#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/74/1507407.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_1507407
loop_
_publ_author_name
'Ma, Yudao'
'Song, Chun'
'Jiang, Wei'
'Xue, Guoping'
'Cannon, John F.'
'Wang, Xiaomei'
'Andrus, Merritt B.'
_publ_section_title
;
 Borylation of aryldiazonium ions with N-heterocyclic carbene-palladium
 catalysts formed without added base.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              4635
_journal_page_last               4638
_journal_paper_doi               10.1021/ol035857q
_journal_volume                  5
_journal_year                    2003
_chemical_formula_moiety         'C54 H76 I4 N4 Pd2'
_chemical_formula_sum            'C54 H76 I4 N4 Pd2'
_chemical_formula_weight         1501.59
_chemical_name_systematic        ?
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.479(10)
_cell_angle_beta                 93.757(11)
_cell_angle_gamma                104.671(12)
_cell_formula_units_Z            1
_cell_length_a                   10.3173(16)
_cell_length_b                   12.3785(17)
_cell_length_c                   12.5477(17)
_cell_measurement_reflns_used    63
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      14.00
_cell_measurement_theta_min      4.78
_cell_volume                     1431.1(4)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '2θ/ω 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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7494
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.33
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.822
_exptl_absorpt_correction_T_max  0.5511
_exptl_absorpt_correction_T_min  0.4815
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            RED-ORANGE
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.857
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         6421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0340P)²+0.7335P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0789
_reflns_number_gt                5370
_reflns_number_total             6421
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol035857qrom20030924_034343.cif
_cod_data_source_block           PdI2-5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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      P-1
_cod_database_code               1507407
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Pd1 Pd 0.93087(2) 0.338620(19) 0.383433(19) 0.03409(7) Uani 1 1 d .
I1 I 1.05620(3) 0.17815(2) 0.29537(2) 0.05417(8) Uani 1 1 d .
I2 I 1.16652(2) 0.49003(2) 0.50365(2) 0.05218(8) Uani 1 1 d .
N1 N 0.6756(3) 0.1387(2) 0.3221(2) 0.0353(5) Uani 1 1 d .
N2 N 0.6571(2) 0.2641(2) 0.2410(2) 0.0341(5) Uani 1 1 d .
C1 C 0.7434(3) 0.2362(2) 0.3050(2) 0.0317(6) Uani 1 1 d .
C2 C 0.5284(3) 0.1073(3) 0.2832(3) 0.0445(7) Uani 1 1 d .
H2A H 0.4822 0.1382 0.3469 0.053 Uiso 1 1 calc R
H2B H 0.4878 0.0207 0.2450 0.053 Uiso 1 1 calc R
C3 C 0.5250(3) 0.1698(3) 0.2000(3) 0.0453(8) Uani 1 1 d .
H3A H 0.5183 0.1152 0.1211 0.054 Uiso 1 1 calc R
H3B H 0.4501 0.2045 0.2051 0.054 Uiso 1 1 calc R
C4 C 0.7279(3) 0.0627(3) 0.3666(3) 0.0393(7) Uani 1 1 d .
C5 C 0.7612(4) 0.0951(3) 0.4851(3) 0.0481(8) Uani 1 1 d .
C6 C 0.8064(5) 0.0143(4) 0.5204(4) 0.0659(11) Uani 1 1 d .
H6 H 0.8313 0.0336 0.5989 0.079 Uiso 1 1 calc R
C7 C 0.8155(5) -0.0917(4) 0.4442(4) 0.0727(13) Uani 1 1 d .
H7 H 0.8467 -0.1435 0.4708 0.087 Uiso 1 1 calc R
C8 C 0.7789(4) -0.1224(3) 0.3287(4) 0.0625(10) Uani 1 1 d .
H8 H 0.7845 -0.1958 0.2773 0.075 Uiso 1 1 calc R
C9 C 0.7337(4) -0.0473(3) 0.2861(3) 0.0462(8) Uani 1 1 d .
C10 C 0.6930(4) -0.0872(3) 0.1568(3) 0.0550(9) Uani 1 1 d .
H10 H 0.6739 -0.0199 0.1414 0.066 Uiso 1 1 calc R
C11 C 0.5642(5) -0.1944(4) 0.1110(4) 0.0704(12) Uani 1 1 d .
