#------------------------------------------------------------------------------
#$Date: 2016-02-13 13:50:18 +0100 (Sat 13 de Feb de 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/45/7154509.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_7154509
loop_
_publ_author_name
'Reimann, Sebastian'
'Parpart, Silvio'
'Ehlers, Peter'
'Sharif, Muhammad'
'Spannenberg, Anke'
'Langer, Peter'
_publ_section_title
;
 Synthesis of tetraarylpyridines by chemo-selective Suzuki-Miyaura
 reactions of 3,5-dibromo-2,6-dichloropyridine.
;
_journal_issue                   24
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6832
_journal_page_last               6838
_journal_paper_doi               10.1039/c5ob00866b
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C17 H11 Cl2 N'
_chemical_formula_weight         300.17
_chemical_name_systematic
; 
2,6-Dichloro-3,5-diphenylpyridine
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-04-28 deposited with the CCDC.
2015-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.3422(5)
_cell_length_b                   8.1975(2)
_cell_length_c                   8.0145(2)
_cell_measurement_reflns_used    9591
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.69
_cell_measurement_theta_min      3.68
_cell_volume                     1402.16(6)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_data_reduction        SAINT
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa APEX II Duo'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0095
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15714
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    0.450
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0255
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0336P)²+0.5927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0700
_reflns_number_gt                1599
_reflns_number_total             1692
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00866b2.cif
_cod_data_source_block           ax0260
_cod_depositor_comments
'Adding full bibliography for 7154509--7154510.cif.'
_cod_original_sg_symbol_H-M      Pbcn
_cod_database_code               7154509
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'
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
C1 C 0.45236(5) 1.04439(12) 0.31255(13) 0.0182(2) Uani 1 1 d .
C2 C 0.44808(4) 0.87457(13) 0.31494(12) 0.0175(2) Uani 1 1 d .
C3 C 0.5000 0.79258(18) 0.2500 0.0188(3) Uani 1 2 d S
H3 H 0.5000 0.6767 0.2500 0.023 Uiso 1 2 calc SR
C4 C 0.39389(5) 0.78056(14) 0.37983(13) 0.0196(2) Uani 1 1 d .
C5 C 0.40379(6) 0.65538(14) 0.49440(15) 0.0248(2) Uani 1 1 d .
H5 H 0.4449 0.6336 0.5338 0.030 Uiso 1 1 calc R
C6 C 0.35379(6) 0.56225(15) 0.55135(16) 0.0317(3) Uani 1 1 d .
H6 H 0.3607 0.4783 0.6309 0.038 Uiso 1 1 calc R
C7 C 0.29381(6) 0.59167(16) 0.49224(17) 0.0336(3) Uani 1 1 d .
H7 H 0.2597 0.5271 0.5304 0.040 Uiso 1 1 calc R
C8 C 0.28350(5) 0.71530(17) 0.37751(17) 0.0321(3) Uani 1 1 d .
H8 H 0.2424 0.7350 0.3368 0.039 Uiso 1 1 calc R
C9 C 0.33315(5) 0.81058(14) 0.32187(15) 0.0248(2) Uani 1 1 d .
H9 H 0.3258 0.8962 0.2444 0.030 Uiso 1 1 calc R
Cl1 Cl 0.393882(12) 1.16480(3) 0.39987(4) 0.02523(10) Uani 1 1 d .
