#------------------------------------------------------------------------------
#$Date: 2016-03-21 10:52:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178671 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/82/4078258.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_4078258
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            'C30 H30 N O5 P Pd'
_chemical_formula_weight         621.92
_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                66.454(2)
_cell_angle_beta                 79.382(2)
_cell_angle_gamma                77.703(2)
_cell_formula_units_Z            2
_cell_length_a                   10.1867(5)
_cell_length_b                   12.514(6)
_cell_length_c                   13.6052(7)
_cell_measurement_reflns_used    7402
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.23
_cell_measurement_theta_min      2.46
_cell_volume                     1543.9(7)
_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 0.993
_diffrn_measured_fraction_theta_max 0.918
_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  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17799
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.10
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.689
_exptl_absorpt_correction_T_max  0.9343
_exptl_absorpt_correction_T_min  0.8075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.021
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment
'NH2  and OH free with DFIX, rigid methyls others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         6909
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0377
_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)+(0.0504P)²+0.9939P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0927
_refine_ls_wR_factor_ref         0.0950
_reflns_number_gt                6106
_reflns_number_total             6909
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om300141b_si_002.cif
_cod_data_source_block           ist323sq
_cod_database_code               4078258
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.678788(19) 0.444964(17) 0.784601(16) 0.02168(7) Uani 1 1 d . . .
P1 P 0.79522(6) 0.26612(6) 0.86981(5) 0.02141(14) Uani 1 1 d . . .
N1 N 0.5679(2) 0.6092(2) 0.6955(2) 0.0281(5) Uani 1 1 d D B .
H01A H 0.621(3) 0.634(3) 0.6414(18) 0.030(9) Uiso 1 1 d D . .
H01B H 0.559(4) 0.639(3) 0.741(2) 0.045(11) Uiso 1 1 d D . .
O1 O 0.3407(2) 0.32422(19) 1.15158(17) 0.0311(4) Uani 1 1 d D . .
H02 H 0.265(2) 0.346(3) 1.173(3) 0.050(12) Uiso 1 1 d D . .
O4 O 0.84222(19) 0.51645(19) 0.67324(16) 0.0324(5) Uani 1 1 d . . .
O5 O 0.9028(2) 0.5965(3) 0.7743(2) 0.0529(7) Uani 1 1 d . . .
C1 C 0.5040(3) 0.4051(2) 0.8744(2) 0.0231(5) Uani 1 1 d . . .
C2 C 0.3904(3) 0.4346(2) 0.8177(2) 0.0246(5) Uani 1 1 d . . .
C3 C 0.2631(3) 0.4234(2) 0.8753(2) 0.0289(6) Uani 1 1 d . . .
H3 H 0.1870 0.4425 0.8368 0.035 Uiso 1 1 calc R . .
C4 C 0.2432(3) 0.3857(2) 0.9860(2) 0.0289(6) Uani 1 1 d . . .
H4 H 0.1553 0.3773 1.0235 0.035 Uiso 1 1 calc R . .
C5 C 0.3549(3) 0.3600(2) 1.0419(2) 0.0261(6) Uani 1 1 d . . .
C6 C 0.4837(3) 0.3688(2) 0.9865(2) 0.0237(5) Uani 1 1 d . . .
H6 H 0.5591 0.3497 1.0256 0.028 Uiso 1 1 calc R . .
C7 C 0.4044(3) 0.4888(3) 0.6967(2) 0.0315(6) Uani 1 1 d . B .
H7A H 0.3197 0.4911 0.6695 0.038 Uiso 1 1 calc R . .
H7B H 0.4790 0.4419 0.6663 0.038 Uiso 1 1 calc R . .
C8 C 0.4348(3) 0.6156(3) 0.6634(2) 0.0322(6) Uani 1 1 d . . .
H8 H 0.3622 0.6625 0.6966 0.039 Uiso 1 1 calc R A 1
O2 O 0.5384(6) 0.6722(8) 0.4789(5) 0.0404(17) Uiso 0.478(16) 1 d P B 1
O3 O 0.3234(6) 0.6972(7) 0.5051(5) 0.0363(16) Uiso 0.478(16) 1 d P B 1
C9 C 0.4411(8) 0.6696(7) 0.5393(6) 0.0212(19) Uiso 0.478(16) 1 d P B 1
C10 C 0.3106(8) 0.7525(8) 0.3952(6) 0.0329(19) Uiso 0.478(16) 1 d P B 1
H10A H 0.2148 0.7698 0.3841 0.040 Uiso 0.478(16) 1 calc PR B 1
H10B H 0.3594 0.7003 0.3581 0.040 Uiso 0.478(16) 1 calc PR B 1
H10C H 0.3485 0.8262 0.3660 0.040 Uiso 0.478(16) 1 calc PR B 1
O2' O 0.5356(5) 0.7101(7) 0.4820(4) 0.0375(15) Uiso 0.522(16) 1 d P B 2
O3' O 0.3064(5) 0.7283(5) 0.5211(4) 0.0256(13) Uiso 0.522(16) 1 d P B 2
C9' C 0.4275(8) 0.6904(8) 0.5507(6) 0.030(2) Uiso 0.522(16) 1 d P B 2
C10' C 0.2855(8) 0.7869(8) 0.4092(6) 0.040(2) Uiso 0.522(16) 1 d P B 2
H10D H 0.1885 0.8122 0.4028 0.048 Uiso 0.522(16) 1 calc PR B 2
H10E H 0.3217 0.7326 0.3717 0.048 Uiso 0.522(16) 1 calc PR B 2
H10F H 0.3321 0.8560 0.3768 0.048 Uiso 0.522(16) 1 calc PR B 2
C11 C 0.9181(3) 0.5723(3) 0.6922(3) 0.0334(7) Uani 1 1 d . . .
