#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:39:45 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179856 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/52/7015268.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_7015268
loop_
_publ_author_name
'Luo, Qun-Li'
'Tan, Jian-Ping'
'Li, Zhi-Fu'
'Qin, Yue'
'Ma, Lin'
'Xiao, Dong-Rong'
_publ_section_title
;
 Novel bis(azole) pincer palladium complexes: synthesis, structures and
 applications in Mizoroki-Heck reactions.
;
_journal_issue                   14
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3601
_journal_page_last               3609
_journal_paper_doi               10.1039/c0dt01414a
_journal_volume                  40
_journal_year                    2011
_chemical_formula_sum            'C14 H11 Br N2 O2 Pd'
_chemical_formula_weight         425.56
_chemical_name_systematic
;
?
;
_space_group_IT_number           36
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_space_group_name_H-M   'C m c 21'
_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                   6.7355(13)
_cell_length_b                   11.269(2)
_cell_length_c                   18.178(4)
_cell_measurement_reflns_used    5015
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.24
_cell_volume                     1379.8(5)
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX 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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5015
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    4.242
_exptl_absorpt_correction_T_max  0.7278
_exptl_absorpt_correction_T_min  0.3265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.049
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.164
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.028(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.831
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1760
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.830
_refine_ls_R_factor_all          0.0202
_refine_ls_R_factor_gt           0.0188
_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0392
_refine_ls_wR_factor_ref         0.0395
_reflns_number_gt                1643
_reflns_number_total             1760
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt01414a.txt
_cod_data_source_block           compound-1
_cod_original_cell_volume        1379.7(5)
_cod_original_sg_symbol_H-M      Cmc2(1)
_cod_database_code               7015268
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, z+1/2'
'-x, y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 1.0000 0.32589(2) 0.931740(16) 0.03111(7) Uani 1 2 d S . .
Br1 Br 1.0000 0.36862(5) 1.06908(3) 0.05576(15) Uani 1 2 d S . .
O1 O 1.0000 0.6828(3) 0.8526(2) 0.0514(11) Uani 1 2 d S . .
O2 O 1.0000 -0.0513(3) 0.9476(2) 0.0504(9) Uani 1 2 d S . .
N1 N 1.0000 0.4965(3) 0.88967(17) 0.0332(7) Uani 1 2 d S . .
N2 N 1.0000 0.1414(2) 0.9348(3) 0.0367(6) Uani 1 2 d S . .
C1 C 1.0000 0.6595(4) 0.9855(3) 0.0431(13) Uani 1 2 d S . .
H1A H 0.9009 0.7206 0.9887 0.043 Uiso 0.50 1 calc PR . .
H1B H 1.1282 0.6928 0.9960 0.043 Uiso 0.50 1 calc PR . .
H1C H 0.9709 0.5982 1.0205 0.043 Uiso 0.50 1 calc PR . .
C2 C 1.0000 0.6087(4) 0.9104(3) 0.0384(10) Uani 1 2 d S . .
C3 C 1.0000 0.6132(4) 0.7907(3) 0.0470(10) Uani 1 2 d S . .
H3A H 1.0000 0.6406 0.7425 0.056 Uiso 1 2 calc SR . .
C4 C 1.0000 0.4998(4) 0.8114(2) 0.0396(8) Uani 1 2 d S . .
C5 C 1.0000 0.3833(4) 0.7764(2) 0.0391(10) Uani 1 2 d S . .
C6 C 1.0000 0.3569(4) 0.7014(3) 0.0588(13) Uani 1 2 d S . .
H6A H 1.0000 0.4178 0.6669 0.071 Uiso 1 2 calc SR . .
C7 C 1.0000 0.2407(5) 0.6786(3) 0.0691(14) Uani 1 2 d S . .
H7A H 1.0000 0.2240 0.6285 0.083 Uiso 1 2 calc SR . .
C8 C 1.0000 0.1472(4) 0.7290(3) 0.0556(13) Uani 1 2 d S . .
H8A H 1.0000 0.0689 0.7129 0.067 Uiso 1 2 calc SR . .
C9 C 1.0000 0.1732(3) 0.8033(3) 0.0388(8) Uani 1 2 d S . .
C10 C 1.0000 0.2912(3) 0.8274(2) 0.0346(8) Uani 1 2 d S . .
C11 C 1.0000 0.0890(4) 0.8645(2) 0.0383(10) Uani 1 2 d S . .
