#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:12:26 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178693 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/04/4080475.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_4080475
loop_
_publ_author_name
'Frutos-Pedreño, Roberto'
'González-Herrero, Pablo'
'Vicente, José'
'Jones, Peter G.'
_publ_section_title
;
 Synthesis and Reactivity of Ortho-Palladated 3-Phenylpropanamides.
 Insertion of CO, XyNC, and Alkynes into the Pd--C Bond. Synthesis of
 Seven- and Nine-Membered Palladacycles and Benzazepine- and
 Benzazonine-Based Heterocycles
;
_journal_issue                   6
_journal_name_full               Organometallics
_journal_page_first              1892
_journal_paper_doi               10.1021/om4000192
_journal_volume                  32
_journal_year                    2013
_chemical_formula_sum            'C16 H28 I N3 O Pd'
_chemical_formula_weight         511.71
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 108.468(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.8170(4)
_cell_length_b                   11.4064(4)
_cell_length_c                   12.3040(4)
_cell_measurement_reflns_used    35124
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      30.7706
_cell_measurement_theta_min      2.3624
_cell_volume                     1839.27(11)
_computing_cell_refinement
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) 
(compiled Oct 25 2010,18:11:34) 
;
_computing_data_collection
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) 
(compiled Oct 25 2010,18:11:34) 
;
_computing_data_reduction
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) 
(compiled Oct 25 2010,18:11:34) 
;
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      103(2)
_diffrn_detector_area_resol_mean 16.1419
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0137
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            57558
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.84
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    2.693
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) 
(compiled Oct 25 2010,18:11:34) 
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         2.519
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    'NH free, rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         5534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0195
_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)+(0.0145P)²+3.1055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0433
_refine_ls_wR_factor_ref         0.0445
_reflns_number_gt                5140
_reflns_number_total             5534
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om4000192_si_002.cif
_cod_data_source_block           otrebor
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1839.27(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4080475
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
Pd Pd 0.216414(10) 0.595406(11) 0.291578(11) 0.01012(3) Uani 1 1 d .
I I 0.121790(9) 0.698053(10) 0.100280(10) 0.01427(3) Uani 1 1 d .
N1 N 0.23045(14) 1.04089(16) 0.46885(15) 0.0198(3) Uani 1 1 d .
H01 H 0.228(2) 0.971(3) 0.493(2) 0.027(7) Uiso 1 1 d .
N2 N 0.08257(12) 0.50028(14) 0.30738(13) 0.0145(3) Uani 1 1 d .
N3 N 0.29344(11) 0.51484(14) 0.45123(13) 0.0127(3) Uani 1 1 d .
O O 0.23970(13) 1.15838(13) 0.32547(14) 0.0247(3) Uani 1 1 d .
C1 C 0.34639(15) 0.66731(16) 0.28127(16) 0.0159(3) Uani 1 1 d .
C2 C 0.38584(14) 0.77385(17) 0.33317(16) 0.0151(3) Uani 1 1 d .
C3 C 0.48153(15) 0.81052(18) 0.32879(18) 0.0191(4) Uani 1 1 d .
H3 H 0.5106 0.8807 0.3668 0.023 Uiso 1 1 calc R
C4 C 0.53478(15) 0.74660(19) 0.27022(18) 0.0209(4) Uani 1 1 d .
H4 H 0.5992 0.7731 0.2675 0.025 Uiso 1 1 calc R
C5 C 0.49267(15) 0.64359(19) 0.21582(17) 0.0198(4) Uani 1 1 d .
H5 H 0.5263 0.5992 0.1732 0.024 Uiso 1 1 calc R
C6 C 0.39825(14) 0.60664(18) 0.22562(16) 0.0170(4) Uani 1 1 d .
H6 H 0.3703 0.5347 0.1907 0.020 Uiso 1 1 calc R
C7 C 0.32959(16) 0.85333(17) 0.39066(17) 0.0174(4) Uani 1 1 d .
H7A H 0.3780 0.8846 0.4624 0.021 Uiso 1 1 calc R
H7B H 0.2768 0.8077 0.4109 0.021 Uiso 1 1 calc R
C8 C 0.27886(15) 0.95565(17) 0.31214(16) 0.0167(3) Uani 1 1 d .
H8A H 0.3264 0.9829 0.2718 0.020 Uiso 1 1 calc R
H8B H 0.2171 0.9253 0.2533 0.020 Uiso 1 1 calc R
C9 C 0.24796(14) 1.06091(17) 0.36897(17) 0.0168(3) Uani 1 1 d .
C10 C 0.20135(17) 1.13364(19) 0.53251(19) 0.0230(4) Uani 1 1 d .
H10A H 0.2479 1.2002 0.5403 0.035 Uiso 1 1 calc R
H10B H 0.2051 1.1048 0.6087 0.035 Uiso 1 1 calc R
H10C H 0.1314 1.1587 0.4916 0.035 Uiso 1 1 calc R
C11 C 0.01141(15) 0.58366(19) 0.33390(18) 0.0203(4) Uani 1 1 d .
