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#$Date: 2016-03-21 04:15:30 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178463 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/84/4028475.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_4028475
loop_
_publ_author_name
'Victor Mamane'
'Emmanuel Aubert'
'Paola Peluso'
'Sergio Cossu'
_publ_section_title
;
 Lithiation of Prochiral 2,2'-Dichloro-5,5'-dibromo-4,4'-bipyridine as a
 Tool for the Synthesis of Chiral Polyhalogenated 4,4'-Bipyridines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7683
_journal_page_last               7689
_journal_paper_doi               10.1021/jo401255q
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C10 H3 Br Cl2 I2 N2'
_chemical_formula_sum            'C10 H3 Br Cl2 I2 N2'
_chemical_formula_weight         555.75
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 119.9080(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   26.6463(3)
_cell_length_b                   8.86220(10)
_cell_length_c                   13.57710(10)
_cell_measurement_reflns_used    63132
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      35.0239
_cell_measurement_theta_min      3.0190
_cell_volume                     2779.19(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR_92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.4508
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) x-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0602
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            87960
_diffrn_reflns_theta_full        34.16
_diffrn_reflns_theta_max         34.16
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    7.762
_exptl_absorpt_correction_T_max  0.673
_exptl_absorpt_correction_T_min  0.387
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.656
_exptl_crystal_description       prism
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.1594
_exptl_crystal_size_mid          0.1047
_exptl_crystal_size_min          0.0664
_refine_diff_density_max         1.284
_refine_diff_density_min         -0.698
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         11433
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0158
_refine_ls_R_factor_gt           0.0152
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0106P)²+5.0174P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0348
_refine_ls_wR_factor_ref         0.0350
_reflns_number_gt                11267
_reflns_number_total             11433
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401255q_si_003.cif
_cod_data_source_block           bipylpeak1
_cod_original_cell_volume        2779.19(5)
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               4028475
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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
I4 I 0.227302(5) 0.433157(16) 0.608095(11) 0.01840(2) Uani 1 1 d .
I1 I 0.134069(5) 1.021609(14) 0.131717(10) 0.01556(2) Uani 1 1 d .
I2 I 0.032966(6) 0.667970(17) -0.107428(11) 0.02110(3) Uani 1 1 d .
I3 I 0.113326(6) 0.750072(16) 0.344249(12) 0.02096(3) Uani 1 1 d .
Br1 Br 0.193820(9) 0.57497(2) -0.119332(18) 0.01969(4) Uani 1 1 d .
Br2 Br 0.082728(12) 0.30553(3) 0.63264(2) 0.02584(5) Uani 1 1 d .
Cl1 Cl 0.14911(3) 1.25270(6) -0.04722(5) 0.02594(10) Uani 1 1 d .
Cl4 Cl 0.00607(2) 0.15557(8) 0.15578(5) 0.03143(12) Uani 1 1 d .
Cl3 Cl 0.07095(3) 0.98326(6) 0.48529(6) 0.03296(13) Uani 1 1 d .
Cl2 Cl 0.26743(3) 0.47005(8) 0.35599(5) 0.03221(14) Uani 1 1 d .
N13 N 0.06373(8) 0.7629(2) 0.60155(16) 0.0215(3) Uani 1 1 d .
C20 C 0.06353(9) 0.2327(2) 0.27657(16) 0.0170(3) Uani 1 1 d .
N19 N 0.11541(8) 0.1759(2) 0.30803(14) 0.0170(3) Uani 1 1 d .
N1 N 0.16934(8) 1.0321(2) -0.14660(15) 0.0210(3) Uani 1 1 d .
C15 C 0.08902(8) 0.6858(2) 0.46244(16) 0.0162(3) Uani 1 1 d .
C23 C 0.15455(8) 0.3513(2) 0.46375(15) 0.0146(3) Uani 1 1 d .
C9 C 0.21259(9) 0.6362(2) 0.16431(16) 0.0179(3) Uani 1 1 d .
H9 H 0.2492 0.6806 0.1864 0.021 Uiso 1 1 calc R
C16 C 0.08909(8) 0.5340(2) 0.49057(15) 0.0146(3) Uani 1 1 d .
C6 C 0.17942(10) 0.8884(3) -0.15981(18) 0.0206(4) Uani 1 1 d .
H6 H 0.1874 0.8639 -0.2187 0.025 Uiso 1 1 calc R
C22 C 0.09963(8) 0.4107(2) 0.42871(15) 0.0139(3) Uani 1 1 d .
C21 C 0.05245(8) 0.3493(2) 0.33189(16) 0.0168(3) Uani 1 1 d .
