#------------------------------------------------------------------------------
#$Date: 2016-03-21 06:55:12 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178540 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/46/4064655.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_4064655
loop_
_publ_author_name
'Serrano, José Luis'
'García, Luis'
'Pérez, José'
'Pérez, Eduardo'
'García, Joaquín'
'Sánchez, Gregorio'
'Sehnal, Petr'
'De Ornellas, Sara'
'Williams, Thomas J.'
'Fairlamb, Ian J. S.'
_publ_section_title
;
 Synthesis and Characterization of Imine-Palladacycles Containing Imidate
 “Pseudohalide” Ligands: Efficient Suzuki--Miyaura
 Cross-Coupling Precatalysts and Their Activation To Give Pd0LnSpecies (L
 = Phosphine)
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              5095
_journal_paper_doi               10.1021/om2002443
_journal_volume                  30
_journal_year                    2011
_chemical_formula_moiety         'C38 H33 N2 O5 P Pd'
_chemical_formula_sum            'C38 H33 N2 O5 P Pd'
_chemical_formula_weight         735.03
_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     Patterson
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.1770(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3096(4)
_cell_length_b                   12.4295(5)
_cell_length_c                   23.3800(9)
_cell_measurement_temperature    100(2)
_cell_volume                     3277.9(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.000
_diffrn_measured_fraction_theta_max 0.940
_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  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            37001
_diffrn_reflns_theta_full        0.50
_diffrn_reflns_theta_max         28.24
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  0.9367
_exptl_absorpt_correction_T_min  0.7964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.889
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         7619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.889
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0295
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0505P)²+3.9894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0777
_reflns_number_gt                7150
_reflns_number_total             7619
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om2002443_si_002.cif
_cod_data_source_block           malmeos(3c)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4064655
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 0.362793(11) 0.274572(10) 0.818991(5) 0.01495(5) Uani 1 1 d .
P1 P 0.21376(4) 0.28152(4) 0.87752(2) 0.01664(10) Uani 1 1 d .
N1 N 0.50251(14) 0.29418(13) 0.76497(6) 0.0181(3) Uani 1 1 d .
O2 O 0.20501(14) 0.34614(12) 0.69460(6) 0.0306(3) Uani 1 1 d .
C32 C 0.07189(16) 0.24059(15) 0.84268(8) 0.0189(3) Uani 1 1 d .
O1 O 0.25197(14) 0.02850(12) 0.78961(7) 0.0315(3) Uani 1 1 d .
C34 C -0.08747(17) 0.28053(15) 0.77098(8) 0.0225(4) Uani 1 1 d .
H34 H -0.1231 0.3271 0.7438 0.027 Uiso 1 1 calc R
C30 C 0.1778(2) 0.21552(17) 0.99163(9) 0.0289(4) Uani 1 1 d .
H30 H 0.1327 0.2774 0.9950 0.035 Uiso 1 1 calc R
C8 C 0.49522(16) 0.28296(15) 0.70377(8) 0.0202(4) Uani 1 1 d .
C25 C 0.23298(16) 0.19689(15) 0.94090(8) 0.0192(3) Uani 1 1 d .
N2 N 0.25189(14) 0.20303(13) 0.75508(7) 0.0187(3) Uani 1 1 d .
C2 C 0.48695(17) 0.35482(15) 0.93571(8) 0.0201(4) Uani 1 1 d .
H2 H 0.4184 0.3416 0.9542 0.024 Uiso 1 1 calc R
C5 C 0.69489(17) 0.39700(16) 0.88308(8) 0.0226(4) Uani 1 1 d .
H5 H 0.7639 0.4108 0.8650 0.027 Uiso 1 1 calc R
C7 C 0.59439(16) 0.33922(15) 0.79027(8) 0.0192(3) Uani 1 1 d .
H7 H 0.6589 0.3586 0.7700 0.023 Uiso 1 1 calc R
C9 C 0.45908(17) 0.18501(17) 0.67894(9) 0.0237(4) Uani 1 1 d .
H9 H 0.4420 0.1268 0.7019 0.028 Uiso 1 1 calc R
C16 C 0.12117(18) 0.16993(18) 0.67519(9) 0.0289(4) Uani 1 1 d .
H16 H 0.0751 0.1815 0.6412 0.035 Uiso 1 1 calc R
C6 C 0.59395(16) 0.35871(14) 0.85141(8) 0.0187(3) Uani 1 1 d .
C22 C 0.22391(18) 0.60962(16) 0.89692(8) 0.0241(4) Uani 1 1 d .
H22 H 0.2737 0.6654 0.8874 0.029 Uiso 1 1 calc R
C18 C 0.18010(16) 0.41813(15) 0.89897(7) 0.0187(3) Uani 1 1 d .
C33 C 0.01746(16) 0.30879(16) 0.80087(8) 0.0208(4) Uani 1 1 d .
H33 H 0.0528 0.3743 0.7932 0.025 Uiso 1 1 calc R
C4 C 0.69169(17) 0.41431(16) 0.94161(8) 0.0235(4) Uani 1 1 d .
