#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:22:22 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178561 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/69/4066967.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_4066967
loop_
_publ_author_name
'Vicente, José'
'Saura-Llamas, Isabel'
'García-López, José-Antonio'
'Bautista, Delia'
_publ_section_title
;
 Eight-Membered Palladacycles Derived from the Insertion of Olefins into
 the Pd−C Bond of Ortho-Palladated Pharmaceuticals Phenethylamine
 and Phentermine. Synthesis of Stable Heck-Type Intermediates Containing
 Accessible β-Hydrogens and Its Use in the Synthesis of
 2-Styrylphenethylamines, Tetrahydroisoquinolines, and Eight-Membered
 Cyclic Amidines†
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              4320
_journal_paper_doi               10.1021/om100738z
_journal_volume                  29
_journal_year                    2010
_chemical_formula_sum            'C36 H42 Cl2 N2 Pd'
_chemical_formula_weight         680.02
_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                101.558(2)
_cell_angle_beta                 96.832(2)
_cell_angle_gamma                104.834(2)
_cell_formula_units_Z            1
_cell_length_a                   6.0466(5)
_cell_length_b                   10.1257(8)
_cell_length_c                   13.9180(11)
_cell_measurement_reflns_used    5543
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.95
_cell_measurement_theta_min      2.31
_cell_volume                     793.89(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker ShelXTL'
_computing_publication_material  'Bruker ShelXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.917
_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  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9186
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.15
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_T_max  0.9547
_exptl_absorpt_correction_T_min  0.8853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.803
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment
'NH2 free with SADI, rigid methyls others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3551
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0271
_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)+(0.0327P)²+0.3802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0649
_refine_ls_wR_factor_ref         0.0657
_reflns_number_gt                3452
_reflns_number_total             3551
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om100738z_si_002.cif
_cod_data_source_block           jae191s
_cod_database_code               4066967
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 0.5000 0.5000 1.0000 0.01255(7) Uani 1 2 d S
Cl1 Cl 0.82507(7) 0.67736(5) 0.99972(3) 0.01812(10) Uani 1 1 d .
N1 N 0.3077(3) 0.60265(17) 0.92589(12) 0.0154(3) Uani 1 1 d D
H01A H 0.186(3) 0.599(2) 0.9510(17) 0.021(6) Uiso 1 1 d D
H01B H 0.398(4) 0.685(2) 0.9453(17) 0.026(6) Uiso 1 1 d D
C1 C 0.2384(3) 0.56439(19) 0.81356(13) 0.0161(4) Uani 1 1 d .
C2 C 0.0340(3) 0.4280(2) 0.78464(14) 0.0177(4) Uani 1 1 d .
H2A H 0.0697 0.3620 0.8236 0.021 Uiso 1 1 calc R
H2B H -0.1070 0.4509 0.8036 0.021 Uiso 1 1 calc R
C3 C -0.0188(3) 0.3548(2) 0.67484(14) 0.0192(4) Uani 1 1 d .
C4 C 0.0836(3) 0.2497(2) 0.63597(15) 0.0210(4) Uani 1 1 d .
C5 C 0.0320(4) 0.1909(2) 0.53278(16) 0.0270(5) Uani 1 1 d .
H5 H 0.1032 0.1220 0.5055 0.032 Uiso 1 1 calc R
C6 C -0.1194(4) 0.2305(2) 0.46989(16) 0.0306(5) Uani 1 1 d .
H6 H -0.1524 0.1882 0.4004 0.037 Uiso 1 1 calc R
C7 C -0.2232(4) 0.3317(2) 0.50787(16) 0.0295(5) Uani 1 1 d .
H7 H -0.3283 0.3590 0.4650 0.035 Uiso 1 1 calc R
C8 C -0.1719(3) 0.3926(2) 0.60933(15) 0.0238(4) Uani 1 1 d .
H8 H -0.2429 0.4623 0.6352 0.029 Uiso 1 1 calc R
C9 C 0.2326(4) 0.1976(2) 0.70199(15) 0.0227(4) Uani 1 1 d .
H9 H 0.2164 0.2128 0.7701 0.027 Uiso 1 1 calc R
C10 C 0.3883(4) 0.1308(2) 0.67522(16) 0.0261(4) Uani 1 1 d .
H10 H 0.4099 0.1192 0.6079 0.031 Uiso 1 1 calc R
C11 C 0.5288(4) 0.0739(2) 0.74032(17) 0.0245(4) Uani 1 1 d .