H21 H 0.0142 0.3857 0.3049 0.020 Uiso 1 1 calc R
C10 C 0.16268(8) 0.6818(2) 0.06582(16) 0.0143(3) Uani 1 1 d .
C4 C 0.16556(8) 0.8045(2) -0.00616(15) 0.0132(3) Uani 1 1 d .
N7 N 0.15819(9) 0.4521(2) 0.20286(16) 0.0238(4) Uani 1 1 d .
C24 C 0.16048(8) 0.2347(2) 0.40126(16) 0.0167(3) Uani 1 1 d .
H24 H 0.1980 0.1952 0.4258 0.020 Uiso 1 1 calc R
C11 C 0.11078(9) 0.6080(2) 0.03709(16) 0.0159(3) Uani 1 1 d .
C3 C 0.15472(8) 0.9559(2) 0.00797(15) 0.0142(3) Uani 1 1 d .
C8 C 0.20662(10) 0.5231(3) 0.22882(16) 0.0211(4) Uani 1 1 d .
C17 C 0.07794(8) 0.5022(2) 0.57880(16) 0.0172(3) Uani 1 1 d .
C2 C 0.15785(9) 1.0630(2) -0.06420(16) 0.0171(3) Uani 1 1 d .
C14 C 0.07495(9) 0.7954(2) 0.51987(18) 0.0195(4) Uani 1 1 d .
C18 C 0.06551(9) 0.6196(3) 0.63151(17) 0.0202(4) Uani 1 1 d .
H18 H 0.0580 0.5962 0.6912 0.024 Uiso 1 1 calc R
C5 C 0.17874(9) 0.7731(2) -0.09172(16) 0.0156(3) Uani 1 1 d .
C12 C 0.11062(10) 0.4933(2) 0.10664(19) 0.0214(4) Uani 1 1 d .
H12 H 0.0753 0.4419 0.0851 0.026 Uiso 1 1 calc R
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C14 N13 C18 118.62(19)
N19 C20 C21 125.12(18)
N19 C20 Cl4 116.28(15)
C21 C20 Cl4 118.59(15)
C20 N19 C24 117.10(17)
C2 N1 C6 117.23(18)
C16 C15 C14 118.48(18)
C16 C15 I3 120.91(14)
C14 C15 I3 120.54(15)
C24 C23 C22 119.29(17)
C24 C23 I4 119.72(14)
C22 C23 I4 120.99(13)
C8 C9 C10 117.28(19)
C8 C9 H9 121.4
C10 C9 H9 121.4
C15 C16 C17 117.07(17)
C15 C16 C22 121.83(17)
C17 C16 C22 121.10(18)
N1 C6 C5 123.05(19)
N1 C6 H6 118.5
C5 C6 H6 118.5
C23 C22 C21 118.14(17)
C23 C22 C16 123.04(16)
C21 C22 C16 118.82(17)
C20 C21 C22 117.55(18)
C20 C21 H21 121.2
C22 C21 H21 121.2
C9 C10 C11 117.99(18)
C9 C10 C4 120.26(17)
C11 C10 C4 121.74(17)
C5 C4 C3 117.17(17)
C5 C4 C10 121.09(17)
C3 C4 C10 121.73(16)
C8 N7 C12 117.09(19)
N19 C24 C23 122.81(18)
N19 C24 H24 118.6
C23 C24 H24 118.6
C12 C11 C10 119.40(19)
C12 C11 I2 119.09(15)
C10 C11 I2 121.51(14)
C2 C3 C4 117.72(17)
C2 C3 I1 120.36(14)
C4 C3 I1 121.93(13)
N7 C8 C9 125.5(2)
N7 C8 Cl2 116.05(16)
C9 C8 Cl2 118.46(18)
C18 C17 C16 119.76(19)
C18 C17 Br2 118.86(15)
C16 C17 Br2 121.32(15)
N1 C2 C3 124.79(19)
N1 C2 Cl1 114.61(16)
C3 C2 Cl1 120.57(15)
N13 C14 C15 123.4(2)
N13 C14 Cl3 115.64(16)
C15 C14 Cl3 120.93(17)
N13 C18 C17 122.6(2)
N13 C18 H18 118.7
C17 C18 H18 118.7
C6 C5 C4 120.01(19)
C6 C5 Br1 118.76(15)
C4 C5 Br1 121.21(15)
N7 C12 C11 122.7(2)
N7 C12 H12 118.7
