#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:54:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178587 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/98/4069819.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_4069819
loop_
_publ_author_name
'Nagai, Yusuke'
'Kochi, Takuya'
'Nozaki, Kyoko'
_publ_section_title
;
 Synthesis of N-Heterocyclic Carbene-Sulfonate Palladium Complexes
;
_journal_issue                   20
_journal_name_full               Organometallics
_journal_page_first              6131
_journal_paper_doi               10.1021/om9004252
_journal_volume                  28
_journal_year                    2009
_chemical_formula_sum            'C13 H16 I2 N2'
_chemical_formula_weight         454.08
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.193(10)
_cell_length_b                   17.064(17)
_cell_length_c                   22.80(3)
_cell_measurement_reflns_used    8647
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      3.0631
_cell_volume                     3188(7)
_computing_cell_refinement       'RIGAKU CrystalClear'
_computing_data_collection       'RIGAKU CrystalClear'
_computing_data_reduction        'RIGAKU CrystalClear'
_computing_molecular_graphics    ORTEP-III
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR-97
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.1028
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            18917
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    3.930
_exptl_absorpt_correction_T_max  0.6738
_exptl_absorpt_correction_T_min  0.2933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Jacobson, R. (1998). Private communication to the Rigaku Corporation'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.893
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.060
_refine_diff_density_min         -1.330
_refine_diff_density_rms         0.248
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         3621
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0499
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0773P)²+15.7851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1362
_reflns_number_gt                3378
_reflns_number_total             3621
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om9004252_si_002.cif
_cod_data_source_block           9b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3187(6)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4069819
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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 0.3547(6) 0.1679(3) 0.6034(2) 0.0175(9) Uani 1 1 d .
H1 H 0.4166 0.2117 0.6164 0.021 Uiso 1 1 calc R
N1 N 0.3244(5) 0.1488(2) 0.54769(18) 0.0175(8) Uani 1 1 d .
C2 C 0.2307(7) 0.0814(3) 0.5461(2) 0.0237(11) Uani 1 1 d .
H2 H 0.1927 0.0551 0.5120 0.028 Uiso 1 1 calc R
C3 C 0.2038(6) 0.0601(3) 0.6023(2) 0.0225(10) Uani 1 1 d .
H3 H 0.1424 0.0161 0.6151 0.027 Uiso 1 1 calc R
N2 N 0.2823(5) 0.1144(2) 0.6380(2) 0.0197(8) Uani 1 1 d .
C4 C 0.3782(6) 0.1942(3) 0.4974(2) 0.0201(9) Uani 1 1 d .
H4 H 0.4017 0.2485 0.5101 0.024 Uiso 1 1 calc R
H5 H 0.2889 0.1963 0.4682 0.024 Uiso 1 1 calc R
I1 I 0.59345(4) 0.14572(2) 0.456289(14) 0.02346(14) Uani 1 1 d .
C5 C 0.2816(6) 0.1151(3) 0.7011(2) 0.0176(9) Uani 1 1 d .
C6 C 0.2155(6) 0.1803(3) 0.7298(2) 0.0202(9) Uani 1 1 d .
C7 C 0.2172(6) 0.1797(4) 0.7913(2) 0.0248(11) Uani 1 1 d .
H6 H 0.1760 0.2239 0.8119 0.030 Uiso 1 1 calc R
C8 C 0.2775(7) 0.1166(4) 0.8228(2) 0.0271(11) Uani 1 1 d .
C9 C 0.3416(7) 0.0516(3) 0.7923(2) 0.0259(11) Uani 1 1 d .
H7 H 0.3828 0.0081 0.8136 0.031 Uiso 1 1 calc R
C10 C 0.3452(6) 0.0505(3) 0.7309(2) 0.0218(10) Uani 1 1 d .
C11 C 0.1434(7) 0.2498(3) 0.6981(2) 0.0260(11) Uani 1 1 d .
H8 H 0.0710 0.2785 0.7247 0.039 Uiso 1 1 calc R
H9 H 0.0810 0.2315 0.6641 0.039 Uiso 1 1 calc R
H10 H 0.2314 0.2845 0.6849 0.039 Uiso 1 1 calc R
C12 C 0.2757(10) 0.1167(5) 0.8893(3) 0.0417(17) Uani 1 1 d .
H11 H 0.2466 0.1691 0.9035 0.063 Uiso 1 1 calc R
H12 H 0.3842 0.1026 0.9040 0.063 Uiso 1 1 calc R
H13 H 0.1953 0.0786 0.9034 0.063 Uiso 1 1 calc R
C13 C 0.4162(7) -0.0195(3) 0.6996(3) 0.0291(12) Uani 1 1 d .
