#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/69/2016975.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2016975
loop_
_publ_author_name
'Calmuschi-Cula, Beatrice'
'Kalf, Irmgard'
'Timofte, Claudia'
'Englert, Ulli'
_publ_section_title
;
 Robust packing in cyclopalladated primary amines: isomorphous crystal
 structures of four complexes with varying substitution patterns
;
_journal_coeditor_code           LG3003
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m48
_journal_page_last               m51
_journal_paper_doi               10.1107/S0108270108043631
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Pd Br (C8 H9 Br N) (C6 H7 N)]'
_chemical_formula_moiety         'C14 H16 Br2 N2 Pd'
_chemical_formula_sum            'C14 H16 Br2 N2 Pd'
_chemical_formula_weight         478.51
_chemical_name_systematic
;
(SP-4-4)-[rac-2-(1-aminoethyl)-5-bromophenyl-
κ²C¹,N]bromido(4-methylpyridine-κN)palladium(II)
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :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            16
_cell_length_a                   18.5329(13)
_cell_length_b                   18.5329(13)
_cell_length_c                   18.071(3)
_cell_measurement_reflns_used    1895
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.16
_cell_measurement_theta_min      2.70
_cell_volume                     6206.8(12)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1999)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full .985
_diffrn_measured_fraction_theta_max .985
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '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  0.0671
_diffrn_reflns_av_sigmaI/netI    0.0874
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13256
_diffrn_reflns_theta_full        27.11
_diffrn_reflns_theta_max         27.11
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        'no decay'
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.334
_exptl_absorpt_correction_T_max  0.4931
_exptl_absorpt_correction_T_min  0.2442
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.048
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3680
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.13
_refine_diff_density_max         .692
_refine_diff_density_min         -.594
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         3374
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0422
_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)+(0.0200P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0717
_refine_ls_wR_factor_ref         0.0750
_reflns_number_gt                1916
_reflns_number_total             3374
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            lg3003.cif
_cod_data_source_block           III
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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_sg_symbol_H-M      I41/a
_cod_database_code               2016975
_cod_database_fobs_code          2016975
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+3/4, x+1/4, z+1/4'
'-x+1/2, -y, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'-x+1, -y+1/2, z+1'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'y-3/4, -x-1/4, -z-1/4'
'x-1/2, y, -z-1/2'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'x, y+1/2, -z'
'-y-1/4, x-1/4, -z-1/4'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd Pd1 0.00428(2) 0.14605(2) 0.30708(2) 0.04295(15) Uani d . 1 B .
Br Br1 -0.09198(3) 0.13378(3) 0.20809(3) 0.05454(19) Uani d . 1 . .
Br Br2 0.13075(4) 0.19745(4) 0.59829(4) 0.0838(3) Uani d . 1 . .
N N1 -0.0643(2) 0.1079(2) 0.3863(2) 0.0417(11) Uani d . 1 . .
N N2 0.0816(2) 0.1808(2) 0.2347(2) 0.0500(13) Uani d D 1 . .
H H2A 0.0775 0.1546 0.1917 0.060 Uiso calc R 1 A 1
H H2B 0.0725 0.2284 0.2233 0.060 Uiso calc R 1 A 1
C C1 -0.1233(3) 0.1435(3) 0.4062(3) 0.0568(17) Uani d . 1 . .
H H1 -0.1336 0.1899 0.3825 0.074 Uiso calc R 1 . .
C C2 -0.1710(3) 0.1175(4) 0.4594(3) 0.0640(18) Uani d . 1 . .
H H2 -0.2137 0.1460 0.4724 0.083 Uiso calc R 1 . .
C C3 -0.1591(4) 0.0531(3) 0.4935(3) 0.0525(16) Uani d . 1 . .
C C4 -0.1013(3) 0.0172(3) 0.4704(3) 0.0567(17) Uani d . 1 . .
H H4 -0.0917 -0.0308 0.4908 0.074 Uiso calc R 1 . .
C C5 -0.0544(3) 0.0451(3) 0.4185(3) 0.0542(17) Uani d . 1 . .
H H5 -0.0117 0.0168 0.4051 0.070 Uiso calc R 1 . .
