#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:02:18 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178690 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/01/4080105.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_4080105
loop_
_publ_author_name
'Sabater, Sara'
'Mata, Jose A.'
'Peris, Eduardo'
_publ_section_title
;
 Chiral Palladacycles with N-Heterocyclic Carbene Ligands as Catalysts for
 Asymmetric Hydrophosphination
;
_journal_issue                   4
_journal_name_full               Organometallics
_journal_page_first              1112
_journal_paper_doi               10.1021/om400007a
_journal_volume                  32
_journal_year                    2013
_chemical_formula_sum            'C17 H20 I N3 Pd'
_chemical_formula_weight         499.66
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 103.859(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.5601(8)
_cell_length_b                   7.4175(7)
_cell_length_c                   14.2238(16)
_cell_measurement_temperature    150(2)
_cell_volume                     876.84(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.931
_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    0.0882
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10007
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.97
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    2.818
_exptl_crystal_density_diffrn    1.892
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_refine_diff_density_max         1.132
_refine_diff_density_min         -1.023
_refine_diff_density_rms         0.157
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         4104
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0430
_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)+(0.0220P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0894
_reflns_number_gt                3476
_reflns_number_total             4104
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400007a_si_001.cif
_cod_data_source_block           compound_23_str1392
_cod_database_code               4080105
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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
I2 I 0.04360(5) 0.88012(7) 0.40407(3) 0.03403(15) Uani 1 1 d .
Pd1 Pd 0.17449(6) 0.81142(6) 0.25476(4) 0.02116(13) Uani 1 1 d .
N4 N 0.3542(7) 0.5054(9) 0.3744(4) 0.0311(15) Uani 1 1 d .
N8 N 0.5091(7) 0.7240(8) 0.3604(4) 0.0257(14) Uani 1 1 d .
N10 N 0.0079(6) 0.9707(8) 0.1577(4) 0.0259(14) Uani 1 1 d .
H10A H -0.0839 0.9051 0.1330 0.031 Uiso 1 1 calc R
H10B H -0.0195 1.0693 0.1896 0.031 Uiso 1 1 calc R
C3 C 0.3543(8) 0.6720(9) 0.3350(5) 0.0224(15) Uani 1 1 d .
C5 C 0.2093(9) 0.3958(11) 0.3700(6) 0.0374(18) Uani 1 1 d .
H5A H 0.2382 0.2677 0.3737 0.056 Uiso 1 1 calc R
H5B H 0.1303 0.4195 0.3090 0.056 Uiso 1 1 calc R
H5C H 0.1628 0.4271 0.4245 0.056 Uiso 1 1 calc R
C6 C 0.5093(9) 0.4580(12) 0.4254(5) 0.0348(19) Uani 1 1 d .
H6 H 0.5406 0.3499 0.4607 0.042 Uiso 1 1 calc R
C7 C 0.6041(9) 0.5943(12) 0.4148(5) 0.0338(19) Uani 1 1 d .
H7 H 0.7172 0.6009 0.4402 0.041 Uiso 1 1 calc R
C9 C 0.5658(8) 0.8947(12) 0.3330(6) 0.040(2) Uani 1 1 d .
H9A H 0.4832 0.9484 0.2808 0.060 Uiso 1 1 calc R
H9B H 0.6643 0.8757 0.3107 0.060 Uiso 1 1 calc R
H9C H 0.5885 0.9758 0.3890 0.060 Uiso 1 1 calc R
C11 C 0.0803(8) 1.0322(9) 0.0764(5) 0.0243(16) Uani 1 1 d .
H11 H -0.0060 1.0574 0.0168 0.029 Uiso 1 1 calc R
C12 C 0.1807(9) 1.1996(10) 0.1083(6) 0.036(2) Uani 1 1 d .
H12A H 0.1108 1.2981 0.1192 0.054 Uiso 1 1 calc R
H12B H 0.2352 1.2347 0.0579 0.054 Uiso 1 1 calc R
H12C H 0.2612 1.1741 0.1685 0.054 Uiso 1 1 calc R
C13 C 0.1864(7) 0.8795(10) 0.0589(4) 0.0176(13) Uani 1 1 d .