H14 H 0.4888 -0.0480 0.7263 0.044 Uiso 1 1 calc R
H15 H 0.4782 -0.0018 0.6653 0.044 Uiso 1 1 calc R
H16 H 0.3277 -0.0542 0.6869 0.044 Uiso 1 1 calc R
I2 I 0.52635(4) 0.368239(19) 0.604888(15) 0.02074(14) Uani 1 1 d .
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'
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
N1 C1 N2 108.1(4)
N1 C1 H1 126.0
N2 C1 H1 126.0
C1 N1 C2 109.3(4)
C1 N1 C4 124.4(4)
C2 N1 C4 126.2(4)
C3 C2 N1 106.8(4)
C3 C2 H2 126.6
N1 C2 H2 126.6
C2 C3 N2 107.5(5)
C2 C3 H3 126.2
N2 C3 H3 126.2
C1 N2 C3 108.2(5)
C1 N2 C5 125.6(4)
C3 N2 C5 126.1(4)
N1 C4 I1 112.7(3)
N1 C4 H4 109.0
I1 C4 H4 109.0
N1 C4 H5 109.0
I1 C4 H5 109.0
H4 C4 H5 107.8
C10 C5 C6 122.9(5)
C10 C5 N2 118.6(4)
C6 C5 N2 118.5(4)
C5 C6 C7 117.3(5)
C5 C6 C11 123.5(5)
C7 C6 C11 119.2(5)
C8 C7 C6 121.8(5)
C8 C7 H6 119.1
C6 C7 H6 119.1
C7 C8 C9 119.2(5)
C7 C8 C12 121.0(6)
C9 C8 C12 119.9(5)
C10 C9 C8 120.8(5)
C10 C9 H7 119.6
C8 C9 H7 119.6
C5 C10 C9 117.9(5)
C5 C10 C13 122.6(5)
C9 C10 C13 119.5(5)
C6 C11 H8 109.5
C6 C11 H9 109.5
H8 C11 H9 109.5
C6 C11 H10 109.5
H8 C11 H10 109.5
H9 C11 H10 109.5
C8 C12 H11 109.5
C8 C12 H12 109.5
H11 C12 H12 109.5
C8 C12 H13 109.5
H11 C12 H13 109.5
H12 C12 H13 109.5
C10 C13 H14 109.5
C10 C13 H15 109.5
H14 C13 H15 109.5
C10 C13 H16 109.5
H14 C13 H16 109.5
H15 C13 H16 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.335(6)
C1 N2 1.345(6)
C1 H1 0.9500
N1 C2 1.383(7)
N1 C4 1.452(6)
C2 C3 1.350(7)
C2 H2 0.9500
C3 N2 1.391(7)
C3 H3 0.9500
N2 C5 1.438(7)
C4 I1 2.161(5)
C4 H4 0.9900
C4 H5 0.9900
C5 C10 1.396(7)
C5 C6 1.399(7)
C6 C7 1.401(7)
C6 C11 1.510(7)
C7 C8 1.386(8)
C7 H6 0.9500
C8 C9 1.411(8)
C8 C12 1.516(8)
C9 C10 1.398(8)
C9 H7 0.9500
C10 C13 1.509(7)
C11 H8 0.9800
C11 H9 0.9800
C11 H10 0.9800
C12 H11 0.9800
C12 H12 0.9800
C12 H13 0.9800
C13 H14 0.9800
C13 H15 0.9800
C13 H16 0.9800
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
N2 C1 N1 C2 -0.1(6)
N2 C1 N1 C4 178.0(4)
C1 N1 C2 C3 0.4(6)
C4 N1 C2 C3 -177.7(5)
N1 C2 C3 N2 -0.5(6)
N1 C1 N2 C3 -0.2(6)
N1 C1 N2 C5 -178.0(4)
C2 C3 N2 C1 0.4(6)
C2 C3 N2 C5 178.2(5)
C1 N1 C4 I1 100.3(5)
C2 N1 C4 I1 -81.9(6)
C1 N2 C5 C10 -122.1(6)
C3 N2 C5 C10 60.4(7)
C1 N2 C5 C6 58.6(7)
C3 N2 C5 C6 -118.9(6)
C10 C5 C6 C7 1.1(7)
N2 C5 C6 C7 -179.6(4)
C10 C5 C6 C11 -178.7(5)
N2 C5 C6 C11 0.5(7)
C5 C6 C7 C8 -1.8(8)
C11 C6 C7 C8 178.1(5)
C6 C7 C8 C9 1.2(8)
C6 C7 C8 C12 -179.0(6)
C7 C8 C9 C10 0.2(8)
C12 C8 C9 C10 -179.6(6)
C6 C5 C10 C9 0.1(8)
N2 C5 C10 C9 -179.1(5)
C6 C5 C10 C13 180.0(5)
N2 C5 C10 C13 0.7(7)
C8 C9 C10 C5 -0.8(8)
C8 C9 C10 C13 179.4(5)