C C6 -0.2067(4) 0.0258(3) 0.5536(3) 0.091(2) Uani d . 1 . .
H H6A -0.2028 -0.0268 0.5565 0.136 Uiso calc R 1 . .
H H6B -0.2568 0.0392 0.5429 0.136 Uiso calc R 1 . .
H H6C -0.1920 0.0471 0.6008 0.136 Uiso calc R 1 . .
C C7 0.1586(4) 0.1748(5) 0.2625(4) 0.046(2) Uiso d PD 0.650(6) B 1
H H7 0.1896 0.2159 0.2459 0.055 Uiso calc PR 0.650(6) B 1
C C14 0.1877(5) 0.1034(4) 0.2395(5) 0.054(2) Uiso d PD 0.650(6) B 1
H H14A 0.1553 0.0651 0.2566 0.081 Uiso calc PR 0.650(6) B 1
H H14B 0.2356 0.0965 0.2612 0.081 Uiso calc PR 0.650(6) B 1
H H14C 0.1913 0.1017 0.1854 0.081 Uiso calc PR 0.650(6) B 1
C C7A 0.1486(7) 0.1422(9) 0.2624(7) 0.046(2) Uiso d PD 0.350(6) B 2
H H7A 0.1434 0.0886 0.2599 0.055 Uiso calc PR 0.350(6) B 2
C C14A 0.2097(8) 0.1680(9) 0.2175(8) 0.054(2) Uiso d PD 0.350(6) B 2
H H14D 0.2024 0.1541 0.1657 0.081 Uiso calc PR 0.350(6) B 2
H H14E 0.2546 0.1465 0.2359 0.081 Uiso calc PR 0.350(6) B 2
H H14F 0.2128 0.2207 0.2210 0.081 Uiso calc PR 0.350(6) B 2
C C8 0.1521(3) 0.1703(3) 0.3451(3) 0.0584(18) Uani d D 1 . .
C C9 0.0844(3) 0.1623(3) 0.3779(3) 0.0439(14) Uani d . 1 B .
C C10 0.0775(3) 0.1706(3) 0.4535(3) 0.0447(14) Uani d . 1 . .
H H10 0.0305 0.1657 0.4779 0.058 Uiso calc R 1 B .
C C11 0.1403(3) 0.1863(3) 0.4945(3) 0.0486(15) Uani d . 1 B .
C C12 0.2071(3) 0.1944(3) 0.4636(3) 0.0556(17) Uani d . 1 . .
H H12 0.2495 0.2056 0.4939 0.072 Uiso calc R 1 B .
C C13 0.2120(3) 0.1862(3) 0.3885(4) 0.0631(18) Uani d . 1 B .
H H13 0.2591 0.1917 0.3646 0.082 Uiso calc R 1 . .
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'
Br Br -0.2901 2.4595 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 Pd1 N1 . . 93.80(19) ?
C9 Pd1 N2 . . 80.83(19) ?
N1 Pd1 N2 . . 174.04(16) ?
C9 Pd1 Br1 . . 174.41(16) ?
N1 Pd1 Br1 . . 91.46(12) ?
N2 Pd1 Br1 . . 94.01(11) ?
C5 N1 C1 . . 115.9(5) ?
C5 N1 Pd1 . . 122.0(4) ?
C1 N1 Pd1 . . 122.0(4) ?
C7 N2 C7A . . 24.0(7) ?
C7 N2 Pd1 . . 115.1(4) ?
C7A N2 Pd1 . . 102.4(6) ?
C7 N2 H2A . . 108.5 ?
C7A N2 H2A . . 95.5 ?
Pd1 N2 H2A . . 108.5 ?
C7 N2 H2B . . 108.5 ?
C7A N2 H2B . . 132.4 ?
Pd1 N2 H2B . . 108.5 ?
H2A N2 H2B . . 107.5 ?
N1 C1 C2 . . 122.6(6) ?
N1 C1 H1 . . 118.7 ?
C2 C1 H1 . . 118.7 ?
C3 C2 C1 . . 120.8(6) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C4 C3 C2 . . 115.3(6) ?
C4 C3 C6 . . 122.6(6) ?
