H14 . . 120.4 ?
C13 C14 H14 4 . 120.4 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C8 . 1.340(2) ?
N1 C8 4 1.340(2) ?
C1 C2 . 1.515(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C7 . 1.365(3) ?
C2 C3 . 1.380(3) ?
C3 C4 . 1.381(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.381(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.384(3) ?
C5 C8 . 1.491(2) ?
C6 C7 . 1.384(3) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.386(3) ?
C9 C10 . 1.388(2) ?
C9 H9 . 0.9300 ?
C10 C9 4 1.388(2) ?
C10 C11 . 1.480(4) ?
C11 C12 . 1.387(2) ?
C11 C12 4 1.387(2) ?
C12 C13 . 1.379(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.376(3) ?
C13 H13 . 0.9300 ?
C14 C13 4 1.376(3) ?
C14 H14 . 0.9300 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 C2 C3 C4 . . . . 1.5(4) ?
C1 C2 C3 C4 . . . . 180.0(2) ?
C2 C3 C4 C5 . . . . -0.4(4) ?
C3 C4 C5 C6 . . . . -1.0(3) ?
C3 C4 C5 C8 . . . . 179.96(19) ?
C4 C5 C6 C7 . . . . 1.2(4) ?
C8 C5 C6 C7 . . . . -179.8(2) ?
C3 C2 C7 C6 . . . . -1.3(4) ?
C1 C2 C7 C6 . . . . -179.8(3) ?
C5 C6 C7 C2 . . . . 0.0(5) ?
C8 N1 C8 C9 4 . . . -0.33(12) ?
C8 N1 C8 C5 4 . . . -179.93(18) ?
C4 C5 C8 N1 . . . . 23.1(3) ?
C6 C5 C8 N1 . . . . -155.9(2) ?
C4 C5 C8 C9 . . . . -156.5(2) ?
C6 C5 C8 C9 . . . . 24.5(3) ?
N1 C8 C9 C10 . . . . 0.7(2) ?
C5 C8 C9 C10 . . . . -179.76(15) ?
C8 C9 C10 C9 . . . 4 -0.31(12) ?
C8 C9 C10 C11 . . . . 179.69(12) ?
C9 C10 C11 C12 . . . . 32.62(13) ?
C9 C10 C11 C12 4 . . . -147.38(13) ?
C9 C10 C11 C12 . . . 4 -147.38(13) ?
C9 C10 C11 C12 4 . . 4 32.62(12) ?
C12 C11 C12 C13 4 . . . -0.07(14) ?
C10 C11 C12 C13 . . . . 179.93(14) ?
C11 C12 C13 C14 . . . . 0.1(3) ?
C12 C13 C14 C13 . . . 4 -0.07(14) ?