C12 C 0.6657(4) -0.0065(2) 0.69793(19) 0.0314(5) Uani 1 1 d .
H12 H 0.6648 -0.0227 0.6282 0.038 Uiso 1 1 calc R
C13 C 0.8018(4) -0.0627(2) 0.7554(2) 0.0365(6) Uani 1 1 d .
H13 H 0.8915 -0.1179 0.7248 0.044 Uiso 1 1 calc R
C14 C 0.8083(4) -0.0391(2) 0.85729(19) 0.0317(5) Uani 1 1 d .
H14 H 0.9033 -0.0768 0.8970 0.038 Uiso 1 1 calc R
C15 C 0.6739(4) 0.0406(2) 0.90071(18) 0.0319(5) Uani 1 1 d .
H15 H 0.6777 0.0577 0.9706 0.038 Uiso 1 1 calc R
C16 C 0.5341(4) 0.0955(2) 0.84283(17) 0.0285(5) Uani 1 1 d .
H16 H 0.4412 0.1483 0.8734 0.034 Uiso 1 1 calc R
C17 C 0.4503(3) 0.5471(2) 0.76873(14) 0.0195(4) Uani 1 1 d .
H17A H 0.5788 0.6338 0.7938 0.029 Uiso 1 1 calc R
H17B H 0.4116 0.5277 0.6959 0.029 Uiso 1 1 calc R
H17C H 0.4966 0.4686 0.7877 0.029 Uiso 1 1 calc R
C18 C 0.1631(4) 0.6855(2) 0.78349(15) 0.0217(4) Uani 1 1 d .
H18A H 0.0374 0.7026 0.8181 0.032 Uiso 1 1 calc R
H18B H 0.1080 0.6611 0.7113 0.032 Uiso 1 1 calc R
H18C H 0.2957 0.7707 0.8018 0.032 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'
Cl Cl 0.1484 0.1585 '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
N1 Pd1 N1 180.000(1) 2_667 .
N1 Pd1 Cl1 87.47(5) 2_667 2_667
N1 Pd1 Cl1 92.53(5) . 2_667
N1 Pd1 Cl1 92.53(5) 2_667 .
N1 Pd1 Cl1 87.47(5) . .
Cl1 Pd1 Cl1 180.0 2_667 .
C1 N1 Pd1 122.36(11) . .
N1 C1 C17 108.17(14) . .
N1 C1 C18 107.70(15) . .
C17 C1 C18 109.87(16) . .
N1 C1 C2 107.38(15) . .
C17 C1 C2 112.77(15) . .
C18 C1 C2 110.76(15) . .
C3 C2 C1 114.33(15) . .
C8 C3 C4 118.60(18) . .
C8 C3 C2 119.37(17) . .
C4 C3 C2 122.03(17) . .
C5 C4 C3 118.39(18) . .
C5 C4 C9 120.31(18) . .
C3 C4 C9 121.24(18) . .
C6 C5 C4 121.7(2) . .
C5 C6 C7 120.1(2) . .
C6 C7 C8 119.1(2) . .
C7 C8 C3 122.10(19) . .
C10 C9 C4 126.29(19) . .
C9 C10 C11 126.0(2) . .
C16 C11 C12 117.8(2) . .
C16 C11 C10 123.47(19) . .
C12 C11 C10 118.7(2) . .
C13 C12 C11 121.4(2) . .
C12 C13 C14 120.4(2) . .
C13 C14 C15 119.1(2) . .
C16 C15 C14 120.6(2) . .
C15 C16 C11 120.7(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 N1 2.0638(16) 2_667
Pd1 N1 2.0638(16) .
Pd1 Cl1 2.2991(5) 2_667
Pd1 Cl1 2.2991(5) .
N1 C1 1.513(2) .
C1 C17 1.524(2) .
C1 C18 1.528(3) .
C1 C2 1.543(3) .
C2 C3 1.515(3) .
C3 C8 1.398(3) .
C3 C4 1.412(3) .
C4 C5 1.404(3) .
C4 C9 1.475(3) .
C5 C6 1.380(3) .
C6 C7 1.384(3) .
C7 C8 1.386(3) .
C9 C10 1.339(3) .
C10 C11 1.467(3) .
C11 C16 1.395(3) .
C11 C12 1.402(3) .
C12 C13 1.381(3) .
C13 C14 1.384(4) .
C14 C15 1.390(3) .
C15 C16 1.390(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 H01A Cl1 0.845(18) 2.625(19) 3.4171(16) 157(2) 1_455