H11A H 0.5793 -0.2600 0.1289 0.106 Uiso 1 1 calc R
H11B H 0.5418 -0.2193 0.0289 0.106 Uiso 1 1 calc R
H11C H 0.4907 -0.1713 0.1465 0.106 Uiso 1 1 calc R
C12 C 0.8034(5) -0.1215(5) 0.0904(4) 0.0888(16) Uani 1 1 d .
H12A H 0.8837 -0.0535 0.1154 0.133 Uiso 1 1 calc R
H12B H 0.7727 -0.1456 0.0094 0.133 Uiso 1 1 calc R
H12C H 0.8238 -0.1873 0.1045 0.133 Uiso 1 1 calc R
C13 C 0.7475(4) 0.2087(4) 0.5730(3) 0.0574(10) Uani 1 1 d .
H13 H 0.7236 0.2567 0.5314 0.069 Uiso 1 1 calc R
C14 C 0.6321(6) 0.1799(5) 0.6384(5) 0.0906(16) Uani 1 1 d .
H14A H 0.5478 0.1402 0.5853 0.136 Uiso 1 1 calc R
H14B H 0.6264 0.2535 0.6955 0.136 Uiso 1 1 calc R
H14C H 0.6496 0.1280 0.6756 0.136 Uiso 1 1 calc R
C15 C 0.8794(6) 0.2852(4) 0.6570(4) 0.0881(16) Uani 1 1 d .
H15A H 0.9037 0.2414 0.7011 0.132 Uiso 1 1 calc R
H15B H 0.8672 0.3590 0.7082 0.132 Uiso 1 1 calc R
H15C H 0.9505 0.3033 0.6147 0.132 Uiso 1 1 calc R
C16 C 0.6872(3) 0.3517(3) 0.1874(2) 0.0351(6) Uani 1 1 d .
C17 C 0.6172(4) 0.4381(3) 0.2110(3) 0.0441(7) Uani 1 1 d .
C18 C 0.6367(5) 0.5139(4) 0.1500(4) 0.0680(12) Uani 1 1 d .
H18 H 0.5914 0.5723 0.1641 0.082 Uiso 1 1 calc R
C19 C 0.7212(6) 0.5045(4) 0.0699(5) 0.0803(15) Uani 1 1 d .
H19 H 0.7323 0.5559 0.0299 0.096 Uiso 1 1 calc R
C20 C 0.7887(4) 0.4208(4) 0.0487(4) 0.0650(11) Uani 1 1 d .
H20 H 0.8471 0.4168 -0.0050 0.078 Uiso 1 1 calc R
C21 C 0.7734(4) 0.3400(3) 0.1050(3) 0.0458(8) Uani 1 1 d .
C22 C 0.8465(4) 0.2459(4) 0.0712(3) 0.0579(10) Uani 1 1 d .
H22 H 0.8435 0.2118 0.1311 0.069 Uiso 1 1 calc R
C23 C 0.9961(5) 0.3001(7) 0.0695(6) 0.109(2) Uani 1 1 d .
H23A H 1.0035 0.3330 0.0105 0.164 Uiso 1 1 calc R
H23B H 1.0410 0.2385 0.0536 0.164 Uiso 1 1 calc R
H23C H 1.0380 0.3630 0.1431 0.164 Uiso 1 1 calc R
C24 C 0.7752(7) 0.1426(5) -0.0417(4) 0.108(2) Uani 1 1 d .
H24A H 0.6857 0.1034 -0.0332 0.163 Uiso 1 1 calc R
H24B H 0.8263 0.0855 -0.0619 0.163 Uiso 1 1 calc R
H24C H 0.7685 0.1735 -0.1015 0.163 Uiso 1 1 calc R
C25 C 0.5164(4) 0.4520(3) 0.2928(3) 0.0506(8) Uani 1 1 d .
H25 H 0.5216 0.4007 0.3364 0.061 Uiso 1 1 calc R
C26 C 0.3728(4) 0.4098(4) 0.2271(4) 0.0682(11) Uani 1 1 d .
H26A H 0.3632 0.4629 0.1887 0.102 Uiso 1 1 calc R
H26B H 0.3096 0.4104 0.2799 0.102 Uiso 1 1 calc R
H26C H 0.3548 0.3293 0.1708 0.102 Uiso 1 1 calc R
C27 C 0.5442(5) 0.5815(4) 0.3796(4) 0.0720(12) Uani 1 1 d .