N1 N 0.5000 1.12815(16) 0.2500 0.0196(2) Uani 1 2 d S
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
C1 0.0159(4) 0.0215(5) 0.0172(4) -0.0013(4) -0.0019(4) 0.0030(4)
C2 0.0139(4) 0.0216(5) 0.0171(4) 0.0001(4) -0.0018(4) -0.0005(4)
C3 0.0160(6) 0.0188(6) 0.0215(7) 0.000 -0.0012(5) 0.000
C4 0.0162(5) 0.0213(5) 0.0213(5) -0.0046(4) 0.0030(4) -0.0021(4)
C5 0.0254(5) 0.0235(5) 0.0256(5) -0.0018(4) 0.0017(4) -0.0026(4)
C6 0.0403(7) 0.0235(5) 0.0312(6) -0.0019(5) 0.0106(5) -0.0075(5)
C7 0.0289(6) 0.0304(6) 0.0416(7) -0.0137(6) 0.0175(5) -0.0126(5)
C8 0.0166(5) 0.0372(7) 0.0426(7) -0.0142(6) 0.0072(5) -0.0041(5)
C9 0.0168(5) 0.0288(5) 0.0289(5) -0.0050(5) 0.0021(4) 0.0001(4)
Cl1 0.02188(15) 0.02555(16) 0.02826(16) -0.00302(10) 0.00385(9) 0.00624(9)
N1 0.0189(6) 0.0202(6) 0.0195(6) 0.000 -0.0020(5) 0.000
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'
Cl Cl 0.1484 0.1585 '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_1
_geom_angle_site_symmetry_3
N1 C1 C2 124.92(10) . .
N1 C1 Cl1 114.13(8) . .
C2 C1 Cl1 120.93(8) . .
C1 C2 C3 115.02(10) . .
C1 C2 C4 125.04(9) . .
C3 C2 C4 119.94(10) . .
C2 C3 C2 122.47(13) . 3_655
C2 C3 H3 118.8 . .
C2 C3 H3 118.8 3_655 .
C5 C4 C9 119.28(10) . .
C5 C4 C2 119.69(9) . .
C9 C4 C2 120.96(10) . .
C6 C5 C4 120.32(11) . .
C6 C5 H5 119.8 . .
C4 C5 H5 119.8 . .
C7 C6 C5 120.10(12) . .
C7 C6 H6 119.9 . .
C5 C6 H6 119.9 . .
C8 C7 C6 120.03(11) . .
C8 C7 H7 120.0 . .
C6 C7 H7 120.0 . .
C7 C8 C9 120.18(11) . .
C7 C8 H8 119.9 . .
C9 C8 H8 119.9 . .
C8 C9 C4 120.08(12) . .
C8 C9 H9 120.0 . .
C4 C9 H9 120.0 . .
C1 N1 C1 117.59(13) . 3_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.3253(12) .
C1 C2 1.3952(15) .
C1 Cl1 1.7383(10) .
C2 C3 1.3967(12) .
C2 C4 1.4838(14) .
C3 C2 1.3967(12) 3_655
C3 H3 0.9500 .
C4 C5 1.3931(16) .
C4 C9 1.3987(15) .
C5 C6 1.3892(16) .
C5 H5 0.9500 .
C6 C7 1.3861(19) .
C6 H6 0.9500 .
C7 C8 1.386(2) .
C7 H7 0.9500 .
C8 C9 1.3900(16) .
C8 H8 0.9500 .
C9 H9 0.9500 .
N1 C1 1.3254(12) 3_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_4
N1 C1 C2 C3 2.17(14) .
Cl1 C1 C2 C3 -176.16(6) .
N1 C1 C2 C4 -177.88(8) .
Cl1 C1 C2 C4 3.79(14) .
C1 C2 C3 C2 -0.97(6) 3_655
C4 C2 C3 C2 179.07(10) 3_655
C1 C2 C4 C5 -129.21(12) .
C3 C2 C4 C5 50.74(13) .
C1 C2 C4 C9 53.79(15) .
C3 C2 C4 C9 -126.25(10) .
C9 C4 C5 C6 -0.48(17) .
C2 C4 C5 C6 -177.53(10) .
C4 C5 C6 C7 1.08(18) .
C5 C6 C7 C8 -0.70(19) .
C6 C7 C8 C9 -0.27(18) .
C7 C8 C9 C4 0.87(18) .
C5 C4 C9 C8 -0.49(17) .
C2 C4 C9 C8 176.52(10) .
C2 C1 N1 C1 -1.17(7) 3_655
Cl1 C1 N1 C1 177.26(8) 3_655
