#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:53:49 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178410 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/31/4023140.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_4023140
loop_
_publ_author_name
'Stéphane Diring'
'Pascal Retailleau'
'Raymond Ziessel'
_publ_section_title
;
 A Rational Protocol for the Synthesis of Arylated Bipyridine
 Ligands via a Cycloaddition Pathway
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10181
_journal_page_last               10193
_journal_paper_doi               10.1021/jo7019866
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C16 H10 Cl I N2 Pt'
_chemical_formula_sum            'C16 H10 Cl I N2 Pt'
_chemical_formula_weight         587.70
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                   8.169(1)
_cell_length_b                   12.543(2)
_cell_length_c                   14.364(2)
_cell_measurement_reflns_used    3391
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.407
_cell_volume                     1471.9(4)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft, 1998)'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) COLLECT (Hooft, 1998)'
_computing_data_reduction        'HKL package (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1980-2004)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .985
_diffrn_measured_fraction_theta_max .985
_diffrn_measurement_device_type  'Nonius kappa-CCD diffractometer'
_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     0.71070
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0305
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15790
_diffrn_reflns_theta_full        27.68
_diffrn_reflns_theta_max         27.68
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    11.805
_exptl_absorpt_correction_T_max  0.310
_exptl_absorpt_correction_T_min  0.22
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL SCALEPACK, Blessing'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.048
_refine_diff_density_min         -1.482
_refine_diff_density_rms         .159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3184
_refine_ls_number_restraints     186
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0359P)²+3.5587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0725
_refine_ls_wR_factor_ref         0.0842
_reflns_number_gt                2131
_reflns_number_total             3184
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7019866-File004.cif
_cod_data_source_block           compound_23_sd114
_cod_database_code               4023140
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'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
Pt Pt 0.24931(5) 0.091685(18) 0.49910(12) 0.03073(9) Uani 1 1 d U
I I 0.25377(12) 0.63121(4) 0.4992(2) 0.05260(15) Uani 1 1 d U
Cl Cl 0.2505(4) -0.09197(13) 0.4991(8) 0.0538(5) Uani 1 1 d U
N2 N 0.2456(9) 0.2464(4) 0.5004(13) 0.0287(10) Uani 1 1 d U
N1 N 0.3866(10) 0.1178(9) 0.6174(8) 0.039(2) Uani 1 1 d U
C1 C 0.4103(13) 0.2265(11) 0.6347(8) 0.037(2) Uani 1 1 d U
C2 C 0.4996(12) 0.2632(13) 0.7113(8) 0.046(3) Uani 1 1 d U
H2 H 0.5144 0.3357 0.7220 0.056 Uiso 1 1 calc R
C3 C 0.5660(13) 0.1863(13) 0.7713(10) 0.051(3) Uani 1 1 d U
H3 H 0.6223 0.2082 0.8242 0.062 Uiso 1 1 calc R
C4 C 0.5494(12) 0.0785(12) 0.7532(11) 0.047(3) Uani 1 1 d U
H4 H 0.5951 0.0282 0.7931 0.056 Uiso 1 1 calc R
C5 C 0.4594(12) 0.0446(13) 0.6707(10) 0.046(3) Uani 1 1 d U
H5 H 0.4527 -0.0273 0.6553 0.055 Uiso 1 1 calc R
C6 C 0.3320(12) 0.2983(9) 0.5697(9) 0.034(2) Uani 1 1 d U
C7 C 0.3331(13) 0.4114(9) 0.5687(10) 0.038(2) Uani 1 1 d U
H7 H 0.3853 0.4498 0.6155 0.045 Uiso 1 1 calc R
C8 C 0.2538(14) 0.4633(6) 0.496(2) 0.0396(16) Uani 1 1 d U
C9 C 0.1715(14) 0.4062(9) 0.4275(10) 0.041(2) Uani 1 1 d U
H9 H 0.1164 0.4418 0.3801 0.049 Uiso 1 1 calc R