C2 C3 C6 . . 122.1(6) ?
C3 C4 C5 . . 122.3(6) ?
C3 C4 H4 . . 118.8 ?
C5 C4 H4 . . 118.8 ?
N1 C5 C4 . . 123.0(6) ?
N1 C5 H5 . . 118.5 ?
C4 C5 H5 . . 118.5 ?
C3 C6 H6A . . 109.5 ?
C3 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C3 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C14 C7 C8 . . 105.0(6) ?
C14 C7 N2 . . 108.3(6) ?
C8 C7 N2 . . 105.0(6) ?
C14 C7 H7 . . 112.7 ?
C8 C7 H7 . . 112.7 ?
N2 C7 H7 . . 112.7 ?
C14A C7A N2 . . 107.2(11) ?
C14A C7A C8 . . 112.4(11) ?
N2 C7A C8 . . 100.9(8) ?
C14A C7A H7A . . 111.9 ?
N2 C7A H7A . . 111.9 ?
C8 C7A H7A . . 111.9 ?
C7A C14A H14D . . 109.5 ?
C7A C14A H14E . . 109.5 ?
H14D C14A H14E . . 109.5 ?
C7A C14A H14F . . 109.5 ?
H14D C14A H14F . . 109.5 ?
H14E C14A H14F . . 109.5 ?
C13 C8 C9 . . 120.0(5) ?
C13 C8 C7 . . 119.1(6) ?
C9 C8 C7 . . 120.0(6) ?
C13 C8 C7A . . 129.4(7) ?
C9 C8 C7A . . 109.2(7) ?
C7 C8 C7A . . 23.4(7) ?
C10 C9 C8 . . 119.4(5) ?
C10 C9 Pd1 . . 125.9(4) ?
C8 C9 Pd1 . . 114.5(4) ?
C9 C10 C11 . . 117.8(5) ?
C9 C10 H10 . . 121.1 ?
C11 C10 H10 . . 121.1 ?
C12 C11 C10 . . 123.8(5) ?
C12 C11 Br2 . . 118.5(4) ?
C10 C11 Br2 . . 117.7(4) ?
C11 C12 C13 . . 117.0(5) ?
C11 C12 H12 . . 121.5 ?
C13 C12 H12 . . 121.5 ?
C12 C13 C8 . . 122.0(6) ?
C12 C13 H13 . . 119.0 ?
C8 C13 H13 . . 119.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Pd1 C9 . 1.983(5) ?
Pd1 N1 . 2.042(4) ?
Pd1 N2 . 2.044(4) ?
Pd1 Br1 . 2.5365(7) ?
Br2 C11 . 1.895(5) ?
N1 C5 . 1.314(6) ?
N1 C1 . 1.326(6) ?
N2 C7 . 1.517(8) ?
N2 C7A . 1.519(12) ?
N2 H2A . 0.9200 ?
N2 H2B . 0.9200 ?
C1 C2 . 1.392(7) ?
C1 H1 . 0.9800 ?
C2 C3 . 1.363(8) ?
C2 H2 . 0.9800 ?
C3 C4 . 1.327(7) ?
C3 C6 . 1.487(7) ?
C4 C5 . 1.380(7) ?
C4 H4 . 0.9800 ?
C5 H5 . 0.9800 ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
C7 C14 . 1.488(10) ?
C7 C8 . 1.499(9) ?
C7 H7 . 1.0000 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C7A C14A . 1.472(14) ?
C7A C8 . 1.584(13) ?
C7A H7A . 1.0000 ?
C14A H14D . 0.9800 ?
C14A H14E . 0.9800 ?
C14A H14F . 0.9800 ?
C8 C13 . 1.391(7) ?
C8 C9 . 1.397(7) ?
C9 C10 . 1.381(7) ?
C10 C11 . 1.410(7) ?
C10 H10 . 0.9800 ?
C11 C12 . 1.366(7) ?
C12 C13 . 1.369(8) ?
C12 H12 . 0.9800 ?
C13 H13 . 0.9800 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 Pd1 N1 C5 . . . . -69.9(4) ?
N2 Pd1 N1 C5 . . . . -44.4(18) ?
Br1 Pd1 N1 C5 . . . . 112.1(4) ?
