#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:22:22 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178561 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/69/4066978.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_4066978
loop_
_publ_author_name
'Xu, Xiangya'
'Xu, Baochang'
'Li, Yongxin'
'Hong, Soon Hyeok'
_publ_section_title
;
 Abnormal N-Heterocyclic Carbene Promoted Suzuki−Miyaura Coupling
 Reaction: A Comparative Study
;
_journal_issue                   23
_journal_name_full               Organometallics
_journal_page_first              6343
_journal_paper_doi               10.1021/om100746r
_journal_volume                  29
_journal_year                    2010
_chemical_formula_moiety         'C19 H20 I2 N2 Pd, C H2 Cl2'
_chemical_formula_sum            'C20 H22 Cl2 I2 N2 Pd'
_chemical_formula_weight         721.50
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 100.348(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6740(3)
_cell_length_b                   19.8592(6)
_cell_length_c                   12.6490(4)
_cell_measurement_reflns_used    6217
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      2.62
_cell_volume                     2390.57(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'CCD area detector'
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            28870
_diffrn_reflns_theta_full        26.59
_diffrn_reflns_theta_max         26.59
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    3.591
_exptl_absorpt_correction_T_max  0.7153
_exptl_absorpt_correction_T_min  0.5337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.005
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.510
_refine_diff_density_min         -1.226
_refine_diff_density_rms         0.408
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.211
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         4922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.211
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0288
_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)+(0.0581P)²+1.4674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.1076
_reflns_number_gt                4034
_reflns_number_total             4922
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100746r_si_001.cif
_cod_data_source_block           compound8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4066978
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
Pd1 Pd 1.02328(3) 0.428734(16) 0.60248(3) 0.02534(12) Uani 1 1 d .
C1 C 0.8945(5) 0.3582(2) 0.6358(4) 0.0265(10) Uani 1 1 d .
C2 C 0.7847(5) 0.3655(2) 0.6901(4) 0.0271(10) Uani 1 1 d .
C3 C 0.7471(5) 0.4261(2) 0.7461(4) 0.0318(11) Uani 1 1 d .
C4 C 0.8528(6) 0.4605(3) 0.8152(5) 0.0413(13) Uani 1 1 d .
H4 H 0.9453 0.4426 0.8306 0.050 Uiso 1 1 calc R
C5 C 0.8222(7) 0.5212(3) 0.8616(5) 0.0555(17) Uani 1 1 d .
H5 H 0.8945 0.5443 0.9086 0.067 Uiso 1 1 calc R
C6 C 0.6918(7) 0.5477(3) 0.8410(5) 0.0573(17) Uani 1 1 d .
H6 H 0.6730 0.5896 0.8718 0.069 Uiso 1 1 calc R
C7 C 0.5852(7) 0.5133(3) 0.7744(5) 0.0515(15) Uani 1 1 d .
H7 H 0.4927 0.5313 0.7616 0.062 Uiso 1 1 calc R
C8 C 0.6122(6) 0.4533(3) 0.7265(4) 0.0398(12) Uani 1 1 d .
H8 H 0.5386 0.4306 0.6803 0.048 Uiso 1 1 calc R
C9 C 0.5870(5) 0.2890(3) 0.7307(4) 0.0367(12) Uani 1 1 d .
H9A H 0.5021 0.2986 0.6778 0.055 Uiso 1 1 calc R
H9B H 0.5873 0.3167 0.7949 0.055 Uiso 1 1 calc R
H9C H 0.5883 0.2412 0.7505 0.055 Uiso 1 1 calc R
C10 C 0.7753(5) 0.2608(2) 0.6272(4) 0.0273(10) Uani 1 1 d .
C11 C 0.7302(5) 0.1907(2) 0.6044(4) 0.0296(10) Uani 1 1 d .
C12 C 0.6121(6) 0.1771(3) 0.5284(4) 0.0393(12) Uani 1 1 d .
H12 H 0.5570 0.2129 0.4931 0.047 Uiso 1 1 calc R
C13 C 0.5750(6) 0.1109(3) 0.5044(5) 0.0468(15) Uani 1 1 d .
H13 H 0.4957 0.1011 0.4505 0.056 Uiso 1 1 calc R
C14 C 0.6517(7) 0.0595(3) 0.5577(5) 0.0505(15) Uani 1 1 d .
H14 H 0.6252 0.0143 0.5400 0.061 Uiso 1 1 calc R
C15 C 0.7665(7) 0.0721(3) 0.6365(5) 0.0445(14) Uani 1 1 d .
H15 H 0.8178 0.0361 0.6744 0.053 Uiso 1 1 calc R
C16 C 0.8058(6) 0.1385(3) 0.6596(4) 0.0355(11) Uani 1 1 d .
H16 H 0.8851 0.1481 0.7136 0.043 Uiso 1 1 calc R
C17 C 0.9794(5) 0.2670(2) 0.5233(4) 0.0297(10) Uani 1 1 d .
H17 H 1.0397 0.3057 0.5093 0.036 Uiso 1 1 calc R
C18 C 1.0782(6) 0.2127(3) 0.5739(5) 0.0514(15) Uani 1 1 d .
H18A H 1.0246 0.1719 0.5831 0.077 Uiso 1 1 calc R
H18B H 1.1279 0.2281 0.6441 0.077 Uiso 1 1 calc R
H18C H 1.1464 0.2028 0.5274 0.077 Uiso 1 1 calc R
C19 C 0.8968(6) 0.2469(3) 0.4165(4) 0.0459(14) Uani 1 1 d .
H19A H 0.8467 0.2047 0.4241 0.069 Uiso 1 1 calc R
H19B H 0.9606 0.2404 0.3654 0.069 Uiso 1 1 calc R
H19C H 0.8288 0.2823 0.3902 0.069 Uiso 1 1 calc R
C20 C 0.3200(7) 0.3706(4) 0.4291(5) 0.0600(17) Uani 1 1 d .