H11A H -0.0171 0.6361 0.2684 0.030 Uiso 1 1 calc R
H11B H 0.0481 0.6300 0.4015 0.030 Uiso 1 1 calc R
H11C H -0.0440 0.5402 0.3494 0.030 Uiso 1 1 calc R
C12 C 0.02412(16) 0.43158(19) 0.20505(18) 0.0209(4) Uani 1 1 d .
H12A H 0.0694 0.3742 0.1866 0.031 Uiso 1 1 calc R
H12B H -0.0034 0.4847 0.1399 0.031 Uiso 1 1 calc R
H12C H -0.0321 0.3905 0.2212 0.031 Uiso 1 1 calc R
C13 C 0.12549(15) 0.41660(17) 0.40270(17) 0.0177(4) Uani 1 1 d .
H13A H 0.1517 0.3465 0.3737 0.021 Uiso 1 1 calc R
H13B H 0.0712 0.3910 0.4340 0.021 Uiso 1 1 calc R
C14 C 0.21079(15) 0.47337(18) 0.49636(16) 0.0168(4) Uani 1 1 d .
H14A H 0.1836 0.5407 0.5284 0.020 Uiso 1 1 calc R
H14B H 0.2393 0.4162 0.5589 0.020 Uiso 1 1 calc R
C15 C 0.36159(15) 0.59219(17) 0.53954(16) 0.0173(4) Uani 1 1 d .
H15A H 0.4153 0.6234 0.5114 0.026 Uiso 1 1 calc R
H15B H 0.3927 0.5471 0.6098 0.026 Uiso 1 1 calc R
H15C H 0.3219 0.6571 0.5559 0.026 Uiso 1 1 calc R
C16 C 0.35471(16) 0.41505(18) 0.43217(18) 0.0195(4) Uani 1 1 d .
H16A H 0.3102 0.3603 0.3773 0.029 Uiso 1 1 calc R
H16B H 0.3868 0.3746 0.5050 0.029 Uiso 1 1 calc R
H16C H 0.4076 0.4442 0.4017 0.029 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'
O O 0.0106 0.0060 '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
C1 Pd N3 92.23(6)
C1 Pd N2 174.32(7)
N3 Pd N2 83.92(6)
C1 Pd I 87.83(5)
N3 Pd I 178.51(4)
N2 Pd I 96.14(4)
C9 N1 C10 122.12(18)
C11 N2 C13 111.55(15)
C11 N2 C12 107.80(15)
C13 N2 C12 107.74(15)
C11 N2 Pd 109.77(12)
C13 N2 Pd 104.49(11)
C12 N2 Pd 115.51(12)
C16 N3 C15 108.14(15)
C16 N3 C14 110.95(15)
C15 N3 C14 107.36(14)
C16 N3 Pd 109.28(11)
C15 N3 Pd 115.87(12)
C14 N3 Pd 105.21(11)
C6 C1 C2 119.37(18)
C6 C1 Pd 117.17(14)
C2 C1 Pd 123.40(15)
C1 C2 C3 118.44(18)
C1 C2 C7 123.48(17)
C3 C2 C7 118.06(17)
C4 C3 C2 121.59(19)
C5 C4 C3 119.04(18)
C4 C5 C6 118.02(19)
C1 C6 C5 123.45(19)
C2 C7 C8 111.23(16)
C9 C8 C7 116.78(16)
O C9 N1 122.35(19)
O C9 C8 121.22(18)
N1 C9 C8 116.43(17)
N2 C13 C14 110.36(16)
N3 C14 C13 110.84(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd C1 2.015(2)
Pd N3 2.1240(15)
Pd N2 2.2052(16)
Pd I 2.5827(2)
N1 C9 1.345(3)
N1 C10 1.447(3)
N2 C11 1.477(2)
N2 C13 1.482(2)
N2 C12 1.486(2)
N3 C16 1.481(2)
N3 C15 1.482(2)
N3 C14 1.496(2)
O C9 1.223(2)
C1 C6 1.331(3)
C1 C2 1.400(3)
C2 C3 1.404(3)
C2 C7 1.508(3)
C3 C4 1.389(3)
C4 C5 1.386(3)
C5 C6 1.412(3)
C7 C8 1.536(3)
C8 C9 1.517(3)
C13 C14 1.509(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H01 I 0.85(3) 2.98(3) 3.7196(18) 147(2) 4_576
C13 H13A O 0.99 2.63 3.608(3) 172.0 1_545
C16 H16A O 0.98 2.50 3.391(3) 150.4 1_545
C11 H11B I 0.98 3.05 4.013(2) 168.4 4_576
C14 H14A I 0.99 3.30 4.265(2) 166.2 4_576
C10 H10C I 0.98 3.35 4.304(2) 165.3 2
