#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:45:10 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178699 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/10/4081006.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_4081006
loop_
_publ_author_name
'Lin, Yong-Chieh'
'Hsueh, Hsin-Hsueh'
'Kanne, Shanker'
'Chang, Li-Kuang'
'Liu, Fu-Chen'
'Lin, Ivan J. B.'
'Lee, Gene-Hsiang'
'Peng, Shie-Ming'
_publ_section_title
;
 Efficient PEPPSI-Themed Palladium N-Heterocyclic Carbene Precatalysts for
 the Mizoroki--Heck Reaction
;
_journal_issue                   14
_journal_name_full               Organometallics
_journal_page_first              3859
_journal_paper_doi               10.1021/om4003297
_journal_volume                  32
_journal_year                    2013
_chemical_formula_sum            'C15 H16 Br2 N4 O Pd'
_chemical_formula_weight         534.54
_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                77.8590(10)
_cell_angle_beta                 87.1520(10)
_cell_angle_gamma                81.7860(10)
_cell_formula_units_Z            2
_cell_length_a                   7.6666(3)
_cell_length_b                   9.1375(3)
_cell_length_c                   13.1036(5)
_cell_measurement_temperature    298(2)
_cell_volume                     888.03(6)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_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  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0388
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5960
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    5.552
_exptl_absorpt_correction_T_max  0.6650
_exptl_absorpt_correction_T_min  0.2148
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.999
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.948
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4267
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0620P)²+0.1992P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1063
_reflns_number_gt                3479
_reflns_number_total             4267
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om4003297_si_002.cif
_cod_data_source_block           1
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4081006
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 1.11718(3) 0.91271(3) 0.19819(2) 0.03606(10) Uani 1 1 d .
Br1 Br 1.38423(5) 0.73407(5) 0.24399(4) 0.05176(13) Uani 1 1 d .
Br2 Br 0.84218(5) 1.06858(5) 0.14357(4) 0.05461(14) Uani 1 1 d .
C1 C 0.9835(4) 0.7473(4) 0.2556(3) 0.0358(7) Uani 1 1 d .
N2 N 0.9128(4) 0.7220(3) 0.3533(2) 0.0359(6) Uani 1 1 d .
N1 N 0.9539(4) 0.6338(3) 0.2113(2) 0.0404(7) Uani 1 1 d .
N4 N 1.2580(4) 1.0965(4) 0.1519(2) 0.0417(7) Uani 1 1 d .
C10 C 0.7407(4) 0.8993(4) 0.4570(3) 0.0370(7) Uani 1 1 d .
C9 C 0.9165(5) 0.8156(5) 0.4290(3) 0.0400(8) Uani 1 1 d .
C7 C 0.8651(5) 0.5317(4) 0.2822(3) 0.0402(8) Uani 1 1 d .
C2 C 0.8391(4) 0.5871(4) 0.3725(3) 0.0379(7) Uani 1 1 d .
C3 C 0.7520(5) 0.5117(5) 0.4589(4) 0.0489(9) Uani 1 1 d .
C8 C 1.0070(8) 0.6213(7) 0.1049(4) 0.0576(11) Uani 1 1 d .
C6 C 0.8097(6) 0.3960(5) 0.2740(4) 0.0531(10) Uani 1 1 d .
C5 C 0.7250(6) 0.3211(5) 0.3610(5) 0.0654(13) Uani 1 1 d .
C15 C 1.3415(6) 1.1305(5) 0.0600(3) 0.0520(10) Uani 1 1 d .
C11 C 1.2670(7) 1.1827(5) 0.2200(4) 0.0566(11) Uani 1 1 d .
N3 N 0.7345(4) 0.9534(4) 0.5341(2) 0.0445(8) Uani 1 1 d .
H3A H 0.6381 1.0038 0.5514 0.053 Uiso 1 1 calc R
H3B H 0.8265 0.9415 0.5715 0.053 Uiso 1 1 calc R
C13 C 1.4429(7) 1.3393(5) 0.1074(5) 0.0646(13) Uani 1 1 d .
C14 C 1.4348(7) 1.2537(6) 0.0360(4) 0.0655(13) Uani 1 1 d .
C12 C 1.3574(7) 1.3057(6) 0.2010(4) 0.0655(13) Uani 1 1 d .
