#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/74/1507408.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_1507408
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 Cl4 N4 Pd2'
_chemical_formula_sum            'C54 H76 Cl4 N4 Pd2'
_chemical_formula_weight         1135.83
_chemical_name_systematic        ?
_space_group_IT_number           92
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_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            4
_cell_length_a                   15.9400(18)
_cell_length_b                   15.9400(18)
_cell_length_c                   26.756(3)
_cell_measurement_reflns_used    72
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      11.86
_cell_measurement_theta_min      5.12
_cell_volume                     6798.3(13)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0595
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            7877
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.62
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            YELLOW-ORANGE
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BIPYRAMID
_exptl_crystal_F_000             2352
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.42
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         5975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0424
_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)+(0.0522P)²+1.3465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1104
_reflns_number_gt                4647
_reflns_number_total             5975
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol035857qrom20030924_034402.cif
_cod_data_source_block           PdCl2-5
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
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_cell_volume        6798.1(14)
_cod_original_sg_symbol_H-M      P4(1)2(1)2
_cod_database_code               1507408
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -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 0.21664(2) 0.36456(2) 0.009604(14) 0.05307(13) Uani 1 1 d .
Cl1 Cl 0.14723(10) 0.45163(10) -0.04265(5) 0.0758(4) Uani 1 1 d .
Cl2 Cl 0.28138(9) 0.26507(9) 0.05939(5) 0.0673(4) Uani 1 1 d .
N1 N 0.2379(3) 0.4676(3) 0.09802(15) 0.0590(11) Uani 1 1 d .
C17 C 0.3875(4) 0.4467(4) 0.1154(2) 0.0683(16) Uani 1 1 d .
C18 C 0.4702(4) 0.4681(4) 0.1049(3) 0.0791(18) Uani 1 1 d .
H18 H 0.5134 0.4442 0.1234 0.095 Uiso 1 1 calc R
N2 N 0.1068(3) 0.4413(3) 0.08494(15) 0.0563(11) Uani 1 1 d .
C16 C 0.3254(3) 0.4857(4) 0.0874(2) 0.0581(14) Uani 1 1 d .
C20 C 0.4279(4) 0.5616(4) 0.0410(3) 0.0794(18) Uani 1 1 d .
H20 H 0.4427 0.5990 0.0158 0.095 Uiso 1 1 calc R
C22 C 0.2775(4) 0.5952(4) 0.0238(2) 0.0754(16) Uani 1 1 d .
H22 H 0.2243 0.5645 0.0258 0.091 Uiso 1 1 calc R
C25 C 0.3695(4) 0.3863(4) 0.1574(2) 0.0767(16) Uani 1 1 d .
H25 H 0.3109 0.3683 0.1550 0.092 Uiso 1 1 calc R
C4 C 0.0308(3) 0.4136(3) 0.0625(2) 0.0577(13) Uani 1 1 d .
C5 C 0.0085(4) 0.3305(4) 0.0667(2) 0.0650(15) Uani 1 1 d .
C23 C 0.2989(6) 0.6087(6) -0.0315(3) 0.116(3) Uani 1 1 d .
H23A H 0.3490 0.6419 -0.0341 0.175 Uiso 1 1 calc R
H23B H 0.2534 0.6373 -0.0477 0.175 Uiso 1 1 calc R
H23C H 0.3078 0.5553 -0.0473 0.175 Uiso 1 1 calc R
C1 C 0.1840(3) 0.4307(3) 0.06763(18) 0.0531(13) Uani 1 1 d .
C19 C 0.4887(4) 0.5229(5) 0.0682(3) 0.089(2) Uani 1 1 d .
H19 H 0.5446 0.5346 0.0612 0.107 Uiso 1 1 calc R
C21 C 0.3433(4) 0.5454(4) 0.0507(2) 0.0663(15) Uani 1 1 d .
C10 C -0.0022(4) 0.5649(4) 0.0387(2) 0.0838(18) Uani 1 1 d .