C11 C12 H12 118.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I4 C23 2.0823(18)
I1 C3 2.0945(18)
I2 C11 2.092(2)
I3 C15 2.087(2)
Br1 C5 1.8802(19)
Br2 C17 1.870(2)
Cl1 C2 1.728(2)
Cl4 C20 1.731(2)
Cl3 C14 1.719(2)
Cl2 C8 1.743(2)
N13 C14 1.316(3)
N13 C18 1.327(3)
C20 N19 1.326(3)
C20 C21 1.393(3)
N19 C24 1.342(3)
N1 C2 1.327(3)
N1 C6 1.332(3)
C15 C16 1.399(3)
C15 C14 1.408(3)
C23 C24 1.395(3)
C23 C22 1.397(3)
C9 C8 1.391(3)
C9 C10 1.395(3)
C9 H9 0.9500
C16 C17 1.399(3)
C16 C22 1.487(3)
C6 C5 1.384(3)
C6 H6 0.9500
C22 C21 1.399(3)
C21 H21 0.9500
C10 C11 1.398(3)
C10 C4 1.489(3)
C4 C5 1.399(3)
C4 C3 1.406(3)
N7 C8 1.316(3)
N7 C12 1.340(3)
C24 H24 0.9500
C11 C12 1.389(3)
C3 C2 1.396(3)
C17 C18 1.393(3)
C18 H18 0.9500
C12 H12 0.9500
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
C21 C20 N19 C24 0.8(3)
Cl4 C20 N19 C24 179.79(15)
C14 C15 C16 C17 -3.2(3)
I3 C15 C16 C17 173.66(14)
C14 C15 C16 C22 175.88(18)
I3 C15 C16 C22 -7.2(2)
C2 N1 C6 C5 -0.5(3)
C24 C23 C22 C21 0.4(3)
I4 C23 C22 C21 -179.13(14)
C24 C23 C22 C16 179.40(18)
I4 C23 C22 C16 -0.2(3)
C15 C16 C22 C23 92.1(2)
C17 C16 C22 C23 -88.8(2)
C15 C16 C22 C21 -88.9(2)
C17 C16 C22 C21 90.2(2)
N19 C20 C21 C22 -0.5(3)
Cl4 C20 C21 C22 -179.44(15)
C23 C22 C21 C20 -0.2(3)
C16 C22 C21 C20 -179.19(18)
C8 C9 C10 C11 -1.9(3)
C8 C9 C10 C4 178.75(18)
C9 C10 C4 C5 87.2(2)
C11 C10 C4 C5 -92.1(2)
C9 C10 C4 C3 -93.4(2)
C11 C10 C4 C3 87.3(2)
C20 N19 C24 C23 -0.5(3)
C22 C23 C24 N19 -0.1(3)
I4 C23 C24 N19 179.47(15)
C9 C10 C11 C12 0.0(3)
C4 C10 C11 C12 179.36(18)
C9 C10 C11 I2 179.27(14)
C4 C10 C11 I2 -1.4(2)
C5 C4 C3 C2 0.1(3)
C10 C4 C3 C2 -179.38(17)
C5 C4 C3 I1 179.76(14)
C10 C4 C3 I1 0.3(3)
C12 N7 C8 C9 -0.6(3)
C12 N7 C8 Cl2 178.65(16)
C10 C9 C8 N7 2.3(3)
C10 C9 C8 Cl2 -176.88(15)
C15 C16 C17 C18 2.2(3)
C22 C16 C17 C18 -176.95(18)
C15 C16 C17 Br2 -174.94(14)
C22 C16 C17 Br2 6.0(3)
C6 N1 C2 C3 -1.0(3)
C6 N1 C2 Cl1 176.68(17)
C4 C3 C2 N1 1.2(3)
I1 C3 C2 N1 -178.46(16)
C4 C3 C2 Cl1 -176.37(15)
I1 C3 C2 Cl1 3.9(2)
C18 N13 C14 C15 -0.2(3)
C18 N13 C14 Cl3 179.32(17)
C16 C15 C14 N13 2.4(3)
I3 C15 C14 N13 -174.49(16)
C16 C15 C14 Cl3 -177.14(15)
I3 C15 C14 Cl3 6.0(2)
C14 N13 C18 C17 -1.0(3)
C16 C17 C18 N13 0.0(3)
Br2 C17 C18 N13 177.13(17)
N1 C6 C5 C4 1.7(3)
N1 C6 C5 Br1 -179.90(17)
C3 C4 C5 C6 -1.4(3)
C10 C4 C5 C6 178.01(19)
C3 C4 C5 Br1 -179.78(14)
C10 C4 C5 Br1 -0.3(3)
C8 N7 C12 C11 -1.5(3)
C10 C11 C12 N7 1.8(3)
I2 C11 C12 N7 -177.44(16)