C12 C 1.0343(3) 0.6110(4) 0.6081(3) 0.0484(9) Uani 1 1 d . . .
H12A H 1.0000 0.6739 0.5433 0.073 Uiso 1 1 calc R . .
H12B H 1.0838 0.5439 0.5899 0.073 Uiso 1 1 calc R . .
H12C H 1.0951 0.6405 0.6360 0.073 Uiso 1 1 calc R . .
C21 C 0.9744(3) 0.2515(2) 0.8170(2) 0.0254(6) Uani 1 1 d . . .
C22 C 1.0097(3) 0.2863(3) 0.7059(2) 0.0349(7) Uani 1 1 d . . .
H22 H 0.9411 0.3179 0.6586 0.042 Uiso 1 1 calc R . .
C23 C 1.1443(3) 0.2751(3) 0.6640(3) 0.0419(8) Uani 1 1 d . . .
H23 H 1.1678 0.2991 0.5883 0.050 Uiso 1 1 calc R . .
C24 C 1.2449(3) 0.2287(3) 0.7328(3) 0.0368(7) Uani 1 1 d . . .
H24 H 1.3373 0.2210 0.7041 0.044 Uiso 1 1 calc R . .
C25 C 1.2108(3) 0.1941(3) 0.8418(3) 0.0321(6) Uani 1 1 d . . .
H25 H 1.2797 0.1623 0.8887 0.038 Uiso 1 1 calc R . .
C26 C 1.0764(3) 0.2053(2) 0.8844(2) 0.0266(6) Uani 1 1 d . . .
H26 H 1.0539 0.1810 0.9603 0.032 Uiso 1 1 calc R . .
C31 C 0.8043(2) 0.2279(2) 1.0129(2) 0.0224(5) Uani 1 1 d . . .
C32 C 0.7824(3) 0.1188(3) 1.0912(2) 0.0291(6) Uani 1 1 d . . .
H32 H 0.7565 0.0618 1.0719 0.035 Uiso 1 1 calc R . .
C33 C 0.7985(3) 0.0933(3) 1.1977(2) 0.0366(7) Uani 1 1 d . . .
H33 H 0.7819 0.0193 1.2516 0.044 Uiso 1 1 calc R . .
C34 C 0.8388(3) 0.1754(3) 1.2259(2) 0.0364(7) Uani 1 1 d . . .
H34 H 0.8505 0.1570 1.2988 0.044 Uiso 1 1 calc R . .
C35 C 0.8619(3) 0.2841(3) 1.1483(2) 0.0326(6) Uani 1 1 d . . .
H35 H 0.8906 0.3400 1.1674 0.039 Uiso 1 1 calc R . .
C36 C 0.8427(3) 0.3106(3) 1.0422(2) 0.0283(6) Uani 1 1 d . . .
H36 H 0.8560 0.3858 0.9890 0.034 Uiso 1 1 calc R . .
C41 C 0.7423(3) 0.1387(2) 0.8629(2) 0.0222(5) Uani 1 1 d . . .
C42 C 0.6057(3) 0.1336(2) 0.8692(2) 0.0287(6) Uani 1 1 d . . .
H42 H 0.5395 0.1970 0.8762 0.034 Uiso 1 1 calc R . .
C43 C 0.5657(3) 0.0362(3) 0.8652(3) 0.0330(6) Uani 1 1 d . . .
H43 H 0.4722 0.0329 0.8707 0.040 Uiso 1 1 calc R . .
C44 C 0.6600(3) -0.0554(3) 0.8534(2) 0.0321(6) Uani 1 1 d . . .
H44 H 0.6320 -0.1212 0.8496 0.039 Uiso 1 1 calc R . .
C45 C 0.7958(3) -0.0515(3) 0.8472(3) 0.0352(7) Uani 1 1 d . . .
H45 H 0.8612 -0.1152 0.8399 0.042 Uiso 1 1 calc R . .