H10 H 0.0557 0.5726 0.0502 0.101 Uiso 1 1 calc R
C2 C 0.1951(3) 0.5109(4) 0.1395(2) 0.0689(16) Uani 1 1 d .
H2A H 0.1999 0.5714 0.1362 0.083 Uiso 1 1 calc R
H2B H 0.2180 0.4939 0.1715 0.083 Uiso 1 1 calc R
C13 C 0.0558(4) 0.2687(4) 0.0985(2) 0.0772(17) Uani 1 1 d .
H13 H 0.1107 0.2936 0.1059 0.093 Uiso 1 1 calc R
C7 C -0.1169(4) 0.3620(6) 0.0203(3) 0.105(2) Uani 1 1 d .
H7 H -0.1662 0.3442 0.0051 0.126 Uiso 1 1 calc R
C11 C -0.0094(5) 0.6025(5) -0.0142(3) 0.120(3) Uani 1 1 d .
H11A H -0.0645 0.5921 -0.0273 0.180 Uiso 1 1 calc R
H11B H 0.0316 0.5770 -0.0357 0.180 Uiso 1 1 calc R
H11C H 0.0004 0.6619 -0.0127 0.180 Uiso 1 1 calc R
C6 C -0.0665(4) 0.3053(4) 0.0443(3) 0.085(2) Uani 1 1 d .
H6 H -0.0824 0.2492 0.0457 0.102 Uiso 1 1 calc R
C12 C -0.0599(5) 0.6102(5) 0.0755(3) 0.107(3) Uani 1 1 d .
H12A H -0.1173 0.6025 0.0656 0.161 Uiso 1 1 calc R
H12B H -0.0468 0.6690 0.0757 0.161 Uiso 1 1 calc R
H12C H -0.0519 0.5876 0.1085 0.161 Uiso 1 1 calc R
C8 C -0.0951(4) 0.4440(5) 0.0187(3) 0.0856(19) Uani 1 1 d .
H8 H -0.1307 0.4822 0.0032 0.103 Uiso 1 1 calc R
C24 C 0.2659(5) 0.6797(5) 0.0490(3) 0.109(3) Uani 1 1 d .
H24A H 0.2473 0.6713 0.0828 0.164 Uiso 1 1 calc R
H24B H 0.2247 0.7117 0.0311 0.164 Uiso 1 1 calc R
H24C H 0.3182 0.7094 0.0491 0.164 Uiso 1 1 calc R
C9 C -0.0210(4) 0.4719(4) 0.0395(2) 0.0694(16) Uani 1 1 d .
C26 C 0.3825(5) 0.4317(6) 0.2083(2) 0.112(3) Uani 1 1 d .
H26A H 0.4368 0.4576 0.2089 0.169 Uiso 1 1 calc R
H26B H 0.3785 0.3916 0.2350 0.169 Uiso 1 1 calc R
H26C H 0.3400 0.4738 0.2125 0.169 Uiso 1 1 calc R
C27 C 0.4248(5) 0.3096(5) 0.1558(3) 0.099(2) Uani 1 1 d .
H27A H 0.4159 0.2803 0.1249 0.148 Uiso 1 1 calc R
H27B H 0.4111 0.2733 0.1832 0.148 Uiso 1 1 calc R
H27C H 0.4825 0.3263 0.1582 0.148 Uiso 1 1 calc R
C15 C 0.0106(6) 0.2566(5) 0.1483(3) 0.111(3) Uani 1 1 d .
H15A H 0.0005 0.3103 0.1634 0.167 Uiso 1 1 calc R
H15B H 0.0448 0.2233 0.1702 0.167 Uiso 1 1 calc R
H15C H -0.0419 0.2287 0.1427 0.167 Uiso 1 1 calc R
C14 C 0.0719(5) 0.1838(4) 0.0733(3) 0.105(3) Uani 1 1 d .
H14A H 0.0193 0.1578 0.0652 0.158 Uiso 1 1 calc R
H14B H 0.1029 0.1482 0.0956 0.158 Uiso 1 1 calc R
H14C H 0.1037 0.1922 0.0432 0.158 Uiso 1 1 calc R
C3 C 0.1071(4) 0.4834(4) 0.1340(2) 0.0702(16) Uani 1 1 d .