H4 H 0.7583 0.4396 0.9631 0.028 Uiso 1 1 calc R
C17 C 0.19656(17) 0.25213(16) 0.70780(8) 0.0220(4) Uani 1 1 d .
C37 C 0.01861(17) 0.14228(16) 0.85268(8) 0.0233(4) Uani 1 1 d .
H37 H 0.0540 0.0959 0.8801 0.028 Uiso 1 1 calc R
C1 C 0.48681(16) 0.33567(14) 0.87681(8) 0.0175(3) Uani 1 1 d .
C19 C 0.07319(17) 0.44224(16) 0.92332(8) 0.0216(4) Uani 1 1 d .
H19 H 0.0218 0.3869 0.9315 0.026 Uiso 1 1 calc R
C23 C 0.25330(17) 0.50324(16) 0.88619(8) 0.0213(4) Uani 1 1 d .
H23 H 0.3242 0.4886 0.8699 0.026 Uiso 1 1 calc R
C21 C 0.11901(18) 0.63106(16) 0.92208(8) 0.0234(4) Uani 1 1 d .
C3 C 0.58765(18) 0.39338(16) 0.96743(8) 0.0228(4) Uani 1 1 d .
H3 H 0.5848 0.4052 1.0066 0.027 Uiso 1 1 calc R
C26 C 0.30102(18) 0.10484(16) 0.93730(8) 0.0247(4) Uani 1 1 d .
H26 H 0.3393 0.0914 0.9042 0.030 Uiso 1 1 calc R
C20 C 0.04372(18) 0.54713(16) 0.93513(8) 0.0241(4) Uani 1 1 d .
H20 H -0.0266 0.5620 0.9519 0.029 Uiso 1 1 calc R
C28 C 0.25627(19) 0.05050(16) 1.03203(9) 0.0262(4) Uani 1 1 d .
C36 C -0.08714(17) 0.11173(16) 0.82231(9) 0.0239(4) Uani 1 1 d .
H36 H -0.1215 0.0455 0.8292 0.029 Uiso 1 1 calc R
C14 C 0.21797(16) 0.09709(15) 0.75483(8) 0.0215(4) Uani 1 1 d .
C13 C 0.51990(17) 0.37000(17) 0.66998(8) 0.0254(4) Uani 1 1 d .
H13 H 0.5449 0.4348 0.6867 0.030 Uiso 1 1 calc R
C11 C 0.4720(2) 0.2630(2) 0.58571(9) 0.0347(5) Uani 1 1 d .
H11 H 0.4639 0.2567 0.5460 0.042 Uiso 1 1 calc R
C12 C 0.5070(2) 0.3597(2) 0.61064(9) 0.0335(5) Uani 1 1 d .
H12 H 0.5220 0.4184 0.5876 0.040 Uiso 1 1 calc R
C10 C 0.44895(18) 0.17539(19) 0.61960(9) 0.0303(5) Uani 1 1 d .
H10 H 0.4267 0.1101 0.6027 0.036 Uiso 1 1 calc R
C27 C 0.3128(2) 0.03193(17) 0.98280(9) 0.0281(4) Uani 1 1 d .
H27 H 0.3591 -0.0294 0.9798 0.034 Uiso 1 1 calc R
C15 C 0.13214(18) 0.07901(17) 0.70334(9) 0.0276(4) Uani 1 1 d .
H15 H 0.0938 0.0148 0.6934 0.033 Uiso 1 1 calc R
C29 C 0.1893(2) 0.14360(18) 1.03689(9) 0.0313(5) Uani 1 1 d .
H29 H 0.1524 0.1574 1.0704 0.038 Uiso 1 1 calc R
O5 O -0.24403(12) 0.16138(12) 0.75022(6) 0.0282(3) Uani 1 1 d .
O3 O 0.07993(15) 0.73214(12) 0.93486(7) 0.0313(3) Uani 1 1 d .
C35 C -0.14017(16) 0.18149(16) 0.78181(8) 0.0223(4) Uani 1 1 d .
C38 C -0.2975(2) 0.05918(19) 0.75818(10) 0.0345(5) Uani 1 1 d .
H38A H -0.3696 0.0540 0.7340 0.052 Uiso 1 1 calc R
H38B H -0.3150 0.0514 0.7975 0.052 Uiso 1 1 calc R
H38C H -0.2440 0.0033 0.7484 0.052 Uiso 1 1 calc R
C24 C 0.1443(3) 0.8211(2) 0.91411(17) 0.0579(8) Uani 1 1 d .
H24A H 0.1090 0.8871 0.9257 0.087 Uiso 1 1 calc R
H24B H 0.1420 0.8182 0.8730 0.087 Uiso 1 1 calc R
H24C H 0.2251 0.8179 0.9297 0.087 Uiso 1 1 calc R
O4 O 0.26069(16) -0.01633(13) 1.07830(7) 0.0372(4) Uani 1 1 d .
C31 C 0.3249(3) -0.1140(2) 1.07454(12) 0.0551(8) Uani 1 1 d .
