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#$Date: 2016-03-21 10:52:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178671 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/82/4078260.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_4078260
loop_
_publ_author_name
'Oliva-Madrid, María-José'
'Garc\?ía-López, José-Antonio'
'Saura-Llamas, Isabel'
'Bautista, Delia'
'Vicente, José'
_publ_section_title
;
 Ortho Palladation of the Phenethylamines of Biological
 Relevancel-Tyrosine Methyl Ester and Homoveratrylamine. Reactivity of the
 Palladacycles toward CO and Isocyanides. Synthesis of the Natural
 Alkaloid Corydaldine
;
_journal_issue                   9
_journal_name_full               Organometallics
_journal_page_first              3647
_journal_paper_doi               10.1021/om300141b
_journal_volume                  31
_journal_year                    2012
_chemical_formula_sum            'C24 H40 N2 O10 Pd'
_chemical_formula_weight         622.98
_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                 109.139(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   16.5114(7)
_cell_length_b                   5.3548(2)
_cell_length_c                   16.3972(7)
_cell_measurement_reflns_used    8119
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      2.52
_cell_volume                     1369.63(10)
_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_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ω-scan
_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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14946
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.13
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  0.9369
_exptl_absorpt_correction_T_min  0.8378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment
'water H free with SADI, NH2 free, rigid methyls others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3168
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0254P)²+1.6359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0671
_reflns_number_gt                2979
_reflns_number_total             3168
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om300141b_si_002.cif
_cod_data_source_block           jad693si
_cod_original_sg_symbol_H-M      'P 2(1)/c'
_cod_database_code               4078260
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
Pd1 Pd 0.5000 0.0000 0.0000 0.01332(7) Uani 1 2 d S
N1 N 0.58155(11) 0.2920(3) 0.04792(12) 0.0169(3) Uani 1 1 d .
H01A H 0.5787(17) 0.394(5) 0.0077(18) 0.025(7) Uiso 1 1 d .
H01B H 0.5637(16) 0.373(5) 0.0830(17) 0.024(7) Uiso 1 1 d .
O1 O 0.40917(9) 0.2043(3) 0.02659(9) 0.0171(3) Uani 1 1 d .
O2 O 0.42547(12) -0.0043(3) 0.14860(11) 0.0302(4) Uani 1 1 d .
O3 O 1.03057(10) 0.0570(3) 0.39169(10) 0.0248(3) Uani 1 1 d .
O4 O 0.92814(10) 0.3873(3) 0.41778(10) 0.0252(3) Uani 1 1 d .
C1 C 0.67336(12) 0.2421(4) 0.09448(13) 0.0186(4) Uani 1 1 d .
H1A H 0.7038 0.4019 0.1135 0.022 Uiso 1 1 calc R
H1B H 0.6993 0.1586 0.0552 0.022 Uiso 1 1 calc R
C2 C 0.68333(13) 0.0763(4) 0.17282(14) 0.0204(4) Uani 1 1 d .
H2A H 0.6481 0.1443 0.2062 0.024 Uiso 1 1 calc R
H2B H 0.6621 -0.0935 0.1531 0.024 Uiso 1 1 calc R
C3 C 0.77590(13) 0.0609(4) 0.23050(14) 0.0192(4) Uani 1 1 d .
C4 C 0.80723(13) 0.2337(4) 0.29803(13) 0.0196(4) Uani 1 1 d .
H4 H 0.7696 0.3556 0.3078 0.023 Uiso 1 1 calc R
C5 C 0.89223(13) 0.2290(4) 0.35058(13) 0.0207(4) Uani 1 1 d .
C6 C 0.94802(13) 0.0490(4) 0.33595(14) 0.0204(4) Uani 1 1 d .
C7 C 0.91813(14) -0.1197(4) 0.26946(14) 0.0227(4) Uani 1 1 d .
H7 H 0.9558 -0.2409 0.2594 0.027 Uiso 1 1 calc R
C8 C 0.83174(14) -0.1124(4) 0.21643(14) 0.0230(4) Uani 1 1 d .