H3A H 0.0914 0.4449 0.1605 0.084 Uiso 1 1 calc R
H3B H 0.0691 0.5309 0.1343 0.084 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'
Pd Pd -0.9988 1.0072 '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_3
C1 Pd1 Cl1 91.71(16) .
C1 Pd1 Cl2 91.79(15) .
Cl1 Pd1 Cl2 174.62(6) .
C1 Pd1 Cl2 176.45(16) 7
Cl1 Pd1 Cl2 91.20(5) 7
Cl2 Pd1 Cl2 85.45(5) 7
Pd1 Cl2 Pd1 91.38(5) 7
C1 N1 C16 126.3(4) .
C1 N1 C2 111.8(4) .
C16 N1 C2 119.9(4) .
C16 C17 C18 117.1(6) .
C16 C17 C25 123.6(5) .
C18 C17 C25 119.3(6) .
C19 C18 C17 121.0(7) .
C1 N2 C4 127.1(4) .
C1 N2 C3 111.5(4) .
C4 N2 C3 121.4(4) .
C17 C16 C21 122.6(5) .
C17 C16 N1 119.3(5) .
C21 C16 N1 118.0(5) .
C19 C20 C21 120.3(7) .
C21 C22 C24 110.0(6) .
C21 C22 C23 112.4(6) .
C24 C22 C23 109.4(6) .
C27 C25 C17 112.7(6) .
C27 C25 C26 109.0(6) .
C17 C25 C26 109.2(5) .
C5 C4 C9 121.8(5) .
C5 C4 N2 119.0(5) .
C9 C4 N2 119.1(5) .
C4 C5 C6 117.6(6) .
C4 C5 C13 123.1(5) .
C6 C5 C13 118.9(6) .
N1 C1 N2 109.4(4) .
N1 C1 Pd1 123.9(4) .
N2 C1 Pd1 126.6(4) .
C18 C19 C20 121.9(6) .
C20 C21 C16 117.0(6) .
C20 C21 C22 119.2(6) .
C16 C21 C22 123.7(5) .
C9 C10 C12 109.6(6) .
C9 C10 C11 112.3(6) .
C12 C10 C11 111.3(6) .
N1 C2 C3 103.0(4) .
C5 C13 C15 109.9(6) .
C5 C13 C14 114.3(5) .
C15 C13 C14 110.6(6) .
C8 C7 C6 120.2(6) .
C7 C6 C5 120.8(7) .
C7 C8 C9 121.2(6) .
C8 C9 C4 118.2(6) .
C8 C9 C10 118.7(6) .
C4 C9 C10 123.0(5) .
N2 C3 C2 103.1(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C1 1.947(5) .
Pd1 Cl1 2.2595(15) .
Pd1 Cl2 2.3139(15) .
Pd1 Cl2 2.4001(14) 7
Cl2 Pd1 2.4001(14) 7
N1 C1 1.322(6) .
N1 C16 1.452(7) .
N1 C2 1.474(6) .
C17 C16 1.390(8) .
C17 C18 1.390(8) .
C17 C25 1.508(8) .
C18 C19 1.347(9) .
N2 C1 1.326(6) .
N2 C4 1.422(6) .
N2 C3 1.474(6) .
C16 C21 1.397(8) .
C20 C19 1.359(9) .
C20 C21 1.397(8) .
C22 C21 1.500(8) .
C22 C24 1.517(9) .
C22 C23 1.534(8) .
C25 C27 1.507(9) .
C25 C26 1.556(9) .
C4 C5 1.376(8) .
C4 C9 1.386(8) .
C5 C6 1.396(8) .
C5 C13 1.505(8) .
C10 C9 1.512(8) .
C10 C12 1.529(9) .
C10 C11 1.544(9) .
C2 C3 1.478(8) .
C13 C15 1.527(9) .
C13 C14 1.535(8) .
C7 C8 1.352(10) .
C7 C6 1.369(10) .
C8 C9 1.380(8) .