C12 C 1.0000 -0.0292(4) 0.8733(3) 0.0500(11) Uani 1 2 d S . .
H12A H 1.0000 -0.0857 0.8360 0.060 Uiso 1 2 calc SR . .
C13 C 1.0000 0.0536(4) 0.9811(3) 0.0409(11) Uani 1 2 d S . .
C14 C 1.0000 0.0535(4) 1.0624(3) 0.0528(11) Uani 1 2 d S . .
H14A H 0.9080 -0.0050 1.0800 0.053 Uiso 0.50 1 calc PR . .
H14B H 0.9612 0.1304 1.0800 0.053 Uiso 0.50 1 calc PR . .
H14C H 1.1308 0.0351 1.0800 0.053 Uiso 0.50 1 calc PR . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 Pd1 N1 79.96(14) . . ?
C10 Pd1 N2 79.89(18) . . ?
N1 Pd1 N2 159.85(16) . . ?
C10 Pd1 Br1 179.27(11) . . ?
N1 Pd1 Br1 100.77(9) . . ?
N2 Pd1 Br1 99.38(14) . . ?
C2 O1 C3 106.7(3) . . ?
C13 O2 C12 106.9(4) . . ?
C2 N1 C4 105.1(3) . . ?
C2 N1 Pd1 141.7(3) . . ?
C4 N1 Pd1 113.2(3) . . ?
C13 N2 C11 105.6(4) . . ?
C13 N2 Pd1 141.2(4) . . ?
C11 N2 Pd1 113.3(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 O1 111.8(4) . . ?
N1 C2 C1 129.4(4) . . ?
O1 C2 C1 118.8(4) . . ?
C4 C3 O1 108.5(4) . . ?
C4 C3 H3A 125.7 . . ?
O1 C3 H3A 125.7 . . ?
C3 C4 N1 107.9(4) . . ?
C3 C4 C5 137.8(5) . . ?
N1 C4 C5 114.4(4) . . ?
C10 C5 C6 119.5(4) . . ?
C10 C5 C4 112.4(4) . . ?
C6 C5 C4 128.2(4) . . ?
C7 C6 C5 119.9(5) . . ?
C7 C6 H6A 120.1 . . ?
C5 C6 H6A 120.1 . . ?
C6 C7 C8 121.4(5) . . ?
C6 C7 H7A 119.3 . . ?
C8 C7 H7A 119.3 . . ?
C9 C8 C7 118.8(4) . . ?
C9 C8 H8A 120.6 . . ?
C7 C8 H8A 120.6 . . ?
C8 C9 C10 120.4(4) . . ?
C8 C9 C11 127.3(4) . . ?
C10 C9 C11 112.2(4) . . ?
C5 C10 C9 120.0(4) . . ?
C5 C10 Pd1 120.1(3) . . ?
C9 C10 Pd1 119.9(3) . . ?
C12 C11 N2 107.9(4) . . ?
C12 C11 C9 137.3(5) . . ?
N2 C11 C9 114.7(4) . . ?
C11 C12 O2 107.3(4) . . ?
C11 C12 H12A 126.4 . . ?
O2 C12 H12A 126.4 . . ?
N2 C13 O2 112.3(4) . . ?
N2 C13 C14 130.4(5) . . ?
O2 C13 C14 117.3(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 C10 1.937(4) . ?
Pd1 N1 2.069(3) . ?
Pd1 N2 2.080(2) . ?
Pd1 Br1 2.5425(8) . ?
O1 C2 1.343(5) . ?
O1 C3 1.370(6) . ?
O2 C13 1.329(6) . ?
O2 C12 1.373(7) . ?
N1 C2 1.320(5) . ?
N1 C4 1.423(5) . ?
N2 C13 1.300(6) . ?
N2 C11 1.408(6) . ?
C1 C2 1.480(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C3 C4 1.332(6) . ?
C3 H3A 0.9300 . ?
C4 C5 1.459(6) . ?
C5 C10 1.392(5) . ?
C5 C6 1.396(8) . ?
C6 C7 1.373(7) . ?
C6 H6A 0.9300 . ?
C7 C8 1.397(7) . ?
C7 H7A 0.9300 . ?
C8 C9 1.381(7) . ?
C8 H8A 0.9300 . ?
C9 C10 1.400(5) . ?
C9 C11 1.462(6) . ?
C11 C12 1.341(6) . ?