H8 H 0.8116 -0.2283 0.1703 0.028 Uiso 1 1 calc R
C9 C 0.87298(15) 0.5667(5) 0.43696(15) 0.0264(5) Uani 1 1 d .
H9A H 0.8484 0.6753 0.3868 0.040 Uiso 1 1 calc R
H9B H 0.9060 0.6677 0.4866 0.040 Uiso 1 1 calc R
H9C H 0.8267 0.4801 0.4506 0.040 Uiso 1 1 calc R
C10 C 1.08524(14) -0.1431(5) 0.38699(15) 0.0281(5) Uani 1 1 d .
H10A H 1.0586 -0.3021 0.3935 0.042 Uiso 1 1 calc R
H10B H 1.1404 -0.1261 0.4333 0.042 Uiso 1 1 calc R
H10C H 1.0945 -0.1394 0.3310 0.042 Uiso 1 1 calc R
C11 C 0.39390(13) 0.1661(4) 0.09720(13) 0.0202(4) Uani 1 1 d .
C12 C 0.33254(15) 0.3515(5) 0.11475(16) 0.0271(5) Uani 1 1 d .
H12A H 0.3142 0.2904 0.1622 0.041 Uiso 1 1 calc R
H12B H 0.2824 0.3713 0.0628 0.041 Uiso 1 1 calc R
H12C H 0.3613 0.5131 0.1306 0.041 Uiso 1 1 calc R
O99 O 0.53819(12) 0.5869(3) 0.17428(11) 0.0281(4) Uani 1 1 d D
H09A H 0.549(2) 0.552(6) 0.2249(16) 0.046(10) Uiso 1 1 d D
H09B H 0.509(2) 0.714(6) 0.165(2) 0.061(11) Uiso 1 1 d 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'
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'
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
O1 Pd1 O1 180.0 3_655 .
O1 Pd1 N1 86.83(7) 3_655 3_655
O1 Pd1 N1 93.17(7) . 3_655
O1 Pd1 N1 93.17(7) 3_655 .
O1 Pd1 N1 86.83(7) . .
N1 Pd1 N1 180.0 3_655 .
C1 N1 Pd1 119.58(13) . .
C11 O1 Pd1 119.35(13) . .
C6 O3 C10 116.82(17) . .
C5 O4 C9 117.18(17) . .
N1 C1 C2 110.42(16) . .
C3 C2 C1 111.48(17) . .
C8 C3 C4 118.77(19) . .
C8 C3 C2 121.7(2) . .
C4 C3 C2 119.47(19) . .
C5 C4 C3 120.9(2) . .
O4 C5 C4 125.1(2) . .
O4 C5 C6 115.37(18) . .
C4 C5 C6 119.5(2) . .
O3 C6 C7 124.7(2) . .
O3 C6 C5 115.36(19) . .
C7 C6 C5 119.98(19) . .
C6 C7 C8 119.9(2) . .
C3 C8 C7 120.9(2) . .
O2 C11 O1 124.8(2) . .
O2 C11 C12 121.0(2) . .
O1 C11 C12 114.23(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 O1 2.0161(14) 3_655
Pd1 O1 2.0161(14) .
Pd1 N1 2.0451(17) 3_655
Pd1 N1 2.0451(17) .
N1 C1 1.481(3) .
O1 C11 1.280(2) .
O2 C11 1.236(3) .
O3 C6 1.370(2) .
O3 C10 1.420(3) .
O4 C5 1.362(3) .
O4 C9 1.428(3) .
C1 C2 1.525(3) .
C2 C3 1.513(3) .
C3 C8 1.380(3) .
C3 C4 1.405(3) .
C4 C5 1.386(3) .
C5 C6 1.407(3) .
C6 C7 1.377(3) .
C7 C8 1.407(3) .
C11 C12 1.512(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 H01B O99 0.85(3) 2.03(3) 2.876(3) 172(2) .
N1 H01A O1 0.85(3) 2.25(3) 2.985(2) 146(2) 3_665
O99 H09A O2 0.81(2) 2.00(2) 2.809(2) 175(3) 2_655
O99 H09B O2 0.82(2) 2.00(2) 2.814(2) 172(4) 1_565