C10 C 0.1721(13) 0.2998(9) 0.4303(9) 0.034(2) Uani 1 1 d U
C11 C 0.0957(13) 0.2258(11) 0.3624(8) 0.037(2) Uani 1 1 d U
C12 C 0.0090(13) 0.2595(11) 0.2850(9) 0.044(3) Uani 1 1 d U
H12 H 0.0013 0.3319 0.2718 0.052 Uiso 1 1 calc R
C13 C -0.0675(13) 0.1851(12) 0.2265(9) 0.047(3) Uani 1 1 d U
H13 H -0.1281 0.2070 0.1751 0.056 Uiso 1 1 calc R
C14 C -0.0504(14) 0.0803(12) 0.2470(13) 0.055(4) Uani 1 1 d U
H14 H -0.1031 0.0301 0.2100 0.067 Uiso 1 1 calc R
C15 C 0.0394(12) 0.0474(13) 0.3183(10) 0.042(3) Uani 1 1 d U
H15 H 0.0550 -0.0253 0.3279 0.051 Uiso 1 1 calc R
C16 C 0.1112(12) 0.1212(10) 0.3795(9) 0.033(2) Uani 1 1 d U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pt Pt -1.7033 8.3905 '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
N2 Pt N1 80.9(6)
N2 Pt C16 79.8(6)
N1 Pt C16 160.7(2)
N2 Pt Cl 179.1(5)
N1 Pt Cl 99.0(4)
C16 Pt Cl 100.3(4)
C10 N2 C6 122.0(6)
C10 N2 Pt 119.7(10)
C6 N2 Pt 118.0(9)
C5 N1 C1 120.4(12)
C5 N1 Pt 127.3(10)
C1 N1 Pt 112.1(8)
C2 C1 N1 122.2(12)
C2 C1 C6 122.3(13)
N1 C1 C6 115.5(10)
C1 C2 C3 117.4(15)
C1 C2 H2 121.3
C3 C2 H2 121.3
C4 C3 C2 121.3(14)
C4 C3 H3 119.4
C2 C3 H3 119.4
C3 C4 C5 119.1(13)
C3 C4 H4 120.5
C5 C4 H4 120.5
N1 C5 C4 119.4(14)
N1 C5 H5 120.3
C4 C5 H5 120.3
N2 C6 C7 117.9(10)
N2 C6 C1 113.4(10)
C7 C6 C1 128.7(11)
C8 C7 C6 118.2(12)
C8 C7 H7 120.9
C6 C7 H7 120.9
C9 C8 C7 121.0(7)
C9 C8 I 122.1(15)
C7 C8 I 116.8(14)
C10 C9 C8 119.5(13)
C10 C9 H9 120.2
C8 C9 H9 120.2
C9 C10 N2 121.3(12)
C9 C10 C11 127.2(12)
N2 C10 C11 111.5(10)
C16 C11 C12 119.6(12)
C16 C11 C10 116.9(11)
C12 C11 C10 123.5(13)
C11 C12 C13 120.4(14)
C11 C12 H12 119.8
C13 C12 H12 119.8
C14 C13 C12 117.9(13)
C14 C13 H13 121.0
C12 C13 H13 121.0
C15 C14 C13 121.9(13)
C15 C14 H14 119.0
C13 C14 H14 119.0
C14 C15 C16 120.6(15)
C14 C15 H15 119.7
C16 C15 H15 119.7
C11 C16 C15 119.4(12)
C11 C16 Pt 112.0(9)
C15 C16 Pt 128.6(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pt N2 1.940(5)
Pt N1 2.062(11)
Pt C16 2.088(13)
Pt Cl 2.3036(16)
I C8 2.106(7)
N2 C10 1.351(18)
N2 C6 1.383(17)
N1 C5 1.335(16)
N1 C1 1.399(16)
C1 C2 1.398(15)
C1 C6 1.446(15)
C2 C3 1.402(17)
C2 H2 0.9300
C3 C4 1.38(2)
C3 H3 0.9300
C4 C5 1.46(2)
C4 H4 0.9300
C5 H5 0.9300
C6 C7 1.419(15)
C7 C8 1.39(3)
C7 H7 0.9300
C8 C9 1.39(3)
C9 C10 1.336(14)
C9 H9 0.9300
C10 C11 1.483(15)
C11 C16 1.341(17)
C11 C12 1.384(15)
C12 C13 1.404(17)
C12 H12 0.9300
C13 C14 1.35(2)
C13 H13 0.9300
C14 C15 1.33(2)
C14 H14 0.9300
C15 C16 1.405(17)
C15 H15 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
N1 Pt N2 C10 176.6(10)
C16 Pt N2 C10 -2.9(9)
N1 Pt N2 C6 2.3(9)
C16 Pt N2 C6 -177.2(10)
N2 Pt N1 C5 -177.1(10)
C16 Pt N1 C5 -175.6(11)
Cl Pt N1 C5 3.8(10)
N2 Pt N1 C1 -2.1(8)
C16 Pt N1 C1 -1(2)
Cl Pt N1 C1 178.7(7)
C5 N1 C1 C2 -4.8(16)
Pt N1 C1 C2 179.9(7)
C5 N1 C1 C6 177.1(9)
Pt N1 C1 C6 1.7(12)
N1 C1 C2 C3 0.0(15)
C6 C1 C2 C3 178.1(9)
C1 C2 C3 C4 2.6(15)
C2 C3 C4 C5 -0.7(17)
C1 N1 C5 C4 6.6(16)
Pt N1 C5 C4 -178.9(8)
C3 C4 C5 N1 -4.0(17)
C10 N2 C6 C7 3.9(19)
Pt N2 C6 C7 178.1(9)
C10 N2 C6 C1 -176.2(9)
Pt N2 C6 C1 -2.0(13)
C2 C1 C6 N2 -178.2(10)
N1 C1 C6 N2 0.0(14)
C2 C1 C6 C7 1.8(18)
N1 C1 C6 C7 179.9(11)
N2 C6 C7 C8 -2.9(17)
C1 C6 C7 C8 177.2(12)
C6 C7 C8 C9 2(2)
C6 C7 C8 I 178.6(9)
C7 C8 C9 C10 -2(2)
I C8 C9 C10 -178.2(11)
C8 C9 C10 N2 2.7(19)
C8 C9 C10 C11 -178.1(12)
C6 N2 C10 C9 -4(2)
Pt N2 C10 C9 -178.0(9)
C6 N2 C10 C11 176.8(9)
Pt N2 C10 C11 2.7(13)
C9 C10 C11 C16 -179.7(12)
N2 C10 C11 C16 -0.4(14)
C9 C10 C11 C12 -0.8(18)
N2 C10 C11 C12 178.4(10)
C16 C11 C12 C13 2.2(15)
C10 C11 C12 C13 -176.6(10)
C11 C12 C13 C14 -1.4(16)
C12 C13 C14 C15 -2(2)
C13 C14 C15 C16 5(2)
C12 C11 C16 C15 0.2(16)
C10 C11 C16 C15 179.1(9)
C12 C11 C16 Pt 179.4(7)
C10 C11 C16 Pt -1.8(12)
C14 C15 C16 C11 -3.6(17)
C14 C15 C16 Pt 177.4(9)
N2 Pt C16 C11 2.4(8)
N1 Pt C16 C11 1(2)
Cl Pt C16 C11 -178.4(8)
N2 Pt C16 C15 -178.6(10)
N1 Pt C16 C15 180.0(11)
Cl Pt C16 C15 0.6(10)