C9 Pd1 N1 C1 . . . . 113.0(4) ?
N2 Pd1 N1 C1 . . . . 138.4(16) ?
Br1 Pd1 N1 C1 . . . . -65.1(4) ?
C9 Pd1 N2 C7 . . . . 20.2(4) ?
N1 Pd1 N2 C7 . . . . -5.5(19) ?
Br1 Pd1 N2 C7 . . . . -161.9(4) ?
C9 Pd1 N2 C7A . . . . 41.8(6) ?
N1 Pd1 N2 C7A . . . . 16.1(19) ?
Br1 Pd1 N2 C7A . . . . -140.4(6) ?
C5 N1 C1 C2 . . . . 1.8(8) ?
Pd1 N1 C1 C2 . . . . 179.1(4) ?
N1 C1 C2 C3 . . . . -0.3(10) ?
C1 C2 C3 C4 . . . . -2.4(9) ?
C1 C2 C3 C6 . . . . 176.5(6) ?
C2 C3 C4 C5 . . . . 3.7(9) ?
C6 C3 C4 C5 . . . . -175.2(6) ?
C1 N1 C5 C4 . . . . -0.5(8) ?
Pd1 N1 C5 C4 . . . . -177.8(4) ?
C3 C4 C5 N1 . . . . -2.4(10) ?
C7A N2 C7 C14 . . . . 29.3(12) ?
Pd1 N2 C7 C14 . . . . 91.3(6) ?
C7A N2 C7 C8 . . . . -82.4(14) ?
Pd1 N2 C7 C8 . . . . -20.4(7) ?
C7 N2 C7A C14A . . . . -50.4(13) ?
Pd1 N2 C7A C14A . . . . -175.5(10) ?
C7 N2 C7A C8 . . . . 67.4(13) ?
Pd1 N2 C7A C8 . . . . -57.8(9) ?
C14 C7 C8 C13 . . . . 85.3(8) ?
N2 C7 C8 C13 . . . . -160.6(6) ?
C14 C7 C8 C9 . . . . -105.3(7) ?
N2 C7 C8 C9 . . . . 8.8(8) ?
C14 C7 C8 C7A . . . . -37.5(13) ?
N2 C7 C8 C7A . . . . 76.6(14) ?
C14A C7A C8 C13 . . . . -30.8(16) ?
N2 C7A C8 C13 . . . . -144.7(7) ?
C14A C7A C8 C9 . . . . 162.9(10) ?
N2 C7A C8 C9 . . . . 49.0(10) ?
C14A C7A C8 C7 . . . . 41.0(13) ?
N2 C7A C8 C7 . . . . -72.9(14) ?
C13 C8 C9 C10 . . . . 0.2(9) ?
C7 C8 C9 C10 . . . . -169.0(6) ?
C7A C8 C9 C10 . . . . 168.0(7) ?
C13 C8 C9 Pd1 . . . . 176.2(5) ?
C7 C8 C9 Pd1 . . . . 7.0(8) ?
C7A C8 C9 Pd1 . . . . -15.9(8) ?
N1 Pd1 C9 C10 . . . . -21.5(5) ?
N2 Pd1 C9 C10 . . . . 161.1(5) ?
Br1 Pd1 C9 C10 . . . . 138.4(14) ?
N1 Pd1 C9 C8 . . . . 162.8(4) ?
N2 Pd1 C9 C8 . . . . -14.6(4) ?
Br1 Pd1 C9 C8 . . . . -37.3(19) ?
C8 C9 C10 C11 . . . . -0.6(8) ?
Pd1 C9 C10 C11 . . . . -176.1(4) ?
C9 C10 C11 C12 . . . . 0.6(8) ?
C9 C10 C11 Br2 . . . . -179.9(4) ?
C10 C11 C12 C13 . . . . -0.3(9) ?
Br2 C11 C12 C13 . . . . -179.8(4) ?
C11 C12 C13 C8 . . . . 0.0(9) ?
C9 C8 C13 C12 . . . . 0.1(9) ?
C7 C8 C13 C12 . . . . 169.4(6) ?
C7A C8 C13 C12 . . . . -165.0(9) ?