H31A H 0.3214 -0.1537 1.1096 0.083 Uiso 1 1 calc R
H31B H 0.4061 -0.0982 1.0683 0.083 Uiso 1 1 calc R
H31C H 0.2906 -0.1561 1.0432 0.083 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 N2 173.20(7)
C1 Pd1 N1 80.99(7)
N2 Pd1 N1 93.33(6)
C1 Pd1 P1 95.33(5)
N2 Pd1 P1 90.81(4)
N1 Pd1 P1 171.15(4)
C25 P1 C18 109.30(8)
C25 P1 C32 104.63(9)
C18 P1 C32 100.90(9)
C25 P1 Pd1 115.06(6)
C18 P1 Pd1 112.64(6)
C32 P1 Pd1 113.13(6)
C7 N1 C8 119.15(16)
C7 N1 Pd1 113.00(12)
C8 N1 Pd1 126.55(12)
C37 C32 C33 118.36(18)
C37 C32 P1 123.36(15)
C33 C32 P1 118.14(14)
C33 C34 C35 119.68(18)
C29 C30 C25 121.24(19)
C13 C8 C9 120.70(18)
C13 C8 N1 119.71(17)
C9 C8 N1 119.55(17)
C26 C25 C30 118.19(17)
C26 C25 P1 117.55(14)
C30 C25 P1 124.15(15)
C14 N2 C17 108.21(16)
C14 N2 Pd1 124.58(13)
C17 N2 Pd1 127.17(13)
C1 C2 C3 121.58(17)
C4 C5 C6 119.73(18)
N1 C7 C6 117.73(16)
C10 C9 C8 119.4(2)
C15 C16 C17 107.60(18)
C5 C6 C1 122.48(17)
C5 C6 C7 121.17(17)
C1 C6 C7 116.35(16)
C21 C22 C23 118.82(19)
C23 C18 C19 117.94(17)
C23 C18 P1 120.77(14)
C19 C18 P1 120.94(14)
C34 C33 C32 121.17(18)
C3 C4 C5 118.97(17)
O2 C17 N2 126.35(18)
O2 C17 C16 125.30(19)
N2 C17 C16 108.35(17)
C32 C37 C36 121.25(18)
C2 C1 C6 116.04(16)
C2 C1 Pd1 132.31(14)
C6 C1 Pd1 111.60(13)
C20 C19 C18 120.69(18)
C18 C23 C22 122.08(18)
O3 C21 C22 124.55(19)
O3 C21 C20 115.21(18)
C22 C21 C20 120.23(18)
C4 C3 C2 121.20(17)
C25 C26 C27 120.83(18)
C19 C20 C21 120.22(18)
O4 C28 C27 124.72(19)
O4 C28 C29 115.52(18)
C27 C28 C29 119.76(18)
C35 C36 C37 119.21(18)
O1 C14 N2 126.39(18)
O1 C14 C15 125.53(18)
N2 C14 C15 108.07(17)
C8 C13 C12 119.22(19)
C12 C11 C10 120.2(2)
C11 C12 C13 120.5(2)
C11 C10 C9 120.0(2)
C28 C27 C26 120.25(18)
C16 C15 C14 107.75(18)
C30 C29 C28 119.71(19)
C35 O5 C38 116.71(16)
C21 O3 C24 117.07(19)
O5 C35 C36 124.56(18)
O5 C35 C34 115.13(17)
C36 C35 C34 120.31(18)
C28 O4 C31 117.47(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 C1 2.0236(18)
Pd1 N2 2.0794(15)
Pd1 N1 2.1076(15)
Pd1 P1 2.2488(5)
P1 C25 1.8173(19)
P1 C18 1.8187(19)
P1 C32 1.8182(19)
N1 C7 1.286(2)
N1 C8 1.434(2)
O2 C17 1.214(2)
C32 C37 1.390(3)
C32 C33 1.402(3)
O1 C14 1.221(2)
C34 C33 1.378(3)
C34 C35 1.399(3)
C30 C29 1.384(3)
C30 C25 1.399(3)
C8 C13 1.380(3)
C8 C9 1.397(3)
C25 C26 1.385(3)
N2 C14 1.371(2)
N2 C17 1.373(3)
C2 C1 1.397(2)
C2 C3 1.398(3)
C5 C4 1.388(3)
C5 C6 1.398(3)
C7 C6 1.450(2)
C9 C10 1.389(3)
C16 C15 1.309(3)
C16 C17 1.502(3)
C6 C1 1.417(3)
C22 C21 1.388(3)
C22 C23 1.391(3)
C18 C23 1.389(3)
C18 C19 1.406(3)
C4 C3 1.386(3)
C37 C36 1.398(3)
C19 C20 1.378(3)
C21 O3 1.372(2)
C21 C20 1.394(3)
C26 C27 1.397(3)
C28 O4 1.362(2)
C28 C27 1.376(3)
C28 C29 1.392(3)
C36 C35 1.388(3)
C14 C15 1.507(3)
C13 C12 1.390(3)
C11 C12 1.382(3)
C11 C10 1.382(4)
O5 C35 1.364(2)
O5 C38 1.425(3)
O3 C24 1.428(3)
O4 C31 1.421(3)