C14 C 0.2498(7) 0.7637(9) 0.1349(5) 0.0199(15) Uani 1 1 d .
C15 C 0.3542(7) 0.6238(9) 0.1182(5) 0.0231(15) Uani 1 1 d .
H15 H 0.3993 0.5436 0.1696 0.028 Uiso 1 1 calc R
C16 C 0.3915(7) 0.6014(9) 0.0313(5) 0.0222(15) Uani 1 1 d .
H16 H 0.4625 0.5071 0.0235 0.027 Uiso 1 1 calc R
C17 C 0.3267(8) 0.7155(9) -0.0475(5) 0.0216(15) Uani 1 1 d .
C18 C 0.3638(8) 0.6937(10) -0.1372(5) 0.0280(17) Uani 1 1 d .
H18 H 0.4331 0.5982 -0.1456 0.034 Uiso 1 1 calc R
C19 C 0.3033(8) 0.8057(13) -0.2130(6) 0.0353(18) Uani 1 1 d .
H19 H 0.3290 0.7861 -0.2735 0.042 Uiso 1 1 calc R
C20 C 0.2012(8) 0.9528(12) -0.2017(5) 0.0361(19) Uani 1 1 d .
H20 H 0.1603 1.0326 -0.2541 0.043 Uiso 1 1 calc R
C21 C 0.1637(8) 0.9763(10) -0.1149(5) 0.0284(17) Uani 1 1 d .
H21 H 0.0947 1.0733 -0.1080 0.034 Uiso 1 1 calc R
C22 C 0.2231(7) 0.8623(10) -0.0340(5) 0.0201(14) Uani 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'
I I -0.4742 1.8119 '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
C3 Pd1 C14 92.0(3)
C3 Pd1 N10 171.5(2)
C14 Pd1 N10 81.1(2)
C3 Pd1 I2 93.30(19)
C14 Pd1 I2 174.21(18)
N10 Pd1 I2 93.85(15)
C3 N4 C6 110.4(7)
C3 N4 C5 124.7(6)
C6 N4 C5 124.7(7)
C3 N8 C7 111.3(6)
C3 N8 C9 123.6(6)
C7 N8 C9 125.1(6)
C11 N10 Pd1 109.7(4)
N8 C3 N4 104.4(6)
N8 C3 Pd1 125.9(5)
N4 C3 Pd1 129.6(5)
C7 C6 N4 106.3(7)
C6 C7 N8 107.5(7)
N10 C11 C13 105.8(5)
N10 C11 C12 109.0(6)
C13 C11 C12 110.1(5)
C14 C13 C22 122.2(6)
C14 C13 C11 118.4(6)
C22 C13 C11 119.4(6)
C13 C14 C15 117.7(6)
C13 C14 Pd1 114.2(4)
C15 C14 Pd1 128.0(5)
C16 C15 C14 122.3(6)
C15 C16 C17 121.1(6)
C18 C17 C16 121.7(6)
C18 C17 C22 119.2(6)
C16 C17 C22 119.0(6)
C19 C18 C17 121.8(7)
C18 C19 C20 120.2(7)
C21 C20 C19 118.9(7)
C20 C21 C22 122.8(7)
C21 C22 C13 125.3(6)
C21 C22 C17 117.0(6)
C13 C22 C17 117.7(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I2 Pd1 2.6768(7)
Pd1 C3 1.975(7)
Pd1 C14 1.993(6)
Pd1 N10 2.095(5)
N4 C3 1.357(9)
N4 C6 1.397(9)
N4 C5 1.472(9)
N8 C3 1.344(8)
N8 C7 1.372(9)
N8 C9 1.443(10)
N10 C11 1.508(9)
C6 C7 1.328(11)
C11 C13 1.510(9)
C11 C12 1.517(10)
C13 C14 1.385(9)
C13 C22 1.436(8)
C14 C15 1.426(9)
C15 C16 1.359(9)
C16 C17 1.407(9)
C17 C18 1.397(10)
C17 C22 1.446(9)
C18 C19 1.360(10)
C19 C20 1.431(11)
C20 C21 1.360(10)
C21 C22 1.420(9)