O1 O 0.6065(4) 0.9118(4) 0.3951(3) 0.0634(8) Uani 1 1 d .
C4 C 0.6967(6) 0.3777(5) 0.4501(4) 0.0600(12) Uani 1 1 d .
H9B H 1.000(5) 0.881(5) 0.414(3) 0.040(10) Uiso 1 1 d .
H15 H 1.329(6) 1.065(5) 0.007(4) 0.057(12) Uiso 1 1 d .
H4 H 0.645(7) 0.317(6) 0.507(4) 0.068(14) Uiso 1 1 d .
H6 H 0.824(7) 0.366(6) 0.209(4) 0.074(16) Uiso 1 1 d .
H3 H 0.727(6) 0.552(5) 0.512(3) 0.045(12) Uiso 1 1 d .
H8A H 1.075(8) 0.546(7) 0.101(4) 0.077(18) Uiso 1 1 d .
H11 H 1.204(8) 1.180(7) 0.271(5) 0.09(2) Uiso 1 1 d .
H9A H 0.956(7) 0.758(6) 0.484(4) 0.074(17) Uiso 1 1 d .
H13 H 1.508(7) 1.416(6) 0.090(4) 0.072(15) Uiso 1 1 d .
H5 H 0.683(5) 0.224(5) 0.362(3) 0.051(11) Uiso 1 1 d .
H12 H 1.353(8) 1.374(7) 0.241(5) 0.10(2) Uiso 1 1 d .
H8B H 0.915(8) 0.614(7) 0.076(4) 0.084(19) Uiso 1 1 d .
H14 H 1.510(8) 1.255(7) -0.023(5) 0.094(19) Uiso 1 1 d .
H8C H 1.031(12) 0.740(11) 0.047(8) 0.19(4) Uiso 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C1 Pd1 N4 173.99(13)
C1 Pd1 Br2 88.45(10)
N4 Pd1 Br2 91.65(9)
C1 Pd1 Br1 87.42(10)
N4 Pd1 Br1 92.97(9)
Br2 Pd1 Br1 173.576(17)
N1 C1 N2 107.4(3)
N1 C1 Pd1 128.0(3)
N2 C1 Pd1 124.5(2)
C1 N2 C2 109.8(3)
C1 N2 C9 126.0(3)
C2 N2 C9 124.2(3)
C1 N1 C7 109.8(3)
C1 N1 C8 124.4(4)
C7 N1 C8 125.9(3)
C11 N4 C15 118.0(4)
C11 N4 Pd1 117.1(3)
C15 N4 Pd1 124.9(3)
N3 C10 O1 124.1(3)
N3 C10 C9 117.3(3)
O1 C10 C9 118.5(3)
N2 C9 C10 116.4(3)
C2 C7 C6 121.7(4)
C2 C7 N1 106.9(3)
C6 C7 N1 131.4(4)
C7 C2 C3 121.4(3)
C7 C2 N2 106.1(3)
C3 C2 N2 132.5(4)
C4 C3 C2 116.6(4)
C5 C6 C7 116.4(5)
C4 C5 C6 121.8(4)
N4 C15 C14 121.3(4)
N4 C11 C12 123.5(5)
C14 C13 C12 119.6(4)
C13 C14 C15 119.5(5)
C13 C12 C11 118.2(5)
C5 C4 C3 122.2(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 C1 1.946(3)
Pd1 N4 2.092(3)
Pd1 Br2 2.4185(5)
Pd1 Br1 2.4437(5)
C1 N1 1.341(4)
C1 N2 1.353(4)
N2 C2 1.399(4)
N2 C9 1.444(4)
N1 C7 1.397(5)
N1 C8 1.455(5)
N4 C11 1.319(5)
N4 C15 1.334(5)
C10 N3 1.211(4)
C10 O1 1.319(5)
C10 C9 1.519(5)
C7 C2 1.376(5)
C7 C6 1.393(5)
C2 C3 1.390(5)
C3 C4 1.381(6)
C6 C5 1.384(7)
C5 C4 1.369(8)
C15 C14 1.392(6)
C11 C12 1.376(6)
C13 C14 1.348(8)
C13 C12 1.360(8)