C12 H12A 0.9300 . ?
C13 C14 1.477(8) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 Pd1 N1 C2 180.000(3) . . . . ?
N2 Pd1 N1 C2 180.000(3) . . . . ?
Br1 Pd1 N1 C2 0.000(3) . . . . ?
C10 Pd1 N1 C4 0.000(1) . . . . ?
N2 Pd1 N1 C4 0.000(2) . . . . ?
Br1 Pd1 N1 C4 180.000(1) . . . . ?
C10 Pd1 N2 C13 180.000(3) . . . . ?
N1 Pd1 N2 C13 180.000(2) . . . . ?
Br1 Pd1 N2 C13 0.000(3) . . . . ?
C10 Pd1 N2 C11 0.000(1) . . . . ?
N1 Pd1 N2 C11 0.000(2) . . . . ?
Br1 Pd1 N2 C11 180.000(1) . . . . ?
C4 N1 C2 O1 0.000(2) . . . . ?
Pd1 N1 C2 O1 180.000(2) . . . . ?
C4 N1 C2 C1 180.000(3) . . . . ?
Pd1 N1 C2 C1 0.000(4) . . . . ?
C3 O1 C2 N1 0.000(2) . . . . ?
C3 O1 C2 C1 180.000(2) . . . . ?
C2 O1 C3 C4 0.000(2) . . . . ?
O1 C3 C4 N1 0.000(2) . . . . ?
O1 C3 C4 C5 180.000(3) . . . . ?
C2 N1 C4 C3 0.000(2) . . . . ?
Pd1 N1 C4 C3 180.000(2) . . . . ?
C2 N1 C4 C5 180.000(2) . . . . ?
Pd1 N1 C4 C5 0.000(2) . . . . ?
C3 C4 C5 C10 180.000(2) . . . . ?
N1 C4 C5 C10 0.000(2) . . . . ?
C3 C4 C5 C6 0.000(4) . . . . ?
N1 C4 C5 C6 180.000(2) . . . . ?
C10 C5 C6 C7 0.000(3) . . . . ?
C4 C5 C6 C7 180.000(2) . . . . ?
C5 C6 C7 C8 0.000(2) . . . . ?
C6 C7 C8 C9 0.000(2) . . . . ?
C7 C8 C9 C10 0.000(2) . . . . ?
C7 C8 C9 C11 180.000(2) . . . . ?
C6 C5 C10 C9 0.000(2) . . . . ?
C4 C5 C10 C9 180.000(2) . . . . ?
C6 C5 C10 Pd1 180.000(1) . . . . ?
C4 C5 C10 Pd1 0.000(2) . . . . ?
C8 C9 C10 C5 0.000(2) . . . . ?
C11 C9 C10 C5 180.000(2) . . . . ?
C8 C9 C10 Pd1 180.000(1) . . . . ?
C11 C9 C10 Pd1 0.000(1) . . . . ?
N1 Pd1 C10 C5 0.000(1) . . . . ?
N2 Pd1 C10 C5 180.000(1) . . . . ?
Br1 Pd1 C10 C5 180.00(6) . . . . ?
N1 Pd1 C10 C9 180.000(1) . . . . ?
N2 Pd1 C10 C9 0.000(1) . . . . ?
Br1 Pd1 C10 C9 0.00(6) . . . . ?
C13 N2 C11 C12 0.000(2) . . . . ?
Pd1 N2 C11 C12 180.000(2) . . . . ?
C13 N2 C11 C9 180.000(2) . . . . ?
Pd1 N2 C11 C9 0.000(2) . . . . ?
C8 C9 C11 C12 0.000(3) . . . . ?
C10 C9 C11 C12 180.000(2) . . . . ?
C8 C9 C11 N2 180.000(1) . . . . ?
C10 C9 C11 N2 0.000(2) . . . . ?
N2 C11 C12 O2 0.000(2) . . . . ?
C9 C11 C12 O2 180.000(2) . . . . ?
C13 O2 C12 C11 0.000(2) . . . . ?
C11 N2 C13 O2 0.000(2) . . . . ?
Pd1 N2 C13 O2 180.000(2) . . . . ?
C11 N2 C13 C14 180.000(2) . . . . ?
Pd1 N2 C13 C14 0.000(4) . . . . ?
C12 O2 C13 N2 0.000(2) . . . . ?
C12 O2 C13 C14 180.000(2) . . . . ?