C46 C 0.8372(3) 0.0450(3) 0.8517(2) 0.0311(6) Uani 1 1 d . . .
H46 H 0.9309 0.0472 0.8469 0.037 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'
P P 0.1023 0.0942 '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
C1 Pd1 O4 169.49(9)
C1 Pd1 N1 86.83(10)
O4 Pd1 N1 82.66(9)
C1 Pd1 P1 93.73(8)
O4 Pd1 P1 96.72(6)
N1 Pd1 P1 175.86(7)
C31 P1 C41 105.00(12)
C31 P1 C21 101.98(12)
C41 P1 C21 102.40(12)
C31 P1 Pd1 115.30(9)
C41 P1 Pd1 117.24(9)
C21 P1 Pd1 113.05(9)
C8 N1 Pd1 120.99(18)
C11 O4 Pd1 122.73(19)
C6 C1 C2 118.6(2)
C6 C1 Pd1 124.49(19)
C2 C1 Pd1 116.1(2)
C3 C2 C1 119.1(3)
C3 C2 C7 120.0(2)
C1 C2 C7 120.7(2)
C4 C3 C2 122.4(3)
C3 C4 C5 118.5(3)
O1 C5 C6 118.7(2)
O1 C5 C4 121.0(2)
C6 C5 C4 120.3(3)
C5 C6 C1 121.1(2)
C2 C7 C8 107.1(2)
C9' C8 N1 110.5(4)
C9' C8 C9 12.8(4)
N1 C8 C9 109.4(3)
C9' C8 C7 115.6(4)
N1 C8 C7 109.1(2)
C9 C8 C7 105.2(4)
C9 O3 C10 120.4(6)
O2 C9 O3 120.0(7)
O2 C9 C8 126.0(6)
O3 C9 C8 113.1(6)
C9' O3' C10' 121.1(6)
O3' C9' O2' 122.3(6)
O3' C9' C8 115.5(6)
O2' C9' C8 122.0(6)
O5 C11 O4 124.8(3)
O5 C11 C12 118.9(3)
O4 C11 C12 116.2(3)
C26 C21 C22 118.8(2)
C26 C21 P1 122.0(2)
C22 C21 P1 119.2(2)
C23 C22 C21 120.3(3)
C22 C23 C24 120.0(3)
C25 C24 C23 119.8(3)
C24 C25 C26 120.5(3)
C25 C26 C21 120.5(3)
C32 C31 C36 119.6(3)
C32 C31 P1 122.8(2)
C36 C31 P1 117.5(2)
C33 C32 C31 119.7(3)
C34 C33 C32 120.3(3)
C35 C34 C33 120.4(3)
C34 C35 C36 119.3(3)
C35 C36 C31 120.7(3)
C42 C41 C46 118.7(2)
C42 C41 P1 120.4(2)
C46 C41 P1 120.9(2)
C43 C42 C41 120.3(3)
C44 C43 C42 120.6(3)
C43 C44 C45 119.7(3)
C44 C45 C46 120.3(3)
C45 C46 C41 120.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 C1 2.001(3)
Pd1 O4 2.119(2)
Pd1 N1 2.120(2)
Pd1 P1 2.2500(10)
P1 C31 1.825(3)
P1 C41 1.829(3)
P1 C21 1.833(3)
N1 C8 1.476(4)
O1 C5 1.365(3)
O4 C11 1.265(4)
O5 C11 1.245(4)
C1 C6 1.394(4)
C1 C2 1.411(4)
C2 C3 1.390(4)
C2 C7 1.501(4)
C3 C4 1.375(4)
C4 C5 1.394(4)
C5 C6 1.390(4)
C7 C8 1.551(4)
C8 C9' 1.448(8)
C8 C9 1.542(8)
O2 C9 1.163(9)
O3 C9 1.294(9)
O3 C10 1.392(9)
O2' C9' 1.303(9)
O3' C9' 1.301(8)
O3' C10' 1.435(8)
C11 C12 1.499(4)
C21 C26 1.388(4)
C21 C22 1.395(4)
C22 C23 1.385(4)
C23 C24 1.389(5)
C24 C25 1.367(5)
C25 C26 1.386(4)
C31 C32 1.389(4)
C31 C36 1.393(4)
C32 C33 1.387(4)
C33 C34 1.387(5)
C34 C35 1.385(5)
C35 C36 1.387(4)
C41 C42 1.392(4)
C41 C46 1.393(4)
C42 C43 1.388(4)
C43 C44 1.372(4)
C44 C45 1.380(4)
C45 C46 1.387(4)
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 O1 0.831(15) 2.16(2) 2.885(3) 146(3) 2_667
O1 H02 O5 0.802(18) 1.842(19) 2.642(3) 175(4) 2_667
C44 H44 O1 0.95 2.50 3.394(4) 156.2 2_657