H27A H 0.6382 0.6130 0.4149 0.108 Uiso 1 1 calc R
H27B H 0.4883 0.5820 0.4379 0.108 Uiso 1 1 calc R
H27C H 0.5234 0.6306 0.3403 0.108 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'
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'
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 89.45(8) . 2_766
C1 Pd1 I1 97.57(8) . .
I2 Pd1 I1 171.816(12) 2_766 .
C1 Pd1 I2 173.64(8) . .
I2 Pd1 I2 84.386(17) 2_766 .
I1 Pd1 I2 88.460(17) . .
Pd1 I2 Pd1 95.614(17) 2_766 .
C1 N1 C4 128.8(3) . .
C1 N1 C2 111.4(2) . .
C4 N1 C2 119.7(2) . .
C1 N2 C16 128.7(2) . .
C1 N2 C3 111.1(2) . .
C16 N2 C3 118.2(2) . .
N1 C1 N2 108.5(2) . .
N1 C1 Pd1 125.1(2) . .
N2 C1 Pd1 125.7(2) . .
N1 C2 C3 101.5(2) . .
N2 C3 C2 101.5(2) . .
C5 C4 C9 122.5(3) . .
C5 C4 N1 120.3(3) . .
C9 C4 N1 117.0(3) . .
C4 C5 C6 116.4(4) . .
C4 C5 C13 123.5(3) . .
C6 C5 C13 120.1(3) . .
C7 C6 C5 122.2(4) . .
C6 C7 C8 120.0(4) . .
C7 C8 C9 121.6(4) . .
C8 C9 C4 117.2(3) . .
C8 C9 C10 119.1(3) . .
C4 C9 C10 123.7(3) . .
C12 C10 C9 112.8(4) . .
C12 C10 C11 108.5(3) . .
C9 C10 C11 110.9(3) . .
C5 C13 C15 112.6(4) . .
C5 C13 C14 110.8(4) . .
C15 C13 C14 110.5(4) . .
C17 C16 C21 122.0(3) . .
C17 C16 N2 118.1(3) . .
C21 C16 N2 119.6(3) . .
C18 C17 C16 117.5(3) . .
C18 C17 C25 117.0(3) . .
C16 C17 C25 125.4(3) . .
C19 C18 C17 121.4(4) . .
C20 C19 C18 120.3(4) . .
C19 C20 C21 122.0(4) . .
C20 C21 C16 116.9(3) . .
C20 C21 C22 118.2(3) . .
C16 C21 C22 124.9(3) . .
C21 C22 C24 111.8(4) . .
C21 C22 C23 111.9(4) . .
C24 C22 C23 112.2(4) . .
C17 C25 C26 110.8(3) . .
C17 C25 C27 113.5(3) . .
C26 C25 C27 108.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C1 1.989(3) .
Pd1 I2 2.5844(5) 2_766
Pd1 I1 2.6060(5) .
Pd1 I2 2.6329(6) .
I2 Pd1 2.5844(5) 2_766
N1 C1 1.328(4) .
N1 C4 1.440(4) .
N1 C2 1.472(4) .
N2 C1 1.346(4) .
N2 C16 1.447(4) .
N2 C3 1.472(4) .
C2 C3 1.504(4) .
C4 C5 1.390(4) .
C4 C9 1.402(5) .
C5 C6 1.391(5) .
C5 C13 1.499(5) .
C6 C7 1.357(6) .
C7 C8 1.364(6) .
C8 C9 1.378(5) .
C9 C10 1.517(5) .
C10 C12 1.515(6) .
C10 C11 1.526(6) .
C13 C15 1.524(6) .
C13 C14 1.528(6) .
C16 C17 1.396(5) .
C16 C21 1.400(5) .
C17 C18 1.391(5) .
C17 C25 1.507(5) .
C18 C19 1.367(6) .
C19 C20 1.350(6) .
C20 C21 1.398(5) .
C21 C22 1.500(5) .
C22 C24 1.518(6) .
C22 C23 1.524(6) .
C25 C26 1.514(5) .
C25 C27 1.530(5) .