H20A H 0.2828 0.4087 0.3821 0.072 Uiso 1 1 calc R
H20B H 0.2832 0.3744 0.4970 0.072 Uiso 1 1 calc R
Cl1 Cl 0.5018(2) 0.37357(12) 0.45594(17) 0.0869(7) Uani 1 1 d .
Cl2 Cl 0.2651(2) 0.29398(12) 0.36509(17) 0.0919(7) Uani 1 1 d .
I1 I 1.17653(3) 0.531301(16) 0.55117(3) 0.03686(12) Uani 1 1 d .
I2 I 1.22000(3) 0.380212(17) 0.75083(3) 0.03909(13) Uani 1 1 d .
N1 N 0.7130(4) 0.3048(2) 0.6837(3) 0.0281(9) Uani 1 1 d .
N2 N 0.8863(4) 0.29287(18) 0.5974(3) 0.0248(8) 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 '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'
Cl Cl 0.1484 0.1585 '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'
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
C1 Pd1 I2 89.49(13) . .
C1 Pd1 I1 87.90(13) . 3_766
I2 Pd1 I1 175.973(17) . 3_766
C1 Pd1 I1 174.66(13) . .
I2 Pd1 I1 95.258(15) . .
I1 Pd1 I1 87.491(14) 3_766 .
C2 C1 N2 106.0(4) . .
C2 C1 Pd1 127.4(3) . .
N2 C1 Pd1 126.2(3) . .
C1 C2 N1 107.6(4) . .
C1 C2 C3 127.3(4) . .
N1 C2 C3 125.0(4) . .
C8 C3 C4 118.6(5) . .
C8 C3 C2 122.3(5) . .
C4 C3 C2 118.9(5) . .
C5 C4 C3 119.9(6) . .
C5 C4 H4 120.1 . .
C3 C4 H4 120.1 . .
C6 C5 C4 121.1(6) . .
C6 C5 H5 119.4 . .
C4 C5 H5 119.4 . .
C5 C6 C7 119.6(6) . .
C5 C6 H6 120.2 . .
C7 C6 H6 120.2 . .
C8 C7 C6 120.8(6) . .
C8 C7 H7 119.6 . .
C6 C7 H7 119.6 . .
C7 C8 C3 120.0(6) . .
C7 C8 H8 120.0 . .
C3 C8 H8 120.0 . .
N1 C9 H9A 109.5 . .
N1 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
N1 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
N1 C10 N2 107.2(4) . .
N1 C10 C11 125.2(4) . .
N2 C10 C11 127.6(4) . .
C12 C11 C16 120.2(5) . .
C12 C11 C10 119.9(5) . .
C16 C11 C10 119.9(4) . .
C11 C12 C13 119.2(5) . .
C11 C12 H12 120.4 . .
C13 C12 H12 120.4 . .
C14 C13 C12 120.4(5) . .
C14 C13 H13 119.8 . .
C12 C13 H13 119.8 . .
C13 C14 C15 121.2(5) . .
C13 C14 H14 119.4 . .
C15 C14 H14 119.4 . .
C14 C15 C16 118.7(5) . .
C14 C15 H15 120.7 . .
C16 C15 H15 120.7 . .
C11 C16 C15 120.3(5) . .
C11 C16 H16 119.8 . .
C15 C16 H16 119.8 . .
C19 C17 N2 111.8(4) . .
C19 C17 C18 112.9(5) . .
N2 C17 C18 112.7(4) . .
C19 C17 H17 106.3 . .
N2 C17 H17 106.3 . .
C18 C17 H17 106.3 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C17 C19 H19A 109.5 . .
C17 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C17 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
Cl1 C20 Cl2 109.4(4) . .
Cl1 C20 H20A 109.8 . .
Cl2 C20 H20A 109.8 . .
Cl1 C20 H20B 109.8 . .
Cl2 C20 H20B 109.8 . .
H20A C20 H20B 108.2 . .
Pd1 I1 Pd1 92.509(14) 3_766 .
C10 N1 C2 109.3(4) . .
C10 N1 C9 123.9(4) . .
C2 N1 C9 126.8(4) . .
C10 N2 C1 109.9(4) . .
C10 N2 C17 127.2(4) . .
C1 N2 C17 122.5(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C1 1.971(5) .
Pd1 I2 2.6055(5) .
Pd1 I1 2.6065(4) 3_766
Pd1 I1 2.6672(5) .
C1 C2 1.372(7) .
C1 N2 1.383(6) .
C2 N1 1.386(6) .
C2 C3 1.475(7) .
C3 C8 1.393(7) .
C3 C4 1.398(7) .
C4 C5 1.397(8) .
C4 H4 0.9500 .
C5 C6 1.347(9) .
C5 H5 0.9500 .
C6 C7 1.388(10) .
C6 H6 0.9500 .
C7 C8 1.384(8) .
C7 H7 0.9500 .
C8 H8 0.9500 .
C9 N1 1.483(6) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 N1 1.339(6) .
C10 N2 1.359(6) .
C10 C11 1.472(6) .
C11 C12 1.381(7) .
C11 C16 1.383(7) .
C12 C13 1.382(8) .
C12 H12 0.9500 .
C13 C14 1.366(9) .
C13 H13 0.9500 .
C14 C15 1.375(9) .
C14 H14 0.9500 .
C15 C16 1.389(7) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 C19 1.494(7) .
C17 N2 1.503(6) .
C17 C18 1.505(7) .
C17 H17 1.0000 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 Cl1 1.731(7) .
C20 Cl2 1.760(7) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
I1 Pd1 2.6065(4) 3_766
